polymers

Review
Jojoba Oil: An Updated Comprehensive Review on Chemistry,
Pharmaceutical Uses, and Toxicity
Heba A. Gad 1 , Autumn Roberts 2 , Samirah H. Hamzi 3 , Haidy A. Gad 4 , Ilham Touiss 5 , Ahmed E. Altyar 6 ,
Osama A. Kensara 7 and Mohamed L. Ashour 3,4, *

1 Department of Pharmaceutics and Industrial Pharmacy, Faculty of Pharmacy, Ain Shams University,
Cairo 11566, Egypt; [Link]@[Link]
2 Independent Researcher, La Route de la Haule, St. Peter, Jersey JE3 7BA, UK; autumnggroberts@[Link]
3 Department of Pharmaceutical Sciences, Pharmacy Program, Batterjee Medical College, P.O. Box 6231,
Jeddah 21442, Saudi Arabia; [Link]@[Link]
4 Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, Cairo 11566, Egypt;
haidygad@[Link]
5 Laboratory of Bioresources, Biotechnologies, Ethnopharmacology, and Health, Faculty of Sciences,
University Mohamed I, Oujda 60000, Morocco; [Link]@[Link]
6 Department of Pharmacy Practice, Faculty of Pharmacy, King Abdulaziz University, P.O. Box 80260,
Jeddah 21589, Saudi Arabia; aealtyar@[Link]
7 Department of Clinical Nutrition, Faculty of Applied Medical Sciences, Umm Al-Qura University,
P.O. Box 7067, Makkah 21955, Saudi Arabia; oakensara@[Link]
* Correspondence: [Link]@[Link]; Tel.: +966-54-9255-376



Abstract: Jojoba is a widely used medicinal plant that is cultivated worldwide. Its seeds and oil


have a long history of use in folklore to treat various ailments, such as skin and scalp disorders,
Citation: Gad, H.A.; Roberts, A.; superficial wounds, sore throat, obesity, and cancer; for improvement of liver functions, enhancement
Hamzi, S.H.; Gad, H.A.; Touiss, I.;
of immunity, and promotion of hair growth. Extensive studies on Jojoba oil showed a wide range of
Altyar, A.E.; Kensara, O.A.; Ashour,
pharmacological applications, including antioxidant, anti-acne and antipsoriasis, anti-inflammatory,
M.L. Jojoba Oil: An Updated
antifungal, antipyretic, analgesic, antimicrobial, and anti-hyperglycemia activities. In addition, Jojoba
Comprehensive Review on
Chemistry, Pharmaceutical Uses, and
oil is widely used in the pharmaceutical industry, especially in cosmetics for topical, transdermal,
Toxicity. Polymers 2021, 13, 1711. and parenteral preparations. Jojoba oil also holds value in the industry as an anti-rodent, insecticides,
[Link] lubricant, surfactant, and a source for the production of bioenergy. Jojoba oil is considered among
13111711 the top-ranked oils due to its wax, which constitutes about 98% (mainly wax esters, few free fatty
acids, alcohols, and hydrocarbons). In addition, sterols and vitamins with few triglyceride esters,
Academic Editor: Bramasta Nugraha flavonoids, phenolic and cyanogenic compounds are also present. The present review represents
an updated literature survey about the chemical composition of jojoba oil, its physical properties,
Received: 28 April 2021 pharmacological activities, pharmaceutical and industrial applications, and toxicity.
Accepted: 21 May 2021
Published: 24 May 2021
Keywords: jojoba; Simmondsia; chemistry; liquid wax; biology; toxicity; pharmaceutical/industrial uses

Publisher’s Note: MDPI stays neutral

with regard to jurisdictional claims in
published maps and institutional affil-
1. Introduction
iations.
The plant kingdom continues to hold considerable importance in our daily life. In ad-
dition to supplying humanity with food, it is considered as a potential source of thousands
of novel materials such as fragrances, flavoring agents, dyes, fibers, beverages, building
materials, heavy metal chelators, and many useful compounds of great therapeutic value.
Copyright: © 2021 by the authors.
Early studies of plants helped humankind make use of local flora for healing ailments.
Licensee MDPI, Basel, Switzerland.
These studies have continued until now to seek out new agents for the treatment of various
This article is an open access article
distributed under the terms and
diseases. Recent investigations regarding plants with centuries of use in folk medicine
conditions of the Creative Commons
have generated a great deal of information about the biologically active chemical compo-
Attribution (CC BY) license (https://
nents responsible for many claimed medicinal effects. As a result of thorough research
[Link]/licenses/by/ involving the isolation and structure characterization techniques, many lead compounds,
4.0/). and prototypes from natural products have assumed reputable roles in medicine. Despite

Polymers 2021, 13, 1711. [Link] [Link]

Polymers 2021, 13, 1711 2 of 22

the huge number of synthetic and semisynthetic drugs, the most valuable medicinal agents
still in use are obtained from medicinal plants.
There is high consumption of natural resources due to the increasing population. The
resultant demand for green energy amidst fossil fuel shortages has rekindled interest in
Jojoba oil (Simmondsia chinensis (Link) Schneider). Jojoba oil is the only unsaturated liquid
wax readily extractable in large quantities from plant sources (≈52% of the total seed
weight), which shows a high structure similarity with the sperm whale oil. This similarity
has increased the interest in Jojoba oil as a replacement for sperm whale oil (spermaceti
wax) since the 1970s [1].
Simmondsia chinensis (Link) Schneider is native to North and Central American deserts
but cultivated worldwide in Chile, Egypt, and Argentina [2]. Jojoba was widely used by
Native Americans in the Sonora desert (California) as a foodstuff in the form of cooked
fruits and in oil form as a therapeutic for multiple ailments: cancer therapy, liver and kidney
disorders, obesity, parturition, sore throat, superficial wound healing, warts, psoriasis,
acne, sunburn, and treatment of poison ivy exposure [3–6]. Jojoba oil is widely used in
the pharmaceutical industry, especially in cosmetics, to restore the ordinary health of hair
and skin. The leaf extract, combined with extracts from other plants, also acts as anti-
inflammatory agents to treat sensitive skin stress [7]. Jojoba cosmetic products currently
on the market include the following: bath oil, body oil, cleansing creams, cleansing pads,
cleansing scrubs, nourishing facial cream, facial oil, hair conditioner, hair oil, makeup
remover, and shaving cream [8–11].
In addition, the oil has many industrial applications that include an extreme tem-
perature/extreme pressure lubricant in the form of sulfurized oil, which can bear high
temperature and pressure without changing its viscosity [6,12]. Other industrial uses
include the extraction and separation of isotopes such as Uranium (VI), Thorium (IV), and
Plutonium (IV); in the leather industry as a fat liquor with good tanning properties [5]; as a
surfactant, fire retardant, lamp oil, candle wax, polishes [13], and antifoaming agents in
isolation of penicillin and tetracycline [9].
An updated and in-depth review about jojoba oil chemistry, its pharmaceutical and
industrial uses, and toxicity was conducted and is presented in this work to supplement
the lack of comprehensive reviews covering the plant since the 1990s. The keywords jojoba,
Simmondsia, chemistry, pharmaceutical preparations, emulgels, nanoparticles, toxicity, and
biological activity were used in many combinations to search Scifinder® , PubMed® , Web
of Science ® starting 1990 until 2021. English language was used as the only filter.

2. Common Names and Botanical Characteristics

The word jojoba, pronounced “ho-ho-ba”, is a distortion of the native Papago Indian
word “howhowi”. Jojoba is known by many other names such as bucknut, coffee nut,
goatnut, pignut, nutpush, goatberry, sheepnut, and lemon leaf [14]. The seeds of the jojoba
plant are dark brown, akin to large coffee beans.
Plants of the order Euphorbiales are usually herbs, shrubs, or sometimes trees [15].
They are widely distributed globally, especially in temperate, subtropical, and tropical
regions [16]. They have frequently unisexual (rarely bisexual) hypogynous flowers, which
are generally regular with a single whorl of a green perianth. The stamens are equal in
number to perianth leaves or numerous. The pistil is composed of three carpels forming a
trilocular ovary, with each chamber containing one or two anatropous, pendulous ovules in
the inner angle with ventral or dorsal raphe [17]. Simmondsiaceae is a small family of one
genus, Simmondsia, which is abundant in Southern Arizona, Sonora, and Baja California.
Plants that belong to “Simmondsiaceae” are mostly woody branched shrubs that reach
2–4 m in height [4–6]. A photograph of male and female trees, flowers, and seeds of
Simmondsia chinensis are displayed in Figure 1.
Polymers 2021, 13, x FOR PEER REVIEW 3 of 22

Polymers 2021, 13, 1711 3 of 22

reach 2–4 m in height [4–6]. A photograph of male and female trees, flowers, and seeds of
Simmondsia chinensis are displayed in Figure 1.

Figure
Figure 1.1. A
A photograph
photograph showing
showingdifferent
differentorgans
organsof
ofSimmondsia
Simmondsiachinensis,
chinensis,(A)
(A)Branch
Branchofofthe
theplant
plant
(X 0.8), (B) Male flowers (X 1.0), (C) Old male and female trees (X 0.02), (D) Female flower (X(X
(X 0.8), (B) Male flowers (X 1.0), (C) Old male and female trees (X 0.02), (D) Female flower 0.5),
0.5), (E)
(E) Ripe fruit (X 0.5) and (F) Seed (X 0.8) (Photographer Eng. Nabil Elmougi, the jojoba farms of
Ripe fruit (X 0.5) and (F) Seed (X 0.8) (Photographer Eng. Nabil Elmougi, the jojoba farms of The
The Egyptian Natural Oil Company, Ismailia Desert Road, Egypt).
Egyptian Natural Oil Company, Ismailia Desert Road, Egypt).
3.
3. Chemical
Chemical Constituents
Constituents
Jojoba
Jojoba oil is
oil composed of
is composed almost 98%
of almost 98% pure
pure waxes
waxes (mainly
(mainly wax
wax esters,
esters, few
few free
free fatty
fatty
acids,
acids, alcohols, and hydrocarbons), sterols, and vitamins with few triglyceride esters, soso
alcohols, and hydrocarbons), sterols, and vitamins with few triglyceride esters, it
it
is is widely
widely known
known asas liquid
liquid wax
wax rather
rather than
than oiloil
oror
fatfat [18].
[18].

3.1. Jojoba Wax

Investigation of the different organs of the jojoba plant for the presence of the wax
Investigation
that the
revealed that theseeds
seedscontain
containmost
mostofofthe
thewaxwax content
content in in
thethe plant
plant (almost
(almost 50–52%
50–52% of
of the
the seed
seed weight)
weight) [5]. Jojoba
[5]. Jojoba wax wax is composed
is composed mainly mainly of esters
of esters and,
and, to to a lesser
a lesser extent,extent, free
free acids,
acids,alcohols,
free free alcohols, and hydrocarbons
and hydrocarbons [4]. [4]. Esters
Esters areare composed
composed bybythe
theassociation
association of of long
straight-chain fatty acids with long straight-chain or higher molecular weight monohydric
alcohols, C20
alcohols, C20 and
and C22;
C22; both
both the
the acids
acids and
and alcohols
alcohols are
are cis-monounsaturated
cis-monounsaturated at at the
the (ω-9)
(ω-9)
position. Small triglyceride esters are also present [19–22].
position. Small triglyceride esters are also present [19–22].

3.1.1. Wax
3.1.1. Wax Esters
Esters
The main components
The main components ofof the
the wax
wax esters
esters that
thathave
havebeen
beenisolated
isolatedand
andpreviously
previouslyidenti-
iden-
fied are docosenyl eicosenoate “erucyl jojobenoate” (1), eicosenyl eicosenoate “jojobenyl
tified are docosenyl eicosenoate “erucyl jojobenoate” (1), eicosenyl eicosenoate “jojobenyl
jojobenoate” (2), eicosenyl docosenoate “jojobenyl erucate” (3), docosenyl docosenoate (4),
jojobenoate” (2), eicosenyl docosenoate “jojobenyl erucate” (3), docosenyl docosenoate (4),
eicosenyl oleate (5), and docosenyl oleate (6) (Table 1) [23]. Many other wax esters and free
eicosenyl oleate (5), and docosenyl oleate (6) (Table 1) [23]. Many other wax esters and
fatty alcohols and acids components are present in small quantities [19,24].
free fatty alcohols and acids components are present in small quantities [19,24].
It was initially thought that jojoba wax esters were made up of random combinations
It was initially thought that jojoba wax esters were made up of random combinations
of alcohols and acids until Miwa conducted a study on these combinations [13]. He showed
of alcohols and acids until Miwa conducted a study on these combinations [13]. He
a significant difference between the observed results and those calculated by a random
showed a significant difference between the observed results and those calculated by a
association of acids and alcohols. For instance, it was observed that (acid/alcohol, %
experimental (% random)): (C20:1/C’20:1, 28.0% (31.8%)), (C20:1/C’22:1, 10.3% (5.7%)),
(C22:1/C’20:1, 41.4% (32.0%)), (C22:1/C’22:1, 1.9% (5.7%)) indicating that eicosenyl do-
Polymers 2021, 13, x FOR PEER REVIEW 4 of 22

Polymers 2021, 13, 1711

random association of acids and alcohols. For instance, it was observed that (acid/alcohol, 4 of 22
% experimental (% random)): (C20:1/C’20:1, 28.0% (31.8%)), (C20:1/C’22:1, 10.3% (5.7%)),
(C22:1/C’20:1, 41.4% (32.0%)), (C22:1/C’22:1, 1.9% (5.7%)) indicating that eicosenyl do-
cosenoate ester is preferably biosynthesized by the association of eicosenoic acid and do-
cosenoate
cosenol. Theseester is preferably
combinations biosynthesized
demonstrate by thefavor
that plants association
specificofassociations,
eicosenoic acid
which and
docosenol.
correspond to These combinations
their genome. From demonstrate
an analytical that
pointplants favor
of view, thisspecific associations,
observation which
constitutes
correspond
a valuable tooltofor
their genome.
detecting From an analytical
adulterated pointdiscrimination
oil and good of view, this observation constitutes
between natural Jo- a
valuable tool for detecting adulterated oil and good discrimination between natural
joba wax and its synthetic substitutes. In the latter case, associations between fatty acids Jojoba
andwax and itsare
alcohols synthetic
governedsubstitutes. In the latterrules,
by thermodynamic case, and
associations
random between fatty acids
results would be ob-and
alcohols are governed by thermodynamic rules, and random results would be observed.
served.

Table
Table 1. Chemical
1. Chemical structures
structures forfor
thethe most
most abundant
abundant waxwax ester
ester components
components in in jojoba
jojoba wax.
wax.

R1= C20H41, R2= C17 H35

R1 = C20 H41 , R2 = C17 H35
Docosenyl eicosenoate (1)
Docosenyl eicosenoate (1)
RR 1= C18H37, R2= C17 H35
1 = C18 H37 , R2 = C17 H35
Eicosenyl
Eicosenyl eicosenoate (2)
eicosenoate (2)
RR = CC1818H
1 1= H37 R22==C
37, R 19H
C19 H3939 Eicosenyl
Eicosenyl docosenoate
docosenoate (3)(3)
RR1 1=
= CC1616H
H33 , R = C19H
33, R22= C19
H3939 Docosenyl docosenoate
Docosenyl docosenoate (4) (4)
R1 = C18 H37 , R2 = C17 H33 (C9) Eicosenyl oleate (5)
R1= C18H37, R2= C17 H33 (C9) Eicosenyl oleate (5)
R1 = C20 H41 , R2 = C17 H33 (C9) Docosenyl oleate (6)
R1= C20H41, R2= C17 H33 (C9) Docosenyl oleate (6)

3.1.2. Free Fatty Acids and Alcohols

3.1.2. Free Fatty Acids and Alcohols
It was reported that the natural oil contains small quantities of free fatty acids (0.96%)
It was reported that the natural oil contains small quantities of free fatty acids (0.96%)
and free alcohols (1.11%), as seen in (Table 2) [13].
and free alcohols (1.11%), as seen in (Table 2) [13].
Table 2. The composition of free fatty alcohols and fatty acids derived from jojoba oil.
Table 2. The composition of free fatty alcohols and fatty acids derived from jojoba oil.
Alcohols (%) Acids (%)
Alcohols (%) Acids (%)
Tetradecanol
Tetradecanol trace trace Dodecanoic
Dodecanoic trace
trace
Hexadecanol 0.1 Tetradecanoic trace
Hexadecanol 0.1 Tetradecanoic trace
Heptadec-8-enol trace Pentadecanoic trace
Heptadec-8-enol
Octadecanol 0.2 trace Pentadecanoic
Hexadecanoic trace
1.2
Octadecanol
Octadec-9-enol 0.7 0.2 Hexadecanoic
Hexadec-7-onoic 0.11.2
Octadec-11-enol
Octadec-9-enol 0.4 0.7 Hexadec-9-enoic
Hexadec-7-onoic 0.20.1
Eicosanol trace Heptadecenoic trace
Octadec-11-enol 0.4 Hexadec-9-enoic 0.2
Eicos-11-enol 43.8 Octadecanoic 0.1
Eicosanol
Hecos-12-enol trace trace Heptadecenoic
Octadec-9-enoic trace
10.1
Eicos-11-enol
Docosanol 1.0 43.8 Octadecanoic
Octadec-11-enoic 1.10.1
Docos-12-enol
Hecos-12-enol 44.9 trace Octadecadienoic
Octadec-9-enoic 0.110.1
Tetracos-15-enol
Docosanol 8.9 1.0 Octadecatrienoic
Octadec-11-enoic trace1.1
Hexacosenol trace Nonadecenoic trace
Docos-12-enol 44.9 Octadecadienoic
Eicosanoic 0.10.1
Tetracos-15-enol 8.9 Octadecatrienoic
Eicos-l1-enoic trace
71.3
Hexacosenol trace Nonadecenoic
Eicosadienoic trace
trace
Docosanoic
Eicosanoic 0.20.1
Docos-13-enoic 13.6
Eicos-l1-enoic
Tricosenoic trace
71.3
Eicosadienoic
Tetracosenoic trace
trace
Docosanoic
Tetracos-15-enoic 1.30.2
Docos-13-enoic 13.6
3.2. Sterols Tricosenoic trace
Tetracosenoic trace
There are many reports concerning the sterol content of jojoba oil [5,19]. The major
Tetracos-15-enoic
content of the sterols fraction is cholesterol (7), β-Sitosterol (8), campesterol (9),1.3stigmas-
terol (10), and isofucosterol (11). Most of these sterols are sketched in Figure 2, and the
composition is tabulated in Table 3 [22].
 3.2. Sterols
There are many reports concerning the sterol content of jojoba oil [5,19]. The major
Polymers 2021, 13, 1711 content of the sterols fraction is cholesterol (7), β-Sitosterol (8), campesterol (9), stigmas-
5 of 22
terol (10), and isofucosterol (11). Most of these sterols are sketched in Figure 2, and the
composition is tabulated in Table 3 [22].

Figure
Figure 2.
2. Structures
Structures of
of major
major sterols
sterols content
content of
of jojoba oil.

Table
Table 3.
3. The
The average
average percentage
percentage of
of sterols
sterols content
content in
in jojoba oil.
jojoba oil.
Sterol
Sterol
Sterol Fraction (%)
Sterol Fraction (%)
Total Wax (mg/kg Seed)
Total Wax (mg/kg Seed)
Unidentified 0.4 16
Unidentified 0.4 16
Stigmasta-5,25-dien-3β-ol
Stigmasta-5,25-dien-3β-ol 0.6
0.6 2424
Fucosterol
Fucosterol 0.6
0.6 2424
Isofucosterol
Isofucosterol 4.1
4.1 163
163
Cholesterol
Cholesterol 0.8
0.8 3232
Stigmasterol 6.7 266
Stigmasterol
Campesterol
6.7
16.9
266
672
Campesterol
Sitosterol 16.9
69.9 672
2780
Sitosterol 69.9 2780
3.3. Flavonoids, Phenolic, and Cyanogenic Compounds
3.3. Flavonoids, Phenolic, and Cyanogenic Compounds
Although phenolic compounds are the most common secondary metabolites dis-
Although
tributed phenolic
in nature, theycompounds are the in
are only present most common
small secondary
quantities metabolites
in jojoba, distrib-
as reported in
uted in nature, they are only present in small quantities in jojoba, as
Table 4 [25]. Ten flavonoids have been identified as quercetin (12), quercetin 3 methyl reported in Table
0 4
[25]. Ten flavonoids have been identified as quercetin (12), quercetin 0
ether (isorhamnetin), quercetin 3-methyl ether (14), quercetin 3,3 -dimethyl ether (15),3′methyl ether (iso-
rhamnetin),
isorhamnetin quercetin 3-methyl
3-O-glucoside ether
(16), (14), quercetin
quercetin 3,3′-dimethyl
3-O-glucoside ether (15), isorhamnetin
(17), typhaneoside (18), isorham-
3-O-glucoside (16), quercetin
netin 3-O-rutinoside 3-O-glucoside
(19), quercetin (17), typhaneoside
3-O-rutinoside (20). Some (18), isorhamnetin
lignans 3-O-ru-
are also present:
tinoside
(+)-lyoniresinol 4,40 -bis-O-β-
(19), quercetin 3-O-rutinoside (20). Some lignans
D -glucopyranoside are also present:
(21), salvadoraside (22),(+)-lyoniresinol
and eleuthero-
4,4′-bis-O-β-D-glucopyranoside
side E (23) [26]. Simmondisin (24), (21), simmonosides
salvadoraside A (22), and
(25), eleutherosideB E(26),
simmonosides (23)and
[26].
4,
Simmondisin (24), simmonosides A (25), simmonosides B (26), and
5-dimethyl-4-O-alpha-D-glucopyranosylsimmondsin (27) are the main cyanogenic glyco- 4, 5-dimethyl-4-O-al-
pha-D-glucopyranosylsimmondsin
sides [20,21,27]. (27) are the main cyanogenic glycosides [20,21,27].
 Polymers 2021, 13, x FOR PEER REVIEW 6 of 22
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22

Table 4. Chemical structures for the most abundant flavonoids in jojoba.

Table 4. Chemical structures for the most abundant flavonoids in jojoba.
Table 4. Chemical structures for the most abundant flavonoids in jojoba.
Table 4. Chemical structures for
for the
the most
most abundant
abundant flavonoids
flavonoids in
in jojoba.
jojoba.

R1 R2 R3
R1 R2 R3
Quercetin (12) R1
H R2
H R3
H
Quercetin (12) H
R1 H
R2 H
R3
Quercetin (12)
Isorhamnetin (13) HR1 HR2
Me H
R3
Isorhamnetin
Quercetin (12)(13) HH Me
H HH
Isorhamnetin
Quercetin 3-methyl
Quercetin (13)
ether (14)
(12) HH Me
HH H
Me
H
Quercetin 3-methyl(13)
Isorhamnetin ether (14) HH H
Me HMe
Quercetin
Quercetin 3-methyl(13)
Isorhamnetin
3,3′-methyl ether
ether(14)
(15) HH HMe
Me H
Me
Quercetin
Quercetin 3,3′-methyl
3-methyl
Quercetin 3-methyl ether
ether
ether (15)
(14)
(14) HH MeH
H Me
Me
Quercetin 3,3′-methyl
isorhamnetin 3-O-glucoside ether (15)
(16) HH Me Me
Me
Glc
isorhamnetin 0 -methyl ether (15)
3,33-O-glucoside (16)
Quercetin
Quercetin 3,3′-methyl
isorhamnetin ether
3-O-glucoside
Quercetin-3-O-glucoside (15)
(16)
(17) HH
HH
H MeMe
Me
Me
H
Glc
Me
Me
Glc
isorhamnetin 3-O-glucoside(17)
Quercetin-3-O-glucoside (16) H HMe Glc
Glc
isorhamnetin 3-O-glucoside (17)
Quercetin-3-O-glucoside (16) HH Me
HH Glc
Glc
Quercetin-3-O-glucoside (17) H Glc
Quercetin-3-O-glucoside
Typhaneoside (18) (17) H
Me HH Glc
Typhaneoside (18) Me H
Typhaneoside
Typhaneoside (18) (18) MeMe HH
Typhaneoside (18) Me H
Isorhamnetin 3-O-rutinoside (19) Me H
Isorhamnetin
Isorhamnetin3-O-rutinoside (19)
3-O-rutinoside (19) MeMe HH
Isorhamnetin 3-O-rutinoside (19) Me H
Isorhamnetin 3-O-rutinoside (19) Me H
Quercetin3 O-rutinoside (20)
Quercetin 3-O-rutinoside H H
Quercetin3 O-rutinoside(20)
(20) HH HH
Quercetin3 O-rutinoside (20) H H
Quercetin3 O-rutinoside (20) H H
3.4. Fat-SolubleVitamins
3.4. Vitamins
[Link]-Soluble
Fat-Soluble Vitamins
3.4. Fat-Soluble
Vitamin DVitamins and its derivatives
derivatives viz. α, γ, and δδ tocopherol were isolated and quantita-
Vitamin
VitaminDD
3.4. Fat-Soluble
and
andits
Vitamins its derivatives viz. α, γ,
viz. α, and δ
γ, and tocopherolwere
tocopherol wereisolated
isolatedand andquantita-
quanti-
tively
tatively Vitamin
estimated D
estimatedinin and
in theits
the derivatives
oil where viz. α,
γ-tocopherol γ, and δ
makes tocopherol
up were
approximately isolated79% and
of quantita-
these com-
tively estimated
Vitamin D and the
its oiloil where
where
derivatives
γ-tocopherol
γ-tocopherol
viz. α, γ, and makes
δ
makes
tocopherol
up approximately
up approximately
were isolated 79%and 79% of these
of these com-
quantita-
tively
pounds.
compounds. estimated
Other in the
fat-soluble
Other oil
fat-soluble where
vitamins γ-tocopherol
vitamins such suchas makes
vitamin
as vitamin Aup areapproximately
A arealso found 79%
[22]. of these com-
pounds.
tively Other
estimated fat-soluble
in the oil where vitamins such
γ-tocopherol as vitamin
makes up A are alsoalso
found
approximately
found [22]. [22].
79% of these com-
pounds. Other fat-soluble vitamins such as vitamin A are also found [22].
pounds.
[Link]
PhysicalOther fat-soluble
Characters
Characters of
ofthevitamins
theOil Oil such as vitamin A are also found [22].
4. Physical Characters of the Oil
4. Physical
Crude Characters
Crudejojobajojobaoil obtainedOil
of
oilobtained the directly
directlyby byeither
eithercold
coldexpression
expressionororsolvent solventextraction
extractionofof
4. CrudeCharacters
Physical jojoba oil obtained the Oildirectly
ofmodifications, by either cold expression or solvent extraction of
the seeds,
Crude without
jojoba
the seeds, without any any
oil obtained directly yields
by an
either oil
cold with a golden
expression
yields an oil with a golden light yellow or or light
solvent yellow
extraction color.
color. of
It
the seeds,
Crude without
jojoba any
oil modifications,
obtained directly yields
by an oil
either cold with a goldenororsolvent
expression light yellowextraction [Link]
Ithas
has a
the seeds,pleasant,
without
a pleasant, slightly nutty
any modifications,
slightly taste [6].
nutty taste [6]. yields The
The thermalthermal
an oil with and oxidative
a golden or
and oxidative stabilities
light yellow
stabilities of the
of thecolor. oil
oil areIt
hasseeds,
the a pleasant,
without slightly nutty tastehigh
[6].yields
The thermal andaoxidative orstabilities of the oil are
are
hashigh;
high; therefore,
a therefore,
pleasant, theanyoil modifications,
the
slightly oil
nutty
shows showstaste resistance
high [6]. The an
resistance oil toward
thermal
toward withand golden
rancidity
oxidative
rancidity due light
duetheto
stabilities
to yellow
the
presence thecolor.
of presence It
oilnat-
of are
high;
has therefore,
a antioxidants
pleasant, the oil nutty
slightly shows highδ[6].
resistance toward rancidity or due to theoil, presence of are
nat-
of natural
high;
ural antioxidants
therefore, the(α,oil andγ,δtaste
(α,
γ, shows and The[6].
tocopherol)
high resistance
tocopherol) thermal[6]. and
toward
Refined oroxidative
Refined
rancidity
bleached due stabilities
bleached
oil,toobtained of
the presence the
obtained oil by
of nat-
by passing
ural
high;
passing antioxidants
therefore,
the naturalthe (α,
oil γ, and
shows
over δ tocopherol)
high
activated resistance
charcoal[6]. Refined
toward
and or bleached
rancidity
treating withdue oil,
to
caustic obtained
the presence
alkali by passing
of
substances,nat-
ural antioxidants (α, γ, and δ tocopherol) [6]. Refined or bleached
the natural oil over activated charcoal and treating with caustic alkali substances, is nearly oil, obtained by passing
isthe
ural
the
white
natural
natural
with
oil with
antioxidants
nearly whiteoil
low
over
over(α, activated
γ, and
low
oxidative oxidative
activated
charcoal
δstability
tocopherol) and
stability
charcoal due and [6].treating
todue Refined with
to subsequent
treating
subsequent with
caustic
or bleached
caustic
removal
alkali
oil,
removal
alkali
of the
substances,
obtained
of antioxidants. is nearly
by passing
the antioxidants.
substances, is nearly
The
white
The with
thermal low oxidative
stability of both stability
natural due
and to subsequent
bleached forms removal
is high, of
which the antioxidants.
is indicated The
the natural
white with
thermal oil over activated
low oxidative
stability of both natural charcoal
stabilityanddueand treating
to subsequent
bleached with
forms is high,caustic
removal alkali
which of is substances,
theindicated
[Link] aby
bynearly The
higha
thermal
high
white flash
withstability
point
low of both natural
reaching
oxidative 295 ◦ C and
stability [28].
duebleached
The
to oil’sforms
viscosity
subsequent isremoval
high, which
favors using
of is indicated
the the oil by a The
and/or
antioxidants. high
its
thermal
flash pointstability
reaching of both295 °C natural
[28]. and
The bleached
oil’s viscosityformsfavors is high, which
using theisoilindicated
and/or its byderiva-
a high
flash point
derivatives
thermal reaching
as
stability anofextreme
both 295natural
°C [28].andThe oil’s viscosity
temperature/pressure favors
lubricant using
[6,12]. the isisoil
Jojoba and/or
oil is in its aderiva-
soluble in
flash as
tives point reaching
an extreme 295 °C [28]. Thebleached
temperature/pressure forms
oil’s lubricant
viscosity is high,
favors
[6,12]. which
using
Jojoba the
oil indicated
oil and/or
soluble by high
itscommon
deriva-
tives
common
flash as an extreme
solvents temperature/pressure
such295as°Cbenzene and lubricant
chloroform. [6,12].
However, Jojoba oil
it the
isoil is soluble
essentially in
and/orimmisciblecommon
tivespoint
as an
solvents reaching
suchextreme
as benzene and[28].
temperature/pressure The oil’s
chloroform. viscosity
lubricant
However, favors
[6,12]. using
Jojoba
it is essentially oil
is soluble
immiscible itsincommon
in deriva-
metha-
insolvents
methanol.
tives as ansuch
extremeas benzene
The solubility andof
temperature/pressure chloroform.
jojoba in However,
different
lubricant organic it issolvents
[6,12]. essentially
Jojoba (Table
oil is immiscible
5)
soluble [29]in in metha-
and
commonother
solvents such as benzene and chloroform. However, it is
nol. The solubility of jojoba in different organic solvents (Table 5) [29] and other physical essentially immiscible in metha-
nol. Thesuch
physical
solvents solubility
properties
as of jojoba
(Table
benzene 6)
and inchloroform.
are different
listed in organic
many
However, solvents
previous it is (Table[4–6,13,29–31].
works
essentially5) [29] and other
immiscible in physical
metha-
nol. The solubility
properties (Table 6)ofare jojoba
listed inin different organic solvents
many previous (Table 5) [29] and other physical
works [4–6,13,29–31].
properties
nol. (Table 6)
The solubility are listed in many previous works [4–6,13,29–31].
properties (Table of jojoba
6) are listedin different
in many organic
previoussolvents (Table 5) [29] and other physical
works [4–6,13,29–31].
Table 5. Solubility
properties (Tablecharacteristics
6) are listed in of many
jojoba oil in common
previous works organic solvents at 15 ◦ C a .
[4–6,13,29–31].
Solvent mL of Solvent Observation b
5.0 I
Water
10.0 I
10.0 I
Acetic acid 40.0 I
50.0 S
Polymers 2021, 13, 1711 7 of 22

Table 5. Cont.

Solvent mL of Solvent Observation b

1.0 I
Methanol 10.0 I
40.0 S
1.0 I
Ethanol 5.0 I
20.0 S
t-Amyl Alcohol 1.0 S
1-Butanol 1.0 S
1.0 I
Acetone 3.0 I
8.0 I
Benzene 1.0 I
Toulene 1.0 I
Carbon Tetrachloride 1.0 I
s-Tetrachlocthane 1.0 I
Diethylether 1.0 I
Tetrahydrofuran 1.0 I
Hexane 1.0 I
Cyclohexane 1.0 I
1.0 I
Dimethylformamide 10.0 I
30.0 S
1.0 I
Dimethylsulfoxide 5.0 I
20.0 S
1.0 I
Acetonitrile 10.0 I
30.0 S
Aniline 2.0 S
m-Cresol 2.0 S
a all measurement used 0.2 g b I = insoluble; S = soluble.

Table 6. Some physical properties of jojoba oil as reported in the literature [31].

Freezing point, ◦ C 10.6–7.0

Melting point, ◦ C 6.8–7.0
Boiling point at 757 mm under N2, ◦ C 389
Heat of fusion by DSC, Cal/g 21
Refractive index at 25 ◦ C 1.465
Dielectric constant, 27 ◦ C 2.680
Specific conductivity, 27 ◦ C, mho/cm 8.86.10–13
Specific gravity, 25/25 ◦ C 0.863
MV-1 rotor in MY cup, cp 35
Plate and cone with PK-1, cp 33
Brookfield, spindle #1, 25 ◦ C, cp 37
Cannon–Fenske, 25 ◦ C, cp 50
Cannon–Fenske, 100 ◦ C centistokes 27
Smoke point, ◦ C 195
Flash point, ◦ C 295
Fire point, ◦ C 338
Iodine value 82
Saponification value 92
Acid value <2
Acetyl value 2
Unsaponifiable matter, % 51
Total acids, % 52
Iodine value of alcohols 77
Iodine value of acids <76
Average molecular weight of wax esters 606
Polymers 2021, 13, 1711 8 of 22

5. Chemical Properties of the Oil

Jojoba molecules contain two double bonds at ω-9 positions in both alcohol and
acid sides, which are separated by an ester bond. While in typical plant oils, double
bonds are usually close to each other; in jojoba molecules, they are far apart and uneven
from the center. These three active sites have been proven to be the source of many
intermediates and final products with different physical and chemical characters. These
derivatives are described with particular reference to the reaction that leads to the formation
of a wide potential of industrial and pharmaceutical applications: the production of
semisoft waxes by geometrical isomerization in the manufacture of suppository bases,
production of hard waxes by hydrogenation in the manufacture of candles, production of
additives by sulfurization for high-pressure/high-temperature lubricants, production of
selective exectrants for the nuclear industry by phosphonation of chemically bonded jojoba
oil [5,32,33].
These chemical modifications provide a wide range of polymers with diverse proper-
ties that could serve as good candidates in industrial application, especially those related
to the polyhydroxyurethanes polymers that will be discussed in detail in Section 8.1.
Shani continued his basic research on the possible reaction schemes at the double bond.
All-trans jojoba oil was prepared by the straight chemical route, involving the anti-addition
of bromine or chlorine to the double bonds followed by displacement and elimination of
the halogens with Na I. All-trans jojoba was obtained at a yield greater than 75% and had
a melting point of 52–54 ◦ C. Similar to those obtained from natural liquid oil, a series of
products were prepared from the semisolid all-trans jojoba under the same conditions used
for the natural liquid oil [34,35].
Thorough investigations of the all-trans derivatives and their physical and chemi-
cal characteristics revealed that the all-trans derivatives of jojoba oil had essentially the
same melting points as those of the cis configuration. Based on these observations, Shani
concluded that the polar groups played a more significant role than the geometrical config-
uration of the double bonds in determining the strength of the packing of the molecules in
the solid phase.

5.1. Cis/Trans Isomerization

Unsaturated fatty materials can be converted into solid materials by geometrical
isomerization of the double bonds. The trans isomer of jojoba is thermodynamically more
stable than the cis form. Moreover, it has a substantially higher melting point, and its
soaps have superior wetting and detergency properties. The reaction has never had any
commercial significance, which is most likely because the same results can be achieved by
partial hydrogenation with the additional advantages of higher oxidation stability. This
phenomenon could expand the uses of this isomerized material, especially as a suppository
base in the pharmaceutical industry due to its natural creamy appearance coupled with a
melting point close to human body temperature [6].
Wisniak and Alfandary were the first to report on the geometrical isomerization of
jojoba oil with selenium and NO2 catalysts under a wide range of conditions. Melting
points of the resultant product varied between 36 and 42 ◦ C. Proper adjustment of the
operating conditions could, if necessary, allow the preparation of a material with a melting
point close to average human body temperature [36]. Later, Galun and coworkers described
the thermal and photosensitized isomerization of jojoba oil. The absorption of light at
wavelengths of 366 nm or more via the allowance of sensitizers enables the acquisition
of the isomerized form of jojoba oil. However, this is dependent on the fact that the cis
isomer can transform into the trans form if heated to a temperature sufficiently high and
that the double bonds present in jojoba oil absorb light of wavelengths below 200 nm as a
result [37,38].
Polymers 2021, 13, 1711 9 of 22

5.2. Hydrogenation
Hydrogenation is a standard technique for improving the properties of vegetable
and animal oils. In addition, it increases the softening and melting points of the fats
and improves their color, odor, and stability. The reaction involves the chemical addition
of hydrogen to the unsaturated carbon-to-carbon double bonds in fatty alcohol or the
fatty acid molecule. This addition occurs by mixing the heated oil and hydrogen in the
presence of nickel as a catalyst, at pressures in the order of 0–120 psi, and in hydrogenation
conditions widely used in industrial purposes [5]. Total hydrogenation of the oil produces
highly lustrous, pearly white crystalline laminae that are very hard. Solid wax has been
suggested as a potential ingredient in polish waxes, carbon paper, waxing of fruit, and
candles component [5].
In 1959, a comparison was made by Knoepfler et al. between the hydrogenation
characteristics of jojoba oil obtained by extracting the oil with solvents and those obtained
by the cold-hydraulic pressing of the jojoba seeds. The results revealed no significant
difference between both hydrogenated forms, except in the melting point. Those prepared
from cold-hydraulic pressing have a melting point of 67–68 ◦ C, while those prepared from
oil extracted by solvents have a higher melting point of 74–76 ◦ C [32]. Wisniak and Holin
have studied the hydrogenation of jojoba oil under a wide range of operating conditions
and reaction kinetics in the preparation of different types of solid waxes and compared the
characters of the hydrogenated jojoba oil with Beeswax and Carnauba wax. It was observed
that jojoba oil is substantially better than Beeswax and relatively equal with Carnauba wax
regarding hydrogenation [39]. Simpson and Miwa have done an in-depth X-ray diffraction
study of hydrogenated jojoba oil to determine fatty acid and alcohol chain conformation,
unit cell, and angle of tilt of the chains [40].

5.3. Halogenation
Halogenated fatty materials find extensive uses in preparing quaternary compounds,
anti-rotting, flame proofing, and fungicide additives. In addition, brominated vegetable
oils have long been used as weighting oil in carbonated beverages [41]. In 1979, Wisniak
and Alfandary conducted an extensive study of the chlorination and bromination of jojoba
oil. Their main objective was to determine the kinetics of the reaction and evaluate the
influence of the operating variables. The experimental results indicated that in the dark
and the temperature range used (−15 to +5 ◦ C), a direct addition to the double bond with
essentially no substitution occurred. The rate of halogenation decreased with the increase
in temperature [42].

5.4. Sulfurization and Sulfur Halogenation

The sulfurization of fatty material with sulfur or other reagents containing sulfur and
halogen yields various products with different physical and chemical properties. In general,
when sulfur content is low (<5%), the products will be liquid and be used as additives.
Increasing the sulfur content will increase the viscosity until a rubber-like mass is obtained.
In 1975, Gisser et al. conducted a deep study about the mechanical properties of
sulfurized jojoba oil and sulfurized sperm oil. The results obtained revealed that there
is no difference between both oils [5]. Furthermore, sulfurized jojoba oil has additional
advantageous properties regarding its appearance and high viscosity; the same result was
obtained by Miwa et al. [13].

5.5. Phosphonation
Dialkyl alkylphosphantes are stable organic phosphorus esters possessing unique
properties and offer considerable potential for commercial exploitation. Thus, they have
been recommended for use in many applications. As plasticizers, they hold great poten-
tial due to their superior stability and other unique characteristics compared to organic
phosphates. They have been suggested as synthetic lubricants, additives to improve the ex-
treme pressure properties of lubricants, functional fluids, oil, or fuel additives; pour-point
Polymers 2021, 13, 1711 10 of 22

depressants, pesticides, synergists, or carriers for pesticides and fertilizers, intermediates

for the synthesis of corrosion inhibitors, and metal extractants. In general, several dialkyl
alkylphosphantes are useful as flame-retardants, softeners, textile treating agents, and heat
transfer media [5]. Wisniak has reported preliminary experimental data on the phosphona-
tion of jojoba oil with different dialkylphosphites, using tert-butyl perbenzoate as a radical
generator. The average ester chain in jojoba oil contains two double bonds so that the final
product may contain up to two atoms of phosphorus per chain [33,42].

5.6. Oxidation, Epioxidation, and Ozonolysis

Jojoba oil shows good thermal stability up to a relatively high temperature. Generally,
the cosmetic formulations containing jojoba oil have superior stability toward oxidation
than other lipids used for this purpose. A comparative study of the relative oxidation sta-
bility of jojoba oil, sperm whale oil, carnauba wax esters, Limnanthes douglassi wax esters,
and behenyl arachidate revealed that jojoba oil has high oxidative stability comparing all
other oils [43]. Kampf conducted an in-depth study of the accelerated oxidation of crude
jojoba oil and bleached and stripped oils. He found that crude jojoba oil contains natural
antioxidants that counted for the high oxidative stability of the natural oil. The removal
of these antioxidants through bleaching or stripping of the oil leads to a sharp decline in
the oxidative stability of the products [5]. Epoxides of unsaturated glycerides and simple
fatty acid esters are currently used as plasticizers and stabilizers for polyvinyl chloride
plastics [5].
Ozonolysis is an important technique for studying the structure of unsaturated com-
pounds such as those present in jojoba oil. Ozonides in general, but particularly jojoba
ozonides, are viable intermediates for many synthetic paths. Zabicky previously used
ozone as a reagent to attain intermediates to synthesize different derivatives that are widely
used for industrial purposes [5].

6. Biological Activity
Extensive biological and pharmacological investigations, based on the uses of jojoba
oil in folk medicine, revealed that jojoba oil and its derivatives exhibit vast biological
activities in different pharmaceutical forms, whether used topically or internally. These
Polymers 2021, 13, x FOR PEER REVIEW 11 Most
activities can be attributed to the unique chemical composition of the wax esters [4]. of 22
of the relevant activities were grouped in Figure 3.

Figure
Figure 3.
3. Summary
Summary of
of the
the main
main biological
biological activities of jojoba
activities of jojoba oil.
oil.

6.1. Traditional and Folk Medicinal Uses

Jojoba has a rich ethnobotanical history due to its wide use by natives of the arid
southwestern deserts of the USA and northwest of Mexico. Jesuit priests in this area rec-
orded tribal uses of jojoba for many skin and scalp disorders. It was first reported in 1789
Polymers 2021, 13, 1711 11 of 22

6.1. Traditional and Folk Medicinal Uses

Jojoba has a rich ethnobotanical history due to its wide use by natives of the arid
southwestern deserts of the USA and northwest of Mexico. Jesuit priests in this area
recorded tribal uses of jojoba for many skin and scalp disorders. It was first reported in
1789 by the Mexican historian Francisco J. Clavijero that the Amerindians of Baja California
highly prized the fruit for food and the oil as a medication [10,33]. “Two to three jojoba
seeds taken in the morning are said to be good for the stomach. Seeds when ground and
mixed with chocolate facilitate parturition for women. Toasted and ground seeds are found
to be specific against sores that erupt on the face. The unguent oil stops chills and if eaten
in certain quantity gradually eliminates them”. He was also the first to describe how the
Indians use the nuts to treat the wounds, where jojoba nuts were put in hot ashes until the
oil starts oozing. “They were then ground on rocks, with the resultant salve-like substance
applied to the wound. This salve is claimed to cure cuts, scratches and sores rapidly” [5].
Other early mentioned medical uses include curing the suppression of urine, helping
in weight loss, improvement of liver functions, elevating body immunity, remedy for
cancer, and promotion of growth of hair [5].

6.2. Pharmacological Uses

6.2.1. Emollient Agent
Skin surface-softening effects are represented by an increase in the extensibility or
suppleness of the surface. These changes contribute to the overall softness of the skin
and make it possible to accommodate stretching and movement without cracks and tears,
perceived as scaliness, developing on the surface. That surface suppleness changes rapidly
in response to the application of water or known emollients [6,8,10,11,44]. Jojoba oil in
single-phase and emulsion systems shows an excellent lubricity without the oily, greasy
feel of other lipids, especially lanolin and petrolatum [45]. It can also contribute to superior
transpirational water control in the skin, thus reducing evaporation without blocking the
passage of gases and water vapor. This character is due to its high molecular weight and
low viscosity, and structural similarity with skin sebum, leading to a smoothing effect on
dry skins and the inhibition of excess flaking of epidermal cells [5,33]. Skin indentation
tests showed that the oil enhanced skin elasticity, similar to the effect of lanolin. Jojoba oil
also showed a keratoplastic effect and seemed to restore the skin’s natural shine [5].
Many studies have been carried out to evaluate the penetration rates, slip, and occlu-
sive of various emollients, including jojoba oil and fully hydrogenated jojoba oil in many
pharmaceutical skin care products. It was found that the derivatives of jojoba oil have
excellent lubricity characteristics. It was also demonstrated that hydrogenated jojoba oil
has a faster penetration rate and good occlusive properties. Thus, it is recommended to use
jojoba oil alone or with other natural oils to maintain the natural appearance of the skin
and the safety of that derivative as an emollient in the cosmetic formulation [7,10].
Christensen et al. in 1988 examined jojoba oil, both hydrogenated and ozonized
derivatives, for their emollient activity. He found that a marked increase in skin surface
suppleness appeared after 5 min which persisted for many hours, implying a potential use
in dry skin products. In addition, ozonized jojoba derivatives make the skin surface water
repellent and resistant to the stiffening effect encountered after washing with soap and
water [6,10].

6.2.2. Anti-Acne and Antipsoriasis Activities

The historic use of jojoba oil by Mexican Indians to treat sores has recently highlighted
its potential in treating acne and psoriasis. Miwa gave the scientific evidence of its use
as anti-acne in 1973, who clinically examined the wax on patients suffering from acne
vulgaris. The results revealed that jojoba oil could be used successfully to treat these
conditions [10,13]. Its properties as a liquid wax allow the dissolution of sebum deposits
within hair follicles due to an ability to penetrate the follicles and remove the comedome,
thus clearing the skin.
Polymers 2021, 13, 1711 12 of 22

Mosovich studied the effect of jojoba wax in the treatment of both acne vulgaris
and psoriasis. He found that jojoba has high effectiveness in acne, with no secondary
effects noted and no reports made of burning or itching. This efficacy indicates that jojoba
oil may be used alone or in addition to other treatments. The antipsoriasis activity of
jojoba oil is related to the positive keratoplastic and the slight keratolytic effect required
to treat excessive scaling of the skin. Therefore, jojoba oil may be used as an additional
treatment [6].

6.2.3. Anti-Inflammatory, Antipyretic, and Analgesic Activities

Possible anti-inflammatory effects of jojoba oil were investigated against both acute
and chronic inflammation of the skin. The possibility that jojoba oil could be beneficial
in treating pain and reducing edema resulting from thermal and sunburns was demon-
strated [10]. Habashy et al. conducted a study in 2005 that demonstrated this reduction
of edema and prostaglandin E2 content in rats, further supporting this potential of jojoba.
The anti-inflammatory effect of jojoba oil involved the blockage of both cyclooxygenase II
and lipoxygenase enzymes [7,26].
This work is confirmed by a controlled clinical trial evaluating the short-term effec-
tiveness of jojoba liquid wax as local treatment of Napkin rash. The results were compared
to standard treatment of a combination of triamcinolone acetonide, nystatin, neomycin,
and gramicidin. Jojoba liquid wax was found as effective as the use of that combination in
the treatment of Napkin rash. However, jojoba had the advantage of being safer due to
the lack of systemic side effects that are usually present using the combination mentioned
above [10].

6.2.4. Antimicrobial Activity

Jojoba oil has been shown to have an intense inhibitory action on the growth of
Tubercle bacilli, leprosy bacilli, and Brucelli [11]. The liquid wax could help dissolve the solid
wax coatings around the bacilli due to the chemical structure similarity between jojoba
waxes and the fats forming the sheath of the bacilli, which prevents the penetration of the
antibiotics. A combination of antibiotics and jojoba oil as penetrating oil may be effective in
treating those serious diseases [6,46]. Furthermore, alcoholic extracts of the jojoba root have
demonstrated antimicrobial activity against several pathogens, including Bacillus cereus,
Salmonella typhimurium, and Candida albicans. This activity is attributed to the alkaloid,
saponin, and steroid content of the root extract.

6.2.5. Other Activities

Jojoba oil has also demonstrated a beneficial effect against hyperglycemia-induced
oxidative stress. Cyanogenic glycosides and other components found in the seed extract
markedly decreased ROS and caspase-3 activation and improved antioxidant defense,
inhibiting p22phox and increasing nuclear factors—this activity may serve as a useful tool
for combating diabetes [46,47]. Manoharan et al. support this theory, having conducted a
report in 2016 that discussed the potential of jojoba oil to inhibit or manage diabetes due
to its antioxidant properties. Jojobenoic acid present in the alcoholic seed extract has also
demonstrated protection against FB1-induced hepatotoxicity in rat liver. Similar results
were confirmed in a recent study that indicated jojoba seeds induced a decrease in body
weight, fat mass, insulin resistance, oxidative stress, liver steatosis and renal complications.
The results demonstrated the beneficial effect of jojoba against metabolic syndrome and
oxidative stress [48].
Clarke and Yermanos were the first to study the lowering effect of jojoba oil on the
serum cholesterol by their studies on the blood cholesterol level in rabbits where blood
cholesterol level was reduced 40% in rabbits given 2% jojoba oil and 1% cholesterol in the
diet for 30 days compared to the result obtained when 1% cholesterol is given alone [49].
The concomitant administration of jojoba oil with fipronil ameliorated the toxic effects
of fipronil on liver, brain, and kidney with improvement of the antioxidant status, the rate
Polymers 2021, 13, 1711 13 of 22

of apoptosis, and the histopathological alterations. This positive effects were evidenced
by the combating effect on the oxidative stress in liver, brain, and kidney as indicated
by lowering the malondialdehyde (MDA) and nitric oxide (NO) levels with elevating in
glutathione (GSH) level and activities of superoxide dismutase (SOD) and catalase (CAT). In
addition, there is a marked lowering of the elevated serum levels of hepatic markers alanine
aminotransferase (ALT), aspartate transaminase (AST), alkaline phosphatase (ALP), and
lactate dehydrogenase (LDH) and the γ-aminobutyric acid (GABA) level in the brain [50].
Biorefinery processes can be employed to produce jojobyl alcohols from jojoba oil
(11-eicosenol, 13-docosenol, and 15-tetracosenol), which have been explored as antivirals.
Jojoba oil also holds value in the industry as anti-rodent treatment, insecticides, and bioen-
ergy production. Furthermore, the presence of compounds with cyclooxygenase-2 (COX-2)
inhibitive properties in jojoba leaf extracts holds potential in anticancer treatments. COX-2
inhibitors lead to an increase in the rate of apoptosis and a decrease in the invasiveness of
cancer cells alongside angiogenesis reduction.

7. Pharmaceutical Uses
It is preferred to formulate it into a pharmaceutical preparation to achieve a maximum
benefit of any biologically active natural compound. Owing to jojoba’s high skin moisturiz-
ing ability, high resistance to oxidation, its ability to penetrate the skin, and its ability to
solubilize insoluble drugs, jojoba has been investigated as an excipient in different dosage
forms. In an attempt to compile most of the work done on jojoba oil either as an active
pharmaceutical ingredient or as an excipient, all the efforts published in PubMed have
been collected, and most of the relevant information is reported in the following section. It
is summarized in Table 7.

7.1. Topical Preparations

Jojoba was incorporated in topical preparations to enhance the efficacy of drugs
used to treat skin diseases [1]. A previous study demonstrated the ability of jojoba oil
to solubilize lycopene, which is an important antioxidant with low solubility in both
water and oil. The improved solubility enables the formulation of lycopene into liquid
and transparent products for pharmaceutical uses [2]. Shevachman et al. reported the
successful preparation of microemulsion using jojoba wax as the oily phase using different
surfactants and cosurfactants, in which the content of jojoba oil determined the transition
from the water-in-oil to bicontinuous and to oil-in-water structures [3].
Diclofenac sub-micron emulsion formulated using 20% jojoba oil showed an enhanced
anti-inflammatory effect compared to marketed Voltaren® Emulgel® cream, which was
attributed to jojoba penetrative properties [4]. Thakur et al. reported the preparation of
jojoba oil-based emulsion of benzoyl peroxide for the treatment of acne. Based on jojoba
oil emollient effect, anti-inflammatory, and antibacterial properties, the study resulted
in a significant reduction in skin irritation and dryness caused by benzoyl peroxide. It
enhanced its therapeutic effect [5].
Methotrexate-loaded jojoba oil-based microemulsion was proved to be clinically safe
and effective in treating psoriasis vulgaris due to its moisturizing and anti-inflammatory
effects [6]. Another jojoba oil-based microemulsion loading the synthetic retinoid tazarotene
revealed a better therapeutic effect in psoriatic patients than the marketed product with no
irritation and a double increase in tazarotene skin deposition [7].
Stable valacyclovir solid lipid nanoparticles were successfully prepared using jojoba
oil. The prepared nanoparticles were stable with high entrapment efficiency of valacyclovir,
which can be an effective delivery system in treating viral infections in humans [8]. In ad-
dition, nanostructured lipid carriers (NLC) were developed in semisolid preparation using
jojoba oil as the liquid lipid. The in vivo studies showed a great increase in skin hydration
and reduction of transepidermal water loss, which may result in the improvement in the
symptoms of some skin disorders such as eczema [9].
Polymers 2021, 13, 1711 14 of 22

Previous studies demonstrated the successful use of jojoba oil as an excipient for
different topical antifungal preparations. Shahin et al. revealed the high physical stability
of clotrimazole-loaded jojoba oil-based emulgels with a superior antimycotic activity
against Candida albicans compared to the commercially available formulation Candistan®
and Canesten® [10,11]. In addition, fluconazole dissolved in jojoba oil in the oily phase of
microemulsion gel showed superior antifungal activity against Candida albicans with the
widest zone of inhibition in comparison to fluconazole solution [12]. Moreover, El-Hadidy
et al. explored the use of jojoba oil to formulate the poorly water-soluble voriconazole in
microemulsion (ME) for topical application. Jojoba oil-based MEs showed good physical
and rheological properties upon storage for 12 months at ambient conditions, and in vitro
permeation studies revealed that they were able to sustain voriconazole release up to
42 h. In addition, voriconazole-loaded MEs showed significantly better antifungal activity
against Candida albicans than the drug solution [13].

7.2. Cosmetic Products

Jojoba oil was reported for its use as a conditioning agent due to its emollient proper-
ties. The addition of jojoba oil to thioglycolate-based straightening emulsions benefited
the hair fiber, allowing a little protein loss, protection to hair thread, and improved the
breakage resistance [14]. In an attempt to benefit from the jojoba oil chemical backbone,
Touitou and Godin formulated skin non-penetrating sunscreens (NPSUN) as new photo
protectors from UV harmful radiation. The idea depends on the conjugation of jojoba oil
with UV sunscreen molecules as methoxycinnamate to form new filters. The formulated
NPSUNs exhibited high skin substantivity, decreasing the need for a frequent application
with no in vitro permeation of methoxycinnamate-NPSUN across the skin for 24 h [15,16].

7.3. Transdermal and Intradermal Preparations

Jojoba oil has been investigated as a penetration enhancer in the fabrication of trans-
dermal patches to deliver olanzapine. The fabricated patch was stable with good phys-
ical properties and increased drug skin flux [17]. Intradermally administrated Bacillus
Calmette–Guérin (BCG) vaccine has been successfully encapsulated in small-sized agarose
microcapsules and small-diameter alginate beads prepared by the emulsification of the
hydrogel within jojoba oil. The freeze-drying microcapsules were stable for 12 months of
storage at room temperature [18,19].

7.4. Parenteral Preparations

Novel nanocapsules for parenteral administration were prepared using vegetable oils
such mango, jojoba, pequi, oat, annatto, calendula, and chamomile as the lipid core instead
of the capric/caprylic triglyceride. All the formulated nanosystems were compatible
regardless of the oil type; however, nanocapsules formulated using jojoba were the most
favorable due to their optimum particle size characteristics [20].
Polymers 2021, 13, 1711 15 of 22

Table 7. A summary of pharmaceutical dosage forms containing jojoba oil.

Dosage Form Drug Ingredients Use/effect of Jojoba Oil Ref.

Microemulsion Antioxidant lycopene Jojoba oil, alcohols, nonionic surfactant (Brij 96V) To solubilize lycopene [51]
Jojoba oil, alcohols, different nonionic surfactants, To study the effect of Jojoba oil content on the
Microemulsion - [52]
namely Brij 96V and Tweens, and water type of the microemulsion
Jojoba oil, purified egg lecithin, Cremophor EL To increase the anti-inflammatory effect of
Sub-micron emulsion Diclofenac (Diethyl ammonium) [53]
surfactant, and water topical preparations of diclofenac
Lipophilic surfactant (Span 60), jojoba oil,
hydrophilic surfactant (Tween 20), propylene glycol, To decrease the skin irritation and dryness
Gellified emulsion Anti-acne agent, Benzoyl peroxide [54]
methyl paraben, propyl paraben, disodium EDTA, caused by benzoyl peroxide
butylated hydroxy toluene, Carbopol 940, and water
Microemulsion Methotrexate Jojoba oil, Tween 80, Span-85 and water Treatment of psoriasis vulgaris. [55]
Treatment of psoriasis and increase in skin
Microemulsion Synthetic retinoid tazarotene Jojoba wax, labrasol/plurol isostearique and water [56]
deposition of tazarotene
To benefit from jojoba oil moisturizing and
Valacyclovir Glyceryl monostearate. jojoba oil, polyethylene
Solid lipid nanoparticles stabilizing activity in the treatment of viral [57]
hydrochloride Glycol 400, Tween 80, and water
infections in humans
Glyceryl behenate, jojoba oil, Tween 80, cetrimide,
To improve symptoms of some skin disorders
Nanostructured lipid carriers - glycerine, Carbopol 934 or Carbopol 980, [58]
like eczema
triethanolamine, and water
Jojoba oil, hydroxypropyl methylcellulose (HPMC)
Carbopol 934, Span 60, Brij 35, triethanolamine, [59]
propylene glycol, and water An excipient for different topical antifungal
Emulgels Clotrimazole
Hydrophobically modified co-polymers of acrylic preparations
acid, namely Pemulen TR1 and TR2, jojoba oil, [60]
and water
Cutina lipogels Cutina, Jojoba oil An excipient for fluconazole topical drug
Fluconazole [61]
Microemulsion gel Jojoba oil, Brij 96, Capmul and, water delivery

Jojoba oil, ammonium thioglycolate, self-emulsifying

Straightening emulsions - wax, oleth-3, mineral oil, propylene glycol, aqua, and As a conditioning agent added to the emulsion [62]
preservative blend
Polymers 2021, 13, 1711 16 of 22

Table 7. Cont.

Dosage Form Drug Ingredients Use/effect of Jojoba Oil Ref.

To link UV sunscreen molecules as
Skin non-penetrating sunscreens - Jojoba oil, methoxycinnamate methoxycinnamate to jojoba oil to form [63,64]
new filters
As a penetration enhancer in
Transdermal patch Olanzapine Jojoba oil, Eudragit polymer [65]
transdermal delivery
Small-sized agarose microcapsules Bacillus Calmette–Guérin Agarose, jojoba oil
An excipient [66,67]
Small-diameter alginate beads (BCG) vaccine Calcium alginate matrix, jojoba oil
To study physical stability and the
Jojoba oil, Poly(€-caprolactone) Tween 80,
Nanocapsules hemocompatibility of jojoba oil-based [68]
and Span 60
nanocapsules for parenteral administration
Imiquimod, a Toll-like receptor 7
Solid nanoemulsion Jojoba oil, sucrose fatty ester S-1670 and water An excipient [69]
(TLR7) agonist + SIINFEKL antigen
Jojoba oil, d-α-tocopherol polyethylene glycol 1000 As an excipient to load paclitaxel for cancer
O/W microemulsions Paclitaxel [70]
succinate (TPGS-1000), isobutanol, and water treatment
Cationic lipids Bolaamphiphiles (GLH-58 and
Charged micelles Small interfering RNAs (siRNAs) Starting material for the synthesis of lipids [71]
GLH-60) synthesized from jojoba oil
Polymers 2021, 13, 1711 17 of 22

7.5. Inhalable Preparations

The dry nanoemulsion powder prepared by jojoba oil had a good particle size distri-
bution and an improved mass median aerodynamic diameter. The nanoemulsion showed
higher anti-inflammatory effect on LPS-induced acute lung injury compared to than dex-
amethasone with a decrease in total protein content and downregulation of tumor necrosis
factor-alpha (TNF-α), interleukins-1beta/6 (IL-1β/6), and NF-κB p65. In addition, it
showed higher anti-inflammatory and anti-oxidation effect on H2O2-induced acute lung
injury through the elimination of reactive oxygen species (ROS), increasing of superoxide
dismutase (SOD), decreasing in of lipid peroxide malondialdehyde (MDA) and glutathione
(GSH), and inhibition of caspase-3 expression [72].

7.6. Anticancer Preparations

Jojoba oil was incorporated in anticancer drug delivery systems. Solid nanoemulsion
containing a combination of imiquimod, a Toll-like receptor 7 (TLR7) agonist, and model
peptide antigen SIINFEKL for the topical treatment of different types of precancerous skin
lesions and skin cancer, as a new perspective to avoid invasive technique and enhance
dermal antigen administration [21]. Flores-Villaseñor et al. reported on the formulation
of physically stable biocompatible o/w microemulsions with Jojoba oil as the oily phase
for the delivery of paclitaxel. The microemulsion could load paclitaxel in a concentration
of 0.3 mg/mL, which provides a new alternative nanodevice for cancer treatment [22].
In another study, authors were able to prepare positively charged micelles from bolaam-
phiphiles synthesized using natural jojoba oil. The prepared micelles delivered small
interfering RNAs (siRNAs) to cancer cells with relatively low toxicities in vitro and in vivo
and protected the nucleic acid from degradation [23].

8. Industrial Applications
8.1. Synthesis Polyurethanes Polymers
Jojoba oil has a wide range of industrial applications especially in polymers synthesis.
Polymers are versatile materials that are used in a wide range of industries. Polyurethanes
(Pus) are commonly used synthetic polymers involved in a wide range of applications,
including furniture, automobiles, clothes, shoes, elastomers, coatings, and insulation. The
usefulness of polyurethane is related to its excellent properties, including outstanding
mechanical strength, strong chemical resistance, and light weight [73].
The most popular source of polyols used in the production of PUs is petrol; however,
the researchers were forced to substitute petrol with clean natural resources such as veg-
etable oils, especially seed oils, due to the need for saving the environment. Seed oils are
biodegradable, abundant, inexpensive substituents that entice many researchers to use
them to produce PUs. This process converts different seed oils into reactive polyols by
introducing hydroxyl groups into their structure with the consequent production of PUs
with varying mechanical and thermal properties [74].
Jojoba oil has been used to produce PUs after functionalizing the oil by mercap-
toethanol in a single step reaction to yield a diol with two hydroxyl functions, followed by
catalyst-free reaction with different isocyanates to obtain different polyurethane prepoly-
mers. Then, the chain extenders were added to obtain linear and cross-linked polyurethane
materials characterized by exhibit good flexibility and high thermal stability [75]. The
same group makes a major change through a high reactivity synthesis of cyclic carbonate
monomers to generate biobased PolyHydroxyUrethane (PHU) from jojoba and castor oils.
The first step involved thiol-ene coupling with thioglycolic acid to functionalize jojoba oil,
followed by esterification with glycerol carbonate to yield new dicyclic carbonates. By
aminolysis with different diamines, the dicyclic carbonates were used to synthesize linear
PHUs. The cyclic carbonates produced are recommended due to the absence of solvents
and catalysts during the manufacturing process and the production at low temperatures
and thus with good reactivity [76].
Polymers 2021, 13, 1711 18 of 22

More recent research has extended the development of linear PUs from synthesized
diol Jojoba with different diisocyanates as a catalyst-free polycondensation reaction. PUS
was versatile depending on the nature of the disocyanate used, with good thermal insta-
bility and regulated characteristics. Bio-based PUs are characterized by their improved
solubility, allowing their casting with cellulose nanocrystals or cellulose nanofibrils to
produce strong nanocomposites [77].

8.2. Other Industrial Uses

A rubber-like material is obtained from sulfurized jojoba oil, which is applied in
linoleum manufacturing and ink printing composition, the paint and varnish industries,
and the chewing gum industry [78]. One of the most extensive applications of jojoba oil
includes an extreme temperature/extreme pressure lubricant in the form of sulfurized oil,
which can bear high temperature and pressure without changing its viscosity [6,12,13,79].
Its stability at elevated temperatures permits the constant provision of a thin-film lubricat-
ing border, which is of remarkable necessity in decreasing frictional wear and temperature
increase, which helps directly to extend the life span of the lubricating oil and indirectly to
protect the automobile parts [13]. The study of the utilization of jojoba oil as a lubricant
for some of the petroleum-derived products proved its improvement of certain desirable
characteristics as antirust, antifoam, anti-wear, and friction reduction properties [80,81].
Nasser et al. explored the application of jojoba polymers as a lubricant and evaluated
its viscosity index and pour point depressants when compared to homopolymer. The
results showed that the viscosity index increases with increasing the alkyl chain length of
both α- olefins and acrylate monomers. The pour point improved for additives based on
alkyl acrylate. [82].
Another industrial application is its use as a surfactant due to the long alkenyl (jo-
jobenyl, erucyl) alcohols obtained by hydrolysis, as its combination with polyethylene
glycol chains customizes surfactants with desired hydrophile–lipophile balance [13].
The synthesis of methyl esters from jojoba oil allows its commercial application for
the production of biodiesel. The results explored the promising future of jojoba oil as an oil
feedstock for cultivation in comparatively dry areas [83,84]. The use of ultrasound tech-
nology was successfully applied to reduce the reaction time and temperature and increase
biodiesel yield by reducing the cost and energy, contributing to a cleaner, safer and green
technology for biodiesel production [84]. In addition, Jojoba oil is regarded as an excellent
renewable feedstock to produce replacements for petroleum-derived transportation fuels
and chemicals [85]. A recent study showed that the blend of jojoba oil with diesel fuel leads
to a clear reduction in NOx and hydrocarbon (HC) emissions but indirectly impacts CO
emission due to its high viscosity. Moreover, jojoba oil in the blends adversely influences
thermal radiation to furnace walls due to the less sooting tendency of the flame when jojoba
is present [86].
Moreover, jojoba oil has been used in the leather industry as a fat-liquoring agent,
which verified significant improvement in the mechanical properties of leather, such as
tensile strength and elongation at break [5,87].
The application of jojoba oil as an alternative collector for the selective separation of
apatite and calcite minerals showed high selectivity between calcite and apatite, improving
their selective flotation by using jojoba oil at a slightly acid medium, without the use of
depressants [88].
Jojoba oil has been implemented with castor oil for the synthesis of PolyHydrox-
yUrethane polymer [76]. Other industrial uses include extraction and separation of iso-
topes such as Uranium (VI), Thorium (IV), and Plutonium (IV); and antifoaming agents
in isolation of penicillin and tetracycline [9]. Jojoba oil replaced sperm whale oil as lamp
oil, and it is used as solid wax to mix with and improve paraffin candies, microporous
polyethylene film from microencapsulation of oil, and fatty acid amides as a lubricant for
polyethylene film extrusion [13].
Polymers 2021, 13, 1711 19 of 22

9. Toxicity of Jojoba Oil

No acute toxicity was found when crude jojoba oil was fed to mice; i.e., the LD50 is
more than 160 g/Kg. In ocular irritation tests on rabbits, jojoba oil refined by deodorization
or deodorization and discolorations caused some reversible conjunctival irritation 1 h after
oil application. The reverse action was completely cleared 24 h after ocular application.
In 15- and 30-day-old guinea pigs, patch tests did not cause pathological inflammation.
A light swelling of the epidermis occurred 30 days after topical application, which was
less pronounced than that induced by liquid paraffin and more than that induced by olive
oil. However, the effects on the animal skin were reversible and may have been caused by
the occlusive nature of the oil film. In addition, prolonged daily subcutaneously injections
in rats did not result in any histopathological changes of blood or urine analyses. Only
a mild local reversible granulomatous reaction in the injected area indicated that jojoba
oil is slightly irritant. Patch tests on humans did not reveal allergic reactions except in
hyperallergic people. Prick tests with people exposed earlier to jojoba oil for two years
revealed no allergic reactions to either the crude or refined oil.
A mixture of jojoba oil and hydrogenated jojoba wax was not mutagenic both with
and without activation in the Ames assay [8,10,44,89]. Taguchi measured the safety of
Jobacohol, which was produced by sodium reduction and molecular distillation. No acute
toxicity was found in mice, and eye irritation was quite low. Repeated patch tests in rabbits,
where Jobacohol was compared with oleyl alcohol with both dissolved in jojoba oil, showed
no difference between these materials. Irritation was quite low, and it was concluded that
Jobacohol is quite safe. Jobacohol also showed no irritation in primary skin irritation tests
in marmots and no sensitization in maximization-of-sensitization tests. Negative results
were also obtained in mutagenicity tests with Salmonella typhimurium and Escherichia coli [6].
Tests of primary irritation on humans with either healthy skin or humans suffering
from contact dermatitis were also carried out. The results revealed no skin irritation
concerning Jobacohol or oleyl alcohol. Phototoxicity tests on humans also showed that
Jobacohol was quite free of this effect [6].

10. Conclusions
In this review, we shed light on one of the most economically important crops, jojoba.
Although limited phytochemical work has previously been conducted on the different plant
extracts, the composition of the liquid wax obtained by direct expression of the seeds has
been thoroughly investigated. The plant appears to be a source of golden oil, which shows
high structural similarity to spermaceti wax, involved in many pharmaceutical products.
Traditionally, it is used for many skin and scalp disorders. The seed cake is used safely
as a food and has many applications in the food industry due to its high fat and protein
content. Most of the previously conducted biological work has been directed to prove the
claimed emollient effect and then further extended to evaluate the oil’s anti-inflammatory,
analgesic, and antipyretic properties. In addition, the plant has shown substantial activity
as an antibacterial and antiviral agent. Interestingly, the plant extract shows a promising
antidiabetic and antihypercholesterolemia. In conclusion, the jojoba tree represents an
attractive source for the future development of new medication that could be identified and
characterized using the new tools available in biochemical, physicochemical, and biological
domains.

Author Contributions: H.A.G. (Heba A. Gad), H.A.G. (Haidy A. Gad) and S.H.H. collecting of data
and writing original draft; A.R. revising the whole manuscript; I.T., A.E.A. and O.A.K. reviewing and
editing; M.L.A. conceptualization, writing the original draft supervising and finalizing. All authors
have read and agreed to the published version of the manuscript.
Funding: This research received no external funding.
Institutional Review Board Statement: Not applicable.
Informed Consent Statement: Not applicable.
Polymers 2021, 13, 1711 20 of 22

Data Availability Statement: The data presented in this study are available on request from the
corresponding author.
Conflicts of Interest: The authors declare no conflict of interest.

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