Variation in wax content, fatty acids and fatty alcohols of jojoba seed (Simmondsia chinensis)
Item Type text; Thesis-Reproduction (electronic)
Authors Salazar Zazueta, Alfredo Javier, 1951-
Publisher The University of Arizona.
Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Download date 27/09/2021 18:09:59
Link to Item http://hdl.handle.net/10150/348229 VARIATION IN WAX CONTENT, FATTY ACIDS AND FATTY ALCOHOLS
^ ■ OF JOJOBA SEED (SIMMONDSIA CHINENSIS) . -
'■ . ; by
Alfredo Javier Salazar Zazueta
A Thesis Submitted to the Faculty of the
;DERAR04ENT OF NUTRITION'AND FOOD SCIENCE
In Partial Fulfillment of the' Requirements For the Degree of
MASTER OF SCIENCE • ' WITH A MAJOR IN FOOD SCIENCE
. In the Graduate College ■
THE UNIVERSITY OF ARIZONA
1 9 7 7 STATEMENT BY AUTHOR
This thesis has been submitted in partial fulfillment of re quirements for an advanced degree at The University of Arizona and is deposited in the University Library to be made available to borrowers under rules of the Library.
Brief quotations from this thesis are allowable without special permission, provided that accurate acknowledgment of source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his judg ment the proposed use of the material is in the interests of scholar ship. In all other instances, however, permission must be obtained from the author.
SIGNED:
APPROVAL BY THESIS DIRECTOR
This thesis has been approved on the date shown below:
RALPH L. PRICE Associate Professor ACKNOWLEDGMENTS
I wish to - express gratitude to Dr« Ralph L« Price for his '
advice, encouragement and interest throughout this entire study«
The author also wishes to express his sincere appreciation to
the following members of the University of Arizona, Tucson, Arizona:
Dr0 Jo Warren Stull, Professor of Nutrition and Food Science; Dr= James
Berry, Professor of Nutrition and Food Science; and Dr« Le Moyne Hogan,
Professor of Plant Sciences.
. Acknowledgment is also made to the National Council of Science
and Technology (CONACYT) in Mexico City for sponsoring the author. -' ' TABLE OF CONTENTS
■ ' ■ ' ' ; P a g e XjIST OF TABLES o o b o o e o o o o o .o « o o o © o o © © o o o V
ABSTRACT © © © © © © © © © © © © © ©. © © © © © © © © © © © © © vxi
INTBOLUCTION © © © © © © © © © © © © © © © © © © © ® © © © © © X
Review of Litei?9.tiiiTe ©• © ©. © © © © © © © © © © © © © © © © 2. Jojoba Oil:. Its Description.; and Its Composition © s © 2 Jojoba Oil and Its Potential Uses. © © © © © © © © © © 4 Geographical Variability, in Yields of Jojoba Seeds*. Oil Content Percentage.and Oil Composition © « © * o 4
MATERIALS AMD METHODS : © © © © © © © © « © © © © © © © © © © © ; ' 8
Samples -, o. © © - © © © © © © © © © © © © © © - © © © © © ©, © © 8 ■ Sample C olle c ti on % © © © © © © © © © © © © © © ■■ © © . © © © © 8 . Oil Extraction ■ © • © © © © © © © © © © © © © © © © © © © © © 8 Ethanolysis © © © « © © © © © © ©. © © © © © © .© © © © © © 9. . Gas-Liquii Chromatography © © © © © © © © © © © © © © © © 9 Data Analysis. © © © © ©■ © © © © © © © © © © ©. © « © ©. © © 10
RESULTS. AMD DISCUSSION © © © © © © © © ©' © © © © © © © © © © 11
Conclnsions © © © © © © © © © © © © © © © © ©- © © © © © © 35
APPENDIX As LOCATION OF AREAS SAMPLED- © o- © © © © © © © © © © 35
LIST ■ OF REFERENCES © © © © © © © © © © © © © © © © © © ©. © © © 37
iv- LJST' OF TABLES'
Table Page
1= ■ Variability in jojoba oil fatty acids and fatty alcohols . from different areas of Beer Sheva, Israel „ « «, » , «, c 12
2» . Variability in jojoba oil fatty acids and fatty.alcohols from different sites of Gila County, Arizona . OOO 0 o > 3
3= Variability in jojoba oil fatty acids and fatty alcohols from different sites of Maricopa County, Arizona 14
k0 Variability in jojoba oil fatty acids and fatty alcohols from different sites of San Carlos Indian"Reservation, Arizona o » » d » . » o o » @ o o. o & o o » ® . o © © © © 15
. 5© . Variability in jojoba oil fatty acids and fatty alcohols
from different sites of Yavapai County, Arizona © © © . 16
6= Variability in jojoba oil fatty acids and fatty alcohols from different sites of Pinal County, Arizona © © © © © 17
7© Fatty acid and fatty alcohol composition of Graham County, Arizona, jojoba .seed oil .©©.©©©©©©© 18
8© Fatty acid and fatty alcohol composition of Papagd ■ Reser®, Arizona, jojoba seed, oil © © . « « « » © © © © © 19
9© Fatty.acid and fatty alcohol composition of Yuma County, Arizona, jojoba seed oil . « © . « © . © » ©.©©.© © 20
10© Component means of the analyses of Beer Sheva, Israel, jojoba seed,oil- ©- © © © © © © © © © © © © © © © © © ©. © 21
11© Component means of the analyses of Gila County, Arizona 9 jojoba seed oil o o o ooao o o o o o e . e o o o 22
12® Component means of the analyses of Maricopa County, Arizona, jojoba seed oil. © © © © © © © © © © © © © © © © 23
13© Component means of the analyses of San;Carlos Indian . Reservation, Arizona,jojoba seed oil © © © © © © © © © © 24
l4« Component means of the analyses of Yavapai County, Arizona, jojoba seed oil © © © © © © ©. © © © © © © © © © 25
v vi
LIST OF TABLES— Continued
Table Page
15'= Component means of the analyses of Pinal County, Arizona, jo joba seed oxl a ® » © = = = = = © . © = = © © © © © © © © 26
l6© Oil content and dried seed weight of Beer Sheva, Israel, jojoba seed oil ©©©*©o©©©© © © © © © © © © © © © 31
:17© Oil content and dried seed weight of Gila County, ' Ari2ona, j 0 j oba ■ seed © © © © © © © © © © © © © © © © © © 31
IS© Oil content and dried seed weight of Maricopa County, Arizona,, j 0 j oba. seed © © ©. © © « © © © © © © © . © © © © © ■ 32;
19© Oil content and dried seed weight of Yavapai County, Arizona, jojoba seed © © © © © © © © © © © © © © © © © © 32
20, Oil content and dried seed weight of San Carlos Indian Reservation, Arizona, jojoba seed © © © , © © © © . © © © 32 ABSTRACT
Jojoba is a native shrub of the Sonoran desert which yields a crop of oil seeds each year. The.oil is characterized by a high con tent of monounsaturated C-20 and C-22 acids and alcohols. Seeds from forty-two different sites in Beer Sheva, Israel and in Arizona were analyzed by gas liquid chromatography for fatty acid and fatty alcohol composition. The percentage of wax in each was determined.
Percentages of five fatty acids and four alcohols were measured.
The fatty.acids.were hexadecanoic,■octadecenoic, eicosenoic, decosenoic and tetracosenoic = The fatty alcohols were octadecenol,,eicosenol, docosenol and tetracbsenol. There was a great similarity between all samples that no' variety could be distinguished.on the basis of fatty acids. V .
The jojoba seeds extracted with hexane, the method used in this study, had an average wax content of 40%> or higher. INTRODUCTION
Jojoba, or Simmondsia cMnensls (Link) Schneider, blends quite,
.naturally into the background of the arborescent vegetation of the
Sonoran desert (4, 6, 19). The dense leafy form-and the acorn-shaped,
fruits give it a recognizable image* Mari’s curiosity led him to inves tigate the fruits and to analyze the peanut-sized seeds within, . He has found a unique oil and began getting exploitative ideas, Mirov (11). and Yermanos (19) have characterized jojoba as a plant of numerous uses. For example, oil extracted from jojoba seeds contains up to 50% of liquid wax which possesses properties similar to sperm whale oil (8,
1 6 )o It'can be extracted in. a remarkably pure state■and can be used in many products such as waXj lubricants and cosmetics and has many other potential applications,,
Although jojoba is a wild specie, several attempts have been made during the past few years to establish experimental cultivated ' ■ plantings of jojoba,' There are certain requirements.that any wild plant must meet before it can become a cultivate: (1 ) it must yield a product abundantly; (2) it must respond to the artificial environment of man; and (3) it must have a genetic endowment that will support intensive selection of varieties (4), Jojoba meets.the first two re quirements; whether or not the third requirement can be met is con
jectural because of the.lack of information.
1 Several reports have been published on the chemical and physi
cal properties of the liquid wax extracted from jojoba. The advent of
improved.chromatographic techniques for the qualitative and quantita-.
tive determination of fatty acids has greatly facilitated a study of . ■
this type«-• In this particular, work, seeds from 4$ different areas; in
■ different plots of jojoba plants were analyzed, for the fatty acid and
fatty alcohol composition.
Review of Literature
Jojoba Oil: Its Description and its. Composition
■ Jojoba (Simmondsja.chinensis) oil is a liquid wax, which is re-
■ sistant td oxidation and rancidification (9, 28) = - . It has been de
scribed as:a very unique oil and its uniqueness is a reflection of the
singular architecture of its molecules* When the oil is subjected to .
conventional saponification, only a small fraction is affected, and
analyses of this fraction by gas liquid chromatograph shows a predomi
nance of C-l8 fatty acidso
Jojoba seed oil is not a fat, but a liquid wax. Fats include
. the seed. Oil of all other plants that are triglycerides (a molecule of
glycerol esterified with 3 molecules of fatty acids). Waxes like
jojoba oil and whale sperm oil are wax esters (one-molecule of a long
'chain alcohol esterified with one molecule of a long chain fatty acid)
(22)o Such a vegetable oil has never been.available to industry be
fore* Among the characteristics - that.: should make . jojoba oil valuable
are: its natural purity and molecular simplicity,.its stability (it ; ' - : ' . : ■■ : ■ - : : : ■■ ■ ■ ; ; 3 is: a non-drying. oil) which makes jojoba oil resistant to oxidation, its
being able to be stored for years' without becoming rancid, its lubric- -
ity after sulfuration, its source of chemicals with 20 and 22 carbons,
and its unsaturation (double bonds)=
One of the earliest references to jojoba oil as. a commercial
product was that of McKinney and Jamieson (10) who in 1936 reported
chemical and physical characteristics of jojoba oil* They found that
the oil gave the following characteristics: specific gravity at 25° G
0.8642; refractive index n^ 1.4648; iodine number (Hanus) 81.7; saponi
fication value 92.2; acid value 0.32; aCetyl value unsaponifiable. 171.8;
saturated acids 1.64; unsaponifiable matter 48.3= . The oil contained '
the following percentages of fa.tty acids: saturated acids 1.64, .
palmitoleic acid 0.24, oleic acid 0 .66, eicosahsic acid -30.30, de-
posenoic acid 14.20, eicosenol 14.60, decosenol 33»70.
Because of its chemical similarity to sperm whale oil, jojoba
oil has long been recognized as a possible substitute (16). Still,
jojoba oil possesses several advantageous characteristics over sperm
: whale oil: (l) it has no fishy odor; (2) the crude oil contains no
. stearines and requires little or no treatment for most industrial pur
poses; (3) it is a native vegetable product of North America, not sub-
. . jected to shortages of supply, etc.; (4) 'it takes tip larger amounts of :
sulfur; (5 ) it does not darken on sulfurization; and (6) the highly
sulfurized oil is liquid, whereas sperm whale oil, when highly sul
fur ized, requires additions of mineral oil in order to remain liquid
(17)- : ' • V- • 'i ; V ; . ■ . : ■■■ , . Jojoba Oil and Its Potential Uses
Jojoba (Simmondsiaohinensis) oil can be used as antiwear addi
tive in lubricants for gears, in differentials, transmissions and hy
draulic fluids that need a low coefficient of friction,, It can also be
• used as a source of acids and alcohol which can be used as intermedi
ates in the preparation of disinfectants, surfactants, detergents, .
emulsifiers, resins, protective coatings,and fibers* Jojoba oil's ■.
antioxidation characteristics open other avenues for its use as in
products requiring a stable vegetable oil, as a carrier for pesticides '
and plant hormones, or as a water-evapdration retardant, etc* Jojoba
oil reacts with sulfur chloride, forming products with a wide range of
properties from oils to. rubbery solids known as factices (2, 3)0 It can
also be hydrogenated to a hard, white wax, but it is not yet available .
in quantities suitable for industrial purposes, Due to ■ the rising.
costs and uncertainties of supply of candelilla, carnauba, spermaceti
and beeswaxes, hydrogenated jojoba oil appears to have considerable
commercial promise (1.4, 22) „
Not very much has been reported on jojoba oil as a food. . But
it is worth knowing that its different commercial structure makes it
very resistant to hydrolysis by lipases, the digestive enzyme for fats
(22). Before it is used in food, a great deal of research must be
undertaken to prove its acceptance and effects upon the human body.
Geographical Variability in Yields of Jojoba Seeds, Oil Content Percentage and . Oil Composition . . - V
. The potential yield of jojoba was a crucial question in apprais
ing its economic feasibility. Gentry (6) found that seeds from different shrubs varied in Weight from 336 to 2335,. per- pound» indi
vidual seed yields from eighty.shrubs of jojoba varied from two; ounces
to six pounds,, with a mean of 1 .3 pounds per shrub. Yermanos and
Duncan' (21) conducted•a series of analyses using data from 138 single• native plants located at Aguanga., California. They reported' that yields of seeds from single plants varied from 2 to 12 pounds, with a • mean of five pounds;and'a coefficient of variation of 24oC#. Weights
of single. seeds were reported to vary from 0.15 gr. to I d gr„, with an average of 0o56 go and a coefficient of variation of 32.8^, Forti et alo (5 ) reported that the average seed weight of jojoba seed from
Gilat, Israel, varied from 0.2? g. to 0.68 g0 and total yield from '
1225 g» to 318800 go per planto Yermanos and Holmes. (22) reported
that the average yield of the "Vista” clone in 1963 was 133 g. per . . planto Due to.poor seasonal conditions in 1964, the average yield for
the "Vista" population was only 43 g» per plant, but yields increased
to an average of 350 go per plant in 1963. Comparing the yields indi vidually, it was reported that the seed yield of native plants at
Aguanga,. California, in 1974 was 2.7 times greater than that of 1973.
However, the wax and protein content of the seed did not change sig nificantly (21) o
. Gentry (6) and Jones and Earl (?) reported liquid wax percentage varied from 37=8% to 54%)= The average liquid wax percentage in 1957 was
45=8^, with a standard deviation of 3=19= The percentage of liquid wax
determined by wide-line nuclear magnetic resonance spectroscopy had a
;mean Of 53=1$- and a coefficient of variation-of 5=18® Determination \ , :: 6 of the liquid wax with solvents showed to have the same frequency curve
distribution, but with values from 2-3% below those arrived at with
the nuclear magneticvhesonahce :■ (15)« ^ The average reported for 1954
..was. 53$° The 195? average was k0k% higher0 Yermanos and Duncan (20) :
conducted a single seed analysis at Aguanga and found that variability
in wax content and composition among the seeds within plants was as
large as that-, in bulk sample. They concluded that variability of wax
cpntent and'quality was: not significants - -
Wells, and Tomoff (18) conducted a single seed analysis for oil
content and wax ester composition of seeds as they matured on plants. ,
In addition, they determined the effects of various modes of storage of
the seeds on their oil content and wax ester composition. . They con
cluded that, whatever desirable properties the peculiar wax ester com
position of jojoba oil may have, these properties can be found in the
oil regardless of the stage of maturation of the seed, or the length
of time the seeds are stored. Thus, the exact timing for seed picking ■
is ndt important for the quality of the oil. However, the quantity of
the oil would increase as the seed matures. In order to prevent degra-r
dation it was recommended not to let the seeds set for even short
periods of time under conditions where they can germinate or become •
overgrown by mold, .y
The HCl-rcatalyzed ethanolysis products of jojoba oil have been
successfully chromatographed with a liquid phase of 2(% Apiezon L on
Ohromosorb W (12). GLC analyses of jojoba oil using Miwa*s (12) pro
cedure showed appreciable differences in composition from those reported by-McKinney, and Jamieson (10)= - The seeds analyzed in Miwa’s : stndy were collected from five different areas; the Arizona desert,
Tucson suburbs, California bceanside, California desert and a sample ' of undisclosed origin* The seeds were from the same phenotype, except for the California Oceansida and the;unknowno Results showed that the composition of jojoba oil was essentially the same, but slight differ ences were found in the chemical composition of the seeds from the
California desert and the California Oceanside« The unknown showed a distinct shift in oil composition toward larger molecular size and shorter chain lengths respectively« However, throughout the five seed samples analyzed, the percentage of the major component, eicosanoic ; acid, remained unchanged at 35% of the total of jojoba oil. ■ MATISIAkS AND METHODS
Samples '
Jojoba seeds analyzed v/ere provided by Dr. Le Moyne Hogan,
Professor of Plant Sciences, The University of Arizona. Of the assort ment of seeds provided, 45 were chosen at random.. Each "variety" con- : sisted of 4 seeds. '
Of the 45 areas of jojoba plantings analyzed, 14 were in Gilat, northwest of Beer Sheva, Israel, and 31 were in Arizona. Of the 31 areas in Arizona, 4 were located in the San Carlos Indian Reservation,.
2 in Graham County, 8 in Gila County, 1 in the Papago Reservation, 6 in Maricopa County, 5 in Pinal County, 4 in Yavapai County, and 2 in
Yuma County (see Appendix A).
Sample Collection
Arizona seeds were picked during the 19?4 season. The largest. and healthiest appearing seeds were selected throughout Arizona from / each jojoba planting previously cited,. Seeds from Beer Sheva, Israel,; were received in 1973 = Seeds were stored at room . temperature until■
May 1977 when analyses began.
Oil Extraction
The oil was. extracted by placing the seed in a high speed
Sorvall omnimixer. Two extractions were performed with 50 ml of hexane -
(15) for 5 minutes each. The extract was filtered through filter paper
> ■ ■ 4 ?■ ■■ ': 4 - ' 8 ^ I ' :■ . v : ' : 9 : (Whatman #2) and dried under, nitrogen at 50° G, and the residue weighed '■
as total lipid (TL)o . • ,
Ethanolysis
. For analyses of. fatty alcohols: and ethyl esters of - fatty acids
of the oil, the procedure of rapid ethanolysis (1) was used* Four
• drops of oil were re fluxed with '3>/o HCL in anhydrous ethanol (1 ml) and
anhydrous benzene (0 ,1 ml) for 4 hours at 95$ in 15 x 125 MM test tubes
■v placed ..in a heating block, The oil was washed with alcohol and ethyl '•
ether (2 ml) was added to form a clear homogeneous phase, Water was
added (2 ml) until 2 phases were formed. The water phase was discarded
and the ether extracts were stored at 4? C until analyzed by gas-liquid- .
chromatography,
Gas-Liquid Chromatography .
Gas-liquid chromatography.of ethanolysis products of jojoba oil
was performed, with a Micro-tek DD series model #8818-0001, serial 2?8
gas chromatograph. The following operating parameters were used:
Flow rate' / 30 ml N2/min
; Column 8’ x 34" Glass
Packing 1 . % OV-l? in 100/120 Chromosorb W
Inlet temperature 2506 C
. Column temperature .. 200 ? to 250° at 2°/min
• Detector temperature 300* C '
Injection volumen 2,5 ml of diluted extract
Column was conditioned overnight at 280* C, 10.
Alcohols and acids were identified by comparison with previous chromatograms of jojoba oil ethanolysis products, (12). Peak areas were measured by the disc integrator and each component was expressed as a percentage of total fatty acids and fatty alcohols» ;
Data.Analysis -
Data.from wax determinations, seed weight, fatty acid and fatty alcohol composition of jojoba oil were analyzed with a one-way analysis : of varianceo■ Throughout all of this study dealing with each determi nation, four replications were usedo The 0„05 level of significance : was. usedo -; RESULTS’ AND; DISCUSSION;
. In trying to duplicate Miwa^s ethanolysis procedure in our laboratory with a column of ZOfo Apiezon on Chromosorb W , 0o2 cm iocL,
0*3 cm Oodo, 100 cm long?, we obtained unsatisfactory results due to poor resolution and column bleeding* A column, 1*5K OV-17 on Chromo- sorb W, commonly used in our laboratory for . resolution- of sugars and organic acids, gave excellent separation of jojoba oil fatty acids and fatty alcohols and no column bleeding*
In the preparation of 5% HCL in anhydrous ethanol two methods were tested: by adding 5 ml of concentrated HCL into 95 ml of anhydrous ethanol and by bubbling gaseous HCL into anhydrous ethanol until a 9^ increase in weight was obtained* Both methods of preparation gave the ■ same results*
Jojoba seed oils of the different varieties.analyzed in this study contained predominantly 4 alcohols and 5 acids (Tables 1, 2, 3,
4, 3, 6, 7 8, and 9) *,. The alcohols' identified: were octadecenol,'
(Cl8:i), eicosenol (C20:l), docosenol (022:1), and tetracosenol (024:1)*
The acids were hexadecanoic (Cl6:0 ), octadecenoic (Cl8:l), eicosenoic acid (020 :1 ), docosenoic acid (022:1).and tetracosenoic acid (C24:T)*
Tables 10, 11, 12, 13, l4, and 15 show the component means of each one of these fatty acids and fatty alcohols respectively,
Table 1 shows the composition of jojoba oil fatty acids and fatty alcohols of 14 different sites analyzed in Beer Sheva, Israel*
- ^ V-V'-' 12,
Table lo Variability in jojoba oil fatty acids and fatty alcohols from different areas of Beer Shevav Isfael, -
Chain Length V, Fatty Acids (%) and • Analysis of the different sites (Nb0 of Double Bonds ; ; 1' V ■ ■ . . 2 ■ r;' ■ 3 1 2: ■ . 13 14
• Acids (%) J \ ■ :v '
, Cl6t 0 . . 0 .90 0=52 , 0=4? . 0=67 0=68 0=56 0=90 0=96 0=81 . 0=54 1=09
.., Cl8:1 y : : 8=46 ;' ; 6=55 :: 6=48 : 6=60 7.70 . ' 7.11 8.46 9.49 6.95 . : 7.<
020:1 37.22 40=20 40=15 38.68 39.75 . 40=05 37.30: '37.93: 37.03 38=27 36=61 36.69
022:1 ; . 6=10 7=45 ' 6=57 ' ;7.54 , 6=95 5.34 6=10 6=89 8=95 9.17
024:1 . 0=76 0=58 0=38 0=39 0.50 0=43 0=77 0=62 0=65 . 0=92
Alcohols (%)
, • 018:1 : ' 0=43 ■ 0=38 0=36 0=37 0=36 0=37 ' 0=44 ; ; 0=41 0=41 0=30 0=30 0=30 0=35
020:1 ' . 22=05 21=73 " ■ 22=43 22=83 21=26 , 23=40 22=05 20=80 21=29 21=01 20=82 19.87 21=78
022:1 20=48 20=50 20=81 26=38 19.91 20=05 20=48 ' 19=96 20=07 20=60 21=46 21=90 19=08
. 024:1 ; 3=74 2=74 ■ 2=50 : 2=65 ■ 2=90 : 2=63 3.74 3.33 2=78 2.92 13
Table 2. . Variability in jojoba oil fatty acids and fatty alcohols from ■different sites of Gila County, -Arizona!
Chain Length Fatty Acids (?0 and Analyses of the different sitesi. (No. of sample) Double Bonds ■ 15 % 16 17 "18 19 20 : - 21 22 -
Acids (%)
Cl6:0 0=75 0=79 f 0=93 :■ 1=12 :; 1.19 1=10 ■ 1=10 1=38
Cl8:l - - . 6.53 6=53 . 6=70 6=43 7=84 6=56 6.56 7.35
C20:l 41=06 4l. 06 40=86 36=55 ; 35 = 91 37.43 37.43 35.79
■ 022:1 ' 6.05 6=05 6.05 10.15 7 = 72 8=60 8=60 ■ 8=47
C2k:l , 0=84 0.84 1.00 ■ 0.97 ■ 1=02 - 0=94 . 0=94 1=24
Alcohols (#)
. Cl8:l ; 0=79 0=75 0=77 .0=75' 0=63 o=57 0=57 0=52
C20:l 23.42 23.42 22=42 ; 21=43 22.22 22.65 22=65 21=70
.C22:l 18=58 18=58 18=65 19.01 20=44 19.20 19.20 21=28
C24:l 2=59 2.59 2.62 3.35 3.08 - 2=99 2=99 3.36 Table 3= Variability in jojoba oil fatty acids and fatty alcohols, from different sites of Maricopa County, Arizona*
Chain Length, . ... Fatty Acids {%) and Analyses of the different sites (No* of samples) Double Bonds 23 " ' 24 . 23 t 26 . . 27 . 28
Acids (^) ' 7- V t.
Cl6:0 0.79 0.96 1.02 0.94 0.69 0.62
Cl8:l 8.69 7.52 8.83 9.11 7.56 6.90
020:1 32.67 35.15 34=96 35=31 38.08 37=58
022:1 10.12 9=37 9=86 9=71 9=01 8.71
. 024:1 v ' - 0.867: 1=31 7 1.37 . 1=38 .. 0.91 0.75
Alcohols {%)
Cl8:1 0.40 0.38 . 0.56. 0.53 0.46 0.45
' 020:1 \ 22.39 . 20.39 20.25 21.90 21.10 22.06
022:1 21.25 20.00 19=9 6. 18.91 19=58 20.19
' 024:1 '2.78 . 3=36 3=57 ' 2.62- 2.03 . 2.92 15
Table 4b Variability in jojoba oil fatty acids and fatty alcohols from different sites of San Carlos. Indian Reservation, Arizona*
Chain Length 1 Fatty Acids (.%) and ■ Analyses of different sites (No* of sample) Double Bond . \ 29 30 31 - \ 52
Acids (.%)
Cl6:0 . ; Qo75 l;. : ' ; : 0,75 : 1,07 . 1=07 .
Cl8:l 6 <,53 ' .6,53 6,82 6b82 .
C20;l 41,06 4 1 ,06 K ' . 40 ,09. . 40,09
: C22:l 6,05 6,05 6,90 7=28
024:1 . 0,84 . 0,84 0,75 ' 0,83
Alcohols (.%)
. Cl8:l ; o,79 0,79 : 0,64 0,6!
.C20:1 ■ 23=42 23=42 21,00 ' 21,14
: 022:1 ' ' , 18,58 . 18=58, . 19=97 19=63
- 024:1 . 2,59 2,59 2,69 2,6 9. 16
Table.5= ' Variability in jojoba oil fatty acids, and fatty alcohols from different sites of Yavapai County, Arizona.
Chain Length Fatty Acids {%) and . Analyses of the different sites (No« of sample) Double Bonds 33 ' 34 - / 35 ■' . 36 v 37 Acids {%) .
Cl6;d o,8l 0.93: ' . 1. 00 . ; 1.08 V 0.94
. ci8si 8,24 10.42 7.55 ; 7.87 8.68
C20:l 36,07 •; 33.98 32.58 33.49 32.14
.022:1 ; : 10,02 '.'80.56 - ■ 9.35 9. 0 3 8.86
024:1 ; 0.62 3 0.84 0.99 • 1.21 : 0.56
Alcohols {%)
Cl8:l _ ' 0,38 o,4o . 0.45 0'.48 .: , 0.50
020:1 ' 21.66 22.36 21.89 , 22.47 24.21
022:1 ■ 20.32 20.46 .■ 20.47 20.03 19.80
/.G24il 2.05 2.33 -. 5.43 4ol4 • 3.99 17
Table 6 = Variability in jojoba oil fatty acids and fatty alcohols from different sites of Pinal County, Arizonao
Chain length . Fatty Acids {%)' and, 'Analyses of the different sites (No. of sample) Double Bond - - ; " : - : 1 ' 39 ; . 40 '
Acids (/») .. ■ -
Cl6:0 1.14 ^ 0.99 1.25
018:1 : 7-79 - ■ 6.97 . 7.9i ;
. C20:l 35.18 ■ 4 ■'/ 35.30 35.85
022:1 • 7.90 , 7.02 8.65
C24:l 0.64 0.77 ' . : 1.30 .
Alcohols {%) ' "
V Cl8:l ; 0.42 0.43 • 0.53'
C20:l : 22.25 23.52 22.60
. C22:l ■ 22.22 21.75 19.22
024:1 . 2.36 3.60 2.57 18
Table 7« Fatty acid and fatty alcohol composition of Graham County, Arizona, jojoba seed oil*
Analyses . Sites Analyzed (No, of sample) 41 \ . 4 2 Weight of seed, g, (X) 0,5398 0,4508 Oil content, % (X) ■' 42,07 Acids, %
016:0 1.42 ; • . 1.27
018:1 :. 8,71 / V 8.79
020:1 33.03 ' 33.90
' 022:1 7.78 : 9.00
024:1 0.73 0,81
Alcohols, °/o
018:1 0,76 0.72
020:1 23.25 ; 22,41
022:1 1 8,30 / 19.67
024:1 3.79 . 3.59 19
Table 80 Fatty acid and fatty alcohol composition of Papago Reser®, Arizona, jojoba seed oil® •
Site Analyzed (No® of sample) Analyses . . 43
Weight of seed, (X) 0®5276 ... Oil content, ■% (X) . : 45®.45 Acids, ^ (X)
'. 016:0 - . 1=20
018:1 . , : 7=63 ,
020:1 : ' . : 38=37
022:1: 10=21
. 024:1 ■ 1=18
Alcohols, % (X)
' 018:1 . ’ ■ • ■ : " 0=48
■ 020:1 . :; 20=14
" 022:1 • 18=22
024:1 ' ^ 2=92 20
Table 9= Fatty acid and fatty alcohol composition of Yuma County, Arizona, jojoba seed oilo
: Sites: Analyzed (No0 of sample) ■
Analyses 44 . ■ . 43
Weight of seed, (X) O06160 4 0=6527 ; Oil content, (X) ; 48=06 - 36=32 Acids (90 .
Cl6:0 . 1 *19'' ; ' : . ' 0 = 86
,■ C l S r l . ; i ; ; ■ 7,84 / ; ';;: . 7.00
. 020:1 V ' 34.91 ; .35.46
^ 022:1 ' 8=72 9.27
024:1 1=02 . : ; 1,47
Alcohols (?0
018:1 0=63 0=59
■ G20.:l'; v 22=22 22=78
022:1 20=44 19.54
024:1. • ■ 3.08 , 5.30 21
Table 10= Component means of the analyses of Beer Sheva, Israel, . jojoba seed oil*
Weight of seed, (X) 0„5854 Oil Content, % (X) ' 4$.43 ' Acids^: (3cy:; .
C l6 ;0 0.71
. C l8: l 7-38
, caosl . , 38.46
v ^auv:;;. 7 - 2?
; C 24:l: ■ . - ' " vx ' 4 4 : ' ^ 0..61
Alcohols, % (X)
ci8:i : „ 0.37
C20:l - 21.91 .
■ 022:1 . '20.29
C 2 4 :l .. 3-16
Total 100.16# 22
Table llo Component means of the analyses of Gila County,,Arizona, . jojoba seed oil*
Weight of seed, £, (X) 0=6626 • Oil content, % (X) 42=29 Acids, % (X)
Cl6;0 : 1=04
Cl8:1 6=81 .
• C20:l : ' 38=26
024:1 . , : 0=97
Alcohols, % (X)
. Cl8::l- . ; O .67
■ ' . 020:1 " 22=48
C22:l . 19=37
. 024:1 , ‘ 2=93
■V Total '' 100=26% Table 12* Component means of the analyses of. Maricopa County, Arizona, jojoba seed oil.
Analyses
Weight of seed,-j£,. ,(X) / o 06853 Oil content, % (X) V.:::43cl6-; Acids, % (X)'
' 016:0 0„84
. Cl8:l . • : 8.10
' 020:1 ■- .. 35.63
, 022:1 : . ;-r; 5.46:
024:1 : . ' 1.09
Alcohols, % (X)
Cl8:l 0.46 :
020:1 ' 21.35
022:1 ' 19.98 .
024:1 .. 2.88
Total . 99.79% V 2k
■ Table: 13» Component means- of the. analyses of San Carlos Indian Reservation, Arizona, jojoba seed oil»-
Analyses
Weight of seed, g, (X) o06256 Oil content4 % (X) 43.97 Acids, % (X) '
Cl6s0 . °o9l
■ ciBsi 6.6?
020:1 . V 40=77 . '
... 022:1 . ; , 6.57 y • " ' .
. 024:1 . : - O 081 ': : v .
Alcohols, % (X)
018:1 ■ 0.70
020:1 22.24
' 022:1 19.19
024:1 2.64 ...... Total 101.50% Table l4b.. Component means of the analyses of Yavapai County, Arizona, jojoba seed oilo
Analyses
Weight'of seedy\g, (X) - 0.6940 . Oil content, ^ (X) / 41.75 Acids, % (X)
C16;0 : 0.95
. Cl8;l ' 8.55
' :\ 020:&: /: ; y: '/ 55*65
022:1 9.16
024:1 : ^ . 0.84
Alcohols, % (X)
' 0 1 8 : 1 1 ' ' . v- ; 0.44
C20:1 ' I 22.51
022:1 20.22
024:1 / 5*59
Tbtal ■ 1 99=91% 26
Table 15= Component means of the analyses of Pinal County, Arizona, jojoba seed oil„
Analyses
Weight of seed, _g» (X) ' o06676 Oil content, % (X) 42,53 ; Acids, % (X)
Cl6.: 0 : 1.12
Cl8:l. 7,55
020:1 35.44 :
■ .-0 2 2 :1: . ;■ 7,83^
024:1 Oo90 :
Alcohols, % (X)
018:1. : ■, ■
: 020:1 22.79
C22:i ■ - ; 21.06
024:1; 2,84
Total 100 .00 # In this particular study of variability in the composition of jojoba oil, the content of hexadecanoic acid ranged from 0<,47% to lo09$> with a mean of and standard deviation of 0.09° The F test was signifi- cant at the 0=05 level with S' = 3=6960 These results agree with those reported: by Duncan etalo (1) who made' an-investigation of: comparison between his rapid ethanolysis technique and the one described by Miwa : .
(12)o The average percentage which was the result of 5 optimized runs was 0 o6% with a standard deviation of 0 =lo
The octadecenoic acid (Gl8:l) values found varied from 60210: to 9=490 with a mean of 7 =380 :and a standard deviation of 10 63= ' These results are in excellent agreement with those reported by Duncan et al,
(1) and Miwa (12) 0
The amount of oleic acid in our samples was significantly higher than that, reported- by-McKinney and. Jamieson: :Cl0)o The mean - average of the percentage of eicosenoic acid throughout all sites in
Beer Sheva, Israel were all between 36=61 and 4#=2C0 with a mean of
38=46 and a standard deviation of 2o3 = ■
. The content of docosenoic acid varied from 5=340 to 9ol70 with a mean of 7=270 and a standard deviation of 1<>3= These results gener ally agreed with those reported by Duncan', et al^ (1) and Miwa (1.2) 9
(6ol0 with a standard deviation of 3=9)= The results found by
McKinney and Jamieson (10) were somewhat higher in decosenoic acido
Tetracosenoic acid was detected in proportions from Oo380 to 0=900 with a mean of Oo6l0 and a standard deviation of 0=25= Palmitic acid -y/.- ' ■ : as and hexadecenoic acid were not measured in this particular work because of the small amounts in the analyseSo These acids were included in the. study,of Miwa (12) in 1971, in different individual.jojoba plants from native populations in Southern California; they were present at 0.04 and 0 .1^ respectivelyo
The composition of jojoba oil fatty alcohols was mainly com prised of eicosenol (020:1) and docosenol (C22:l). The content of eicosenol ranged from 20»80 to 23=40 with a mean of 21.91/^ and a stan- dard deviation of 0.94. Docosenol was detected in the proportions from 18o47%. to 21=90^ with a mean of 20=29 and a standard deviation Of
3=860 These values represent more than 90% of the alcohol composition.
The percentage of octadecenpl varied from 0.30^ to 0o44^ with a mean of
Qo37% and.standard deviation of 0.03= Tetracosenol.was detected from
2.30 to 4.2C^ with a mean of 3=16$ and a standard deviation of 0.54.
All of •these'restdtS:are in excellent agreement with those reported by
Duncan et al. (T) and Miwa (13)= They reported 0.6^ for octadecenol with a standard deviation of 0.6 and 3=45^ for tetracosenol with a standard deviation of 4.7.
Tables 2 through 9 show the variability in fatty acids and fatty alcohol composition of the different sites analyzed in Arizona.
All of. these results show a great similarity to those results reported by Miwa (12) who made an investigation on the variability of jojoba oil composition from different areas. The two major components in the fatty acid and:fatty alcohol composition are eicosenoic.acid and eicosenol. . The amount of eicosenoic acid varied from 33<>6^ (Yavapai
County) to k0o77& (San Carlos Indian Reservation) with a mean of 3 7 o21^6
. Eicosenol varied -from 20ol4% (Papago; Resero) to 23=^7^ (Pinal County)
with a mean of 21<,S%0 Miwa (12) reported a value of 3602 ^ with a
standard deviation of 2 „3 for eicosenoic•acid and: 23o3^-with a stan
dard deviation of 1208 ■ for eicosenol» These results are very close0
The:.-range: of • valnes identifie;d fOh;.the: other fatty acids and fatty -
• alcohols: is as follows: hexadecanoic acid ranged from 0«8W (Maricopa
County) to lo3% (Graham County) With a mean of 1.04#. . Oleic acid . . :
varied from 6o8l^ (Gila County) to 8<,75% (Graham County) with a mean
of 7083° This value agrees with that reported by Miwa (13)» but dis- ,•
agrees with that reported by McKinney and Jamieson (10) who reported.
only a'; smallc amounf of: oleic acidy Decosenpic' acid /was fdund -in the ,
proportions from 6o5^ (San Carlos: Indian Reservation) to 10<,21% (Papago
Resero) = The content of tetracosenoic acid varied from 0o8l^ (San
Carlos Indian Reservation) to lo2^ (Yuma County) with a mean of lo02%o
The alcohol fraction was mainly composed of eicosenol and
docosenol which represented more than 8^ of the fatty alcohol compo
sition of jojoba oil* ■The content of docosenol in the different sites
analyzed ranged from l80 22% (Papago Reser» ) to 2100.6%. (Pinal County)
with a mean of 19o640 This value, is very close to: -that reported by.'
- Duncan et alo (1)» The mean average percentage, reported was of 19.5%
vmth,a, standard ’deviation .of .8o-9<. Oleyl and tetracosenol were, identi- :
fied in the following range of proportions: 0.44% (Yavapai County) to
6.74% (Graham County) and 2=64% (San Carlos Indian Reservation) to 3o69^ (Graham County) respectively. There was no palmitoleyl alcohol
.in this particular work, however, this fatty alcohol was included in
Mi'wa' s report. in'very small' amounts as OolG%=
Comparison of,the fatty acid and the fatty alcohol composition
of. Beer Sheva, Israeli jojoba seed oil and Arizona .jojoba seed oil .
showed no significant- differences* • This further corroborates the
assumption that jojoba seed oil does not vary in composition signifi
cantly regardless of the stage of maturation, length of time the seeds
are stored or locale of growth, not even when a particular phenotype
of shrubs has adapted itself to different.-environfflentsb , ■
The determination of wax percentages and dried seed weight ere
included in the results (Tables 16 through 20)„
Wax percentages at the 14 sites analyzed in Beer Sheva, Israel
(Table 1.6) were normally distributed and ranged from 39.09$ to 51 <>72$ '
with a mean of 43o45$= The F test was significant at the 0o05 level
with F = 3<>523=
" -Wax percentages at all sites in Arizona (Tables 17 through 20)
varied from the mean average of 41.75$ (Gila County) to 43ol6?o (Mari
copa County) with a total mean of l2o5i+$o
It is possible that exhaustive Soxhlet extraction of the seeds
in this study may have given slightly higher wax yields<, Additional
extractions in preliminary work gave only slightly higher values.
These were considered quantitatively insignificant.
The tables cited above also show the mean average dried seed
weight in all sites analyzed0 The great majority falls between : ■■■: '\ -• / ; ■ ' ■- ■^' 31 Table 16« Oil content and dried seed weight of Beer Sheva, Israel, jojoba seedo
Sites Analyzed ■ Seed Weight . Oil Content (NOo of sample) (g) ■ . : ;'<*) .
:; 0.2739 41.29 - 2 ; : - 0.6684 46.43 ■ 3 . . : 0.7739 44.28 . 0.5550 43.58
... "5. : 0.5587 51.72 V . 6 ' ' ' . . 0.8026 42.79 7 0.5674 43.19 8 0.4565 45.07 . 9 . 0.7586 39.71 : 10 ; : 0=6822 39.89 11 0.3426 45.06 ■ . 12 0.3675 - 44.82 : : ; .■13': V, :: . 0.6418 : ' ^ 39.09 . -14 . / - : v 0.7468 40.72
: X = 0.5854 43.45
Table 17<, Oil content and dried seed weight of Gila County, Arizona, jojoba seedo
Sites Analyzed Seed Weight Oil Content
(No. of sample) - - (g) . . (%>
. 15 ; y; ; ; 0.7276- - 41.70 ' 16 : 0.6385 44.14 . 17 0.6863 37.84 v 18 >- 0.3529 40.92 : 19 0=5060 ' 43 .16 . 20 : 0.6064 ■ -■ 42.67 : 21 . 0.8346 45.35 22 0.9485 42.61
x = 0.6626 42.29 ■ 32
Table l8„ Oil content and dried seed.weight of Maricopa County, Arizona,jojoba seedc -
Sites Analyzed • Seed Weight . Oil Content (No. of sample) (^) :
23 0.7558 : 45.01 24 0.6588 40=98 25 ... 0.7127 44.29 ' 26 ; 0.5700 44.16 ' 27 V ■ 0.7487 45=85 ' 28 0.6865 . - 42.68
45=16.
Table 19= .Oil center it and dried • seed weight of Y avapai County, ' . Arizona,) 36i joba £seed.
Sites Analyzed . .. Seed Weight ' . Oil Content (No. of.sample) . (g) C : -V;:"-
33 0.5678 4i.o6 ; 34' : ' 0.6586 39=90 35 ■ ■ 0.7685 41.00 3B 0.6144 . 42.05 37 . 0.8610 44.73
ic = 0=6940 : 'v ■ 41.75 v ' -
Table----- —— 200 Oil content----- and — - dried seed weight of San Carlos Indian Reservation-, Ar:izona, jojoba seed.: -
Sites Analyzed . Seed Weight Oil Content (No. of sample) v ; (g) : . - . W - 29 0.8092 41.53 30 O.47I 6 44.72 31 0.7276 41.70 ' 32,, ; - . - 0.6855 . 44.14 • X = 0.6729 42.97 : y ^ . - J ' - :; V'V'; - v . : 33
0o5854 g and 0<,69^0 g as representative of the largest and healthiest
; seed selected from each site* Wells and Tomoff (x8) stated that as the ;
seeds are stored their oil content increases to about 50 & and this is
observed regardless of the stage of maturity seeds are picked* This .
increase is undoubtedly due to loss of moisture* Also of importance
is the observation that once the seeds are dry, prolonged storage does :
not affect the wax ester composition and therefore presumably the
quality of the oil* Although the oil content of these seeds did not
■ vary widely, there was a tendency.for maximum oil content to occur when
. the seed had reached the generally accepted maturity*
Conclusions
10 Jojoba seed oil of the Arizona and Beer SHeva, Israel, varieties
analyzed in this study contain predominantly 5.fatty acids and 4
" fatty alcohols* The fatty acids were hexadecanoic, octadecenoic,
eicosenoic, docosenoic and tetracosenoic acid and the fatty alco
hols were octadecenyl, eicosenol, docosenol and tetracosenol*
2* .Results of the analyses of all different varieties analyzed by . ■
rapid ethanolysis procedure are essentially the same* There was
a remarkable similarity between oils, and they could not be dis
tinguished on the basis of fatty acid or alcohol analyses*
3* The unsaturated acids consist of a mixture of eicosenoic acid
(020:1) , oleic acid (Cl8:l) and docosenoic acid (022:1)., albng
with small quantities of tetracosenoic acid* Hexadecanoic acid
' was the only-saturated identified in this study* The unsaturated ■ " - ' • " ■■■■■■ ' ■ : alcohols are mainly represented by a mixture of eicosenol (G20tl) and doco.senol. (G22:l) =
Throughout all samples-: analyzed the mean average percentage of eicosenoic acid was over
Dried jojoba seeds throughout all samples analyzed contained 4C%> or more total extractable wax<> APPENDIX A
LOCATION OF AREAS SAMPLED
Noo of Sample Site Area ' 1 ' 879/55 Gilat : a ; ■ ' 879/60 vv;;: Giiat.1 /.- .. ' 3 . 879/85 - : v'"'' ' Gilat : • 4; 879/89 Gilat :. : 5 ' .V ' y / .. ' 879/154 \ . Gilat ' y ::- 6/Y' 1176/Noo 3/5 Gilat . y:';::. 7 1176/No. 3/12 Gilat ■ ■ 8 . • 1176/Noo 5/37 Gilat : . 9/ . ■ : ' ' ;il76/No*:y3/48 ^; Gila#yv ■, ' 10 1176/Noo 1/41 Gilat 11 / ■ 1180/No. a/104 Gilat . 12 . . 1 1 8 0 /No. a/106:: Gilat ^ ' ' . / : ; 13 ' . - - . Gilat 14 - ' Gilat . 15 ' - : San. Carlos Indian Beservation 16 1 ■' San Carlos Indian .-Reservation ; 17 2 :: y Gila 18 ; • • • 4.. ; : : 3 . Gila ■ 19 4 San Carlos Indian Reservation • 20 5 San Carlos Indian Reservation .' . 21 . 6 ■ Graham 22 7 Graham ' 23 - ’ - . 8 ' . Gila 24 . 9 PapagO;. Reseryation 25 ' 10 Gila 26 11 . Yuma : : :■ : ; :-35y. ; y-.;y:' ' '' ■ . Hoc of Samples Site ■ Area 27 12 ; ' ; ; ' Gila 28 ; ; 13 v . ■; : Gila. .. 29: r ■ 14 .■ Gila - . 30 15 . . " Gila : 31::/' ' 16 . Maricopa 32 17:' Pinal
, 33 . . 18 V ; ■, . Pinal 34 1 9 / Pinal /:.:39 7 - ^ 20 .Maricopa y// ' 36 . - 21 . • ■ Maricopa ; 37 ■ 22 ; - , v : . Maricopa 38 - . 23 Maricopa:; 39 24 Maricopa . . 40 : ' 25 . Yavapai.; 41 26:: Yavapai 42 ' . 27 /.:/ ■ ;/ ;. ' Yavapai 4328 Yavapai 44 ' ■ 29 Yavapai ■' 45 :. 30 '■ Yuma LIST OF KEFEBENCES
lo Duncan, G» Go, D,' Mi Yermanos, J» Kumamoto» 197^» • Rapid ethanoly- sis procedure for jojoba wax^analyses by gas liquid chroma- tographyo• Journal of the American Oil Chemists' Society 51
( 12): 534- 536o "
2oFore, So Po, F= Co Beeford and Wo Go Beefordo. 1958» Epoxidized jojoba oil as a stabilizer for vinyl chloride containing plasticso: Journal of the American Oil Chemists’ Society 35(9)s469-472o
3o Fore, So Po, H= P 0 Pastor, Jo Po Hughes and Wo G« Be'ckfordo I96O0 ; " Derivatives of jojoba oil as plasticizers for vinyl polymers and bun-N-rubbero Journal of the American Oil Chemists’ ■ Society. 37(8):578-39Qi';'
4o Forti, Ho 1973« Simmondsia studies in Israel« In Jojoba and its uses; an International Conference, June 1972» The Uni- : versity of Arizona, Office of Arid Lands Studies9 Tucsono 81 ppo ■ ' Vv V ;
5o Forti, Ho, Mo Ro Abramovieh, Mo Tal and Eo Biernbaum0 1976» ■ Recent development in jojoba research in Israelc II Con- .. ferencia Sobre Jojoba y su Aprovechamiento, Ensenada, Mexico, February 10-12, 1976<. ; Consijo Internacibnal Sobre . / v Jojoba;,; ■ V. ''
60 Gentry, Ho So 1958« The natural history of jojoba (Simmondsia chinensis) and its cultural aspects= Economy Botany 12(3): " . ^ 261-295o
7o Jones, Ao and Fe Ro Earlo 1966« Chemical analysis of seeds<> Economy Botany 20(2):127-l53o:
80 Knight, Ho.Go 1937= Oil,, fat, and wax investigation, liquid wax ; from jojoba, : TJoS« Department of Agriculture, Bureau of Chemistry and Soils, Annual Report„.
9, Markwood, To K» and I, Ao Markwood, 1942, Jojoba, an oil that ... is different. Domestic Commerce (HoS, Department of Commerce), 50(11) :.2p/%hemur#c:Digast,l(22:174-173).'
10, McKinney, R, S= and G, S, Jamieson, 1936« A non-fatty oil from jojoba oil seed. Oil and Soap 13:289-292,
37 38
11. Mirov, N. T. T. 1950. Simmondsia: desert shrub offers new uses, from cover crop to wax. Chemurgic Digest 9(7):7-9*
12. Miwa, T. K. 1971. Jojoba oil wax esters and derived fatty acids and alcohols: Gas chromatographic analyses. Journal of the American Oil Chemists' Society 48:259-264.
13. Miwa, T. K. 1973. Chemical aspects of jojoba oil, a unique liquid wax from desert shrub simmondsia californica. Cos metic and Perfumery 88:39-41.
14. Miwa, T. K. and I. A. Miwa. 1962. Fatty acids, fatty alcohols, and wax esters from Limmanthes Douglasii (Meadowfoam) seed oil. Journal of the American Oil Chemists' Society 39:320- 322.
15. Spadaro. I960. Direct extraction of jojoba seed. Journal of the American Oil Chemists' Society 37(3):121-124.
16. Thompson, R. F. 1972. Comparison of sperm oil based E.P. addi tives with their replacement products. N.L.G.I. Spokesman 36(6):208-213.
17. Wage, C. Sherbrooke and Edward F. Hoase. 1974. Jojoba: A Wax- producing shrub of the Sonoran desert. The University of Arizona, Office of Arid Lands Studies, Tucson.
18. Wells, M. A. and C. S. Tomoff. 1973. An analyses of the oil content, and the fatty acids, fatty alcohols and wax ester composition during development of jojoba (Simmondsia Californica) seeds. The University of Arizona, Office of Arid Land Studies. 12 pp. (unpublished).
19. Yermanos, D. M. 1974. Agronomic survey of jojoba in California. Economy Botany 28(3):160-174.
2 0 . Yermanos, D. M. and C. C. Duncan. 1976a. Quantitative and quali tative characteristics of jojoba seed obtained from the Aguanga, California population. II Conference Internacional Sobre Jojoba y su Aprovechamiento, Ensenada, Mexico, February 10-12, 1976. Consejo Internacional Sobre Jojoba (Abstract).
21. Yermanos, D. M. and C. C. Duncan. 1976b. Single seed analyses of jojoba — techniques and observations. II Conferencia Inter nacional Sobre Jojoba y su Aprovechamiento, Ensenada, Mexico, February 10-12, 1976. Consejo Internacional Sobre la Jojoba (Abstract).
22. Yermanos, D. M. and R. Holmes. 1973. Jojoba at Vista. Cali fornia Agric. 5:12-14.