U.S. patent number RE44,718 [Application Number 13/776,199] was granted by the patent office on 2014-01-21 for human sebum mimetics derived from botanical sources and methods for making the same.
This patent grant is currently assigned to International Flora Technologies, Ltd.. The grantee listed for this patent is International Flora Technologies, Ltd.. Invention is credited to David A. Ashley, James S. Brown, Robert Kleiman, Sambasivarao Koritala.
United States Patent |
RE44,718 |
Brown , et al. |
January 21, 2014 |
Human sebum mimetics derived from botanical sources and methods for
making the same
Abstract
Human sebum mimetics and methods for producing human sebum
mimetics are provided. In one exemplary embodiment, a human sebum
mimetic comprises a wax ester derived from interesterification
refined botanical oil comprising palmitoleic acid and refined
jojoba oil, a phytosterol, and phytosqualene. A method for
producing a human sebum mimetic comprises mixing refined macadamia
oil and refined jojoba oil, interesterifying the refined macadamia
oil and the refined jojoba oil, adding a phytosterol after the
interesterifying, and adding phytosqualene after the
interesterifying.
Inventors: |
Brown; James S. (Gilbert,
AZ), Kleiman; Robert (Sun Lakes, AZ), Koritala;
Sambasivarao (Sun Lakes, AZ), Ashley; David A. (Phoenix,
AZ) |
Applicant: |
Name |
City |
State |
Country |
Type |
International Flora Technologies, Ltd. |
Chandler |
AZ |
US |
|
|
Assignee: |
International Flora Technologies,
Ltd. (Chandler, AZ)
|
Family
ID: |
43898616 |
Appl.
No.: |
13/776,199 |
Filed: |
February 25, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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61363564 |
Jul 12, 2010 |
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61254909 |
Oct 26, 2009 |
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Reissue of: |
12911150 |
Oct 25, 2010 |
8343468 |
Jan 1, 2013 |
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Current U.S.
Class: |
424/70.1 |
Current CPC
Class: |
A61K
8/31 (20130101); A61Q 5/12 (20130101); A61K
8/361 (20130101); A61Q 19/00 (20130101); A61K
8/922 (20130101); A61K 8/63 (20130101); A61K
8/37 (20130101) |
Current International
Class: |
A61K
8/18 (20060101) |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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2792190 |
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Oct 2000 |
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FR |
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2815254 |
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Apr 2002 |
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FR |
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2847164 |
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May 2004 |
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FR |
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02/11693 |
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Feb 2002 |
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WO |
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02/26207 |
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Apr 2002 |
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WO |
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03/037288 |
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May 2003 |
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WO |
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Other References
Anonymous, Biophytosebum--Obtention du Biophytosebum et Composition
du Biophytosebum, Sophim, Apr. 23, 2001. cited by applicant .
Sivakumar, et al., "Gas chromatography screening of bioactive
phytosterols from mono-cultivar olive oils," Food Chemistry, Apr.
1, 2006, pp. 525-528, vol. 95, No. 3. cited by applicant .
Busson-Breysse, et al, "Jojoba wax: Its Esters and Some of Its
Minor Components," Journal of the American Oil Chemists' Society,
Jan. 1, 1994, pp. 999-1002, vol. 71, No. 9. cited by applicant
.
Soares, et al., "Physical and Chemical Characterization and
Stability Evaluation of Avocado Oil Persea-Americana Mill in
Different Steps of the Refining Process," Revista de Farmacia e
Bioquimica de Universidade de Sao Paulo, Jan. 1, 1991, pp. 70-82,
vol. 27, No. 1. cited by applicant .
Kaijser, et al., "Oxidative stability and lipid composition of
macadamia nuts grown in New Zealand," Food Chemistry, 2000, pp.
67-70, vol. 71, No. 1. cited by applicant .
Lu, et al., "Comparison of artificial sebum with human and hamster
sebum samples, International Journal of Pharaceutics," Feb. 9,
2009, pp. 37-43, vol. 367, Nos. 1-2. cited by applicant.
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Primary Examiner: Wax; Robert A
Assistant Examiner: Mercier; Melissa
Attorney, Agent or Firm: The Noblitt Group, PLLC
Parent Case Text
PRIORITY CLAIMS
This application claims the benefit of U.S. Provisional Application
No. 61/254,909, filed Oct. 26, 2009, and U.S. Provisional
Application No. 61/363,564, filed Jul. 12, 2010, both incorporated
herein by reference.
Claims
What is claimed is:
1. A method for producing a human sebum mimetic comprising the
steps of: mixing a refined macadamia oil and a refined jojoba oil;
interesterifying the refined macadamia oil and the refined jojoba
oil to produce a wax ester; adding a phytosterol; adding
phytosqualene after the step of interesterifying; and producing the
human sebum mimetic.
2. The method of claim 1, wherein the step of mixing comprises
mixing an amount of refined macadamia oil of about 45 to about 65
wt. %. of the human sebum mimetic with the refined jojoba oil.
3. The method of claim 2, wherein the step of mixing comprises
mixing the amount of refined macadamia oil of about 51 to about 55
wt. % of the human sebum mimetic with the refined jojoba oil.
4. The method of claim 1, wherein the step of mixing comprises
mixing an amount of refined jojoba oil of about 20 to about 35 wt.
% of the human sebum mimetic with the refined macadamia oil.
5. The method of claim 4, wherein the step of mixing comprises
mixing the amount of refined jojoba oil of about 20 to about 33 wt.
% of the human sebum mimetic with the refined macadamia oil.
6. The method of claim 1, wherein the step of adding the
phytosterol comprises adding an amount of the phytosterol of about
0.5 to about 10 wt. % of the human sebum mimetic.
7. The method or claim 6, wherein the step of adding the
phytosterol comprises adding the amount of the phytosterol of about
1 to about 5 wt. % of the human sebum mimetic.
8. The method of claim 1, wherein the step of adding the
phytosqualene comprises adding an amount of the phytosqualene of
about 5 to about 20 wt. % of the human sebum mimetic.
9. The method of claim 8, wherein the step of adding the
phytosqualene comprises adding the amount of the phytosqualene of
about 11 to about 15 wt. % of the human sebum mimetic.
10. The method of claim 1, further comprising adding a tocopherol
after the step of interesterifying.
11. The method of claim 1, further comprising adding a functional
additive after the step of interesterifying.
12. The method of claim 1, further comprising bleaching the human
sebum mimetic after the steps of adding the phytosqualene and
adding the phytosterol.
13. The method of claim 1, further comprising the step of
deodorizing the human sebum mimetic after the step of adding the
phytosqualene and adding the phytosterol.
14. The method of claim 1, wherein the adding the phytosterol is
after the step of interesterifying the refined macadamia oil and
the refined jojoba oil.
15. The method of claim 1, wherein the adding the phytosterol is
before the step of interesterifying the refined macadamia oil and
the refined jojoba oil.
16. The method of claim 11, wherein the functional additive is at
least one of a tocopherol, a fragrance, a dye, a pigment, a
preservative, an antioxidant, a moisturizer, an emollient, and a
thickener.
17. The method of claim 1, wherein the human sebum mimetic is added
to a personal care product.
18. The method of claim 17, wherein the personal care product is a
hair conditioning lotion.
Description
TECHNICAL FIELD
The present invention generally relates to personal care
compositions and methods for manufacturing them, and more
particularly relates to human sebum mimetics derived from botanical
sources and methods for making them.
BACKGROUND
Human sebum is secreted by the sebaceous glands that are found over
substantially the entire skin surface (except the palms of the
hands and soles of the feet), but are found predominately on the
scalp, face, chest, and back. Sebum is involved in development of
the epidermal structure and maintenance of the epidermal
permeability barrier, carrying antioxidants to the skin surface,
protecting the skin from microbial colonization, generating body
odor, and producing pheromones.
When secreted, human sebum is a complex mixture of triglycerides,
wax esters, sterol esters, cholesterol, cholesterol esters, and
squalene. As the sebum is secreted, it consists primarily of
triglycerides and wax esters, which are broken down by commensal
microbes into diglycerides, monoglycerides, and the constituent
free fatty acids. The fatty acid chain lengths of human sebum vary
considerably, but have predominantly 16 and 18 carbons, such as in
the case of stearic acid (18 carbons with no double bond
(hereinafter denoted C18:0)), oleic acid (C18:1 with one double
bond on the ninth carbon (hereinafter denoted C18:1.DELTA.9)),
linoleic acid (C18:2.DELTA.9.DELTA.12), palmitic acid (C16:0), and
sapienic acid (16:1.DELTA.6).
Loss of human sebum can be due to a variety of environmental
factors such as bathing, weather conditions, chemical products, and
poor nutrition, and also can be due to genetics. For example, a
natural lack of sebum is observed on the scalp of
African-Americans. A loss of sebum can result in itching, dandruff,
wrinkles, diaper rash and the like on the skin. In addition, the
hair may become brittle and dry without a sufficient amount of
sebum to moisturize it. While a variety of products exist that
attempt to repair the suppleness caused by lack of sebum, many of
these products contain synthetic components or components that are
derived from animals and do not mimic the structure and formulation
of human sebum. In this regard, the products are not absorbed by
the skin as readily as human sebum. In addition, the products are
often made from unstable ingredients that exhibit a short shelf
life.
Accordingly, it is desirable to provide a human sebum mimetic. In
addition, it is desirable to provide a human sebum mimetic produced
from plant sources. It is also desirable to provide a method for
manufacturing a human sebum mimetic. Furthermore, other desirable
features and characteristics of the present invention will become
apparent from the subsequent detailed description of the invention
and the appended claims, taken in conjunction with the accompanying
drawings and this background of the invention.
BRIEF SUMMARY
Human sebum mimetics and methods for producing human sebum mimetics
are provided. In one exemplary embodiment, a human sebum mimetic
comprises a wax ester derived from interesterification of a refined
botanical oil comprising palmitoleic and refined jojoba oil, a
phytosterol, and phytosqualene.
In another exemplary embodiment, a method for producing a human
sebum mimetic comprises mixing refined macadamia oil and refined
jojoba oil, interesterifying the refined macadamia oil and the
refined jojoba oil, adding a phytosterol after the
interesterifying, and adding phytosqualene after the
interesterifying.
In a further exemplary embodiment, a human sebum mimetic comprises
a wax ester comprising a fatty acid having 16 carbons and one
double bond and that is derived from a plant source, a phytosterol,
and phytosqualene.
DETAILED DESCRIPTION
The following detailed description is merely exemplary in nature
and is not intended to limit the invention or the application and
uses of the invention. Furthermore, there is no intention to be
bound by any theory presented in the preceding background or the
following detailed description.
Various embodiments contemplated herein are directed to
compositions that mimic human sebum. The approximate composition of
human sebum includes by weight percent (wt. %) (from Pierre Agache,
"Sebaceous Physiology," Measuring The Skin, Springer-Verlog, 2004,
pp. 271-280):
TABLE-US-00001 Squalene 12 wt % Wax esters 26 wt % Glycerides and
free fatty acids 57.5 wt % Sterols (free and esters) 4.5 wt %.
The human sebum mimetics contemplated herein are plant based, that
is, the components of the mimetics are derived either physically or
chemically from plant sources. In this regard, the mimetics are
plant-derived analogs of human sebum in that they are derived from
phytosqualene, phytosterols, a refined botanical oil such as
macadamia oil, which is the source of the mimetic's triglycerides,
and refined jojoba oil, which is the source of the mimetics' wax
esters. As used herein, the term "refined oil" means crude oil that
has had undesirable compounds such as free fatty acids,
carbohydrates, metals, proteins, and the like removed using caustic
agents, washing, and centrifugation. In one embodiment, the human
sebum mimetic is derived from phytosqualene in an amount of about 5
to about 20 wt. % of the entire mimetic, refined jojoba oil in an
amount of about 20 to about 35 wt. % of the entire mimetic, refined
macadamia oil in an amount of about 45 to about 65 wt. % of the
entire mimetic, and phytosterols in an amount of about 0.5 to about
10 wt. % of the entire mimetic. In preferred embodiment, the human
sebum mimetic is derived from phytosqualene in an amount of about
11 to about 15 wt. % of the entire mimetic, refined jojoba oil in
an amount of about 29 to about 33 wt. % of the entire mimetic,
refined macadamia oil in an amount of about 51 to about 55 wt. % of
the entire mimetic, and, phytosterols in an amount of about 1 to
about 5 wt. % of the entire mimetic. In a more preferred
embodiment, the human sebum mimetic is derived from the following
composition in weight percent:
TABLE-US-00002 Phytosqualene 12.9 wt % Refined jojoba oil 30.8 wt %
Refined macadamia oil 53.2 wt % Phytosterols 3.1 wt %.
Of its fatty acids, human sebum has particularly high levels of
palmitic acid (16:0), sapienic acid (16:1.DELTA.6), and oleic acid
(C18:1.DELTA.9). Analogously, the human sebum mimetics contemplated
herein also comprise high levels of palmitic acid and oleic acid,
as macadamia oil itself comprises about 8.8 wt % palmitic acid and
about 58 wt. % oleic acid. In one embodiment, the human sebum
mimetic comprises about 1 to about 10 wt. % palmitic acid, in a
preferred embodiment about 3 to about 7 wt. % palmitic acid, and in
a more preferred embodiment about 4.8 wt. % palmitic acid. In
another embodiment, the human sebum comprises about 25 to about 35
wt. % oleic acid, in a preferred embodiment about 30 to about 34
wt. % oleic acid, and in a more preferred embodiment about 31.6 wt.
% oleic acid.
However, sapienic acid is unique among mammals. Palmitoleic acid
(16:1.DELTA.9), an analog of sapienic acid, is a substitute for the
sapienic acid. While palmitoleic acid is fairly rare in the plant
kingdom, macadamia oil has the highest palmitoleic acid content of
the currently-available commercial oils, with about 16-22%
palmitoleic acid. Accordingly, the inventors have found that by
interesterifying the refined macadamia oil and the refined jojoba
oil of the human sebum mimetic, a wax ester comprising palmitoleic
acid results. While macadamia oil is preferred, other seed oils
contain greater than 10% palmitoleic acid and also may be
interesterified with refined jojoba oil to produce a wax ester
comprising palmitoleic acid. The genera of these species include
Thunbergia, Doxantha, Alophia, Roureopsis, Telopea, and
Asclepias.
In one embodiment, the human sebum mimetic comprises palmitoleic
acid in an amount of about 5 to about 15 wt. % of the entire
mimetic composition. In a preferred embodiment, the human sebum
mimetic comprises palmitoleic acid in an amount of about 8 to about
12 wt. % of the entire mimetic composition and, in a more preferred
embodiment, the human sebum mimetic comprises palmitoleic acid in
an amount of about 9.7 wt. % of the entire mimetic composition. In
a most preferred embodiment, the human sebum mimetic comprises the
following fatty acids and fatty alcohols in weight percent:
TABLE-US-00003 Fatty acids: Wt. % Fatty Alcohols Wt. % Myristic
acid (14:0) 0.5 cis-11-Eicosenaol (20:1) 5.9 Palmitic acid (16:0)
4.8 cis-13-docosenol (22:1) 6.3 Palmitoleic acid (16:1) 9.7
cis-15-tetracosenol (24:1) 1.9 Stearic acid (18:0) 1.9 Unknown 18:1
(18:1) 0.1 Oleic acid (18:1) 31.6 cis-Vaccenic acid (18:1) 1.6
Linoleic acid (18:2) 1.3 Linolenic acid (18:3) 0.1 Arachidic acid
(20:0) 1.5 cis-11-Eicosenoic acid (20:1) 13.9 Behenic acid (22:0)
0.5 Erucic acid (22:1) 2.9 Lignoceric acid (24:6) 0.2 Nervonic acid
(24:1) 0.3.
In another exemplary embodiment, the human sebum mimetics
contemplated herein comprise additional functional additives, that
is, an ingredient added to perform a particular function. For
example, the human sebum mimetics may comprise tocopherols. In one
embodiment, the human sebum mimetic comprises about 100 to about
2000 parts per million (ppm) of 70% tocopherols, preferably about
1430 ppm. The human sebum mimetics may also comprise fragrances,
dyes, pigments, preservatives, antioxidants, moisturizers, and the
like. By way of a further example, the human sebum mimetics may
comprise emollients or thickeners, such as, FLORAESTERS 20 (FE-20)
available from International Flora Technologies, Ltd. of Chandler,
Ariz. FLORAESTERS 20 may be used to increase the viscosity and/or
the bulk melting/dropping point of the mimetic, to more closely
replicate the wax ester profile of human sebum, etc.
Alternatively, or in addition, the human sebum mimetics may be used
as a component in a wide range of personal care products, such as a
hair care lotions, shampoos, hair conditioners, hair gels, hair
oils, hair colors, hair relaxers, hand lotions, facial lotions, eye
creams, facial soaps, body lotions and creams, body scrubs, shaving
gels, hair removers, sanitary wipes, and the like. Because their
compositions are closely analogous to that of human sebum, the
human sebum mimetics may facilitate the natural healing and
recovery system of the human skin and accelerate cell turn-over and
topical blood circulation, thereby decreasing the appearance of
wrinkles, dark circles under eyes, and age spots. The human sebum
mimetics may also reduce irritation on the scalp through natural
healing and improve hydration of the skin. The human sebum mimetics
could also be used beyond human application and could be used on
animals and to keep fruits and vegetables fresh.
The human sebum mimetics contemplated herein are particularly
suitable as substitutes for lost human sebum due to their
stability. Oil stability is measured according to the American Oil
Chemists' Society's Official Method Cd 12b-92 at 110.degree. C. In
one embodiment, the human sebum mimetics contemplated herein have
an oil stability index greater than 50 hours at 110.degree. C. In
this regard, the mimetics are substantially resistant to oxidation
and have a shelf life that makes them desirable as, and in,
personal care products.
In accordance with an exemplary embodiment, a method for producing
a human sebum mimetic comprises mixing refined macadamia oil and
refined jojoba oil, interesterifying the refined macadamia oil and
the refined jojoba oil to produce a wax ester comprising a fatty
acid having 16 carbons and one double bond, adding a phytosterol,
and adding phytosqualene. Phytosterol can be added to the refined
macadamia oil and the refined jojoba oil before interesterification
and/or after interesterification. The resulting human sebum mimetic
can then be bleached and/or deodorized.
In one exemplary embodiment, a mixture of 53.2 grams (g) refined
macadamia oil, 30.8 g refined jojoba oil and 2.1 g phytosterol are
mixed and heated to 90.degree. C. while stirring under vacuum.
After about 0.5 hours, 0.84 g sodium methoxide is added to the
mixture and the temperature is increased to 130.degree. C. and
maintained at that temperature for about 2 to about 2.5 hours. The
mixture is then cooled to 90.degree. C., and 0.84 g citric acid is
added with stirring for 0.5 hours. The mixture is then filtered, 1
g phytosterol and 12.9 g phytosqualene is added to the filtrate,
which is mixed until homogeneity is achieved, resulting in the
mimetic. 1 wt. % bleaching earth (Clarion 470 bleaching clay
available from American Colloid Company, Arlington Heights, Ill.)
may be added to the mimetic, which is then heated to 95.degree. C.
and maintained for 15 to 30 minutes with stirring under vacuum. The
mixture is filtered. To remove odors and other volatile materials,
the mimetic may be heated to 200-220.degree. C. under high vacuum
while water vapor is injected into it. The temperature is
maintained for about 2 hours and then cooled while still under
vacuum. In a preferred embodiment, 1430 ppm tocopherol (70%) is
added and mixed into the mimetic. Any additional additives also may
be added at this time.
The following are exemplary embodiments of personal care products
comprising the human sebum mimetic produced as described above,
with each of the components set forth in % wt/wt of the personal
care product. The examples are provided for illustration purposes
only and are not meant to limit the various embodiments of the
human sebum mimetic in any way.
Example 1 is a hair conditioning lotion providing multiple
functions including moisturizing, shining, holding, and
anti-breaking functions.
EXAMPLE 1
TABLE-US-00004 Ingredient % wt./wt. Phase A Water 77.95
Polyquaternium-37 0.70 Glycerin 3.00 Sodium PCA 1.00 Panthenol 0.50
Silicone Quaternium-8 2.00 Phase B Human Sebum Mimetic 3.00 Phase C
Sorbitan Stearate (and) 2.00 Sucrose Cocoate Phase D Propanediol
8.00 Quaternium 79 Hydrolyzed 0.50 Keratin Preservative 1.00 Phase
E Fragrance 0.35 Total 100.00
The hair conditioning lotion of Example 1 is manufactured by
heating the water to 45.degree. C. with stirring and adding the
Polyquaternium 37 with medium propeller agitation. The solution is
mixed until a clear gel forms. The remaining ingredients in Phase A
are added to the gel in the order listed. The ingredients in Phase
B are added together at 45.degree. C. The mixture of the Phase B
ingredients is then added to the ingredients of Phase A with rapid
propeller agitation. The Phase A and B ingredients are heated to
60.degree. C., and the Phase C ingredient is added with medium
propeller agitation. All ingredients of Phase D are mixed at
60.degree. C. and are added to the Phase ABC mixture with medium
propeller agitation. The resulting formula is cooled quickly on an
ice-water bath. The fragrance of Phase E is then added.
Example 2 is another hair conditioning lotion providing multiple
functions including moisturizing, shining, holding, and
anti-breaking functions.
EXAMPLE 2
TABLE-US-00005 Ingredient % wt/wt Phase A Water 71.95
Polyquaternium-37 1.00 Glycerin 3.00 Sodium PCA 1.00 Panthenol 0.50
Silicone Quaternium-8 2.00 Phase B Ethyl Macadamiate (and) 2.00
Tocopherol (and) Malic Acid Human Sebum Mimetic 3.00 Isopropyl
Jojobate (and) Jojoba 1.00 Alcohol (and) Jojoba Esters
Phenyltrimethicone 1.00 Phase C Sorbitan Stearate (and) 2.00
Sucrose Cocoate Phase D Propanediol 8.00 Jojoba Oil PEG-150 Esters
1.50 Quaternium-79 Hydrolyzed 0.50 Keratin Preservative 1.00
Hydrolysed Jojoba Esters (and) 1.00 Jojoba Esters (and) Water Phase
E Fragrance 0.35 Total 100.00
The hair conditioning lotion of Example 2 is manufactured using the
same method as described above for Example 1.
Accordingly, human sebum mimetics and methods for producing them
have been provided. The human sebum mimetics are formed from
phytosqualene, phytosterols, refined jojoba oil, and a refined
botanical oil, such as macadamia oil, comprising palmitoleic acid.
Of its fatty acids, human sebum has particularly high levels of
palmitic acid (16:0), sapienic acid (16:1.DELTA.6) , and oleic acid
(C18:1.DELTA.9). Analogously, the human sebum mimetics contemplated
herein also comprise high levels of palmitic acid and oleic acid.
In one embodiment, the human sebum mimetics comprise about 1 to
about 10 wt. % palmitic acid and about 25 to about 35 wt. % oleic
acid. However, sapienic acid is unique among mammals and rarely
found in nature. The inventors have found that by interesterifying
the refined macadamia oil and the refined jojoba oil of the human
sebum mimetics, a wax ester comprising palmitoleic acid, a
substitute for sapienic acid, results. In one embodiment, the human
sebum mimetics comprise palmitoleic acid in an amount of about 5 to
about 15 wt %. of the entire mimetic composition.
While at least one exemplary embodiment has been presented in the
foregoing detailed description of the invention, it should be
appreciated that a vast number of variations exist. It should also
be appreciated that the exemplary embodiment or exemplary
embodiments are only examples, and are not intended to limit the
scope, applicability, or configuration of the invention in any way.
Rather, the foregoing detailed description will provide those
skilled in the art with a convenient road map for implementing an
exemplary embodiment of the invention. It being understood that
various changes may be made in the function and arrangement of
elements described in an exemplary embodiment without departing
from the scope of the invention as set forth in the appended
claims.
* * * * *