Cosmetic compositions containing anise extract and retinoids

Details Cosmetic compositions containing anise extract and retinoids Cosmetic compositions containing anise extract and retinoids

2000-11-15

2002-05-28

Dees, Jose' G. (Department: 1619)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C514S452000, C514S783000

Reexamination Certificate

active

06395286

ABSTRACT:

FIELD OF THE INVENTION
Cosmetic compositions containing anise extract in combination with retinoids and methods of conditioning skin by applying such compositions to the skin.
BACKGROUND OF THE INVENTION
Retinol (vitamin A) is an endogenous compound which occurs naturally in the human body and is essential for normal epithelial cell differentiation. Natural and synthetic vitamin A derivatives have been used extensively in the treatment of a variety of skin disorders and as skin repair and renewal agents. Retinoic acid has been used to treat a variety of skin conditions such as acne, wrinkles, psoriasis, age spots and skin discoloration.
Within the cells, retinol and retinoic acid are bound to specific cellular binding proteins, 2 of the major proteins are CRABP-1 and 2 (Roos et al., Pharmacological reviews: 50, 315-333, 1998). These proteins act in regulating the intracellular concentration of retinoids by acting as both storage or shuttle proteins in retinoid metabolism. The levels of this protein are regulated by the amount of retinoic acid within the cells. Higher cellular levels of retinoids increase the expression of CRABP-2. Therefore, the amount of this protein in the cells, is a measure of the retinoid activity of the cells. Skin cells contain CRABP-2 both in the epidermis and the dermis. CRABP-2 response to retinoid administration in fibroblasts in vitro is used as a reproducible measure of retinoid bioactivity that predict human skin responses (Elder et al., J. Invest. Dermatol., 106: 517-521, 1996). Therefore, CRABP-2 expression of fibroblasts is a measure of retinoid activity leading to various cosmetic skin benefits (antiaging, anti wrinkling, skin conditioning etc.).
Anise (also known as “Sweet cumin,” or by the scientific name
Pimpinella anisum
) seed oil contains several volatile fragrance components. One of the major component of anise seed oil is trans-anethole (up to 75% of the seed) (Embong M B, Hadziyev D, Molnar S., Can. J. Plant Sci, 57: 681-8, 1977). The other constituents of the oil, present in amounts of 1-5% were cis anethole, carvone, beta caryophyllene, dihydcarvyl acetate, estragole and limonene. Agricultural Research Service database on the composition of Anise also include dianethole and photoanethole as other minor components. Anethole, dianethole, photoanethole and estragole are known to have estrogenic activity. Essential oils including that from anise has been described as useful as insect repellents (Shukla H S, Upadhay P D, Tripathi S C, Pesticides, 23: 33-5, 1989); insecticides (Eli S, Uzi R et al., J. Chem. Ecol 17: 499-504, 1991; Craig M and Lichtenstein EP., J. Agric. Food Chem. 30: 563-8, 1982); convulsants (Okuyama E, Nakamura T and Mikio Y., Chem. Pharm. Bull 41: 1670-1, 1993) and as a toxic agent for snails (Maini P, Morallo-Rejesus B., Phillipp. J. Sci., 121:, 391-7, 1992).
WO9112792 describes the use of anethole for promoting hair growth, preventing or minimizing hair loss and enhancing hair color. Several U.S. patents describe the use of cyclodextrin for complexing of essential oils, including anise oil or anethole as components of fragrances, perfumes, oral hygiene compositions, skin care compositions, or laundry detergent compositions (e.g: U.S. Pat. No. 5,543,157). JP 6048934 discloses skin care compositions containing extracts of plants selected from dill, tarragon, Savi, anise, etc., in combination with skin whitening agents or in combination with at least one kind of collagen formation promoter such as retinoic acid.
The present invention is based in part on the discovery that the organic solvent extract of anise seed in combination with retinol or retinyl ester enhances CRABP-2 expression in fibroblasts.
SUMMARY OF THE INVENTION
The present invention includes a cosmetic skin care composition comprising:
(i) an organic solvent extract of anise seed in an amount of from 0.00001 to 10 wt. %,
(ii) from 0.001 to 10% of a retinol selected from the group consisting of retinol, retinyl ester, and mixtures thereof; and
(iii) a cosmetically acceptable vehicle.
The present invention also includes a method of improving or preventing the condition of wrinkled, lined, dry, flaky, aged or photodamaged skin and improving skin thickness, elasticity, flexibility, radiance, glow and plumpness, which method includes applying to the skin the inventive composition. Compositions of the invention are intended for topical application to mammalian skin which is already dry, flaky, lined, wrinkled, aged, photodamaged, or the inventive compositions may be applied prophylactically to reduce the deteriorative changes.
DETAILED DESCRIPTION OF THE INVENTION
Except in the examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and/or use are to be understood as modified by the word “about.” All amounts are by weight of the composition, unless otherwise specified.
Anise seed is suitable for use in the inventive compositions in the form of an organic extract. The anise seed extract is prepared for use in the present invention from dried anise seed, which obtained, may be for instance, from Arrowhead Mills, from health food stores or supermarkets.
The organic extracts of anise seed are prepared by extracting the dried anise seeds with a solvent by stirring 1 part of dried anise seeds with 2 to 5 parts of the solvent for from 4 to 24 hours at room temperature. Suitable solvents are described herein below. The extracts are clarified by filtration and/or centrifugation, then dried by evaporation (optionally, under vacuum) to obtain the organic extract of anise seed.
Solvents suitable for the preparation of anise seed extract for use herein include, but are not limited to: ethanol, methanol, hexane, chloroform, dichloromethane and ethyl acetate. The preferred solvents are dichloromethane, methanol, or ethanol in order to optimize activity. The extract may be further concentrated, fractioned, re-extracted or purified, e.g. by organic solvent extraction or by chromatography.
In general, the amount of the anise seed extract in the inventive compositions is in the range of from 0.0001% to 10% by weight of composition. Preferably in order to lower cost and maximize the effect the amount of the anise seed extract is in the range of from 0.01 to 10% and most preferably is in the range of from 0.1% to 5%.
The inventive compositions further comprise a retinoid selected from the group consisting of retinol or retinyl ester. The term “retinol” includes the following isomers of retinol: all-trans-retinol, 13-cis-retinol, 11-cis-retinol, 9-cis-retinol, 3,4-didehydro-retinol. Preferred isomers are all-trans-retinol, 13-cis-retinol, 3,4-didehydro-retinol, 9-cis-retinol. Most preferred is all-trans-retinol, due to its wide commercial availability.
Retinyl ester is an ester of retinol. The term “retinol” has been defined above. Retinyl esters suitable for use in the present invention are C
1
-C
30
esters of retinol, preferably C
2
-C
20
esters, and most preferably C
2
, C
3
, and C
16
esters because they are more commonly available. Examples of retinyl esters include but are not limited to: retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl hexanoate, retinyl heptanoate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecandate, retinyl laurate, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadeconoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonate, retinyl behenate, retinyl linoleate, retinyl oleate.
The preferred ester for use in the present invention is selected from retinyl palmitate, retinyl acetate and retinyl propionate, because these are the most commercially available and therefore the cheapest. Retinyl linoleate is also preferred due to its efficacy.
Retinol or retinyl ester is employed in the inventive composition in an amount of from about 0.001% to about 10%, preferably in a

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