Skin care formulations comprising phenylpropionic acid derivatives and methods of use thereof

Abstract

There is provided a skin care composition comprising: an emollient; a tackifier; an emulsifier; a wetting agent; and a compound having retinol-like activity. Also provided are methods of treating skin comprising topically applying the skin care composition to the skin. Also provided is a skin care composition comprising: a) a polydimethylsiloxane; b) a tackifier selected from the group consisting of: a polyacrylate cross-linked polymer-6, a polyacrylate 13, sorbitan stearate, and combinations thereof; c) an emulsifier selected from the group consisting of sorbitan olivate, cetyl olivate, and combinations thereof; d) glycerol; and e) a polar plant extract of acronychia pedunculata.

Description

Technical Field

[0001] The present invention generally relates to compositions suitable for use on the skin, and in particular to compositions that activate the retinoic acid pathway. Background Art

[0002] Human skin undergoes certain aging processes, which are partly attributable to intrinsic processes (e.g., chronological aging) and partly to extrinsic factors (e.g., photoaging). In addition, the skin may undergo transient or even persistent changes such as acne, oily or dry skin, keratosis, rosacea, photosensitivity, inflammation, erythema nodosum, and allergic or autoimmune reactions, such as dermatoses and photodermatoses.

[0003] Consequences of the aforementioned aging process may include thinning of the skin, weakening of the interweaving of the epidermis and dermis, and a decrease in the number of cells and blood vessels supplying the skin. These consequences are generally undesirable, and individuals suffering from these problems will seek topical treatments to address them.

[0004] Retinoids have been used to treat skin conditions caused by intrinsic aging, external factors, acne, or skin diseases. However, while retinoid treatment has beneficial effects, their benefits are limited by the fact that retinoids can cause skin irritation. These side effects can limit the use of retinoids, particularly for individuals with sensitive skin.

[0005] To date, the search for alternative compounds to retinoids, and particularly for individuals with sensitive skin, has had limited success in treating skin conditions associated with aging (such as skin atrophy, acne, photoaging) and in reducing the appearance of wrinkles, fine lines, stretch marks or cellulite.

[0006] Therefore, there is a need for alternatives to traditional retinoids that are effective yet mild enough for use in individuals with sensitive skin, and formulations for delivering these alternatives. Summary of the Invention

[0007] Therefore, one aspect of the present invention relates to a skin care composition comprising:

[0008] a. Emollients;

[0009] b. tackifier;

[0010] c. Emulsifier;

[0011] d. Wetting agent; and

[0012] e. Compounds of formula I:

[0013]

[0014] in:

[0015] R1 is selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl and C3-C8 cycloalkyl or aryl;

[0016] R2 is selected from the group consisting of hydrogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl or aryl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl or aryl, thiol, -SC1-C6 alkyl, -SC2-C6 alkenyl, -SC2-C6 alkynyl, -SC3-C8 cycloalkyl or aryl, -NR4C1-C6 alkyl, -NR4C2-C6 alkenyl, -NR4C2-C6 alkynyl and -NR4C3-C8 cycloalkyl or aryl;

[0017] R3 is selected from the group consisting of: -CO2H, -CO2R4 or an isosteric equivalent of a carboxyl group, wherein R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl or aryl; and Y is -(CH2-CH2)-, -(CH=CH)- or -(C ＝ C)-;

[0018] or a cosmetically acceptable salt thereof.

[0019] In one or more embodiments, R1 is selected from the group consisting of: C5-C 16 Alkyl, C5-C 16 Alkenyl and C5-C 16 alkynyl; R2 is selected from the group consisting of: hydrogen, hydroxyl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4, wherein R4 is a C1-C6 alkyl, or an isosteric equivalent of a carboxyl group; and Y is -(CH2-CH2)- or -(CH=CH)-. In some embodiments, R1 is selected from the group consisting of: C5-C 16alkenyl; and R2 is selected from the group consisting of: hydrogen or -OC1-C3 alkyl. In one or more embodiments, the compound of Formula I is selected from the group consisting of: 3-(4-farnesyloxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-hydroxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-methoxyphenyl)-propionic acid, their ethyl esters, and combinations of two or more thereof. In some embodiments, the compound of Formula I comprises 3-(4-farnesyloxyphenyl)-propionic acid. In one or more embodiments, the concentration of the compound of Formula I is present in an amount ranging from about 0.0001% to about 1% by weight of the total weight of the composition. In some embodiments, the skin care composition comprises a plant extract containing a compound of Formula I. In one or more embodiments, the plant extract includes an extract of a plant of the genus Acronychia. In some embodiments, the plant extract is an extract of Acronychia acidula. In one or more embodiments, the plant extract is a polar extract. In some embodiments, the plant extract is present in an amount ranging from about 0.01% to about 5% by weight of the total weight of the composition. In one or more embodiments, the extract of Citrus aurantium contains 3-(4-farnesyloxyphenyl)-propionic acid in a concentration ranging from about 0.01% to about 0.5% by weight of the total weight of the composition. In some embodiments, the emollient is a silicone or a silicone-based emollient. In one or more embodiments, the emollient is selected from the group consisting of dimethicone, dimethicone crosspolymer, phenyl trimethicone, cetyl trimethicone, amino-terminated dimethicone, caprylyl methicone, and combinations thereof. In some embodiments, the emollient is present in a concentration of from about 0.1% to about 1.5% by weight. In one or more embodiments, the tackifier is a rheology modifier that provides yield stress to the composition and has compatibility at a pH of less than about 5. In some embodiments, the viscosity increasing agent is selected from the group consisting of polyacrylate crosspolymer-6, polyacrylate-13, sorbitan stearate, polyacrylamide, C13-14 isoparaffin, laureth-7, ammonium acryloyldimethyltaurate / VP copolymer, carbomer, and combinations thereof. In one or more embodiments, the viscosity increasing agent is present at a concentration of about 0.1% to about 5% by weight. In some embodiments, the emulsifier comprises a liquid crystal emulsifier. In one or more embodiments, the emulsifier is selected from the group consisting of sorbitan olivate, cetyl olivate, C12-20 alkyl glucoside, C14-22 alcohol, sorbitan stearate, sorbitan laurate, polyglyceryl-6 pentaoleate, and combinations thereof. In some embodiments, the emulsifier is present at a concentration of about 0.1% to about 5% by weight.In one or more embodiments, the humectant comprises a polar humectant. In some embodiments, the humectant is selected from the group consisting of glycerol, sorbitol, xylitol, hyaluronic acid, lactic acid, and combinations thereof. In one or more embodiments, the humectant is present in a concentration of about 0.5% by weight to about 1.5% by weight.

[0020] Another aspect of the present invention is directed to a method of treating skin comprising topically applying to the skin any one of the skin care compositions described herein.

[0021] In some embodiments, the method comprises increasing CRABP2 expression in skin cells.

[0022] Another aspect of the present invention relates to a skin care composition comprising:

[0023] a. Polydimethylsiloxane;

[0024] b. a viscosity increasing agent selected from the group consisting of: polyacrylate crosspolymer-6, polyacrylate-1 3, sorbitan stearate, and combinations thereof;

[0025] c. an emulsifier selected from the group consisting of sorbitan olivate, cetyl olivate, and combinations thereof;

[0026] d. glycerol; and

[0027] e. Polar plant extract of Citrus aurantium. DETAILED DESCRIPTION

[0028] It is believed that one skilled in the art can, based on the description herein, utilize the present invention to its fullest extent.The following specific embodiments are to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.

[0029] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention belongs. In addition, all publications, patent applications, patents and other references mentioned herein are incorporated by reference.

[0030] Unless otherwise indicated, percentages used to express the amount of an ingredient are weight percentages (referred to as "weight %", "wt %", "% by weight", or "% (W / W)"). Similarly, weight ratios used to express the relative proportions of ingredients are also determined using weight percentages (i.e., the weight ratio is calculated by dividing the weight percentage of one ingredient by the weight percentage of another ingredient). Unless otherwise indicated, all ranges are inclusive, e.g., "4 to 9" includes the values 4 and 9.

[0031] As used herein, a composition that is "substantially free" of an ingredient refers to a composition having about 2% or less of that ingredient by weight (based on the total weight of the composition). Preferably, a composition that is substantially free of an ingredient has about 1% or less, more preferably about 0.5% or less, more preferably about 0.1% or less, more preferably about 0.05% or less, and more preferably about 0.01% or less of that ingredient by weight (based on the total weight of the composition). In certain more preferred embodiments, a composition that is substantially free of an ingredient is free of that ingredient, that is, the composition is completely free of that ingredient.

[0032] As used herein, "cosmetically / dermatologically acceptable" means that the ingredients such term describes are suitable for use in contact with tissue (e.g., skin or hair) without undue toxicity, incompatibility, instability, irritation, allergic response, etc. As will be appreciated by those skilled in the art, cosmetically / dermatologically acceptable salts are either acidic / anionic or basic / cationic salts.

[0033] As used herein, the term "safe and effective amount" refers to an amount of an extract or composition that is sufficient to produce the desired effect but insufficient to avoid serious side effects. The safe and effective amount of a compound, extract, or composition will vary depending on factors such as the age, health, and environmental exposures of the end user, the duration and nature of the treatment, the specific extract, ingredient, or composition employed, and the specific pharmaceutically acceptable carrier employed.

[0034] As used herein, the term "about" means within 5 weight percent, within 4 weight percent, within 3 weight percent, within 2.5 weight percent, within 2 weight percent, or within 1 weight percent of the disclosed value.

[0035] In general, IUPAC nomenclature is used herein and the following terms are defined.

[0036] The term "substituted" refers to one or more hydrogen atoms on the core molecule that have been replaced by a substituent group in the amount permitted by the available valence. Substitution is not limited to the core molecule but can also be carried out on a substituent group such that the group becomes a linking group.

[0037] The term "independently selected" refers to two or more substituents that can be selected from a variable group of substituents, wherein the selected substituents may be the same or different.

[0038] The term "dependently selected" refers to one or more substituent variables being designated for substitution in the core molecule in the indicated combination (eg, variables relating to groups of substituents appearing in a tabular listing of a compound).

[0039] Acceptable salts derived from inorganic bases include, for example, sodium or potassium salts, etc. Acceptable salts derived from organic bases include, for example, salts formed with primary, secondary, tertiary amines, etc.

[0040] One aspect of the present invention relates to a skin care composition comprising:

[0041] (a) Emollients;

[0042] (b) a tackifier;

[0043] (c) emulsifiers;

[0044] (d) wetting agents; and

[0045] (e) Compounds of formula I:

[0046]

[0047] in:

[0048] R1 is selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl and C3-C8 cycloalkyl or aryl;

[0049] R2 is selected from the group consisting of hydrogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl or aryl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl or aryl, thiol, -SC1-C6 alkyl, -SC2-C6 alkenyl, -SC2-C6 alkynyl, -SC3-C8 cycloalkyl or aryl, -NR4C1-C6 alkyl, -NR4C2-C6 alkenyl, -NR4C2-C6 alkynyl and -NR4C3-C8 cycloalkyl or aryl;

[0050] R3 is selected from the group consisting of: -CO2H, -CO2R4 or an isosteric equivalent of a carboxyl group, wherein R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl or aryl; and Y is -(CH2-CH2)-, -(CH=CH)- or -(C ＝ C)-;

[0051] or a cosmetically acceptable salt thereof.

[0052] Surprisingly, the compositions described herein have been found to activate various biomarkers associated with retinoids, which are known for their anti-acne, anti-aging, and skin barrier properties. Additionally, the formulation ingredients as a whole can enhance the delivery of retinol-like compounds.

[0053] Emollients

[0054] As used herein, "emollient" refers to a compound that helps maintain the soft, smooth, and pliable appearance of the skin (e.g., by remaining on the surface of the skin or in the stratum corneum to act as a lubricant). Examples of emollients include those found in "Handbook of Cosmetic Science and Technology" (edited by A. Barel, M. Paye, and H. Maibach, published in 2001 by Marcel Dekker, Inc., New York), Chapter 35, pages 399 to 415 (G Zocchi's Skin Feel Agents), and include, but are not limited to, esters (e.g., isopropyl palmitate), petrolatum, hexyldecyl stearate, and plant, nut, and vegetable oils and butters, such as avocado (Butyrospermum parkii / shea) butter, candelilla (Euphorbia cerifera / candelilla) wax; hydrogenated vegetable oils, macadamia nut oil, rice bran oil, grapeseed oil, palm oil, evening primrose oil, hydrogenated peanut oil, and avocado oil.

[0055] In one or more embodiments, the emollient comprises silicone or a silicone-based emollient (i.e., a compound containing silicone units). In further embodiments, the emollient is selected from the group consisting of dimethicone, dimethicone crosspolymer, phenyl trimethicone, cetyl trimethicone, amodimethicone, caprylyl methicone, and combinations thereof.

[0056] The emollient may be present in an amount of from about 0.5% to about 15%, from about 1% to about 10%, from about 1% to about 8%, from about 1% to about 6%, from about 1% to about 5%, from about 1% to about 4%, from about 1% to about 3%, or from about 1.5% to about 3.5%, by weight of the total composition. In one or more embodiments, the emollient comprises dimethicone and by It is present in an amount from about 0.5% to about 15%, from about 1% to about 10%, from about 1% to about 8%, from about 1% to about 6%, from about 1% to about 5%, from about 1% to about 4%, from about 1% to about 3%, or from about 1.5% to about 3.5% by weight of the total composition.

[0057] Tackifier

[0058] As used herein, "viscosifier" (also known as thickener) refers to a compound used as a rheology modifier that provides yield stress to the composition. Examples of such thickeners include: carbomers (e.g., CARBOPOL ULTREZ 30 polymer), cetyl alcohol, electrolytes (e.g., sodium chloride, ammonium chloride, magnesium chloride); polysaccharides of natural origin (e.g., xanthan gum, dehydroxanthan gum, guar gum, cassia gum, carrageenan, alginic acid and alginate gums (algin, calcium alginate, etc.), gellan gum, pectin, microcrystalline cellulose); derivatives of natural polysaccharides (e.g., hydroxyethyl cellulose, ethyl hydroxyethyl cellulose, cetyl hydroxyethyl cellulose, methyl cellulose, hydroxypropyl cellulose, sodium carboxymethyl cellulose, hydroxypropyl methyl cellulose, hydroxypropyl guar gum, carboxymethyl hydroxypropyl guar gum, C1 8-22 hydroxyalkyl hydroxypropyl guar gum); alkali swellable emulsion (ASE) polymers (e.g., acrylate copolymers, available under the trade name AQUA SF-1 is commercially available from Noveon Consumer Specialties, Inc., Brecksville, Ohio, USA, and acrylate copolymers are available under the trade name Aculyn TM 33 is commercially available from Dow Personal Care, Springhouse, PA, USA; hydrophobically modified alkali-swellable emulsion (HASE) polymers (e.g., acrylates / steareth-20 methacrylate copolymer, acrylates / steareth-20 methacrylate crosspolymer, and acrylates / ceteth-20 itaconate copolymer); hydrophobically modified acid-swellable emulsion polymers (e.g., acrylates / aminoacrylates / C10-30 alkyl PEG-20 itaconate copolymer and polyacrylate-1 crosspolymer); hydrophobically modified acrylate crosspolymers, such as those available under the trade name 1382 Acrylates C10-30 Alkyl Acrylate Crosspolymer, commercially available from The Lubrizol Corporation of Brecksville, Ohio, U.S.A.; sodium polyacrylate (commercially available as COSMEDIA SP), and a hydrophobic non-ethoxylated micellar thickener such as glyceryl oleate, cocamide MIPA, lauryl lactate, or sorbitan sesquioctanoate.

[0059] In one or more embodiments, the viscosity increasing agent is compatible at a pH of less than about 5. In one or more embodiments, the viscosity increasing agent is selected from the group consisting of: polyacrylate crosspolymer-6, polyacrylate-13, sorbitan stearate, polyacrylamide, C13-14 isoparaffin, laureth-7, ammonium acryloyldimethyltaurate / VP copolymer, carbomer, and combinations thereof. Suitable viscosity increasing agents are available under the trade names: Sepigel 305 (INCI name: polyacrylamide and C13-14 isoparaffin and laureth-7), Aristoflex AVC (INCI name: ammonium acryloyldimethyltaurate / VP copolymer), and CARBOPOL Ultrez 30 (INCI name: carbomer).

[0060] The tackifier can be present in an amount of about 0.1% to about 5%, about 0.2% to about 4.5%, about 0.3% to about 4%, about 0.5% to about 3.5%, about 0.5% to about 3%, about 1% to about 3%, about 1.5% to about 3%, or about 2% to about 2.5% by weight of the total composition. In one or more embodiments, the tackifier is selected from the group consisting of polyacrylate-13, polyisobutylene, polysorbate 20, polyacrylate crosspolymer-6, and combinations thereof, and is present in an amount of about 0.1% to about 5%, about 0.2% to about 4.5%, about 0.3% to about 4%, about 0.5% to about 3.5%, about 0.5% to about 3%, about 1% to about 3%, about 1.5% to about 3%, or about 2% to about 2.5% by weight of the total composition.

[0061] emulsifiers

[0062] As used herein, "emulsifier" (also known as surfactant) refers to a compound that acts to help form and / or stabilize an emulsion. Surfactants / emulsifiers can include anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants. Suitable emulsifiers include those derived from olives, such as olive oil esters. For example, one suitable emulsifier includes Olivem 1000 (sold by Hallstar), which is a combination of cetyl olive oil ester and sorbitan olive oil ester. Examples of suitable nonionic surfactants include, but are not limited to, fatty alcohol acid or amide ethoxylates, monoglyceride ethoxylates, sorbitan ester ethoxylates, alkyl polyglycosides, and mixtures thereof. One suitable nonionic surfactant is a polyoxyethylene derivative of a polyol ester, wherein the polyoxyethylene derivative of the polyol ester (1) is derived from (a) a fatty acid containing from about 8 to about 22, and preferably from about 10 to about 14, carbon atoms, and (b) a polyol selected from the group consisting of sorbitol, sorbitan, glucose, α-methyl glucoside, polyglucose having an average of from about 1 to about 3 glucose residues per molecule, glycerol, pentaerythritol, and mixtures thereof; (2) contains an average of from about 10 to about 120, and preferably from about 20 to about 80, oxyethylene units; and (3) has an average of from about 1 to about 3 fatty acid residues per mole of the polyoxyethylene derivative of the polyol ester.

[0063] Examples of polyoxyethylene derivatives of polyol esters include, but are not limited to, PEG-80, sorbitan laurate, and polysorbate 20. PEG-80 sorbitan laurate (sorbitan laurate monoester ethoxylated with an average of about 80 moles of ethylene oxide) is commercially available from ICI Surfactants of Wilmington, Del., under the trade designation "Atlas G-4280." Polysorbate 20 (the laurate monoester of a mixture of sorbitol and sorbitan anhydride condensed with approximately 20 moles of ethylene oxide) is commercially available from ICI Surfactants of Wilmington, Del., under the trade designation "Tween 20."

[0064] Another class of nonionic surfactants includes long chain alkyl glucosides or polyglucosides, which are condensation products of (a) a long chain alcohol containing from about 6 to about 22, and preferably from about 8 to about 14, carbon atoms and (b) glucose or a glucose-containing polymer. The alkyl glucosides have from about 1 to about 6 glucose residues per molecule of the alkyl glucoside. A preferred glucoside is decyl glucoside, which is a condensation product of decanol and a glucose polymer and is commercially available under the trade name "Plantaren 2000" from Henkel Corporation of Hoboken, NJ.

[0065] Examples of amphoteric surfactants suitable for use in the present invention include, but are not limited to, amphoteric carboxylates, such as alkyl amphoacetates (mono or di); alkyl betaines; alkylamidoalkyl betaines; alkylamidoalkyl sulfobetaines; alkyl amphophosphates; phosphoimidazolines, such as phosphobetaines and pyrophosphobetaines; carboxyalkylalkylpolyamines; alkyliminodipropionates; alkyl amphoglycinates (mono or di); alkyl amphopropionates (mono or di); N-alkyl β-aminopropionic acids; alkyl polyaminocarboxylates; and mixtures thereof. As used herein, the term "ampholytic" refers to: 1) molecules that contain both acidic and basic sites, such as, for example, amino acids that contain both amino (basic) and acid (e.g., carboxylic acid, acidic) functional groups; or 2) zwitterionic molecules that possess both positive and negative charges within the same molecule. The latter charge may be dependent on or independent of the pH of the composition. The amphoteric surfactants disclosed herein do not contain counterions. Those skilled in the art will readily recognize that, at the pH conditions of the compositions of the present invention, amphoteric surfactants are electrically neutral due to having balanced positive and negative charges, or they have counterions such as alkali metal counterions, alkaline earth counterions, or ammonium counterions.

[0066] Cationic surfactants include alkyl quaternary ammonium salts (monoalkyl, dialkyl or trialkyl), benzyl quaternary ammonium salts, ester quaternary ammonium salts, ethoxylated quaternary ammonium salts, alkylamines and mixtures thereof, wherein the alkyl group has from about 6 carbon atoms to about 30 carbon atoms, preferably from about 8 to 22 carbon atoms. These cationic surfactants can be used in the composition of the present invention in an amount of from about 0.01% to about 18%, or from about 0.05% to about 15%, or from about 0.1% to about 10%, based on the total weight of the composition.

[0067] In one or more embodiments, the emulsifier comprises a liquid crystal emulsifier. In one or more embodiments, the emulsifier is selected from the group consisting of sorbitan olivate, cetyl olivate, C12-20 alkyl glucoside, C14-22 alcohol, sorbitan stearate, sorbitan laurate, polyglyceryl-6 pentaoleate, and combinations thereof. Suitable emulsifiers are available under the trade names Montanov L (INCI name C12-20 alkyl glucoside, C14-22 alcohol), Arlacel LC (INCI name Sorbitan stearate (and) sorbitan laurate), and WO (INCI name: Polyglyceryl-6 Pentaoleate).

[0068] The emulsifier can be present in an amount of about 0.1% to about 5%, about 0.1% to about 4.5%, about 0.1% to about 4%, about 0.2% to about 3.5%, about 0.2% to about 3%, about 0.2% to about 2%, about 0.5% to about 1.7%, or about 0.5% to about 1.5% by weight of the total composition. In one or more embodiments, the emulsifier is selected from the group consisting of sorbitan olivate, cetyl olivate, and combinations thereof, and is present in an amount of about 0.1% to about 5%, about 0.1% to about 4.5%, about 0.1% to about 4%, about 0.2% to about 3.5%, about 0.2% to about 3%, about 0.2% to about 2%, about 0.5% to about 1.7%, or about 0.5% to about 1.5% by weight of the total composition.

[0069] Wetting agent

[0070] As used herein, "humectant" refers to a compound that increases the water content of the top layer of the skin (e.g., a hygroscopic compound). Examples of suitable humectants include those found in "Handbook of Cosmetic Science and Technology" (edited by A. Barel, M. Paye, and H. Maibach, published by Marcel Dekker, Inc., New York, 2001), Chapter 35, pages 399 to 415 (Skin Feel Agents by G. Zocchi), and include, but are not limited to, glycerol, sorbitol, or trehalose (e.g., α, α-trehalose, β, β-trehalose, α, β-trehalose) or salts or esters thereof (e.g., trehalose 6-phosphate).

[0071] Any of a variety of commercially available humectants is suitable for use in the present invention. A humectant is a compound intended to increase the water content of the top layer of the skin (e.g., a hygroscopic compound). Examples of suitable humectants include those found in "Handbook of Cosmetic Science and Technology" (edited by A. Barel, M. Paye, and H. Maibach, published by Marcel Dekker, Inc., New York, 2001), Chapter 35, pages 399 to 415 (Skin Feel Agents by G. Zocchi), and include, but are not limited to, glycerol, sorbitol, or trehalose (e.g., α, α-trehalose, β, β-trehalose, α, β-trehalose) or salts or esters thereof (e.g., trehalose 6-phosphate).

[0072] In further embodiments, the humectant comprises a polar humectant.In further embodiments, the humectant is selected from the group consisting of glycerin, sorbitol, xylitol, hyaluronic acid, lactic acid, and combinations thereof.

[0073] The humectant can be present in an amount from about 0.5% to about 15%, from about 0.5% to about 14%, from about 0.8% to about 13%, from about 1% to about 12%, from about 2% to about 12%, from about 2% to about 10%, from about 2.5% to about 8.5%, from about 3% to about 8%, from about 2.5% to about 3.5%, or from 7.5% to about 8.5%, by weight of the total composition. In one or more embodiments, the humectant comprises glycerin and is present in an amount from about 0.5% to about 15%, from about 0.5% to about 14%, from about 0.8% to about 13%, from about 1% to about 12%, from about 2% to about 12%, from about 2% to about 10%, from about 2.5% to about 8.5%, from about 3% to about 8%, from about 2.5% to about 3.5%, or from 7.5% to about 8.5%, by weight of the total composition.

[0074] Compounds of formula I

[0075] As mentioned above, the compound of Formula I is represented by the following structure:

[0076]

[0077] in:

[0078] R1 is selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl and C3-C8 cycloalkyl or aryl;

[0079] R2 is selected from the group consisting of hydrogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl or aryl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl or aryl, thiol, -SC1-C6 alkyl, -SC2-C6 alkenyl, -SC2-C6 alkynyl, -SC3-C8 cycloalkyl or aryl, -NR4C1-C6 alkyl, -NR4C2-C6 alkenyl, -NR4C2-C6 alkynyl and -NR4C3-C8 cycloalkyl or aryl;

[0080] R3 is selected from the group consisting of: -CO2H, -CO2R4 or an isosteric equivalent of a carboxyl group, wherein R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl or aryl; and Y is -(CH2-CH2)-, -(CH=CH)- or -(C ＝ C)-;

[0081] or a cosmetically acceptable salt thereof.

[0082] In one or more embodiments, R1 is selected from the group consisting of: C5-C 16 Alkyl, C5-C 16 Alkenyl and C5-C 16 alkynyl; R2 is selected from the group consisting of hydrogen, hydroxyl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4, wherein R4 is a C1-C6 alkyl, or an isosteric equivalent of a carboxyl group; and Y is -(CH2-CH2)- or -(CH=CH)- (or a cosmetically acceptable salt thereof). In some embodiments, R1 is selected from the group consisting of: C5-C 16 and R2 is selected from the group consisting of hydrogen or -OC1-C3 alkyl. In one or more embodiments, the compound of Formula I is selected from the group consisting of 3-(4-farnesyloxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-hydroxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-methoxyphenyl)-propionic acid, their ethyl esters, and combinations of two or more thereof. In one or more embodiments, the compound of Formula I is 3-(4-farnesyloxyphenyl)-propionic acid and / or its ethyl ester. In a preferred embodiment, the compound of Formula I comprises 3-(4-farnesyloxyphenyl)-propionic acid. 3-(4-farnesyloxyphenyl)-propionic acid and / or its ethyl ester can be synthesized using conventional organic synthesis processes.

[0083] The compound of Formula I can be present in an amount ranging from about 0.00001% to 10%, or about 0.0001% to about 10%, or about 0.001% to about 5%, or about 0.001% to about 1%, or about 0.01% to about 3%, about 0.01% to about 1%, about 0.01% to about 0.5%, or about 0.005% to about 1.5%, or about 0.005% to about 0.06%, or about 0.009% to about 0.06%, or about 0.009% to about 0.03%, based on the total weight of the composition.

[0084] The compounds according to formula I may also be obtained from natural sources. For example, the compounds according to formula I may be present in plant extracts. Thus, the composition may comprise a plant extract containing a compound of formula I.

[0085] In one or more embodiments, the plant extract is an extract of a plant of the genus Citrus. In another embodiment, the plant extract is an extract of Citrus aurantium (also known as lemon aspen). In one or more embodiments, at least one compound of Formula I described above is present in the Citrus aurantium extract at a concentration equal to or greater than about 0.01% to about 30%, or about 0.1% to about 30%, or about 0.1% to about 20%, or about 1% to about 20%, or about 1% to about 10%, or about 1.5% to about 9%, or about 3% to about 9%, based on the weight of the Citrus aurantium extract. In another embodiment, the Citrus aurantium extract comprises 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 1% to about 10%, based on the total weight of the extract.

[0086] Suitable extracts can be obtained using conventional methods including, but not limited to, direct extraction of the material from the biomass by grinding, maceration, pressing, squeezing, mashing, centrifugation, and / or processes such as cold percolation, stirring / distillation, microwave-assisted extraction, supercritical / subcritical CO2 compressed gas extraction with or without polar modifiers, pressurized solvent extraction, accelerated solvent extraction, pressurized or normal hot water extraction, surfactant-assisted pressurized hot water extraction, oil extraction, membrane extraction, Soxhlet extraction, Gold Finger distillation / extraction, and / or the processes disclosed in, for example, U.S. Patent Nos. 7,442,391, 7,473,435, and 7,537,791 to Integrated Botanical Technologies, LLC (each incorporated herein by reference), or by other methods such as solvent extraction.

[0087] Any of a variety of solvents including polar solvents, non-polar solvents, or a combination of two or more thereof can be used in methods including solvent extraction. Suitable polar solvents include polar inorganic solvents such as water, polar organic solvents such as alcohols and corresponding organic acids, for example, C1-C8 alcohols including methanol, ethanol, propanol, butanol, organic acids including acetic acid, formic acid, propionic acid, polyols and glycols including C1-C8 polyols / glycols, and combinations of two or more thereof. Suitable non-polar solvents include non-polar organic solvents such as alkanes (including C1-C8 alkanes), cycloalkanes (including C1-C8 alkanes), alkyl ethers (including C1-C8 alkyl ethers), petroleum ether, ketones (including C1-C8 ketones), dichloromethane, ethyl acetate, xylene, toluene, chloroform, vegetable oils, mineral oils, and the like. In another embodiment, extraction can be obtained by non-polar solvent or supercritical fluid extraction as described above with or without polar modifiers such as C1-C8 alcohols, water, C1-C8 polyols / diols, or C1-C8 organic acids.

[0088] In one or more embodiments, the extract comprises an extract of Citrus aurantium. In some embodiments, the extract of the present invention comprises a combination of polar and non-polar extracts of Citrus aurantium fruit. In another embodiment, the extract of the present invention comprises an alcoholic or glycolic acid extract of Citrus aurantium fruit.

[0089] In one or more embodiments, the extract is a polar extract. In another embodiment, the extract is a polar extract prepared using a polar solvent comprising water, a C1-C8 alcohol, a C1-C8 polyol, or a C1-C8 diol, or a combination of two or more thereof. In certain embodiments, the extract is extracted using one or more C1-C4 alcohols, C1-C4 polyols, and / or C1-C4 diols. In one or more embodiments, the extract is prepared using a solvent comprising methanol, ethanol, or a combination thereof, with or without water. In another embodiment, the extract is a polar extract extracted from the fruit of the citrus aurantium using a combination of alcohol and water.

[0090] In one or more embodiments, the extract is a non-polar extract prepared using a non-polar solvent comprising one or more C1-C8 alkanes, C1-C8 cycloalkanes, C1-C8 alkyl ethers, C1-C8 alkyl esters, and / or chloroform, more preferably one or more C1-C8 alkanes, C1-C8 alkyl esters, and / or chloroform. In other embodiments, the extract is a non-polar extract prepared using hexane, ethyl acetate, chloroform, or a mixture of two or more thereof. In yet other embodiments, the extract is a non-polar extract prepared using ethyl acetate.

[0091] For example, an extract using the fruit of Citrus aurantium can be prepared by homogenizing the fruit in a blender with an amount of denatured alcohol equal to the amount of fruit for 30 seconds. The pulp is then mixed and stirred at ambient temperature (22°C to 26°C) for an additional 24 hours. Additional denatured alcohol may be added as needed to keep the pulp well coated in the alcohol. The mixture is then gravity filtered, and the resulting filter cake is washed with additional amounts of denatured alcohol. The total filtrate can then be dried under reduced pressure to remove the alcohol. The residue can then be freeze-dried to obtain a dry substance free of extraction solvent and water. The extraction can be repeated several times on the filter cake, with a regular extract yield of 5% to 7% being obtained from each extraction.

[0092] Another example of preparing an extract of the fruit of Citrus amygdalus is as follows: 500 g of freeze-dried Citrus amygdalus fruit are cut into approximately 5 mm cubes and soaked with 5 L of ethanol at a ratio of 1:10 (raw material to solvent) and stirred at room temperature for 12 hours. The suspension can then be filtered, and the resulting filtrate can be concentrated under low pressure to obtain a concentrate. The concentrate can then be further dried by freeze drying to obtain 325 g of a residual material called a crude extract (65% yield). A 200 g sample of the crude extract is then dissolved in 1 L of ethanol and stirred at room temperature overnight. The mixture can then be filtered and dried under reduced pressure and low temperature to provide an extract.

[0093] Extract can exist with the amount of about 0.00001 % by weight, 0.0001 % by weight, 0.001 % by weight, 0.01 % by weight, 0.1 % by weight, 0.2 % by weight, 0.3 % by weight, 0.4 % by weight, 0.5 % by weight, 0.75 % by weight, 1 % by weight, 1.5 % by weight or 2 % by weight to about 0.00005 % by weight, 0.0005 % by weight, 0.005 % by weight, 0.05 % by weight, 0.5 % by weight, 1 % by weight, 1.5 % by weight, 2 % by weight, 2.5 % by weight, 3 % by weight, 4 % by weight or 5 % by weight of the gross weight of said composition. In one or more embodiments, this extract exists with the amount of about 0.01 % by weight to about 5 % by weight of the gross weight of said composition. In other embodiments, this extract exists with the amount of about 0.01 % by weight to about 3 % by weight of the gross weight of said composition. In one or more embodiments, the extract is present in an amount of about 0.1% to about 3% by weight based on the total weight of the composition. In further embodiments, the extract is present in an amount of about 0.2% to about 2.5% by weight based on the total weight of the composition. In one or more embodiments, the extract is present in an amount of about 0.5% to about 2% by weight based on the total weight of the composition. In further embodiments, the extract is present in an amount of about 0.5% to about 1.5% by weight based on the total weight of the composition.

[0094] The above embodiments can be combined in any suitable combination. For example, in one exemplary embodiment, the skin care composition comprises

[0095] a. Polydimethylsiloxane;

[0096] b. a viscosity increasing agent selected from the group consisting of: polyacrylate crosspolymer-6, polyacrylate-1 3, sorbitan stearate, and combinations thereof;

[0097] c. an emulsifier selected from the group consisting of sorbitan olivate, cetyl olivate, and combinations thereof;

[0098] d. glycerol; and

[0099] e. Polar plant extract of Citrus aurantium.

[0100] Other ingredients

[0101] Any suitable carrier may be used in the compositions of the present invention. Preferably, for skin care compositions, the carrier is a cosmetically acceptable carrier. As will be appreciated by those skilled in the art, cosmetically acceptable carriers include carriers suitable for use in contact with the body, particularly the skin, for anti-aging applications without causing undue toxicity, incompatibility, instability, irritation, allergic reactions, and the like. A safe and effective amount of carrier comprises from about 50% to about 99.999%, preferably from about 80% to about 99.9%, more preferably from about 99.9% to about 95%, and most preferably from about 99.8% to about 98%, of the composition. The carrier may be present in a wide variety of forms. For example, emulsion carriers including, but not limited to, oil-in-water, water-in-oil, water-in-oil-in-water, and silicone oil-in-water emulsions may be used herein. These emulsions may encompass a range of viscosities, for example, from about 100 centipoise to about 200,000 centipoise. Examples of suitable cosmetically acceptable carriers include cosmetically acceptable solvents and materials suitable for cosmetic solutions, suspensions, lotions, creams, serums, essences, gels, toners, sticks, sprays, ointments, washes and bars, shampoos, hair conditioners, pastes, foams, mousses, powders, shaving creams, wipes, patches, strips, super patches, microneedle patches, bandages, hydrogels, film-forming products, facial and skin masks, foundations, drops, etc. These product types may contain several types of cosmetically acceptable carriers, including but not limited to solutions, suspensions, emulsions such as microemulsions and nanoemulsions, gels, solids, liposomes, other encapsulation technologies, etc. In one or more embodiments, the composition is in the form of a solution, suspension, emulsion, lotion, cream, slurry, gel, stick, spray, ointment, liquid wash, bar, shampoo, conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product. In one or more embodiments, the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid wash, soap bar, shampoo, conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.

[0102] The following are non-limiting examples of such carriers. Other carriers can be formulated by one of ordinary skill in the art. In one embodiment, the carrier comprises water. In another embodiment, the carrier may further comprise one or more aqueous solvents or organic solvents. Examples of organic solvents include, but are not limited to, dimethyl isosorbide; isopropyl myristate; surfactants of cationic, anionic, and nonionic nature; vegetable oils; mineral oils; waxes; gums; synthetic and natural gelling agents; alkanols; glycols; and polyols. Examples of glycols include, but are not limited to, glycerol, propylene glycol, butylene glycol, pentanediol, hexylene glycol, polyethylene glycol, polypropylene glycol, diethylene glycol, triethylene glycol, octanediol, glycerol, butylene glycol, and hexanetriol, and copolymers or mixtures thereof. Examples of alkanols include, but are not limited to, alkanols having from about 2 carbon atoms to about 12 carbon atoms (e.g., from about 2 carbon atoms to about 4 carbon atoms), such as isopropyl alcohol and ethanol. The example of polyol includes but is not limited to polyols having about 2 carbon atoms to about 15 carbon atoms (for example, about 2 carbon atoms to about 10 carbon atoms), such as propylene glycol. Based on the gross weight of the carrier, the organic solvent can be present in the carrier in an amount of about 1% to about 99.99% (for example, about 20% to about 50%). Based on the gross weight of the carrier, water can be present in the carrier (before use) in an amount of about 5% to about 95% (for example, about 50% to about 90%). The solution can include any suitable amount of solvent, including about 40% to about 99.99%. Some preferred solutions include about 50% to about 99.9%, about 60% to about 99%, about 70% to about 99%, about 80% to about 99% or about 90% to 99%.

[0103] Lotions can be prepared from such solutions. In addition to solvents, lotions typically include at least one emollient. Lotions can include about 1% to about 20% (e.g., about 5% to about 10%) of emollient and about 50% to about 90% (e.g., about 60% to about 80%) of water. As used herein, " emollient " refers to a material for preventing or alleviating dryness and for protecting skin or hair. Examples of emollients include, but are not limited to, those listed in the International Cosmetic Ingredient Dictionary and Handbook, edited by Wenninger and McEwen, pp. 1,656 to 61, 1,626, and 1,654 to 55 (U.S. Cosmetic and Fragrance Association, Washington, DC, 7th edition, 1997) (hereinafter, "ICI Handbook").

[0104] Another type of product that can be formulated from a solution is a cream. Creams typically contain from about 5% to about 50% (e.g., from about 10% to about 20%) of an emollient and from about 45% to about 85% (e.g., from about 50% to about 75%) of water.

[0105] Another type of product that can also be formulated from a solution is an ointment. Ointments can contain a simple base of animal, vegetable, or synthetic oils or semisolid hydrocarbons. Ointments can contain from about 2% to about 10% of an emollient and from about 0.1% to about 2% of a thickening agent.

[0106] The compositions useful in the present invention can also be formulated as emulsions. If the carrier is an emulsion, about 1% to about 10% (e.g., about 2% to about 5%) of the carrier comprises an emulsifier. The emulsifier can be nonionic, anionic, or cationic. Examples of emulsifiers include, but are not limited to, those listed in the ICI Handbook, pages 1673 to 1686.

[0107] Lotions and creams can be formulated as emulsions. Typically such lotions contain 0.5% to about 5% emulsifier, while such creams will typically contain about 1% to about 20% (e.g., about 5% to about 10%) of an emollient; about 20% to about 80% (e.g., 30% to about 70%) of water; and about 1% to about 10% (e.g., about 2% to about 5%) of an emulsifier.

[0108] Oil-in-water and water-in-oil single-phase emulsion skin care formulations (such as lotions and creams) are well known in the art and can be used in the present invention. Multiphase emulsion compositions (such as water-in-oil-in-water or oil-in-water-in-oil) can also be used in the present invention. Generally speaking, such single or multiphase emulsions contain water, an emollient, and an emulsifier as the main ingredients.

[0109] The compositions of the present invention may also be formulated as gels (e.g., aqueous gels, alcohol gels, alcohol / hydrogels, or oleogels, using a suitable gelling agent). Suitable gelling agents for aqueous and / or alcohol gels include, but are not limited to, natural gums, acrylic acid and acrylate polymers and copolymers, and cellulose derivatives (e.g., hydroxymethyl cellulose and hydroxypropyl cellulose). Suitable gelling agents for oils such as mineral oil include, but are not limited to, hydrogenated butylene / ethylene / styrene copolymers and hydrogenated ethylene / propylene / styrene copolymers. Such gels typically contain from about 0.1% to 5% by weight of such a gelling agent.

[0110] The compositions of the present invention may also be formulated as solid formulations (e.g., wax-based sticks, soap bar compositions, powders, or wipes). The compositions of the present invention may also be combined with solid, semisolid, or dissolvable substrates (e.g., wipes, masks, pads, gloves, or strips).

[0111] The compositions of the present invention may also contain any of a variety of additional cosmetic active agents, but they are preferably formulated for use on the skin. Examples of suitable additional active agents include additional skin lightening agents, darkening agents, anti-acne agents, shine control agents, antimicrobial agents such as anti-yeast agents, antifungals and antibacterial agents, anti-inflammatory agents, antiparasitic agents, topical analgesics, sunscreens, photoprotectants, antioxidants, keratolytics, detergents / surfactants, moisturizers, nutrients, vitamins, energy enhancers, antiperspirants, astringents, deodorants, depilatories, hair growth promoters, hair growth retardants, firming agents, hydrating agents, synergists, anti-sclerosis agents, skin conditioning agents, anti-cellulite agents, fluoride, tooth whitening agents, anti-plaque agents, as well as plaque dissolving agents, odor control agents (such as odor masking agents) or pH adjusting agents, etc.Examples of various suitable additional cosmetically acceptable actives include hydroxy acids, benzoyl peroxide, D-panthenol, UV filters such as, but not limited to, avobenzone (Parsol 1 789), bisdisulizoledisodium (Neo Heliopan AP), diethylaminohydroxybenzoyl hexyl benzoate (Uvinul A Plus), ecamsule (Mexoryl SX), methyl anthranilate, 4-aminobenzoic acid (PABA), cinoxate, ethylhexyl triazone (Uvinul T1 50), homosalate, 4-methylbenzylidene camphor (Parsol 5000), octyl methoxycinnamate (Octinoxate), octyl salicylate (Octisalate), padimate O (Escalol 507), phenylbenzimidazole sulfonic acid (Ensulizole), polysilicone-1 5 (Parsol SLX), triethanolamine salicylate, bis-ethylethoxyphenol methoxyphenyl triazine (Tinosorb S), benzophenone 1-12, dihydroxybenzone, drometrizole trisiloxane (Mexoryl XL), diethylhexyl butamido triazone (Uvasorb HEB), octocrylene, oxybenzone (Eusolex 4360), sulisophenone, methylene dibenzotriazole tetramethylbutylphenol (Tinosorb M), titanium dioxide, zinc oxide, carotenoids, free radical scavengers, spin traps, retinoids and retinoid precursors (such as retinol, retinoic acid and retinyl palmitate), ceramides, polyunsaturated fatty acids, essential fatty acids, enzymes, enzyme inhibitors, minerals, hormones such as estrogens, steroids such as hydrocortisone, -dimethylaminoethanol, copper salts such as copper chloride, copper-containing peptides such as Cu:Gly-His-Lys, coenzyme Q10, amino acids such as proline, vitamins, lactobionic acid, acetyl-CoA, niacin, riboflavin, thiamine, ribose, electron transporters such as NADH and FADH2, and other plant extracts (such as oat, aloe, feverfew, soybean, shiitake mushroom extract), and their derivatives and mixtures.

[0112] In one or more embodiments, the composition of the present invention is a skin care composition comprising a compound of Formula I and at least one skin lightening active agent. Examples of suitable skin lightening active agents include, but are not limited to, tyrosinase inhibitors, melanin inhibitors, melanin transfer inhibitors (including PAR-2 antagonists), exfoliants, sunscreens, retinoids, antioxidants, tranexamic acid, skin bleaching agents, allantoin, sunscreens, talc and silica, zinc salts, and the like, as well as other agents as described in Solano et al., Pigment Cell Res. 2006, Vol. 19: 550-571. Examples of suitable tyrosinase inhibitors include, but are not limited to, vitamin C and its derivatives, vitamin E and its derivatives, kojic acid, arbutin, resorcinol, hydroquinone, flavonoids (e.g., total flavonoids from licorice, licorice root extract, mulberry root extract, Dioscorea zingiberensis root extract, Saxifraga officinalis extract, etc.), ellagic acid, salicylates and derivatives, glucosamine and derivatives, fullerenes, hinokitiol, dioic acid, acetylglucosamine, magnolia officinalis lignans, and combinations of two or more thereof. Examples of vitamin C derivatives include, but are not limited to, ascorbic acid and salts, ascorbic acid-2-glucoside, sodium ascorbyl phosphate, magnesium ascorbyl phosphate, and natural extracts rich in vitamin C. Examples of vitamin E derivatives include, but are not limited to, α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and mixtures thereof, tocopherol acetate, tocopherol phosphate, and natural extracts rich in vitamin E derivatives. Examples of resorcinol derivatives include, but are not limited to, resorcinol, 4-substituted resorcinols, such as 4-alkylresorcinols (such as 4-n-butylresorcinol (rucinol), 4-hexylresorcinol), phenylethylresorcinol, 1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)-propane, and natural extracts rich in resorcinol. Examples of salicylates include, but are not limited to, salicylic acid, acetylsalicylic acid, 4-methoxysalicylic acid, and salts thereof. In certain preferred embodiments, the tyrosinase inhibitor comprises a 4-substituted resorcinol, a vitamin C derivative, or a vitamin E derivative. In a more preferred embodiment, the tyrosinase inhibitor comprises phenylethylresorcinol, 4-hexylresorcinol, or ascorbic acid-2-glucoside.

[0113] Examples of suitable melanin degrading agents include, but are not limited to, peroxides and enzymes, such as peroxidases and ligninases. In certain preferred embodiments, the melanin inhibitor comprises a peroxide or a ligninase.

[0114] Examples of suitable melanosome transfer inhibitors include PAR-2 antagonists, such as soybean trypsin inhibitor or Bowman-Birk inhibitor, vitamin B3 and derivatives such as nicotinamide, soy essence, whole soybean, soy extract. In certain preferred embodiments, the melanosome transfer inhibitor includes soy extract or nicotinamide.

[0115] Examples of exfoliants include, but are not limited to, alpha-hydroxy acids (such as lactic acid, glycolic acid, malic acid, tartaric acid, citric acid, or any combination of any of the foregoing), beta-hydroxy acids (such as salicylic acid, polyhydroxy acids such as lactobionic acid and gluconic acid), and mechanical exfoliation, such as microdermabrasion. In certain preferred embodiments, the exfoliant comprises glycolic acid or salicylic acid.

[0116] Examples of sunscreens include, but are not limited to, avobenzone (Parsol 1789), disodium phenyldibenzimidazole tetrasulfonate (Neo Heliopan AP), diethylamino hydroxybenzoyl hexyl benzoate (Uvinul A Plus), ecamsule (Mexoryl SX), methyl anthranilate, 4-aminobenzoic acid (PABA), cinoxate, ethylhexyl triazone (Uvinul T150), homosalate, 4-methylbenzylidene camphor (Parsol 5000), octyl methoxycinnamate (Octinoxate), octyl salicylate (Octisalate), padimate O (Escalol 507), phenylbenzimidazole sulfonic acid (Ensulizole), polysilicone-15 (Parsol SLX), triethanolamine salicylate, bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), dibenzophenone 1-12, dihydroxybenzone, drometrizole trialkoxyane (Mexoryl XL), diethylhexyl butamido triazone (UvasorbHEB), octocrylene, oxybenzone (Eusolex 4360), sulibenzophenone, methylene dibenzotriazole tetramethylbutylphenol (Tinosorb M), titanium dioxide, zinc oxide, etc.

[0117] Examples of retinoids include, but are not limited to, retinol, retinal, retinoic acid, retinyl palmitate, isotretinoin, tazarotene, bexarotene, and adapalene. In certain preferred embodiments, the retinoid is retinol. However, in one or more embodiments, the composition is substantially free of a retinoid or a retinoid precursor; and in further embodiments, free of a retinoid or a retinoid precursor.

[0118] Examples of antioxidants include, but are not limited to, water-soluble antioxidants such as sulfhydryl compounds and their derivatives (e.g., sodium metabisulfite and N-acetylcysteine, glutathione), lipoic acid and dihydrolipoic acid, stilbenes such as resveratrol and derivatives, lactoferrin, and ascorbic acid and ascorbic acid derivatives (e.g., ascorbyl-2-glucoside, ascorbyl palmitate, and ascorbic acid polypeptide). Oil-soluble antioxidants suitable for use in the compositions of the present invention include, but are not limited to, butylated hydroxytoluene, retinoids (e.g., retinol and retinyl palmitate), tocopherols (e.g., tocopheryl acetate), tocotrienols, and ubiquinone. Natural extracts containing antioxidants suitable for use in the compositions of the present invention include, but are not limited to, extracts containing flavonoids and isoflavones and their derivatives (e.g., genistein and diadzein), extracts containing resveratrol, and the like. Examples of such natural extracts include grape seed, green tea, pine bark, feverfew, feverfew without parthenol, oat extract, grapefruit extract, malt extract, hesperidin, grape extract, purslane extract, licorice chalcone, chalcone, 2,2'-dihydroxychalcone, primrose extract, propolis, and the like.

[0119] The additional cosmetic active agent may be present in the composition in any suitable amount, for example, in an amount from about 0.0001% to about 20%, for example from about 0.001% to about 10%, such as from about 0.01% to about 5%, by weight of the composition. In certain preferred embodiments, the amount is from 0.1% to 5%, while in other preferred embodiments, the amount is from 1% to 2%.

[0120] Many other substances may also be present in the compositions of the present invention. These include, for example, chelating agents, humectants, sunscreens, conditioners, preservatives, fragrances, and the like. The compositions may contain surfactants, such as those selected from the group consisting of anionic, nonionic, zwitterionic, cationic, or a combination of two or more thereof.

[0121] The compositions of the present invention may also contain chelating agents (e.g., EDTA) and preservatives (e.g., parabens). Examples of suitable preservatives and chelating agents are listed on pages 1626 and 1654-1655 of the ICI Handbook. In addition, the compositions useful herein may contain conventional cosmetic adjuvants, such as colorants such as dyes and pigments, sunscreens (e.g., titanium dioxide), and fragrances.

[0122] In one or more embodiments, the present invention includes applying such materials by a substrate comprising a compound or composition of the present invention. Any suitable substrate can be used in the present invention. For example, examples of suitable substrates and substrate materials are disclosed in U.S. published patent applications 2005 / 022683 and 2009 / 0241242, which are incorporated herein by reference in their entirety. In certain preferred embodiments, the substrate is a wipe or a facial mask.

[0123] Compositions and products comprising such compositions of the present invention can be prepared using methods well known to those of ordinary skill in the art.

[0124] method

[0125] Another aspect of the present invention relates to a method for treating skin comprising topically applying to the skin a composition according to one or more embodiments of the present invention. As used herein, "treating" means improving, preventing or reversing a condition, disease or disorder, or at least one identifiable symptom thereof. In one embodiment, "treating" refers to improving, preventing or reversing at least one measurable physical parameter associated with the condition, disease or disorder being treated, which is not necessarily identifiable in or by the subject being treated. In another embodiment, "treating" refers to inhibiting or slowing the progression of the condition, disease or disorder, which may be physical (e.g., stabilizing an identifiable symptom), physiological (e.g., stabilizing a physical parameter), or both. In another embodiment, "treating" refers to delaying the onset of a condition, disease or disorder.

[0126] The compositions / compounds described herein can be used to treat skin for treating acne, treating signs of aging (e.g., wrinkles), improving skin barrier function, and / or lightening the skin. In one or more embodiments, the treatment is for a subject having a condition or a history of a condition selected from the group consisting of atopic dermatitis, rosacea, seborrheic dermatitis, psoriasis, dry skin, and flaky skin.

[0127] The compositions of the present invention are useful for improving the texture of the skin or improving the firmness of the skin, or any of the following conditions / symptoms.

[0128] As used herein, "improving the texture of the skin" means smoothing the surface of the skin to remove bumps or fissures on the surface of the skin.

[0129] As used herein, "improving the firmness of skin" means increasing the firmness or elasticity of skin, preventing loss of firmness or elasticity of skin, or preventing or treating sagging, loose, and loose skin.

[0130] As used herein, "loss of elasticity" includes loss of elasticity or structural integrity of the skin or tissue, including but not limited to sagging, loose, and loose tissue. Loss of elasticity or tissue structural integrity can be caused by a variety of factors, including but not limited to disease, aging, hormonal changes, mechanical trauma, environmental damage, or as a result of applying products such as cosmetics or medications to the tissue.

[0131] As used herein, "uneven skin tone" refers to a skin condition associated with diffuse or patchy pigmentation, which can be categorized as hyperpigmentation, such as post-inflammatory hyperpigmentation.

[0132] As used herein, "scaly spots" refers to a skin condition that is associated with redness or erythema.

[0133] As used herein, "age spots" refers to a skin condition associated with discrete pigmentation, such as small areas of darker pigmentation that can develop on the face and hands.

[0134] Signs of skin aging also include decreased skin thickness and the presence of abnormal or reduced synthesis of collagen, glycosaminoglycans, proteoglycans, elastin, or glycoproteins including fibronectin. In one embodiment, the signs of aging are selected from abnormal or reduced synthesis of collagen, glycosaminoglycans, proteoglycans, elastin, or glycoproteins (including fibronectin). In another embodiment, the sign of skin aging is reduced synthesis of collagen or elastin.

[0135] Examples of skin aging that can be treated by topical application of the compositions of the present invention include, but are not limited to, wrinkles on the skin. As used herein, the term "wrinkles" includes fine lines, microwrinkles, coarse wrinkles, cellulite, scars, and stretch marks. Examples of wrinkles include, but are not limited to, fine lines around the eyes (e.g., "crow's feet"), forehead and cheek wrinkles, frown lines, and laugh lines around the mouth.

[0136] As used herein, "topical use" and "topical application" mean application or spreading directly to the skin, hair, or nails, for example, by using the hands or an applicator such as a wipe.

[0137] The compositions are also suitable for treating or preventing acne. As used herein, "acne" refers to a disorder caused by the effects of hormones and other substances on the sebaceous glands and hair follicles, typically resulting in clogged pores and the formation of inflammatory or non-inflammatory lesions on the skin. Specifically, it relates to blemishes, lesions or papules, pre-emergent papules, blackheads and / or whiteheads. As used herein, "pre-emergent papules" are inflamed hair follicles that are not visible to the naked eye (e.g., as lesions) on the surface of the skin.

[0138] The compositions of the present invention are also suitable for treating or preventing rosacea.As used herein, "rosacea" means persistent red patches of skin with or without papules, pustules, or nodules.

[0139] The compositions of the present invention are also suitable for reducing epidermal hyperkeratosis. Thus, the compositions can be used to treat or prevent conditions characterized by hyperkeratosis, such as acne or warts.

[0140] In one or more embodiments, one or more of the methods described herein modify the expression of one or more biomarkers. For example, in one or more embodiments, the method can be a method for increasing the expression of CRABP2, HAS3, or HBEGF in the skin. CRABP2 has been well documented in the literature as a highly sensitive marker of retinoid bioactivity and efficacy (Elder JT, Cromie MA, Griffiths CEM, Chambon P, Voorhees JJ, Stimulus-selective induction of CRABP-II mRNA: A marker for retinoic acid action in human skin, J Invest Dermatol. 1993; Vol. 100, No. 4), and is associated with imparting anti-aging benefits to the skin (Bielli A, Scioli MG, D'Amico F, Tarquini C, Agostinelli S, Costanza G, Doldo E, Campione E, Passeri D, Coniglione F, Orlandi A, Cellular retinoic acid binding protein-II expression and its potential role in Skinaging, Aging (Albany, NY, March 18, 2019; Vol. 11, No. 6: pp. 1619-1632). HAS3 is a hyaluronan synthase gene that produces hyaluronic acid, which is associated with skin hydration and plumpness and is indirectly induced by retinol. Skin plumpness confers an anti-aging or youthful appearance. Heparin-binding epidermal growth factor (HbEGF). HbEGF is a marker of cell proliferation, a characteristic associated with retinol.

[0141] The compositions described herein can be applied to any part of the human body where treatment is desired. For example, the compositions can be applied to any one or more of the skin on the face, neck, chest, back, arms, axillae, hands, and / or legs. In certain preferred embodiments, the method comprises applying a composition according to one or more embodiments of the present invention to facial skin.

[0142] Any method suitable for applying the extract to the skin in need thereof can be used in accordance with the present invention. For example, the extract can be applied directly to the skin in need thereof from the packaging, applied by hand to the skin in need thereof, or transferred via a substrate such as a wipe or mask, or a combination of two or more thereof. In other embodiments, the extract can be applied via a dropper, tube, roller, spray, patch, or added to a tub or otherwise added to water for application to the skin, etc.

[0143] In one or more embodiments, the methods of the present invention further comprise the step of allowing the composition to contact the skin for a period of time. For example, in certain preferred embodiments, the compound may be allowed to contact the skin for about 15 minutes or longer after application. In certain more preferred embodiments, the extract is allowed to contact the skin for about 20 minutes or longer, more preferably about 1 hour or longer.

[0144] In some embodiments, the methods of the present invention comprise a course of treatment comprising applying the composition to the skin multiple times over a selected period of time. For example, in certain embodiments, the present invention provides a method of treating signs of aging comprising applying a composition according to one or more embodiments of the present invention to skin in need of anti-aging treatment once or twice daily for at least 12 weeks, preferably at least 8 weeks, and more preferably at least 2 weeks.

[0145] Example

[0146] The following examples evaluate compositions containing Citrus aurantifolia fruit extract. These examples relate to the evaluation of retinol-responsive genes such as CRABP2, HBEGF, and HAS3. Upregulation of these genes is associated with the skin benefits provided by retinoids (e.g., anti-aging effects, wrinkle reduction, acne reduction, and skin tone benefits).

[0147] Example 1: Preparation of composition

[0148] Five compositions of the present invention (Examples 1 to 5) and three comparative compositions (Examples 6 to 8) were prepared in the following manner using the amounts shown in Tables 1 and 2 below. Examples 1 to 5 were prepared using Citrus aurantium fruit extract. Comparative Examples 7 to 8 were compositions prepared without Citrus aurantium fruit extract. The compositions were prepared by adding purified water to a beaker of appropriate size. Mixing was initiated using a propeller-type mixing blade and the water was heated to 75°C to 80°C. Sepimax Zen TM Slowly add to the main batch and mix until fully hydrated and free of visible particles, increasing the mixing speed as needed. Reheat the mixture to 75°C to 80°C, then add chlorphenesin and emulsifier and mix until homogenous and free of undissolved particles. Next, cool the solution to 60°C to 65°C, add glycerin and mix until homogenous. Once the solution has cooled to 55°C to 60°C, add Sepiplus TM 400 and Citrus aurantium fruit extract (except Comparative Examples 7 to 8) are added and mixed until uniform. Continue cooling to 40°C while mixing the solution at a medium speed. Then add dimethicone, phenoxyethanol, and ethylhexylglycerin and mix until uniform. Add an appropriate amount of water and adjust the pH. Mix the solution until uniform and allow it to cool to room temperature. Comparative Example 6 is Citrus aurantium fruit extract (30% extract in a carrier), which was purchased from Southern Cross Botanicals Pty, Knockrow, New South Wales, Australia. The Citrus aurantium fruit extract used in the examples typically contains about 1% to 10% 3-(4-farnesyloxyphenyl)-propionic acid, more specifically about 1% to about 6%, based on the weight of the extract and carrier. 0.01% to 0.06% is calculated based on the total weight of the formulation.

[0149] Table 1: Examples of the present invention

[0150]

[0151] Table 2: Comparative Examples

[0152]

[0153]

[0154] Example 2: Bioactivity Assays of CRABP2, HBEGF, and HAS3 in Human Skin Explants

[0155] Abdominal skin samples were obtained from adults undergoing abdominoplasty. Informed consent was obtained from each patient, and all experimental procedures were approved by the Institutional Review Board (IRB). Subcutaneous fat was carefully removed and a 0.93 cm2 Skin biopsies were obtained from rats and acclimated overnight in DMEM / F12 (1:1) medium, 2% heat-inactivated fetal bovine serum, 10 μg / mL insulin, 10 ng / mL hydrocortisone, 10 ng / mL EGF, 1× ABAM in a humidified atmosphere of 5% CO. Skin explants were topically treated with 4 μL of each formulation for 48 hours.

[0156] At the end of the 48-hour incubation, the skin biopsy was cut in half and either or both halves of the skin biopsy were lysed in 600 μL of lysis buffer consisting of 100 parts RLT buffer (RNA purification kit sold under the trade name RNEASY Mini kit (Qiagen, Valencia, CA)) placed in a reinforced tube with a screw cap and O-ring closure with one part 2-mercaptoethanol and ceramic beads for tissue grinding (sold under the trade name PRECELLYS CKMix50-R, Bertin Corp, Rockville, MD). The tube was shaken at 6300 rpm for 40 seconds. RNA was extracted from the solution using the RNEASY Mini kit (Qiagen, Valencia, CA) according to the manufacturer's instructions and eluted in 30 μL of RNase-free water. Each tissue was transferred to a hard tissue homogenizer Ozyme CK28 tube (Bertin Corp, Rockville, MD) containing ceramic beads, 400 μL RLT buffer and 4 μL β-mercaptoethanol and placed on ice. After thawing, 300 μL water and 10 μL proteinase K (Thermo Fisher Scientific, Bridgewater, NJ) were added to each tube, mixed and incubated at 55°C for 20 minutes.

[0157] Using Applied Biosystems High Capacity Reverse Transcription test kit (ThermoFisherScientific, New Jersey Bridgewater City) to perform reverse transcription (RT).With the gene expression determination for the following items sold under the trade name TAQMAN:Cellular retinoic acid binding protein 2 (CRABP2), heparin-binding epidermal growth factor (HBEGF), hyaluronan synthase 3 (HAS3), polymerase (RNA) II polypeptide A (POLR2A), and with the master mixture sold under the trade name TAQMAN (ThermoFisher Scientific, New Jersey Bridgewater City).Using TAQMAN master mixture to perform qPCR analysis, and run on the real-time PCR system sold under the trade name QUANTSTUDIO 7Flex system (ThermoFisher Scientific, New Jersey Bridgewater City).The expression of these genes is normalized relative to the expression of people's 18S housekeeping gene. Fold changes in CRABP2, HBEGF, and HAS3 gene expression were calculated compared to untreated or vehicle controls, and two-tailed, two-sample Student's t-tests were performed (Microsoft Office Excel 2007; Microsoft, Redmond, WA, USA).

[0158] Table 3: CRABP2 gene expression

[0159]

[0160] Table 4: HBEGF gene expression

[0161]

[0162] Table 5: HAS3 gene expression

[0163]

[0164] As shown in Tables 3 to 4, Examples 1, 2, 3, and 5 of the present invention showed enhanced expression of CRABP2 and HBEGF genes compared to placebo and untreated controls. CRABP2 has been well documented as a highly sensitive marker of retinoid bioactivity and potency (Elder JT, Cromie MA, Griffiths CEM, Chambon P, Voorhees JJ, Stimulus-selective induction of CRABP-II mRNA: A marker for retinoic acid action in human skin, J Invest Dermatol. 1993; Vol. 100 No. 4), and has been associated with imparting anti-aging benefits to the skin (Bielli A, Scioli MG, D'Amico F, Tarquini C, Agostinelli S, Costanza G, Doldo E, Campione E, Passeri D, Coniglione F, Orlandi A, Cellular retinoic acid binding protein-II expression and its potential role in Skinaging, Aging (Albany, NY, March 18, 2019; Vol. 11, No. 6: pp. 1619-1632). Heparin-binding epidermal growth factor (HbEGF) is associated with cell proliferation, a hallmark of retinoid bioactivity. Therefore, this data suggests that the present invention embodiments exhibit increased retinol-like properties and, therefore, have anti-aging benefits.

[0165] As shown in Table 5, HAS3 increased relative to the placebo of Comparative Example 7, and Examples 2 to 3 also increased relative to the untreated control. HAS3, also known as hyaluronan 1 5 synthase 3, encodes a protein involved in the synthesis of hyaluronic acid. Hyaluronic acid is associated with skin hydration and plumping and is indirectly induced by retinol. The plumping of the skin imparts an anti-aging or youthful appearance. Therefore, the upregulation of this gene as shown in the results is also associated with anti-aging and other retinoid behaviors.

[0166] Example 3: Bioactivity Assay of CRABP2 and HBEGF in Human Skin Explants (Epidermis Only)

[0167] Abdominal skin samples were obtained from adults undergoing abdominoplasty. Informed consent was obtained from each patient, and all experimental procedures were approved by the Institutional Review Board (IRB). Subcutaneous fat was carefully removed, and 0.93 cm 2Skin biopsies were transferred to 6-well plates. Skin explants were topically treated with 4 μL of each formulation prepared under sterile conditions and acclimated for 48 h at 37°C and a humidified atmosphere of 5% CO2 in Gold medium supplemented with the following: 1x natural-capped vial with 0.50 mL hydrocortisone, 1x natural-capped vial with 0.50 mL transferrin, 1x amber-capped vial with 0.25 mL epinephrine, 1x red-capped vial with 0.50 mL gentamicin amphotericin B-1000, 1x orange-capped vial with 2.00 mL BPE, 1x green-capped vial with 0.50 mL hEGF, 1x lavender-capped vial with 0.50 mL insulin (KGM) TM Gold Keratinocyte Growth Medium Single Quots TM Supplements and growth factors, (Lonza)).

[0168] At the end of 48 hours of incubation, in order to destroy tissue and make cell homogenization, each explant is placed in the tube containing 100 μ l 60 ℃ of water.After contacting for 50 seconds, epidermis is separated from dermis, and each epidermis is transferred to the Ozyme CK28 tube that contains beads+400 μ L RLT+4 μ L β-mercaptoethanol respectively, and is put into ice.The Ozyme CK28 tube containing epidermal tissue is transferred to tissue grinding device (selling with trade name PRECELLYS CKMix50-R, BertinCorp, Rockville, Maryland), and shaken with 5000rpm for 60 seconds.After micro-spin centrifugation (with 4000rpm), the content in each tube containing epidermis is transferred to 2mL eppendorf tube without RNAse, and is stored in-80 ℃.300 μ L water is added in the tube containing dermis. After homogenization, transfer the contents into 2 ml RNase-free eppendorf tubes and store at -80 °C until further processing.

[0169] RNA was extracted from the solution. After thawing, 300 μL of water plus 10 μL of proteinase K was added to each tube containing epidermal material, mixed, and incubated at 55°C for 20 minutes. RNA was extracted using a Qiacube HT using the epidermal protocol according to the manufacturer's instructions and stored at -80°C. Samples were thawed, and the RNA concentration in 2 μL of RNA extract was assessed using an ultramicrophotometer.

[0170] Reverse transcription (RT) was performed using an Applied Biosystems High Capacity Reverse Transcription Kit (ThermoFisherScientific, Bridgewater, NJ) and a real-time PCR detection system sold under the trade name ICYCLER IQ (Bio-Rad Laboratories, France). Gene expression assays were run for CRABPB2 and HBEGF. qPCR analysis was performed using a master mix sold under the trade name POWER SYBYR Green master mix (ThermoFisherScientific). The expression of these genes was normalized to that of the human 18S housekeeping gene. Fold changes were calculated compared to untreated controls or vehicle controls, and statistical analysis was performed using ANOVA.

[0171] Table 6: CRABP2 gene expression

[0172]

[0173]

[0174] Table 7: HBEGF gene expression

[0175]

[0176] As shown in Tables 6 to 7, Examples 2, 4, and 5 of the present invention showed enhanced expression of CRABP2 and HBEGF genes compared to placebo and untreated controls.

Claims

1. A skin care composition, comprising: a. Emollients; b. tackifier; c. Emulsifier; d. Wetting agent; and e. Compounds of formula I: in: R1 is selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl and C3-C8 cycloalkyl or aryl; R2 is selected from the group consisting of hydrogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl or aryl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl or aryl, thiol, -SC1-C6 alkyl, -SC2-C6 alkenyl, -SC2-C6 alkynyl, -SC3-C8 cycloalkyl or aryl, -NR4C1-C6 alkyl, -NR4C2-C6 alkenyl, -NR4C2-C6 alkynyl and -NR4C3-C8 cycloalkyl or aryl; R3 is selected from the group consisting of: -CO2H, -CO2R4 or an isosteric equivalent of a carboxyl group, wherein R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl or aryl; and Y is -(CH2-CH2)-, -(CH=CH)- or -(C≡C)-; or a cosmetically acceptable salt thereof.

2. The skin care composition according to claim 1, wherein R1 is selected from the group consisting of: C5-C 16 Alkyl, C5-C 16 Alkenyl and C5-C 16 Alkynyl; R2 is selected from the group consisting of hydrogen, hydroxy, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4, wherein R4 is an isosteric equivalent of a C1-C6 alkyl, or a carboxyl group; and Y is -(CH2-CH2)- or -(CH=CH)-.

3. The skin care composition according to claim 1 or 2, wherein R1 is selected from the group consisting of: C5-C 16 alkenyl; and R2 is selected from the group consisting of: hydrogen or -OC1-C3 alkyl.

4. The skin care composition according to any one of claims 1 to 3, wherein the compound of formula I is selected from the group consisting of 3-(4-farnesyloxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-hydroxyphenyl)-propionic acid, 3-(4-farnesyloxy-3-methoxyphenyl)-propionic acid, ethyl esters thereof, and combinations of two or more thereof.

5. The skin care composition according to any one of claims 1 to 4, wherein the compound of formula I comprises 3-(4-farnesyloxyphenyl)-propionic acid.

6. The skin care composition of any one of claims 1 to 5, wherein the concentration of the compound of formula I is present in an amount ranging from about 0.0001% to about 1% by weight of the total composition.

7. The skin care composition according to any one of claims 1 to 6, wherein the skin care composition comprises a plant extract containing the compound of formula I.

8. The skin care composition according to any one of claims 1 to 7, wherein the plant extract comprises an extract of a plant of the genus Citrus.

9. The skin care composition according to any one of claims 1 to 8, wherein the plant extract is an extract of Citrus aurantium.

10. The skin care composition according to any one of claims 1 to 9, wherein the plant extract is a polar extract.

11. The skin care composition of any one of claims 1 to 10, wherein the plant extract is present in an amount ranging from about 0.01% to about 5% by weight of the total composition.

12. The skin care composition of any one of claims 1 to 11, wherein the extract of Citrus aurantium comprises 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 0.01% to about 0.5% by weight of the total composition.

13. A skin care composition according to any one of claims 1 to 12, wherein the emollient is silicone or a silicone-based emollient.

14. The skin care composition of any one of claims 1 to 13, wherein the emollient is selected from the group consisting of dimethicone, dimethicone crosspolymer, phenyl trimethicone, cetyl trimethicone, amodimethicone, caprylyl methicone, and combinations thereof.

15. The skin care composition of any one of claims 1 to 14, wherein the emollient is present at a concentration of from about 0.1% to about 15% by weight.

16. The skin care composition of any one of claims 1 to 15, wherein the viscosity increasing agent is a rheology modifier that provides yield stress to the composition and compatibility at a pH of less than about 5.

17. The skin care composition according to any one of claims 1 to 16, wherein the viscosity increasing agent is selected from the group consisting of polyacrylate crosspolymer-6, polyacrylate-13, sorbitan stearate, polyacrylamide, C13-14 isoparaffin, laureth-7, ammonium acryloyldimethyltaurate / VP copolymer, carbomer, and combinations thereof.

18. The skin care composition of any one of claims 1 to 17, wherein the viscosity increasing agent is present at a concentration of from about 0.1% to about 5% by weight.

19. The skin care composition of any one of claims 1 to 18, wherein the emulsifier comprises a liquid crystal emulsifier.

20. The skin care composition of any one of claims 1 to 19, wherein the emulsifier is selected from the group consisting of sorbitan olivate, cetyl olivate, C12-20 alkyl glucoside, C14-22 alcohol, sorbitan stearate, sorbitan laurate, polyglyceryl-6 pentaoleate, and combinations thereof.

21. The skin care composition of any one of claims 1 to 20, wherein the emulsifier is present at a concentration of from about 0.1% to about 5% by weight.

22. The skin care composition of any one of claims 1 to 21, wherein the humectant comprises a polar humectant.

23. The skin care composition of any one of claims 1 to 22, wherein the humectant is selected from the group consisting of glycerin, sorbitol, xylitol, hyaluronic acid, lactic acid, and combinations thereof.

24. The skin care composition of any one of claims 1 to 231, wherein the humectant is present at a concentration of from about 0.5% to about 15% by weight.

25. A method of treating skin comprising topically applying to the skin a skin care composition according to any one of claims 1 to 24.

26. The method of claim 25, wherein the method comprises increasing CRABP2 expression in skin cells.

27. A skin care composition, comprising: a. Polydimethylsiloxane; b. a viscosity increasing agent selected from the group consisting of: polyacrylate crosspolymer-6, polyacrylate-13, sorbitan stearate, and combinations thereof; c. an emulsifier selected from the group consisting of sorbitan olivate, cetyl olivate, and combinations thereof; d. glycerol; and e. Polar plant extract of Citrus aurantium.

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