Compositions Comprising Compounds Having Retinol-Like Activity and Processed Oat Ingredients
A compound of Formula I, like 3-(4-farnesyloxyphenyl)-propionic acid, combined with processed oats, addresses the need for gentle, effective treatments for aging and acne, enhancing skin texture and firmness without irritation.
Patent Information
- Application Number
- JP2025540463
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-01-11
- Filing Date
- 2024-01-11
- Publication Date
- 2026-02-03
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Figure 2026504051000001 
Figure 2026504051000002 
Figure 2026504051000003
Abstract
Description
[Technical Field]
[0001] The present invention relates generally to compositions suitable for use on the skin, and in particular to compositions comprising a compound having retinol-like activity and a processed oat ingredient. [Background technology]
[0002] Human skin undergoes certain aging processes, some of which are due to intrinsic processes (e.g., chronoaging) and some of which are due to extrinsic factors (e.g., photoaging). In addition, temporary or even permanent changes to the skin can occur, such as acne, oily or dry skin, keratosis, rosacea, photosensitivity, inflammatory, erythematous, and allergic or autoimmune reactions, such as dermatitis and photodermatoses.
[0003] The consequences of the aging process described above can include thinning of the skin, weakening of the epidermis and dermis intertwining, and a decrease in the number of cells and blood vessel supply. These consequences are often undesirable, and individuals suffering from these problems turn to topical treatments to address them.
[0004] Retinoids have been used to treat skin conditions caused by intrinsic aging, extrinsic factors, acne or skin diseases.However, despite the beneficial effects of retinoid treatment, its benefits are limited due to the skin irritation caused by retinoids.These side effects limit the use of retinoids, especially for individuals with sensitive skin.
[0005] To date, the search for alternative compounds to replace retinoids, and particularly for individuals with sensitive skin, has met with some success in treating age-related skin conditions such as skin atrophy, acne, photoaging, and in reducing the appearance of wrinkles, fine lines, stretch marks, or cellulite. Summary of the Invention [Problem to be solved by the invention]
[0006] Therefore, there is a need for alternatives to traditional retinoids that are effective yet sufficiently gentle on the skin and well tolerated. [Means for solving the problem]
[0007] Thus, one aspect of the present invention is Formula I:
[0008] [ka] A compound of the formula: R1 is C1~C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 selected from the group consisting of alkynyl, and C3-C8 cycloalkyl or aryl; R2 is selected from the group consisting of hydrogen, hydroxyl, 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 -CO2H, -CO2R4, or an isosteric equivalent of a carboxy group, and R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, or aryl; Y is,
[0009] [ka] a compound of formula I, or a cosmetically acceptable salt thereof; and a processed oat ingredient.
[0010] In one or more embodiments, R1 is a C5-C 16 Alkyl, C5-C 16 Alkenyl and C5-C 16 In some embodiments, R1 is selected from the group consisting of hydrogen, hydroxyl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, and -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4 where R4 is C1-C6 alkyl, or an isosteric equivalent of a carboxy group; and Y is -(CH2-CH2)- or -(CH=CH)-. In some embodiments, R1 is selected from the group consisting of C5-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, and -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4 where R4 is C1-C6 alkyl, or an isosteric equivalent of a carboxy group; and Y is -(CH2-CH2)- or -(CH=CH)-. 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, ethyl esters thereof, and combinations of two or more thereof. In some embodiments, the compound of Formula I is 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 0.00001% to 10% by weight of the total composition. In some embodiments, the skin care composition comprises a plant extract comprising the compound of Formula I. In one or more embodiments, the plant extract comprises an extract of a plant of the genus Acromicria. In some embodiments, the plant extract is an extract of Paronychia 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 0.00001% to about 5% by weight of the total composition. In one or more embodiments, the extract of Acronychia acidula comprises 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 0.1% to about 30% by weight of the total extract. In some embodiments, the processed oat ingredient is selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof. In one or more embodiments, the composition further comprises an ingredient selected from the group consisting of a surfactant, a chelating agent, an emollient, a moisturizer, a conditioner, a preservative, an opacifier, a fragrance, and combinations of two or more thereof. In some embodiments, the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid wash, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.In one or more embodiments, the compound of formula I is 3-(4-farnesyloxyphenyl)-propionic acid and the processed oat ingredient is selected from the group consisting of fermented oats, oat extract, colloidal oats, and combinations thereof.
[0011] The embodiments described herein can be combined in any suitable manner. For example, in some embodiments, the skin care composition comprises a. 3-(4-farnesyloxyphenyl)-propionic acid, b. a processed oat component selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof; The composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid wash, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.
[0012] Another aspect of the present invention relates to a method for treating skin, comprising topically applying any of the compositions described herein. In some embodiments, the method is for treating signs of aging, treating acne, smoothing skin texture, or brightening skin. In one or more embodiments, the method is for increasing CRABP2 expression. DETAILED DESCRIPTION OF THE INVENTION
[0013] 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 following disclosure in any way.
[0014] 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 this invention belongs. Furthermore, all publications, patent applications, patents, and other references mentioned herein are incorporated by reference.
[0015] Unless otherwise specified, percentages used to express amounts of ingredients are weight percent (also referred to as "weight %, "wt %, "% by weight", or "%(W / W)"). Similarly, weight ratios used to express relative proportions of ingredients are also determined using weight percent (i.e., the weight ratio is calculated by dividing the weight percent of one ingredient by the weight percent of another ingredient). Unless otherwise specified, all ranges are inclusive of their endpoints; for example, "4 to 9" includes the endpoints 4 and 9.
[0016] As used herein, a composition that is "essentially free" or "substantially free" of a component means a composition that has about 2% by weight or less of the component, based on the total weight of the composition. Preferably, a composition that is essentially free of a component has about 1% by weight or less, more preferably about 0.5% by weight or less, more preferably about 0.1% by weight or less, more preferably about 0.05% by weight or less, and more preferably about 0.01% by weight or less of the component, based on the total weight of the composition. In certain more preferred embodiments, a composition that is essentially free of a component does not include the component, i.e., the component is not present in the composition.
[0017] As used herein, "cosmetically / dermatologically acceptable" means that the ingredient it describes is suitable for use in contact with tissue (e.g., skin or hair) without undue toxicity, incompatibility, instability, irritation, allergic reaction, etc. As will be recognized by those skilled in the art, cosmetically / dermatologically acceptable salts are acidic / anionic or basic / cationic salts.
[0018] As used herein, a "safe and effective amount" means an amount of a compound, extract, or composition that is sufficient to induce the desired effect, but low enough to avoid serious side effects. A safe and effective amount of a compound, extract, or composition will vary depending, for example, on the age, health, and environmental exposure of the end user, the duration and nature of the treatment, the particular extract, ingredient, or composition used, the particular pharmaceutically acceptable carrier used, and similar factors.
[0019] As used herein, the term "about" refers to within 5%, within 4%, within 3%, within 2.5%, within 2%, or within 1% by weight of the disclosed value.
[0020] Generally, IUPAC nomenclature is used herein in accordance with the following definitions of terms.
[0021] The term "substituted" refers to a core molecule in which one or more hydrogen atoms have been replaced with a substituent, in the amount permitted by available valences. Substitution is not limited to the core molecule, but can also occur on substituent radicals, thereby rendering the radical a linking group.
[0022] The term "independently selected" refers to two or more substituents that may be selected from a substituent variable group, and the selected substituents may be the same or different.
[0023] The term "dependently selected" refers to one or more substituent variables that are specified in a specified combination for substitution within a core molecule (e.g., a variable that refers to a group of substituents listed in a table of compounds).
[0024] 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, or tertiary amines, etc.
[0025] One aspect of the present invention is (a) Formula I:
[0026] [ka] A compound of the formula: R1 is C1~C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 selected from the group consisting of alkynyl, and C3-C8 cycloalkyl or aryl; R2 is selected from the group consisting of hydrogen, hydroxyl, 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 -CO2H, -CO2R4, or an isosteric equivalent of a carboxy group, and R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, or aryl; Y is,
[0027] [ka] a compound of formula I, or a cosmetically acceptable salt thereof; (b) a processed oat ingredient. Such compositions have been shown to exhibit synergistic effects in various respects compared to the ingredients alone.
[0028] Compounds of formula (I) In one or more embodiments, R1 is a C5-C 16 Alkyl, C5-C 16 Alkenyl and C5-C 16In some embodiments, R1 is selected from the group consisting of hydrogen, hydroxyl, -OC1-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, and -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4 where R4 is C1-C6 alkyl, or an isosteric equivalent of a carboxy 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-C6 alkyl, -OC2-C6 alkenyl, -OC2-C6 alkynyl, and -OC3-C8 cycloalkyl; R3 is selected from -CO2H, -CO2R4 where R4 is C1-C6 alkyl, or an isosteric equivalent of a carboxy group; and Y is -(CH2-CH2)- or -(CH=CH)- (or a cosmetically acceptable salt thereof). 16 alkenyl, 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, ethyl esters thereof, 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 is 3-(4-farnesyloxyphenyl)-propionic acid. 3-(4-farnesyloxyphenyl)-propionic acid and / or its ethyl ester can be synthesized using conventional organic synthesis processes.
[0029] The compound of formula I may be present in an amount ranging from about 0.00001% to 10%, or from about 0.0001 to about 10%, or from about 0.001 to about 5%, or from about 0.001% to about 1%, or from about 0.01% to about 3%, or from about 0.01% to about 1%, or from about 0.01% to about 0.5%, or from about 0.005% to about 1.5%, or from about 0.005% to about 0.06%, or from about 0.009% to about 0.06%, or from about 0.009% to about 0.03%, based on the total weight of the composition.
[0030] The compound according to formula I can also be obtained from natural sources. For example, the compound according to formula I can be found in a plant extract. Thus, the composition can include a plant extract containing the compound of formula I.
[0031] In one or more embodiments, the plant extract is an extract of a plant of the genus Acronychia. In further embodiments, the plant extract is an extract of Acronychia acidula (also known as lemon aspen). In one or more embodiments, at least one compound of Formula I above is present in the Acronychia extract at a concentration of 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% or more by weight of the Acronychia extract. In further embodiments, the Acronychia acidula extract contains 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 1% to about 10% based on the total weight of the extract.
[0032] Suitable extracts can be obtained using conventional methods including, but not limited to, grinding, maceration, pressing, squeezing, grinding, centrifugation, and / or cold irrigation, stirring / distillation, microwave-assisted extraction, supercritical / subcritical CO2 compressed gas extraction with or without polar modifiers, pressurized solvent extraction, accelerated solvent extraction, pressurized or regular hot water extraction, surfactant-assisted pressurized hot water extraction, oil extraction, membrane extraction, Soxhlet extraction, gold finger distillation / extraction, and / or direct extraction of material from biomass by, for example, the processes disclosed in U.S. Pat. Nos. 7,442,391, 7,473,435, and 7,537,791 (Integrated Botanical Technologies, LLC), which are incorporated herein by reference, or by other methods such as solvent extraction.
[0033] Any of a variety of solvents, including polar solvents, nonpolar solvents, or combinations of two or more thereof, may be used in methods involving solvent extraction. Suitable polar solvents include polar inorganic solvents such as water; polar organic solvents such as alcohols and corresponding organic acids, e.g., C1-C8 alcohols, including methanol, ethanol, propanol, butanol, and the like; organic acids, including acetic acid, formic acid, propanoic acid, and the like; polyols and glycols, including C1-C8 polyols / glycols, and the like; and combinations of two or more thereof. Suitable nonpolar solvents include nonpolar organic solvents, e.g., alkanes, including C1-C8 alkanes; cycloalkanes, including C1-C8 alkanes; alkyl ethers, including C1-C8 alkyl ethers; petroleum ether; ketones, including C1-C8 ketones; methylene chloride; ethyl acetate; xylene; toluene; chloroform; vegetable oil; mineral oil; and the like. In another embodiment, the extraction can be obtained by supercritical fluid extraction with or without the use of non-polar solvents as described above or polar modifiers such as C1-C8 alcohols, water, C1-C8 polyols / glycols, or C1-C8 organic acids.
[0034] In one or more embodiments, the extract comprises an extract of Acronychia acidula. In some embodiments, the extract of the present invention comprises a combination of polar and non-polar extracts of the fruit of Acronychia acidula. In other embodiments, the extract of the present invention comprises an alcoholic or glycolic extract of the fruit of Acronychia acidula.
[0035] In one or more embodiments, the extract is a polar extract. In further embodiments, the extract is prepared using a polar solvent including water, a C1-C8 alcohol, a C1-C8 polyol, or a C1-C8 glycol, 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 glycols. In one or more embodiments, the extract is prepared using a solvent including methanol, ethanol, or a combination thereof with or without water. In further embodiments, the extract is a polar extract extracted from the fruit of Acronychia acidula using a combination of alcohol and water.
[0036] 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 further embodiments, the extract is a non-polar extract prepared using hexane, ethyl acetate, chloroform, or a mixture of two or more thereof. In yet further embodiments, the extract is a non-polar extract prepared using ethyl acetate.
[0037] For example, an extract using Acronychia acidula fruit can be prepared by homogenizing the fruit in a blender with an equal volume of denatured alcohol for 30 seconds. The pulp is then mixed and stirred for an additional 24 hours at ambient temperature (22-26°C). Additional denatured alcohol may be added as needed to keep the pulp well covered in alcohol. The mixture is then gravity filtered, and the resulting filter cake can be washed with additional amounts of denatured alcohol. The entire 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 the extractant and water. The extraction can be repeated several times on the filter cake, with each extraction routinely yielding an extract yield of 5-7%.
[0038] Another example of the preparation of Acronychia acidula fruit extract is as follows: 500 gm of freeze-dried Acronychia acidula fruit can be sliced into approximately 5 mm cubes and immersed in 5 L of ethanol at a 1:10 ratio (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 gm of residual material, referred to as the crude extract (65% yield). A 200 gm sample of the crude extract can then be dissolved in 1 L of ethanol and stirred overnight at room temperature. The mixture can then be filtered and dried under reduced pressure and low temperature. The extract may be present in an amount of about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 0.75, 1, 1.5, or 2 to about 0.00005, 0.0005, 0.005, 0.05, 0.5, 1, 1.5, 2, 2.5, 3, 4, or 5 wt.% based on the total weight of the composition. In one or more embodiments, the extract is present in an amount of about 0.01 wt.% to about 5 wt.% based on the total weight of the composition. In further embodiments, the extract is present in an amount of about 0.01 wt.% to about 3 wt.% based on the total weight of the composition. In one or more embodiments, the extract is present in an amount of about 0.1 wt.% to about 3 wt.% based on the total weight of the composition. In further embodiments, the extract is present in an amount of about 0.2 wt.% to about 2.5 wt.% 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. 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 1% by weight, based on the total weight of the composition. In one or more embodiments, the extract is present in an amount of about 0.25% to about 0.5% by weight, based on the total weight of the composition. In further embodiments, the extract is present in an amount of about 0.1% to about 1% by weight, based on the total weight of the composition.
[0039] Processed Oat Ingredients As used herein, the term "processed oat ingredient" refers to an ingredient typically derived from a part of the oat plant (Avena sativa). The ingredient may be a processed (e.g., extracted, milled, fermented) (e.g., extracted) product of one or more parts of the oat plant (e.g., kernel, leaves, stems, seeds), or may be a molecule found in the oat plant (e.g., β-glucan, flavonoids, avenanthramides, lipids, peptides, etc.). This definition is intended to encompass processed oat ingredients derived from sources other than oat (e.g., derived from another plant or chemically synthesized), but otherwise related to oat. In one or more embodiments, the processed oat ingredient is selected from the group consisting of oat extract, colloidal oatmeal (used interchangeably with oat flour), oat bran, oat protein, oat peptides, oat oil, fermented oats, avenanthramides, β-glucan, modified oat kernel material (e.g., chemically, enzymatically, microbially modified), and combinations thereof. As used herein, "colloidal oatmeal" refers to a powder obtained from the grinding and further processing of whole grain oats that meet U.S. standards for first or second oats. The colloidal oatmeal has the following particle size distribution: no more than 3 percent of the total particles exceed 150 micrometers in size, and no more than 20 percent of the total particles exceed 75 micrometers in size. Examples of suitable colloidal oatmeal include, but are not limited to, "Tech-0" available from Beacon Corporation and colloidal oatmeal available from Quaker. In one or more embodiments, the processed oat ingredient comprises oat extract, colloidal oatmeal, and oat oil. In some embodiments, the processed oat ingredient comprises oat extract. In one or more embodiments, the processed oat ingredient comprises colloidal oatmeal. In some embodiments, the processed oat ingredient comprises oat oil. In some embodiments, the processed oat ingredient is selected from the group consisting of oat extract, colloidal oatmeal, oat oil, and combinations thereof.In some embodiments, the processed oat ingredient comprises oat extract, colloidal oatmeal, and oat oil. In one or more embodiments, the processed oat ingredient comprises avenanthramide. In some embodiments, the processed oat ingredient comprises fermented oats. In one or more embodiments, the processed oat ingredient comprises β-glucan. In some embodiments, the oat extract is free or substantially free of protein.
[0040] In a further embodiment, the processed oat ingredient is selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof. In yet a further embodiment, the processed oat ingredient is selected from the group consisting of fermented oats, colloidal oats, oat extract, and combinations thereof.
[0041] The processed oat ingredient may be present in an amount ranging from about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 0.75, 1, 1.5, or 2 to about 0.05, 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight. In one or more embodiments, the processed oat ingredient may be present in an amount ranging from about 0.001 to about 10% by weight. In further embodiments, the processed oat ingredient may be present in an amount ranging from about 0.01 to about 8% by weight. In one or more embodiments, the processed oat ingredient may be present in an amount ranging from about 0.1 to about 6% by weight. In further embodiments, the processed oat ingredient may be present in an amount ranging from about 0.2 to about 5% by weight.
[0042] In embodiments where the processed oat component comprises colloidal oats, the colloidal oats may be present in an amount ranging from about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 0.75, 1, 1.5, or 2 to about 0.05, 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight. In one or more embodiments, the colloidal oats may be present in an amount ranging from about 0.001 to about 10% by weight. In further embodiments, the colloidal oats may be present in an amount ranging from about 0.01 to about 8% by weight. In one or more embodiments, the colloidal oats may be present in an amount ranging from about 0.1 to about 5% by weight. In further embodiments, colloidal oats may be present in an amount ranging from about 0.5 to about 4% by weight. In one or more embodiments, colloidal oats may be present in an amount ranging from about 0.5 to about 2% by weight, or about 1% by weight. In further embodiments, colloidal oats may be present in an amount ranging from about 2 to about 4% by weight, or about 3% by weight.
[0043] In embodiments where the processed oat component comprises fermented oats, the fermented oats may be present in an amount ranging from about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 0.75, 1, 1.5, or 2 to about 0.05, 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight. In one or more embodiments, the fermented oats may be present in an amount ranging from about 0.001 to about 10% by weight. In further embodiments, the fermented oats may be present in an amount ranging from about 0.01 to about 8% by weight. In one or more embodiments, the fermented oats may be present in an amount ranging from about 0.1 to about 6% by weight. In further embodiments, the fermented oats may be present in an amount ranging from about 0.5 to about 5% by weight.
[0044] In embodiments where the processed oat ingredient comprises oat extract, the oat extract may be present in an amount ranging from about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 0.75, 1, 1.5, or 2 to about 0.05, 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight. In one or more embodiments, the oat extract may be present in an amount ranging from about 0.001 to about 10% by weight. In further embodiments, the oat extract may be present in an amount ranging from about 0.01 to about 8% by weight. In one or more embodiments, the oat extract may be present in an amount ranging from about 0.1 to about 5% by weight. In further embodiments, the oat extract may be present in an amount ranging from about 0.5 to about 4% by weight.
[0045] method Another aspect of the present invention relates to a method for treating skin, the method comprising topically applying to the skin a composition according to another embodiment of the present invention. As used herein, "treatment" or "treating" refers to the improvement, prevention, or amelioration of a condition, disease, or disorder, or at least one discernible symptom thereof. In one embodiment, "treatment" or "treating" refers to the improvement, prevention, or amelioration of at least one measurable physical parameter associated with the condition, disease, or disorder being treated, which is not necessarily discernible in or by the subject being treated. In another embodiment, "treatment" or "treating" refers to inhibiting or slowing the progression of the condition, disease, or disorder, either physically (e.g., stabilization of discernible symptoms), physiologically (e.g., stabilization of physical parameters), or both. In another embodiment, "treatment" or "treating" refers to delaying the onset of the condition, disease, or disorder.
[0046] The compositions / compounds described herein may be used to treat skin to treat acne, treat signs of aging (e.g., wrinkles), improve skin barrier function, and / or lighten skin. In one or more embodiments, the treatment is for subjects with 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.
[0047] The compositions of the present invention are suitable for improving skin texture, or for improving skin firmness, or for improving any of the conditions / symptoms described below.
[0048] As used herein, "improving skin texture" means smoothing the surface of the skin to remove either bumps or crevices in the skin surface.
[0049] As used herein, "improving skin firmness" means enhancing skin firmness or elasticity, preventing loss of skin firmness or elasticity, or preventing or treating sagging, loose and lax skin.
[0050] As used herein, "loss of elasticity" includes loss of elasticity or structural integrity of skin or tissue, including, but not limited to, sagging, loose, and flaccid tissue. Loss of elasticity or structural integrity of tissue can be the result of many factors, including, but not limited to, disease, aging, hormonal changes, mechanical trauma, environmental damage, or the application of products, such as cosmetics or pharmaceuticals, to the tissue.
[0051] As used herein, "uneven skin" means a skin condition associated with diffuse or patchy pigmentation that can be classified as hyperpigmentation, such as post-inflammatory hyperpigmentation.
[0052] As used herein, "plaque" means a skin condition associated with redness or erythema.
[0053] As used herein, "age spots" means a skin condition associated with discrete pigmentation, e.g., small areas of darker pigmentation that can occur on the face and hands.
[0054] Signs of skin aging also include a decrease in skin thickness and the presence of abnormal or decreased synthesis of glycoproteins, including collagen, glycosaminoglycans, proteoglycans, elastin, or fibronectin. In one embodiment, the sign of aging is selected from abnormal or decreased synthesis of glycoproteins, including collagen, glycosaminoglycans, proteoglycans, elastin, or fibronectin. In another embodiment, the sign of skin aging is decreased synthesis of collagen or elastin.
[0055] The example of skin aging that can be treated by topical use of the composition of the present invention includes, but is not limited to, skin wrinkles.As used herein, the term "wrinkles" includes fine lines, fine wrinkles, coarse wrinkles, cellulite, scars and stretch marks.Examples of wrinkles include, but are not limited to, the fine lines around the eyes (for example, "crow's feet"), wrinkles on the forehead and cheeks, wrinkles between the eyebrows, and age lines around the mouth.
[0056] As used herein, "topical use" or "topically applying" means to paint or spread directly onto the skin, hair, or nails, for example, by using an applicator such as the hand or a wipe.
[0057] The composition is also suitable for treating or preventing acne.As used herein, "acne" refers to a disorder that results from the action of hormones and other substances on sebaceous glands and hair follicles, and typically leads to the formation of clogged pores and inflammatory or non-inflammatory lesions on the skin.In particular, this relates to blemishes, lesions, or pimples, pre-emergent pimples, blackheads, and / or whiteheads.As used herein, "pre-emergent pimples" are inflammatory vesicles that are not visually apparent to the naked eye (e.g., as lesions) on the surface of the skin.
[0058] The compositions of the present invention are also suitable for treating or preventing rosacea. As used herein, "rosacea" means skin with persistent erythema, with or without papules, pustules, or nodules.
[0059] The compositions of the present invention are also suitable for reducing hyperkeratinization of the epidermis and can therefore be used to treat or prevent conditions characterized by hyperkeratinization, such as acne or warts.
[0060] In one or more embodiments, one or more of the methods described herein alter the expression of one or more biomarkers. For example, in one or more embodiments, the method can be a method of increasing CRABP2, HAS2, or HBEGF expression in the skin.
[0061] The embodiments described herein can be combined in any suitable combination. For example, exemplary embodiments include methods for treating acne, signs of aging, and / or skin lightening. (a) an extract of Acronychia acidula and / or 3-(4-farnesyloxyphenyl)-propionic acid, (b) a processed oat component selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof; The composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid cleanser, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product. In yet further embodiments, the processed oat component is selected from fermented oats, colloidal oats, oat extract, and combinations thereof. In yet further embodiments, the processed oat component is selected from fermented oats, colloidal oats, and combinations thereof. The 3-(4-farnesyloxyphenyl)-propionic acid can be chemically synthesized, naturally occurring in a plant extract, or chemically synthesized and added to the plant extract. In one or more embodiments, the applying step comprises applying to the skin a composition comprising a plant extract that is an extract of a plant of the genus Acronichia. In a further embodiment, the plant extract is an extract of Acronichia acidula. In a still further embodiment, the extract is a polar extract. 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 0.4% to about 1.5% by weight, based on the total weight of the composition.
[0062] The compositions described herein can be applied to any skin in need of treatment in the human body. For example, they can be applied to any one or more of the skin on the face, neck, chest, back, arms, armpits, hands, and / or feet. In certain preferred embodiments, the method comprises applying a composition according to one or more embodiments of the present invention to facial skin.
[0063] Any suitable method of applying the extract to skin in need can be used in accordance with the present invention.For example, the extract can be applied directly from the package to the skin in need, can be applied by hand to the skin in need, can be transferred from a substrate such as a wipe or mask, or can be a combination of two or more of these.In other embodiments, the extract can be applied via a dropper, tube, roller, spray, patch, or can be added to water that is to be bathed or otherwise applied to the skin.
[0064] In one or more embodiments, the method of the present invention further comprises the step of contacting the composition with the skin for a period of time. For example, in certain preferred embodiments, the compound is contacted with the skin for about 15 minutes or more after application. In certain more preferred embodiments, the extract is contacted with the skin for about 20 minutes or more, more preferably about 1 hour or more.
[0065] In some embodiments, the methods of the present invention include a regimen 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.
[0066] composition Any suitable carrier can be used in the compositions of the present invention. Preferably, in skin care compositions, the carrier is a cosmetically acceptable carrier. As will be recognized by those skilled in the art, a cosmetically acceptable carrier includes a carrier suitable for use in contact with the body, particularly the skin, for anti-aging applications without undue toxicity, incompatibility, instability, irritation, allergic reaction, etc. A safe and effective amount of carrier is 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 in a wide variety of forms. For example, emulsion carriers are useful herein, including, but not limited to, oil-in-water, water-in-oil, water-in-oil-in-water, and oil-in-water-in-silicone emulsions. These emulsions may cover a wide range of viscosities, for example, from about 100 cP to about 200,000 cP. Examples of suitable cosmetically acceptable carriers include cosmetically acceptable solvents and materials for cosmetic solutions, suspensions, lotions, creams, serums, essences, gels, toners, sticks, sprays, ointments, cleansing solutions and bar soaps, shampoos, hair conditioners, pastes, foams, mousses, powders, shaving creams, wipes, patches, strips, powered patches, microneedle patches, bandages, hydrogels, film-forming products, facial and skin masks, make-up, liquid 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, serum, gel, stick, spray, ointment, liquid wash, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.
[0067] The following are non-limiting examples of such carriers. Other carriers can be formulated by those skilled in the art. In one embodiment, the carrier comprises water. In a further embodiment, the carrier may further comprise one or more aqueous or organic solvents. Examples of organic solvents include, but are not limited to, dimethyl isosorbide; isopropyl myristate; cationic, anionic, and nonionic surfactants; vegetable oils; mineral oils; waxes; gums; synthetic and natural gelling agents; alkanols; glycols, and polyols. Examples of glycols include, but are not limited to, glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, diethylene glycol, triethylene glycol, capryl glycol, glycerol, butanediol, and hexanetriol, as well as copolymers or mixtures thereof. Examples of alkanols include, but are not limited to, those 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 isopropanol and ethanol. Examples of polyols include, but are not limited to, those having from about 2 carbon atoms to about 15 carbon atoms (e.g., from about 2 carbon atoms to about 10 carbon atoms), such as propylene glycol. The organic solvent may be present in the carrier in an amount of from about 1 percent to about 99.99 percent (e.g., from about 20 percent to about 50 percent) based on the total weight of the carrier. Water may be present in the carrier (prior to use) in an amount of from about 5 percent to about 95 percent (e.g., from about 50 percent to about 90 percent) based on the total weight of the carrier. The solution can contain any suitable amount of solvent, including from about 40 to about 99.99%. Particularly preferred solutions contain from 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 about 99%.
[0068] A lotion can be made from such a solution. Lotions typically contain at least one emollient in addition to a solvent. A lotion may contain about 1% to about 20% (e.g., about 5% to about 10%) of an emollient and about 50% to about 90% (e.g., about 60% to about 80%) of water. As used herein, "emollient" refers to a material used to prevent or reduce dryness and to protect the skin or hair. Examples of emollients include, but are not limited to, those listed in the International Cosmetic Ingredient Dictionary and Handbook, eds. Wenninger and McEwen, pp. 1656-61, 1626, and 1654-55 (The Cosmetic, Toiletry, and Fragrance Assoc., Washington, DC, 7th Edition, 1997) (hereinafter, "ICI Handbook").
[0069] Another type of product that can be formulated from a solution is a cream, which typically contains about 5% to about 50% (e.g., about 10% to about 20%) emollient and about 45% to about 85% (e.g., about 50% to about 75%) water.
[0070] Yet another type of product that can be formulated from a solution is an ointment. Ointments can contain a simple base of animal, vegetable, or synthetic oils, or semi-solid 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.
[0071] The compositions useful in the present invention can also be formulated as emulsions. When the carrier is an emulsion, about 1% to about 10% (e.g., about 2% to about 5%) of the carrier contains an emulsifier. The emulsifier may be nonionic, anionic, or cationic. Examples of emulsifiers include, but are not limited to, those listed on pages 1673 to 1686 of the ICI Handbook.
[0072] Lotions and creams can be formulated as emulsions. Such lotions typically contain 0.5% to about 5% emulsifier, and such creams typically contain about 1% to about 20% (e.g., about 5% to about 10%) emollient, about 20% to about 80% (e.g., about 30% to about 70%) water, and about 1% to about 10% (e.g., about 2% to about 5%) emulsifier.
[0073] Single-phase emulsion skin care formulations, such as lotions and creams, of the oil-in-water and water-in-oil types, are well known in the art and are useful in the present invention. Multiphase emulsion compositions, such as water-in-oil-in-water or oil-in-water-in-oil types, are also useful in the present invention. Generally, such single-phase or multiphase emulsions contain water, emollients, and emulsifiers as essential ingredients.
[0074] The compositions of the present invention can also be formulated as gels (e.g., aqueous, alcohol, alcohol / water, or oil gels using a suitable gelling agent). Suitable gelling agents for aqueous and / or alcoholic gels include, but are not limited to, natural gums, acrylic acid and acrylate polymers and copolymers, and cellulose derivatives (e.g., hydroxymethylcellulose and hydroxypropylcellulose). 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 about 5% by weight of such gelling agents.
[0075] The compositions of the present invention can also be formulated into solid preparations (e.g., wax-based sticks, bar soap compositions, powders, or wipes). The compositions of the present invention can also be combined with solid, semi-solid, or soluble substrates (e.g., wipes, masks, pads, gloves, or strips).
[0076] The compositions of the present invention may further comprise any of a variety of additional cosmetic active agents, which are preferably formulated for use on the skin. Examples of suitable additional active agents include additional skin whitening agents, tanning agents, anti-acne agents, gloss regulators, antimicrobial agents (e.g., anti-yeast, anti-fungal, and anti-bacterial agents), anti-inflammatory agents, anti-parasitic agents, external analgesics, sunscreens, photoprotective agents, antioxidants, keratolytic agents, detergents / surfactants, moisturizers, nutrients, vitamins, energy enhancers, antiperspirants, skin astringents, deodorants, hair removal agents, hair growth enhancers, hair growth retardants, stabilizers, hydration enhancers, efficacy enhancers, anti-callus agents, skin conditioning agents, anti-cellulite agents, fluorides, tooth whitening agents, anti-tartar agents, and tartar dissolving agents, malodor inhibitors (e.g., malodor masking agents), or pH modifiers.Examples of various suitable additional cosmetically acceptable actives include hydroxy acids, benzoyl peroxide, D-panthenol, UV filters, including, but not limited to, avobenzone (Parsol 1789), bisdisulizole disodium (Neo Heliopan AP), diethylaminohydroxybenzoyl hexylbenzoate (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), trolamine salicylate, bemotrizinol (Tinosorb S), benzophenone 1-12, dioxybenzone, drometrizole trisiloxane (Mexoryl XL), iscotrizinol (Uvasorb HEB), octocrylene, oxybenzone (Eusolex 4360), sulisobenzone, bisoctrizole (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 estrogen, steroids such as hydrocortisone, 2-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 coenzyme A, niacin, riboflavin, thiamine, ribose, electron transporters such as NADH and FADH2, and other plant extracts such as oat, aloe vera, feverfew, soybean, and shiitake mushroom extracts, and derivatives and mixtures thereof.
[0077] In one or more embodiments, the compositions of the present invention are skin care compositions 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, melanosome transfer inhibitors (including PAR-2 antagonists), exfoliants, sunscreens, retinoids, antioxidants, tranexamic acid, skin whitening agents, allantoin, opacifiers, talc and silica, zinc salts, and the like, as well as other agents described in Solano et al. Pigment Cell Res. 2006, 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, flavones (e.g., licorice flavanoids, licorice root extract, mulberry root extract, Dioscorea Coposita root extract, Saxifragaceae extract, etc.), ellagic acid, salicylate and derivatives, glucosamine and derivatives, fullerenes, hinokitiol, diacids, acetylglucosamine, magnolignans, combinations of two or more thereof, etc. Examples of vitamin C derivatives include, but are not limited to, ascorbic acid and its salts, ascorbic acid-2-glucoside, sodium ascorbyl phosphate, magnesium ascorbyl phosphate, and vitamin C-rich natural extracts. Examples of derivatives of vitamin E 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 enriched with vitamin E derivatives. Examples of resorcinol derivatives include, but are not limited to, resorcinol, 4-substituted resorcinols such as 4-butylresorcinol (rucinol), 4-hexylresorcinol, phenylethylresorcinol, 4-alkylresorcinols such as 1-(2,4-dihydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)-propane, and natural extracts enriched with 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 includes a 4-substituted resorcinol, a vitamin C derivative, or a vitamin E derivative. In more preferred embodiments, the tyrosinase inhibitor includes phenylethylresorcinol, 4-hexylresorcinol, or ascorbyl-2-glucoside.
[0078] Examples of suitable melanin degrading agents include, but are not limited to, peroxides and enzymes (e.g., peroxidase and ligninase). In certain preferred embodiments, melanin inhibitors include peroxides and ligninase.
[0079] Examples of suitable melanosome transfer inhibitors include PAR-2 antagonists (e.g., soybean trypsin inhibitor or Bowman-Birk inhibitor), vitamin B3 and derivatives (e.g., niacinamide), essential soybean, whole soybean, soybean extract. In certain preferred embodiments, the melanosome transfer inhibitor includes soybean extract or niacinamide.
[0080] Examples of exfoliants include, but are not limited to, alpha-hydroxy acids (e.g., lactic acid, glycolic acid, malic acid, tartaric acid, citric acid, or any combination of any of the foregoing), beta-hydroxy acids (e.g., salicylic acid, polyhydroxy acids such as lactobionic acid and gluconic acid), and mechanical exfoliants (e.g., microdermabrasions). In certain preferred embodiments, the exfoliant includes glycolic acid or salicylic acid.
[0081] Examples of sunscreens include avobenzone (Parsol 1789), bisdisulizole disodium (Neo Heliopan AP), diethylaminohydroxybenzoyl hexylbenzoate (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), trolamine salicylate, and bemotrizinol (Tinosorb S), benzophenone 1-12, dioxybenzone, drometrizole trisiloxane (Mexoryl XL), iscotrizinol (Uvasorb HEB), octocrylene, oxybenzone (Eusolex 4360), sulisobenzone, bisoctrizole (Tinosorb M), titanium dioxide, zinc oxide, and the like.
[0082] Examples of retinoids include, but are not limited to, retinol, retinaldehyde, retinoic acid, retinyl palmitate, tretinoin, tazarotene, bexarotene, and adapalene.In certain preferred embodiments, the retinoid is retinol.Nevertheless, in one or more embodiments, the composition is essentially free of retinoids or retinoid precursors, and in further embodiments, it is free of retinoids or retinoid precursors.
[0083] 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-acetyl-cysteine, glutathione), lipoic acid and dihydrolipoic acid, stilbenoids (e.g., resveratrol and derivatives), lactoferrin, and ascorbic acid and ascorbic acid derivatives (e.g., ascorbyl-2-glucoside, ascorbyl palmitate, and ascorbyl polypeptides). 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., tocopherol 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 isoflavonoids, and their derivatives (e.g., genistein and daidzein), extracts containing resveratrol, etc. Examples of such natural extracts include grape seed, green tea, pine bark, feverfew, parthenolide-free feverfew, oat extract, grapefruit extract, wheat germ extract, hesperidin, grape extract, purslane extract, licochalcone, chalcone, 2,2'-dihydroxychalcone, primrose extract, propolis, and the like.
[0084] The additional cosmetic active agent may be present in the composition in any suitable amount, such as from about 0.0001% to about 20% by weight of the composition, such as from about 0.001% to about 10% by weight, such as from about 0.01% to about 5% by weight, etc. In certain preferred embodiments, the amount is from 0.1% to 5%, and in other preferred embodiments, from 1% to 2%.
[0085] Various other materials may also be present in the compositions of the present invention, including, for example, chelating agents, moisturizing agents, opacifiers, conditioners, preservatives, fragrances, etc. The compositions may also include surfactants, such as those selected from the group consisting of anionic, nonionic, amphoteric, cationic, or combinations of two or more thereof.
[0086] The compositions of the present invention may further contain chelating agents (e.g., EDTA) and preservatives (e.g., parabens). Examples of suitable preservatives and chelating agents are listed on pages 1626 and 1654-55 of the ICI Handbook. Additionally, the compositions useful herein may contain conventional cosmetic adjuvants such as colorants, including dyes and pigments, opacifiers (e.g., titanium dioxide), and fragrances.
[0087] In certain preferred embodiments, the present invention comprises applying the compound or composition of the present invention through a substrate comprising such a material. Any suitable substrate can be used in the present invention. Examples of suitable substrates and substrate materials are disclosed in, for example, U.S. Patent Application Publication Nos. 2005 / 022683 and 2009 / 0241242, the entire contents of which are incorporated herein by reference. In certain preferred embodiments, the substrate is a wipe or a facial mask.
[0088] Compositions and products containing such compositions of the present invention can be prepared using methods well known to those skilled in the art. [Example]
[0089] The following examples evaluate various samples, including processed oat ingredients, lemon aspen extract, and combinations thereof. Some examples involve the evaluation of retinol-responsive genes, such as RARg, CRABP2, HbEGF, HAS2, and HAS3. Upregulation of these genes is associated with skin benefits provided by retinoids, such as anti-aging effects, wrinkle and acne reduction, and skin tone benefits. Some examples involve the evaluation of the gene for IL-8, an inflammatory mediator interleukin. IL-8 gene expression is associated with increased inflammation.
[0090] Example 1: Retinoic Acid Receptor-γ (RARg) Transactivation Assay with Lemon Aspen Extract Alone and in Combination with Colloidal Oats RARg agonism of several samples was assessed using the GENEBLAZER RARgamma-UAS-bla HEK 293T cell-based assay (Thermofisher, Waltham MA), in which activation of RARg leads to transcription of beta-lactamase. When a fluorescence resonance energy transfer (FRET) probe is added to the cells, FRET is observed. However, upon receptor activation and subsequent beta-lactamase expression, the probe is cleaved and FRET is no longer observed.
[0091] Cultured HEK293T cells were washed with phosphate-buffered saline (PBS), trypsinized, and resuspended in growth medium consisting of DMEM supplemented with GlutaMAX (Invitrogen, Waltham, MA), 10% fetal bovine serum (FBS), 0.1 mM non-essential amino acids (NEAA), 25 mM HEPES, 1X Penn / Strep (100 units Penn / 100 μg / mL Strep), 80 μg / mL hygromycin, and 80 μg / mL Zeocin, and then counted using a Vi-Cell cell counter (Breckman Coulter, Brea, CA). Cells were then spun down and resuspended (0.5E6 cells / mL) in assay buffer consisting of phenol red-free DMEM (Invitrogen), 2% charcoal-stripped FBS, 0.1 mM NEAA, 1 mM sodium pyruvate, and 1X Penn / Strep. Using a combi-dispenser, 15,000 cells were seeded per well in 30 μL of assay buffer in a Greiner black-walled, clear, flat-bottom plate. The last two columns were filled with assay buffer. A 30% stock solution of lemon aspen extract, containing 45% polysorbate 20, 21.5% water, and 3.5% butylated hydroxytoluene (Southern Cross Botanicals, Knockrow, NSW, Australia), was diluted 1:30 with medium to make 1% lemon aspen extract in solution. The 1% lemon aspen extract solution was further diluted with medium to give a final concentration (5 × 10 -5 )%, (1.5×10 -4 )%, (4.5×10 -4 )%, (1.4×10 -3 )%, (4.15×10 -3 )%, and (1.25 × 10 -2A concentration of 1.65% lemon aspen extract was prepared. The Acronychia acidula fruit extract used in the examples typically contains approximately 1% to 10% 3-(4-farnesyloxyphenyl)-propionic acid; these samples contain 1.11% 3-(4-farnesyloxyphenyl)-propionic acid by weight of the extract in the carrier. Two hours before use, 100 mg of colloidal oats (Avena Sativa Kernel Flour, Oat Cosmetics, Southampton, United Kingdom) was dissolved in 1.0 mL of medium for a 10% colloidal oat concentration. The 10% colloidal oat solution was then sonicated for 10 minutes and centrifuged for 5 minutes. The colloidal oat solution was further diluted to prepare a 1.65% colloidal oat solution. Ten microliters of test sample was added to the cells to achieve the final concentrations listed in Table 1. The cells were spun down at 800 rpm for 2 minutes without the brake, left at room temperature for 15 minutes, and then incubated at 37°C overnight.
[0092] After 18–20 h of incubation, 8 μL of FRET dye (Invitrogen, K1096) was added using a liquid dispenser sold under the trade name TEMPEST Dispenser (FORMULATRIX, Bedford, MA). The plate was then spun down at 800 rpm for 2 min without the brake and incubated in the dark at room temperature for 2 h. The plate bottom was then cleaned with an antistatic cleaning wipe, and fluorescence was measured using a BMG PHERSTAR (Cary, NC) plate reader (using the FRET module, 10 reads, gain = 1000 for both channels, Ex 409, Em1 460, Em2 530). The average Em1 and Em2 values from assay buffer-only wells were subtracted from the test Em1 and Em2 values, respectively, and subsequent determination of the Em1 / Em2 ratio represented RARg activity. Dimethyl sulfoxide (DMSO) and all-trans retinoic acid (ATRA) were used as neutral and stimulatory controls, respectively, for normalization.
[0093] The combination of colloidal oats and lemon aspen extract was tested for RARg activity in a dose-response format with lemon aspen extract. In the presence of lemon aspen extract, colloidal oats significantly enhanced RARg activity. The results are shown in Table 1 below and graphically in Figure 1. Surprisingly, the results showed that colloidal oats enhanced the retinoid bioactivity of lemon aspen extract. This result is surprising given that oats are not generally known for activating the RARg gene.
[0094] [Table 1]
[0095] Example 2: CRAPB2, IL8 and HAS2 Bioactivity Assays of Fermented Oat and Lemon Aspen Extracts Alone and in Combination in Human Dermal Fibroblasts CRAPB2, IL8, and HAS2 were evaluated in several samples containing various amounts of fermented oats, lemon aspen extract, and a combination of the two. Lemon aspen extract, a 30% stock solution (Southern Cross Botanicals, Knockrow, NSW, Australia, as above) was diluted in DMEM (Dulbecco's Modified Eagle's Medium) containing GlutaMAX medium supplemented with 1% FBS (fetal bovine serum) and 1x Penn / Strep, and incubated at 4°C for 6 hours (6 x 10 -4 )% and (6×10 -5 )% lemon aspen extract. Fermented oats (aurafirm P, Oat Cosmetics, Hampshire, United Kingdom) were diluted with culture medium to obtain 0.2% and 1.0% fermented oat solutions. 100 μL of each test solution was added to each well to achieve the final concentrations listed in Tables 2-4 below.
[0096] Primary human dermal fibroblasts were obtained from Lifeline Cell Technology, LLC (Frederick, MD 21701, Lot 0967). The donor demographics were as follows: 18-year-old, female, Caucasian, fibroblasts isolated from breast tissue. Fibroblasts were cultured and expanded using dermal fibroblast culture medium (Zenbio, Inc., Durham, NC 27713). In preparation for the experiment, fibroblasts were seeded at a concentration of 10,000 cells / well in 96-well plates. Cells were treated with DMEM medium containing GlutaMAX supplemented with 1% FBS and 1x Penn / Strep 6-24 hours after seeding. Thirty hours after treatment, RNA was isolated and converted to cDNA using a Cell-to-CT kit (Invitrogen, Waltham, MA) according to the manufacturer's instructions. The cDNA was evaluated by qPCR (using the QuantStudio™ 7 Flex Real-Time PCR System from Applied Biosystems, Waltham, MA). Gene expression assays for cellular retinoic acid binding protein 2 (CRABP2), interleukin-8 (IL8), and polymerase (RNA) II polypeptide A (POLR2A) sold under the trade name TAQMAN (ThermoFisher Scientific, Bridgewater, NJ) were used. Expression of these genes was normalized to the expression of the human POLR2A housekeeping gene. Fold changes were calculated relative to the untreated control, and a two-tailed, two-sample Student's t-test (Microsoft Office Excel 2007, Microsoft, Redmond, WA, USA) was performed. Synergy calculations were performed as follows: Briefly, the resulting fold changes relative to the untreated control for each component alone were summed, and a 1-fold change was subtracted to account for the contribution of the untreated control. If the result was less than the bioactivity obtained as a result of the combination of ingredients, it was considered synergistic because the result was greater than the sum of its parts. Results are presented in Tables 2-4 as the mean fold change relative to untreated.
[0097] Table 2
[0098] Table 3
[0099] Table 4
[0100] With regard to CRABP2, fermented oats and lemon aspen extract not only complemented each other in terms of bioactivity, but surprisingly also synergistically, with the most pronounced synergy observed for fermented oats combined with lemon aspen extract in samples 2-7, 2-8, and 2-9. CRABP2 is well established in the literature as a 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;100(4)) and is associated with conferring anti-aging benefits on 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 skin aging. Aging (Albany NY). 2019 Mar 18;11(6):1619-1632). This data indicates that the combination of these two ingredients results in a synergistic increase in retinol-like properties and therefore anti-aging benefits. In this example, all synergistic results were statistically significant.
[0101] Similarly, a decrease in synergy with respect to IL8 was observed in most combinations, particularly in samples 2-6, 2-7, and 2-8. Retinoids are known to cause irritation and stinging upon application, which is considered to induce IL8 in vitro. Therefore, a reduction in IL8 corresponds to the clinical outcome of less irritation. The results showed that although the combinations resulted in increased retinol-like activity, it did so without the same degree of inflammatory side effects.
[0102] HAS2 is a hyaluronan synthase gene that produces hyaluronan, which is associated with skin moisturization and plumpness and is indirectly induced by retinol. Skin plumpness provides anti-aging or a youthful appearance. The sample did not exhibit the same hyaluronan synthase-driven moisturizing synergy as CRABP2 and IL8.
[0103] Example 3: Bioactivity assay of CRABP2 and IL8 in human skin fibroblasts (variety of oat and lemon aspen) CRAPB2 and IL8 were evaluated in response to treatment with several types of processed oat products, lemon aspen extract, and various amounts of the two in combination. Fermented oat test samples were prepared as described in Example 2. 2 hours before use, 100 mg of colloidal oats (oat grain flour, Oat Cosmetics, Southampton, United Kingdom) was dissolved in 1.0 mL of medium to achieve a 10% concentration. The 10% oat solution was then sonicated for 10 minutes and centrifuged for 5 minutes. The colloidal oat solution was further diluted to prepare 0.02%, 0.2%, and 1% solutions. Oat oat kernel extract (0.55% oat kernel extract, 25% glycerin, 25% water) (Dragocalm®, Symrise, Holzminden, Germany) was diluted to prepare 0.01%, 0.1%, and 0.5% solutions in medium. 100 μL of each test solution was added to each well to achieve the final concentrations listed below in Tables 5-6. Results are shown in Tables 5-6 as the mean fold change relative to untreated.
[0104] [Table 5]
[0105] [Table 6]
[0106] The results show that all three forms of oats, colloidal oats, fermented oats, and oat extract, when combined with lemon aspen extract, synergistically increased retinoid activity as measured by CRABP2. Again, such synergy is highly advantageous since CRABP2 is a biomarker associated with anti-aging effects.
[0107] Example 4: Bioactivity assay of CRABP2, HBEGF, IL8, and HAS3 in whole tissue of human skin explants for samples containing fermented oat and lemon aspen extracts alone and in combination Propylene glycol / ethanol (PGEtOH) (3:7) (w / w) was used as the vehicle. As previously described, lemon aspen extract and fermented oat material were diluted with PGEtOH to the concentrations shown in Tables 7-10. Combinations were prepared by adding the appropriate amount of test solution to reach the final concentrations shown.
[0108] Abdominal skin samples were obtained from adult humans 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 2 Skin biopsies were prepared under sterile conditions and conditioned 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, and 1x ABAM in a humidified 5% CO atmosphere. Skin explants were treated topically with 4 μL of each formulation for 48 hours.
[0109] At the end of the 48-hour incubation, the skin biopsies were cut in half, and either one half 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) and 1 part 2-mercaptoethanol in a reinforced tube with a screw cap and O-ring closure and ceramic tissue grinding beads (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 the RNA was eluted in 30 μL of RNase-free water.
[0110] Reverse transcription (RT) was performed using the Applied Biosystems High Capacity Reverse Transcription Kit (ThermoFisher Scientific, Bridgewater, NJ). Gene expression assays for cellular retinoic acid-binding protein 2 (CRABP2), heparin-binding epidermal growth factor (HbEGF), hyaluronan 15 synthase 3 (HAS3), interleukin-8 (IL8), polymerase (RNA) II polypeptide A (POLR2A), 18S rRNA (18S), and TATA box-binding protein (TBP) sold under the trade name TAQMAN and the master mix sold under the trade name TAQMAN (ThermoFisher Scientific, Bridgewater, NJ). qPCR analysis was performed using the TAQMAN master mix and run on a real-time PCR system sold under the trade name QUANTSTUDIO 7 Flex System (ThermoFisher Scientific, Bridgewater, NJ). The expression of these genes was normalized to the expression of human POLR2A or to the expression of human 18S rRNA or TBP "housekeeping" genes. These "housekeeping" genes are widely used as controls to normalize specific gene expression levels because their expression is invariant across tissues, cells, and experimental treatments. Methods for normalization include measuring the expression of an internal reference gene or "housekeeping" gene to account for potential errors in RNA / cDNA loading and variations in reverse transcription efficiency. Fold changes were calculated relative to untreated or vehicle controls, and a two-tailed, two-sample Student's t-test (Microsoft Office Excel 2007, Microsoft, Redmond, WA, USA) was performed. Synergy was calculated as described above. Results are presented in Tables 7-10 as the mean fold change relative to untreated.
[0111] [Table 7]
[0112] [Table 8]
[0113] [Table 9]
[0114] [Table 10]
[0115] As can be seen from the results above for Samples 4-11 through 4-14, fermented oats, when combined with lemon aspen extract, synergistically increased retinoid activity as measured by CRABP2, HAS3, and HBEGF, biomarkers associated with anti-aging benefits. Sample 4-12 showed a synergistic decrease in IL-8.
[0116] Example 5: Bioactivity assays of CRABP2, HBEGF, IL8, and HAS3 in human skin explants for samples containing colloidal oat and lemon aspen extracts alone and in combination Bioactivity assays were performed according to the method described in Example 4, except that topically treated explants were cut in half before harvesting (normalized to TBP). One half of each tissue was used to measure gene expression levels in whole tissue, while the other half was separated into its dermis and epidermis by placing it in a tube containing 100 μL of water at 60°C. After 50 seconds of contact, the epidermis was peeled from the dermis and transferred separately to hard tissue homogenizer Ozyme CK28 tubes (Bertin Corp, Rockville, MD) containing ceramic beads, 400 μL of RLT buffer, and 4 μL of beta-mercaptoethanol and placed on ice. For dermal material, 10 μL of proteinase K was added to each tube, mixed, and incubated at 55°C for 2 hours. Gene expression was tested using whole tissue and skin tissue. Dermal tissue made from fibroblasts (as opposed to epidermal tissue made from keratinocytes) compares more accurately with the data obtained with primary fibroblast cultures shown in Example 2. Lemon aspen extract test samples were prepared as described in Example 4. Colloidal oats (oat flour) were dissolved in PgETOH to prepare 1% and 3% solutions. Combinations were prepared by adding the appropriate amount of test solution to reach the final concentrations shown below. Mean fold changes and synergy were calculated as described above. Results are shown in Tables 11-18 as mean fold changes relative to untreated.
[0117] [Table 11]
[0118] [Table 12]
[0119] [Table 13]
[0120] [Table 14]
[0121] [Table 15]
[0122] [Table 16]
[0123] [Table 17]
[0124] [Table 18]
[0125] Example 5 uses a human skin explant model to verify ex vivo synergy, with doses used more closely reflecting in vivo dose usage.
[0126] HBEGF induction was statistically significant compared to untreated for all oat + lemon aspen extract combinations, except for 3% colloidal oat + 0.25% lemon aspen extract, in all tissues. 1% colloidal oat + 0.25% lemon aspen extract was also comparable to 2% lemon aspen extract. In the dermis, HBEGF induction was statistically significant compared to untreated for all oat + LA combinations, except for 1% colloidal oat + 0.25% lemon aspen extract. These results were consistent with the fibroblast data above.
[0127] The combination of 1% colloidal oats and lemon aspen extract showed statistically significant induction of CRABP2 in all tissues compared to untreated. There was no statistically significant difference between treatments for CRABP2 in the dermis. CRABP2 was unchanged compared to untreated, indicating a lower sensitivity or response in this particular marker as opposed to the whole tissue.
[0128] IL8 also showed no significant induction in response to either treatment compared to untreated, further highlighting the mild nature of these components and combinations. The IL8 data showed too much variability to determine synergy, as observed by the high level of standard deviation.
[0129] 1% colloidal oats + 0.25% lemon aspen extract and 3% colloidal oats + 0.5% lemon aspen extract showed statistically significant induction of HAS3 in all tissues compared to untreated. Additionally, 1% colloidal oats + 0.25% lemon aspen extract showed statistically significant induction of HAS3 in all tissues over 0.25% lemon aspen extract.
[0130] In the dermis, 0.25% lemon aspen extract had equivalent induction of HAS3 as 1% and 2% lemon aspen extract. Additionally, 3% colloidal oats plus 0.5% lemon aspen extract had statistically significantly greater induction of HAS3 when compared to 0.5% lemon aspen extract alone.
[0131] [Embodiment] (1) A skin care composition comprising: a. Formula I:
[0132] [ka] A compound of the formula: R1 is C1~C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20selected from the group consisting of alkynyl, and C3-C8 cycloalkyl or aryl; R2 is selected from the group consisting of hydrogen, hydroxyl, 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 -CO2H, -CO2R4, or an isosteric equivalent of a carboxy group, and R4 is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, or aryl; Y is,
[0133] [ka] a compound of formula I, or a cosmetically acceptable salt thereof; b. A skin care composition comprising a processed oat ingredient. (2) R1 is 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 where R4 is C1-C6 alkyl, or an isosteric equivalent of a carboxy group; and Y is -(CH2-CH2)- or -(CH=CH)-. (3) R1 is C5~C 163. The skin care composition of embodiment 1 or 2, wherein R is selected from the group consisting of -C1-C3 alkyl, -C1-C3 alkyl, and R2 is selected from the group consisting of -C1-C3 alkyl. (4) The skin care composition of any one of embodiments 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 of any one of embodiments 1 to 4, wherein the compound of Formula I is 3-(4-farnesyloxyphenyl)-propionic acid.
[0134] (6) The skin care composition of any one of embodiments 1 to 5, wherein the concentration of the compound of formula I is present in an amount ranging from about 0.00001% to 10% by total weight of the composition. (7) The skin care composition of any one of embodiments 1 to 6, wherein the skin care composition comprises a plant extract containing the compound of formula I. (8) The skin care composition of any one of embodiments 1 to 7, wherein the plant extract comprises an extract of a plant of the genus Acronychia. (9) The skin care composition of any one of embodiments 1 to 8, wherein the plant extract is an extract of Acronychia acidula. (10) The skin care composition of any one of embodiments 1 to 9, wherein the plant extract is a polar extract.
[0135] (11) The skin care composition of any one of the preceding claims, wherein the plant extract is present in an amount ranging from about 0.00001% to about 5% by weight of the total composition. (12) The skin care composition of any one of embodiments 1 to 11, wherein the extract of Acronychia acidula comprises 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 0.1% to about 30% based on the total weight of the extract. (13) The skin care composition of any one of the preceding claims, wherein the processed oat ingredient is selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof. (14) The skin care composition of any one of embodiments 1 to 13, further comprising an ingredient selected from the group consisting of a surfactant, a chelating agent, an emollient, a moisturizer, a conditioner, a preservative, an opacifier, a fragrance, and combinations of two or more thereof. (15) The skin care composition of any one of the preceding embodiments, wherein the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid cleanser, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.
[0136] (16) The skin care composition of any one of embodiments 1 to 15, wherein the compound of Formula I is 3-(4-farnesyloxyphenyl)-propionic acid, and the processed oat ingredient is selected from the group consisting of fermented oats, oat extract, colloidal oats, and combinations thereof. (17) A method for treating skin, comprising topically applying a composition according to any one of embodiments 1 to 16. (18) The method according to embodiment 17, wherein the method is a method for treating signs of aging, treating acne, smoothing skin texture, or lightening the skin. (19) The method according to embodiment 17 or 18, wherein the method is a method for increasing CRABP2 expression. (20) A skin care composition comprising: a. 3-(4-farnesyloxyphenyl)-propionic acid, b. a processed oat component selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof; A skin care composition, wherein the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid wash, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.
Claims
1. 1. A skin care composition comprising: Formula I: 【Chemistry 1】 A compound of the formula: R 1 But C 1 ~C 20 Alkyl, C 2 ~C 20 Alkenyl, C 2 ~C 20 Alkynyl, and C 3 ~C 8 selected from the group consisting of cycloalkyl or aryl; R 2 is hydrogen, hydroxyl, C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 3 ~C 8 cycloalkyl or aryl, —OC 1 ~C 6 Alkyl, —OC 2 ~C 6 Alkenyl, —OC 2 ~C 6 Alkynyl, —OC 3 ~C 8 Cycloalkyl or aryl, thiol, —SC 1 ~C 6 Alkyl, -SC 2 ~C 6 Alkenyl, -SC 2 ~C 6 Alkynyl, -SC 3 ~C 8 cycloalkyl or aryl, —NR 4 C 1 ~C 6 Alkyl, —NR 4 C 2 ~C 6 Alkenyl, —NR 4 C 2 ~C 6 Alkynyl, and —NR 4 C 3 ~C 8 selected from the group consisting of cycloalkyl or aryl; R 3 But -CO 2 H, -CO 2 R 4 or an isosteric equivalent of a carboxy group; R 4 But C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 3 ~C 8 cycloalkyl or aryl; Y is, 【Chemistry 2】 A compound of formula I, or a cosmetically acceptable salt thereof; b. a processed oat ingredient.
2. R 1 But C 5 ~C 16 Alkyl, C 5 ~C 16 Alkenyl, and C 5 ~C 16 alkynyl; R 2 is hydrogen, hydroxyl, -OC 1 ~C 6 Alkyl, —OC 2 ~C 6 Alkenyl, —OC 2 ~C 6 Alkynyl, —OC 3 ~C 8 cycloalkyl; R 3 But -CO 2 H, R 4 is C 1 ~C 6 -CO, which is alkyl 2 R 4 or an isosteric equivalent of a carboxy group, and Y is selected from -(CH 2 -CH 2 2. The skin care composition of claim 1, wherein the aryl group is -(CH═CH)- or -(CH═CH)-.
3. R 1 But C 5 ~C 16 alkenyl; R 2 is hydrogen or -OC 1 ~C 3 3. The skin care composition of claim 1, wherein the alkyl group is selected from the group consisting of alkyl.
4. 2. The skin care composition of claim 1, 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. 2. The skin care composition of claim 1, wherein the compound of Formula I is 3-(4-farnesyloxyphenyl)-propionic acid.
6. 10. The skin care composition of claim 1, wherein the concentration of the compound of formula I is present in an amount ranging from about 0.00001% to 10% based on the total weight of the composition.
7. The skin care composition of claim 1 , wherein the skin care composition comprises a plant extract comprising the compound of Formula I.
8. The skin care composition of claim 1 , wherein the plant extract comprises an extract of a plant of the genus Acronychia.
9. 10. The skin care composition of claim 1, wherein the plant extract is an extract of Acronychia acidula.
10. The skin care composition of claim 1 , wherein the plant extract is a polar extract.
11. 10. The skin care composition of claim 1, wherein the plant extract is present in an amount ranging from about 0.00001% to about 5%, based on the total weight of the composition.
12. 10. The skin care composition of claim 1, wherein the extract of Acronychia acidula comprises 3-(4-farnesyloxyphenyl)-propionic acid at a concentration ranging from about 0.1% to about 30% based on the total weight of the extract.
13. 10. The skin care composition of claim 1, wherein the processed oat ingredient is selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof.
14. 10. The skin care composition of claim 1, further comprising an ingredient selected from the group consisting of surfactants, chelating agents, emollients, moisturizers, conditioners, preservatives, opacifiers, fragrances, and combinations of two or more thereof.
15. 10. The skin care composition of claim 1, wherein the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid cleanser, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.
16. 2. The skin care composition of claim 1, wherein the compound of Formula I is 3-(4-farnesyloxyphenyl)-propionic acid and the processed oat ingredient is selected from the group consisting of fermented oats, oat extract, colloidal oats, and combinations thereof.
17. 10. A method for treating skin comprising topically applying the composition of claim 1.
18. 18. The method of claim 17, wherein the method is a method for treating signs of aging, treating acne, smoothing skin texture, or lightening the skin.
19. The method of claim 17 or 18, wherein the method is a method for increasing CRABP2 expression.
20. 1. A skin care composition comprising: a. 3-(4-farnesyloxyphenyl)-propionic acid, b. a processed oat ingredient selected from the group consisting of fermented oats, colloidal oats, oat extract, oat oil, and combinations thereof; A skin care composition, wherein the composition is in the form of a solution, suspension, emulsion, lotion, cream, serum, gel, stick, spray, ointment, liquid wash, bar soap, shampoo, hair conditioner, paste, foam, powder, mousse, shaving cream, hydrogel, or film-forming product.