# US 4,393,044 A · Steroid ester, and cosmetics and ointments containing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,393,044 A - Document ID: US4393044A - Status: Granted - Kind: A - Application number: 06/265,847 - Filed: 1981-05-21 - Granted: 1983-07-12 - Earliest claimed: 1980-05-29 - Assignees: The Nisshin Oil Mills, Ltd. - Inventors: Atsunobu Takada; Yuzo Higaki - Web page: https://patentgrep.com/patent/US4393044A ## CPC - A61K 8/63: Steroids; Derivatives thereof - A61Q 5/00: Preparations for care of the hair - A61Q 19/00: Preparations for care of the skin - A61Q 1/06: Lipsticks - A61Q 1/10: for eyes, e.g. eyeliner, mascara - A61Q 19/10: Washing or bathing preparations - Y10S 424/05: Stick - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Steroid ester is formed by the reaction between a carboxylic component and cholesterol or methylsterol having two methyl groups attached to the 4-position of the sterol skeleton. The carboxylic component is an .alpha.-branched carboxylic acid having a general formula: ##STR1## (where R.sup.1 is an alkyl group having at least two carbon atoms, and R.sup.2 is an alkyl group having at least four carbon atoms) or a reactive derivative of said .alpha.-branched carboxylic acid. The steroid ester is high in resistance to hydrolysis, exhibits an excellent water-embracing property and, thus, provides an effective oil phase material or base material of cosmetics or ointments. ## Claims ### Claim 1 A cosmetic comprising a cosmetic ingredient and a steroid ester obtained by reacting at least one steroid component which is a trimethylsteroid or a mixture comprising said trimethylsteroid, and wherein the trimethylsteroid is dihydrolanosterol, lanosterol, dihydroagnosterol, agnosterol, cycloartanol, cycloartenol, 2,4-methylenecyloartanol, cyclolaudenol, cyclobranol, isocholesterol or a mixture thereof, with at least one carboxylic acid-based component selected from the group consisting of free .alpha.-branched carboxylic acids having a general formula ##STR6## (where R.sup.1 is an alkyl group having at least two carbon atoms, and R.sup.2 is an alkyl group having at least four carbon atoms) and reactive derivatives of said .alpha.-branched carboxylic acid which are acid halides or anhydrides, said cosmetic is a creamy cosmetic for the skin including a cold cream, a nutritive cream, and a cleansing cream, a stick cosmetic for the skin including a lipstick and an eyeshadow, a pasty cosmetic for the hair including a pomade, or a liquefied or emulsified cosmetic for the hair including a hair dresser and a hair rinse. ### Claim 2 (depends on 1) The cosmetic according to claim 1, wherein the total number of carbon atoms contained in R.sup.1 and R.sup.2 is at most 24. ### Claim 3 (depends on 2) The cosmetic according to claim 2, wherein the carboxylic acid-based component is the free acid. ### Claim 4 (depends on 3) The cosmetic according to claim 3, wherein the free acid is selected from the group consisting of 2-ethylhexanoic acid, 2-hexyldecanoic acid, 2-heptylundecanoic acid, acid of the chemical structure: ##STR7## 2-decyltetradecanoic acid, 2-undecyltetradecanoic acid, 2-decylpentadecanoic acid, 2-undecylpentadecanoic acid and a mixture thereof. ### Claim 5 (depends on 2) The cosmetic according to claim 2, wherein the carboxylic acid-based component is the reactive derivative. ### Claim 6 (depends on 5) The cosmetic according to claim 5, wherein the reactive derivative is an acid chloride. ### Claim 7 (depends on 6) The cosmetic according to claim 6, wherein the acid chloride is selected from the group consisting of 2-ethylhexanoic acid chloride, 2-hexyldecanoic acid chloride, 2-heptylundecanoic acid chloride, chloride of acid of the chemical structure: ##STR8## 2-decyltetradecanoic acid chloride, 2-undecyltetradecanoic acid chloride, 2-decylpentadecanoic acid chloride, and a mixture thereof. ### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7) The cosmetic according to any one of claims 1 to 7, further comprising a second steroid component which is cholesterol. ### Claim 9 (depends on 8) The cosmetic according to claim 8, wherein the steroid ester is liquid under room temperature. ### Claim 10 (depends on 8) The cosmetic according to claim 8, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potash is less than 20%. ### Claim 11 (depends on 8) The cosmetic according to claim 8, wherein the steroid ester exhibits a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least two times as much in weight as the ester. ### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7) The cosmetic according to any one of claims 1 to 7, wherein the steroid ester is liquid under room temperature. ### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7) The cosmetic according to any one of claims 1 to 7, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potsh is less than 15%. ### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7) The cosmetic according to any one of claims 1 to 7, wherein the steroid ester exhibits a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least 1.5 times as much in weight as the ester. ### Claim 15 An ointment comprising an ointment ingredient and a steroid ester obtained by reacting at least one steroid component which is a trimethylsteroid or a mixture comprising said trimethylsteroid, and wherein the trimethylsteroid is dihydrolanosterol, lanosterol, dihydroagnosterol, agnosterol, cycloartanol, cycloartenol, 2,4-methylenecycloartanol, cyclolaudenol, cyclobranol, isocholesterol or a mixture thereof, with at least one carboxylic acid-based component selected from the group consisting of free .alpha.-branched carboxylic acids having a general formula ##STR9## (where R.sup.1 is an alkyl group having at least two carbon atoms, and R.sup.2 is an alkyl group having at least four carbon atoms) and reactive derivatives of said .alpha.-branched carboxylic acid which are acid halides or anhydrides ### Claim 16 (depends on 15) The ointment according to claim 15, wherein the total number of carbon atoms contained in R.sup.1 and R.sup.2 is at most 24. ### Claim 17 (depends on 16) The ointment according to claim 16, wherein the carboxylic acid-based component is the free acid. ### Claim 18 (depends on 17) The ointment according to claim 17, wherein the free acid is selected from the group consisting of 2-ethylhexanoic acid, 2-hexyldecanoic acid, 2-heptylundecanoic acid, acid of the chemical structure: ##STR10## 2-decyltetradecanoic acid, 2-undecyltetradecanoic acid, 2-decylpentadecanoic acid, 2-undecylpentadecanoic acid, and a mixture thereof. ### Claim 19 (depends on 15) The ointment according to claim 15, wherein the carboxylic acid-based component is the reactive derivative. ### Claim 20 (depends on 19) The ointment according to claim 19, wherein the reactive derivative is an acid chloride. ### Claim 21 (depends on 20) The ointment according to claim 20, wherein the acid chloride is selected from the group consisting of 2-ethylhexanoic acid chloride, 2-hexyldecanoic acid chloride, 2-heptylundecanoic acid chloride, chloride of acid of the chemical structure: ##STR11## 2-decyltetradecanoic acid chloride, 2-undecyltetradecanoic acid chloride, 2-decylpentadecanoic acid chloride, 2-undecylpentadecanoic acid chloride, and a mixture thereof. ### Claim 22 (depends on 15, 16, 17, 18, 19, 20, 21) The ointment according to any one of claims 15 to 21, further comprising a second steroid component which is cholesterol. ### Claim 23 (depends on 22) The ointment according to claim 22, wherein the steroid ester is liquid under room temperature. ### Claim 24 (depends on 22) The ointment according to claim 22, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potash is less than 20%. ### Claim 25 (depends on 22) The ointment according to claim 22, wherein the steroid ester exhibits a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least two times as much in weight as the ester. ### Claim 26 (depends on 15, 16, 17, 18, 19, 20, 21) The cosmetic according to any one of claims 15 to 21, wherein the steroid ester is liquid under room temperature. ### Claim 27 (depends on 15, 16, 17, 18, 19, 20, 21) The cosmetic according to any one of claims 15 to 21, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potash is less than 15%. ### Claim 28 (depends on 15, 16, 17, 18, 19, 20, 21) The cosmetic according to any one of claims 15 to 21, wherein the steroid ester exhibts a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least 1.5 times as much as in weight as the ester. ### Claim 29 (depends on 1) The cosmetic of claim 1 which is a cold cream, nutritive cream, cleansing cream, lipstick, hair pomade, hair dresser or a hair rinse and the steroid ester is present in an amount of from 0.05 to 50%. ### Claim 30 (depends on 15) The ointment of claim 15 wherein the steroid ester is present in an amount of from 0.05 to 50%. ### Claim 31 (depends on 1, 15, 32) The cosmetic of claim 1, 15, 32, or 42, wherein said cosmetic ingredient is a cosmetic oil, wax, surfactant, wetting agent, pigment, perfume, antioxidant, detergent or mixtures thereof. ### Claim 32 A cosmetic comprising a cosmetic ingredient and a steroid ester obtained by reacting at least one steroid component which is cholesterol with at least one carboxylic acid-based component selected from the group consisting of free .alpha.-branched carboxylic acids having a general formula ##STR12## (where R.sup.1 is an alkyl group having at least two carbon atoms, and R.sup.2 is an alkyl group having at least four carbon atoms) and reactive derivatives of said .alpha.-branched carboxylic acid which are acid halides or anhydrides, said cosmetic is a creamy cosmetic for the skin including a cold cream, a nutritive cream, and a cleansing cream, a stick cosmetic for the skin including a lipstick and an eyeshadow, a pasty cosmetic for the hair including a pomade, or a liquefied or emulsified cosmetic for the hair including a hair dresser and a hair rinse. ### Claim 33 (depends on 32) The cosmetic according to claim 32, wherein the total number of carbon atoms contained in R.sup.1 and R.sup.2 is at most 24. ### Claim 34 (depends on 33) The cosmetic according to claim 33, wherein the carboxylic acid-based component is the free acid. ### Claim 35 (depends on 34) The cosmetic according to claim 34, wherein the free acid is selected from the group consisting of 2-ethylhexanoic acid, 2-hexyldecanoic acid, 2-heptylundecanoic acid, an acid of the chemical structure: ##STR13## 2-decyltetradecanoic acid, 2-undecyltetradecanoic acid, 2-decylpentadecanoic acid, 2-undecylpentadecanoic acid, and mixtures thereof. ### Claim 36 (depends on 33) The cosmetic according to claim 33, wherein the carboxylic acid-based component is the reactive derivative. ### Claim 37 (depends on 36) The cosmetic according to claim 36, wherein the reactive derivative is an acid chloride. ### Claim 38 The cosmetic according to claimm 37, wherein the acid chloride is selected from the group consisting of 2-ethylhexanoic acid chloride, 2-hexyldecanoic acid chloride, 2-heptylundecanoic acid chloride, a chloride of an acid of the chemical structure: ##STR14## 2-decyltetradecanoic acid chloride, 2-undecyltetradecanoic acid chloride, 2-decylpentadecanoic acid chloride, and mixtures thereof. ### Claim 39 (depends on 32, 33, 34, 35, 36, 37, 38) The cosmetic according to any one of claims 32 to 38, wherein the steroid ester is liquid under room temperature. ### Claim 40 (depends on 32, 33, 34, 35, 36, 37, 38) The cosmetic according to any one of claims 32 to 38, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potash is less than 15%. ### Claim 41 (depends on 32, 33, 34, 35, 36, 37, 38) The cosmetic according to any one of claims 32 to 38, wherein the steroid ester exhibits a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least 1.5 times as much in weight as the ester. ### Claim 42 An ointment comprising an ointment ingredient and a steroid ester obtained by reacting at least one steroid component which is cholesterol with at least one carboxylic acid-based component selected from the group consisting of free .alpha.-branched carboxylic acids having a general formula ##STR15## (where R.sup.1 is an alkyl group having at least two carbon atoms, and R.sup.2 is an alkyl group having at least four carbon atoms) and reactive derivatives of said .alpha.-branched carboxylic acid which are acid halides or anhydrides ### Claim 43 (depends on 42) The ointment according to claim 42, wherein the total number of carbon atoms contained in R.sup.1 and R.sup.2 is at most 24. ### Claim 44 (depends on 43) The ointment according to claim 43, wherein the carboxylic acid-based component is the free acid. ### Claim 45 (depends on 44) The ointment according to claim 44, wherein the free acid is selected from the group consisting of 2-ethylhexanoic acid, 2-hexyldecanoic acid, 2-heptylundecanoic acid, an acid of the chemical structure: ##STR16## 2-decyltetradecanoic acid, 2-undecyltetradecanoic acid, 2-decylpentadecanoic acid, 2-undecylpentadecanoic acid, and mixtures thereof. ### Claim 46 (depends on 42) The ointment according to claim 42, wherein the carboxylic acid-based component is the reactive derivative. ### Claim 47 (depends on 46) The ointment according to claim 46, wherein the reactive derivative is an acid chloride. ### Claim 48 (depends on 47) The ointment according to claim 47, wherein the acid chloride is selected from the group consisting of 2-ethylhexanoic acid chloride, 2-hexyldecanoic acid chloride, 2-heptylundecanoic acid chloride, a chloride of an acid of the chemical structure: ##STR17## 2-decyltetradecanoic acid chloride, 2-undecyltetradecanoic acid chloride, 2-decylpentadecanoic acid chloride, 2-undecylpentadecanoic acid chloride, and mixtures thereof. ### Claim 49 (depends on 43, 44, 45, 46, 47, 48) The ointment according to any one of claims 43 to 48, wherein the steroid ester is liquid under room temperature. ### Claim 50 (depends on 43, 44, 45, 46, 47, 48) The ointment according to any one of claims 43 to 48, wherein the rate of hydrolysis of the steroid ester brought about by 1/2 N alcoholic caustic potash is less than 15%. ### Claim 51 (depends on 43, 44, 45, 46, 47, 48) The ointment according to any one of claims 43 to 48, wherein the steroid ester exhibits a water-embracing property enough to permit forming a w/o type emulsion together with water in an amount at least 1.5 times as much in weight as the ester.