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WO2025030260A1 - Nouvelle utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique - Google Patents

Nouvelle utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique Download PDF

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Publication number
WO2025030260A1
WO2025030260A1 PCT/CN2023/111223 CN2023111223W WO2025030260A1 WO 2025030260 A1 WO2025030260 A1 WO 2025030260A1 CN 2023111223 W CN2023111223 W CN 2023111223W WO 2025030260 A1 WO2025030260 A1 WO 2025030260A1
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WO
WIPO (PCT)
Prior art keywords
acid
hydroxystearic acid
cosmetic composition
skin
composition
Prior art date
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Pending
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PCT/CN2023/111223
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English (en)
Inventor
Yulan QU
Qianwen FAN
Huanjun ZHOU
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Estee Lauder Cos Innovation R & D China Co Ltd
ELC Management LLC
Original Assignee
Estee Lauder Cos Innovation R & D China Co Ltd
ELC Management LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Estee Lauder Cos Innovation R & D China Co Ltd, ELC Management LLC filed Critical Estee Lauder Cos Innovation R & D China Co Ltd
Priority to CN202380068264.8A priority Critical patent/CN119923246A/zh
Priority to PCT/CN2023/111223 priority patent/WO2025030260A1/fr
Priority to TW113129117A priority patent/TWI909592B/zh
Publication of WO2025030260A1 publication Critical patent/WO2025030260A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present disclosure relates to the novel use of cosmetic compositions comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for regulating lipid balance in sebocytes, for regulating sebocyte activity, and/or for inhibiting lipogenesis process induced by an inducing agent.
  • 10-hydroxystearic acid (10-HSA) also referred to as 10-hydroxyoctadecanoic acid (10-HOA)
  • 10-hydroxyoctadecanoic acid (10-HOA) is a saturated hydroxy fatty acid having 18 carbon atoms and having a hydroxyl group at the 10-position.
  • the hydroxy group in the 10-HSA molecule imparts special properties to the fatty acid, which has a higher reactivity and is of great value in cosmetics, personal care, food, dietary supplements, and pharmaceutics.
  • 10-HSA can be applied as surfactant, emulsifier, stabilizer, conditioner, anti-oxidant or the like in cosmetic products and also used as antibacterial, anti-inflammatory and anti-tumor actives in the pharmaceutical industry.
  • 10-HSA could boost collagen production and reduce melanin production by activating peroxisome proliferators activated receptor (PPAR) .
  • PPAR peroxisome proliferators activated receptor
  • 10-HSA has been reported to stimulate collagens I and III in cell culture models and improves facial age spots and conspicuous pores in in vivo (see, e.g. "Bio-derived hydroxystearic acid ameliorates skin age spots and conspicuous pores” , Schutz R. et al. Int J Cosmet Sci. 2019; 41: 240) .
  • the efficacy of 10-HSA as a cosmetic active ingredient on the human skin has not been thoroughly developed.
  • 10-hydroxystearic acid shows significant efficacy for sebum control even at a relative low concentration. It has been discovered that 10-HSA could prevent 5 ⁇ -reductase activity in vitro and prevent lipid accumulation in sebocytes, which are two major pathways that contribute to sebum accumulation and secretion.
  • the present disclosure aims to provide a novel use of cosmetic compositions comprising 10-hydroxystearic acid, a salt, ester or amide thereof.
  • the present disclosure provides a non-therapeutic method of cosmetic treatment for regulating lipid balance in sebocytes and/or for regulating sebocyte activity, comprising topically applying to skin a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof.
  • the amount of 10-hydroxystearic acid in the cosmetic composition used in present method for regulating lipid balance in sebocytes and/or for regulating sebocyte activity may be from about 0.000625%to about 20%by weight, and preferably from about 0.00125%to about 0.5%by weight, relative to the total weight of the composition.
  • the present disclosure provides a non-therapeutic method of cosmetic treatment for inhibiting lipogenesis process induced by an inducing agent, comprising topically applying to skin a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof prior to, concurrently with, or after the application of the inducing agent.
  • the inducing agent may be selected from the group consisting of linoleic acid (LA) , dihydrotestosterone (5 ⁇ -dihydrotestosterone, DHT) , insulin, epidermal growth factor (EGF) , palmitic acid (PA) , insulin-like growth factor-1 (IGF) , arachidonic acid, and combinations thereof.
  • LA linoleic acid
  • DHT dihydrotestosterone
  • insulin insulin
  • PA palmitic acid
  • IGF insulin-like growth factor-1
  • arachidonic acid and combinations thereof.
  • the amount of 10-hydroxystearic acid in the cosmetic composition used in present method for inhibiting lipogenesis process induced by an inducing agent may be from about 0.000625%to about 20%by weight, and preferably from about 0.005%to about 0.1%by weight, relative to the total weight of the composition.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for regulating lipid balance in sebocytes and/or for regulating sebocyte activity.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for inhibiting lipogenesis process induced by an inducing agent, e.g. linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, or combinations thereof.
  • an inducing agent e.g. linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, or combinations thereof.
  • FIGURE 1 is a histogram showing the 5 ⁇ reductase activity inhibition effect of 10-HSA at different concentrations
  • FIGURE 2 is a histogram showing the lipid accumulation inhibition effect of 10-HSA at different concentrations under a basal condition tested by the Oil red staining method.
  • FIGURE 3 is a histogram showing the lipid accumulation inhibition effect of 10-HSA at different concentrations under a basal condition tested by the Nile red staining method.
  • FIGURE 4 is a histogram showing the effect of 10-HSA for inhibiting lipogenesis process induced by LA.
  • FIGURE 5 is a histogram showing the effect of 10-HSA for inhibiting lipogenesis process induced by LA plus DHT.
  • ranges stated in this disclosure and the claims are intended to include the entire range specifically and not just the endpoint (s) .
  • a range stated to be 0 to 10 is intended to disclose all whole numbers between 0 and 10 such as, for example 1, 2, 3, 4 and any sub ranges formed by any two values thereof, etc., all fractional numbers between 0 and 10, for example 1.5, 2.3, 4.57, 6.1113 and any sub ranges formed by any two values thereof, etc., and the endpoints 0 and 10.
  • the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. "consisting of” ) .
  • the term "and/or" when used in a list of two or more items, means that any one of the listed items can be employed by itself, or any combination of two or more of the listed items can be employed. For example, if a composition is described as containing components A, B, and/or C, the composition can contain A alone; B alone; C alone; A and B in combination; A and C in combination; B and C in combination; or A, B, and C in combination.
  • compositions for care of the human skin see also the heading "Kosmetika” in Rompp Lexikon Chemie, 10th edition 1997, Georg Thieme Verlag Stuttgart, New York.
  • Sebum is an oily substance excreted by the sebaceous glands in the skin of most mammals.
  • the excretion mechanism is a holocrine mechanism by which sebum is deposited on the surface of the skin.
  • the importance of sebum balance in the skin tissue and cells for the physiological homeostasis of healthy skin is known: an overproduction of sebum, called hyperseborrhea, is responsible for oily skin and greasy hair.
  • hyperseborrhea can also contribute to the development of acne prone skin.
  • certain unsightly discomfort (dry skin) as well as important dermatological disorders (premature photoaging) can be attributed to the absence or insufficiency of sebum on the skin surface. Therefore, a balanced sebum production is desired to cosmetic users.
  • the technology used to regulate the sebocyte activity is critical to deliver such efficacies/benefits.
  • the present disclosure is concerned with a novel use of cosmetic compositions comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for regulating lipid balance in sebocytes, for regulating sebocyte activity, and/or for inhibiting lipogenesis process induced by an inducing agent.
  • 10-hydroxystearic acid (CAS: 638-26-6) has the following formula:
  • Both enantiomers may be used according to the present disclosure, and the preferred enantiomeric form is the (R) -10-hydroxystearic acid.
  • 10-hydroxystearic acid may be formed from 10-hydroxydecanoic acid through dehydration and oxidation with copper chloride and hydrogen peroxide.
  • 10-hydroxystearic acid may be synthesized by recombinant cells, which have been engineered to express the gene for this molecule.
  • the fatty acid can also be produced by corynebacterium glutamicum when grown on a medium containing glucose as the sole carbon source.
  • a commercial product of 10-hydroxystearic acid mention may be made, for example, of the product sold under the tradename "BEAUACTIVE" by DSM Nutritional Products Ltd.
  • the ester or amide are, preferably, an alkyl ester or alkyl amide, wherein the term “alkyl” encompasses straight chain as well as branched alkyl groups, i.e. that “C 1-4 -alkyl” encompasses straight chain C 1-4 -alkyl (methyl, ethyl, n-propyl, n-butyl) as well as branched C 3-4 -alkyl (iso-propyl, iso-butyl, tert-butyl) .
  • the salt may be formed by any cosmetically acceptable cation which means any metal cation as well as any organic cation that is not toxic to the skin and/or does not cause allergic reactions.
  • cosmetically acceptable cation means any metal cation as well as any organic cation that is not toxic to the skin and/or does not cause allergic reactions.
  • cations are ammonium cations and alkyl ammonium cations, alkali metal cations such as sodium and potassium ions, and alkaline earth metal cations such as calcium and magnesium ions.
  • the present disclosure is concerned with a non-therapeutic method of cosmetic treatment for regulating lipid balance in sebocytes and/or for regulating sebocyte activity, comprising topically applying to skin a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof.
  • the amount of 10-hydroxystearic acid or a salt, ester, or amide with the definitions and preferences as given above is suitably from about 0.000625%to about 20%, preferably from about 0.00125%to about 0.5%by weight of the total composition, for example, about 0.000625%, about 0.00125%, about 0.0025%, about 0.005%, about 0.00625%, about 0.01%, about 0.0125%, about 0.025%, about 0.05%, about 0.1%, about 0.2%, about 0.5%, about 1%, about 2%, about 5%, about 10%, and about 20%by weight of the total composition.
  • present composition can achieve a superior effect of regulating lipid balance in sebocytes and/or for regulating sebocyte activity.
  • the present disclosure is concerned with a non-therapeutic method of cosmetic treatment for inhibiting lipogenesis process induced by an inducing agent, comprising topically applying to skin a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof prior to, concurrently with, or after the application of the inducing agent.
  • the inducing agent may be selected from the group consisting of linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, and combinations thereof.
  • the amount of 10-hydroxystearic acid or a salt, ester, or amide with the definitions and preferences as given above is suitably from about 0.000625%to about 20%, preferably from about 0.005%to about 0.1%, and more preferably from about 0.05%to about 0.1%by weight of the total composition, for example, about 0.005%, about 0.01%, about 0.0125%, about 0.025%, about 0.05%, about 0.1%, about 0.2%, about 0.5%, about 1%, about 2%, about 5%, about 10%, and about 20%by weight of the total composition.
  • present composition can achieve a superior effect of inhibiting lipogenesis process induced by an inducing agent.
  • the present disclosure is concerned with a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for regulating lipid balance in sebocytes and/or for regulating sebocyte activity.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for topical application to skin for inhibiting lipogenesis process induced by an inducing agent, e.g. linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, or combinations thereof.
  • an inducing agent e.g. linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, or combinations thereof.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for reducing sebum production of skin.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for treatment of excessive sebum of the skin.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for inhibiting lipid accumulation in sebocytes of skin.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for improving lipid level in sebocytes of skin.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for treating hyperseborrhea.
  • the present disclosure provides a non-therapeutic use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof, for treating acne (or acne prone) skin.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for regulating lipid balance in sebocytes and/or for regulating sebocyte activity.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for inhibiting lipogenesis process induced by an inducing agent.
  • the inducing agent may be selected from the group consisting of linoleic acid, dihydrotestosterone, insulin, epidermal growth factor, palmitic acid, insulin-like growth factor-1, arachidonic acid, and combinations thereof.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for reducing sebum production of skin.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for treatment of excessive sebum of the skin.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for inhibiting lipid accumulation in sebocytes of skin.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for improving lipid level in sebocytes of skin.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for treating hyperseborrhea.
  • the present disclosure provides use of a cosmetic composition comprising 10-hydroxystearic acid, a salt, ester or amide thereof in the manufacture of a cosmetic product for treating acne (or acne prone) skin.
  • the cosmetic composition of the present disclosure may comprise 10-hydroxystearic acid, a salt, ester or amide thereof in an amount efficient to regulate lipid balance in sebocytes, to regulate sebocyte activity, and/or to inhibit lipogenesis process induced by an inducing agent.
  • 10-HSA is used in the cosmetic composition in an amount effective to provide a concentration of 10-HSA in sebocyte cells of skin above 0.01 ⁇ M, preferably above 1 ⁇ M, more preferably between 1 and 20 ⁇ M, in particular between 5 and 10 ⁇ M, when the cosmetic composition is applied to the skin.
  • the application is such that the desired effect occurs and depends on the individuals and the desired effect.
  • the application is such that the amount of sebum on the skin surface is at a suitable level for healthy skin, such as 100 to 200 ⁇ g/cm -2 as indicated by a sebumeter measurement.
  • compositions may also comprise at least one cosmetically acceptable medium, such as additives, excipients, diluents, and/or additional active ingredients, in particular for preventing or reducing excessive sebum, acne, wrinkles, lines, dry skin, photoaging, and inflammation.
  • cosmetically acceptable medium such as additives, excipients, diluents, and/or additional active ingredients, in particular for preventing or reducing excessive sebum, acne, wrinkles, lines, dry skin, photoaging, and inflammation.
  • compositions according to the present disclosure may comprise a total of about 80-99.999375%, preferably about 90-99.95%, and more preferably about 95-99.9%by weight of the composition of one or more additional cosmetically acceptable medium.
  • the usual cosmetic or pharmaceutical adjuvants and additives include but are not limited to preservatives/antioxidants, fatty substances/oils, water, organic solvents, silicones, thickeners, softeners, emulsifiers, sunscreens, antifoaming agents, moisturizers, fragrances, surfactants, fillers, sequestering agents, anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, propellants, acidifying or basifying agents, dyes, colorants, pigments or nanopigments, or any other ingredients usually formulated into cosmetics or medicaments.
  • antioxidants/preservatives are generally preferred. Based on the present disclosure, all known antioxidants usually formulated into cosmetics or medicaments can be used. Especially preferred are antioxidants chosen from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophane) and their derivatives, imidazole (e.g. urocanic acid) and derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine) , carotenoids, carotenes (e.g.
  • amino acids e.g. glycine, histidine, tyrosine, tryptophane
  • imidazole e.g. urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine)
  • carotenoids e.g.
  • ⁇ -carotene, ⁇ -carotene, lycopene and derivatives, chlorogenic acid and derivatives, lipoic acid and derivatives (e.g. dihydrolipoic acid) , aurothioglucose, propylthiouracil and other thiols (e.g.
  • thioredoxine glutathione, cysteine, cystine, cystamine and its glycosyl-, N-acetyl-, methyl-, ethyl-, propyl-, amyl-, butyl-and lauryl-, palmitoyl-; oleyl-, y-linoleyl-, cholesteryl-and glycerylester) and the salts thereof, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and its derivatives (ester, ether, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (such as buthioninsulfoximine, homocysteinsulfoximine, buthioninsulfone, penta-, hexa-, heptathioninsulfoximine) in very low compatible doses (e.g.
  • vitamin E vitamin E, vitamin A and derivatives (vitamin-A-palmitate and -acetate) as well as coniferylbenzoat, rutinic acid and derivatives, ⁇ -glycosylrutin, ferulic acid, furfurylidenglucitol, carnosin, butylhydroxytoluene, butylhydroxyanisole, trihydroxybutyrophenone, urea and its derivatives, mannose and derivatives, zinc and derivatives (e.g. ZnO, ZnSO 4 ) , selen and derivatives (e.g.
  • One or more preservatives/antioxidants may be present in an amount about 0.01 wt%to about 10 wt%of the total weight of the composition of the present disclosure. Preferably, one or more preservatives/antioxidants are present in an amount about 0.1 wt%to about 1 wt%.
  • topical cosmetic compositions also contain surface active ingredients like emulsifiers, solubilizers and the like.
  • An emulsifier enables two or more immiscible components to be combined homogeneously. Moreover, the emulsifier acts to stabilize the composition.
  • Emulsifiers that may be used in the present disclosure in order to form O/W, W/O, O/W/O or W/O/W emulsions/microemulsions include sorbitan oleate, sorbitan sesquioleate, sorbitan isostearate, sorbitan trioleate, polyglyceryl-3-diisostearate, polyglycerol esters of oleic/isostearic acid, polyglyceryl-6 hexaricinolate, polyglyceryl-4-oleate, polygylceryl-4 oleate/PEG-8 propylene glycol cocoate, oleamide DEA, TEA myristate, TEA stearate, magnesium stearate, sodium stearate, potassium laurate, potassium ricinoleate, sodium cocoate, sodium tallowate, potassium castorate, sodium oleate, and mixtures thereof.
  • emulsifiers are phosphate esters and the salts thereof such as cetyl phosphate diethanolamine cetyl phosphate potassium cetyl phosphate sodium glyceryl oleate phosphate, hydrogenated vegetable glycerides phosphate and mixtures thereof.
  • one or more synthetic polymers may be used as an emulsifier.
  • PVP eicosene copolymer acrylates/C 10-30 alkyl acrylate crosspolymer, acrylates/steareth-20 methacrylate copolymer, PEG-22/dodecyl glycol copolymer, PEG-45/dodecyl glycol copolymer, and mixtures thereof.
  • the preferred emulsifiers are cetyl phosphate diethanolamine cetyl phosphate potassium cetyl phosphate PVP Eicosene copolymer, acrylates/C 10-30 -alkyl acrylate crosspolymer, PEG-20 sorbitan isostearate, sorbitan isostearate, and mixtures thereof.
  • the one or more emulsifiers are present in a total amount about 0.01 wt%to about 20 wt%of the total weight of the cosmetic composition of the present disclosure.
  • about 0.1 wt%to about 10 wt%of emulsifiers are used.
  • Exemplary fatty substances which can be incorporated in the oil phase of the emulsion, microemulsion, oleo gel, hydrodispersion or lipodispersion of the present disclosure are advantageously chosen from esters of saturated and/or unsaturated, linear or branched alkyl carboxylic acids with 3 to 30 carbon atoms, and saturated and/or unsaturated, linear and/or branched alcohols with 3 to 30 carbon atoms as well as esters of aromatic carboxylic acids and of saturated and/or unsaturated, linear or branched alcohols of 3-30 carbon atoms.
  • esters can advantageously be selected from octylpalmitate, octylcocoate, octylisostearate, octyldodecylmyristate, cetearylisononanoate, isopropylmyristate, isopropylpalmitate, isopropylstearate, isopropyloleate, n-butylstearate, n-hexyllaureate, n-decyloleat, isooctylstearate, isononylstearate, isononylisononanoate, 2-ethyl hexylpalmitate, 2-ethylhexyllaurate, 2-hexyldecylstearate, 2-octyldodecylpalmitate, stearylheptanoate, oleyloleate, oleylerucate, erucylo
  • fatty components suitable for use in the cosmetic compositions of the present disclosure include polar oils such as lecithines and fatty acid triglycerides, namely thglycerol esters of saturated and/or unsaturated, straight or branched carboxylic acid with 8 to 24 carbon atoms, preferably of 12 to 18 carbon-atoms whereas the fatty acid triglycerides are preferably chosen from synthetic, half synthetic or natural oils (e.g.
  • cocoglyceride olive oil, sun flower oil, soybean oil, peanut oil, rape seed oil, sweet almond oil, palm oil, coconut oil, castor oil, hydrogenated castor oil, wheat oil, grape seed oil, macadamia nut oil and others
  • apolar oils such as linear and/or branched hydrocarbons and waxes e.g.
  • mineral oils vaseline (petrolatum) ; paraffins, squalane and squalene, polyolefines, hydrogenated polyisobutenes and isohexadecanes, favored polyolefines are polydecenes; dialkyl ethers such as dicaprylylether; linear or cyclic silicone oils such as preferably cyclomethicones (octamethylcyclotetrasiloxane; cetyldimethicone, hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane) and mixtures thereof.
  • cyclomethicones octamethylcyclotetrasiloxane
  • cetyldimethicone cetyldimethicone
  • hexamethylcyclotrisiloxane polydimethylsiloxane
  • polydimethylsiloxane poly (methylphenylsiloxane) and mixture
  • the oily phase of the cosmetic compositions of the present disclosure can also contain natural vegetable or animal waxes such as bee wax, china wax, bumblebee wax and other waxes of insects as well as shea butter and cocoa butter.
  • natural vegetable or animal waxes such as bee wax, china wax, bumblebee wax and other waxes of insects as well as shea butter and cocoa butter.
  • a moisturizing agent may be incorporated into a cosmetic composition of the present disclosure to maintain hydration or rehydrate the skin.
  • Moisturizers that prevent water from evaporating from the skin by providing a protective coating are called emollients. Additionally, an emollient provides a softening or soothing effect on the skin surface and is generally considered safe for topical use.
  • Preferred emollients include mineral oils, lanolin, petrolatum, capric/caprylic triglyceraldehydes, cholesterol, silicones such as dimethicone, cyclometicone, almond oil, jojoba oil, avocado oil, castor oil, sesame oil, sunflower oil, coconut oil and grape seed oil, cocoa butter, olive oil aloe extracts, fatty acids such as oleic and stearic, fatty alcohols such as cetyl and hexadecyl (ENJAY) , diisopropyl adipate, hydroxybenzoate esters, benzoic acid esters of C9-15-alcohols, isononyl iso-nonanoate, ethers such as polyoxypropylene butyl ethers and polyoxypropylene cetyl ethers, and C12-15-alkyl benzoates, and mixtures thereof.
  • silicones such as dimethicone, cyclometicone, almond oil,
  • the most preferred emollients are hydroxybenzoate esters, aloe vera, C12-15-alkyl benzoates, and mixtures thereof.
  • An emollient is present in an amount of about 1 wt%to about 20 wt%of the total weight of the composition.
  • the preferred amount of emollient is about 2 wt%to about 15 wt%, and most preferably about 4 wt%to about 10 wt%.
  • humectants Moisturizers that bind water, thereby retaining it on the skin surface are called humectants.
  • Suitable humectants can be incorporated into a cosmetic composition of the present disclosure such as glycerin, polypropylene glycol, 1, 2-pentadiol, polyethylene glycol, lactic acid, pyrrolidone carboxylic acid, urea, phopholipids, collagen, elastin, ceramides, lecithin sorbitol, PEG-4, and mixtures thereof.
  • moisturizers are polymeric moisturizers of the family of water soluble and/or swellable and/or with water gelating polysaccharides such as hyaluronic acid, chitosan and/or a fucose rich polysaccharide which is e.g. available as (CAS-Nr. 178463-23-5) by SOLABIA S.
  • One or more humectants are optionally present at about 0.5 wt%to about 8 wt%in a cosmetic composition of the present disclosure, preferably about 1 wt%to about 5 wt%.
  • the aqueous phase of the preferred topical cosmetic composition of the present disclosure can contain the usual cosmetic additives such as alcohols, especially lower alcohols, preferably ethanol and/or isopropanol, low diols or polyols and their ethers, preferably propyleneglycol, glycerin, ethyleneglycol, ethyleneglycol monoethyl-or monobutylether, propyleneglycol monomethyl-or -monoethyl-or -monobutylether, diethyleneglycol mono-methyl-or -monoethylether and analogue products, polymers, foam stabilizers; electrolytes and especially one or more thickeners.
  • alcohols especially lower alcohols, preferably ethanol and/or isopropanol, low diols or polyols and their ethers
  • ethers preferably propyleneglycol, glycerin, ethyleneglycol, ethyleneglycol monoethyl-or mono
  • Thickeners that may be used in formulations of the present disclosure to assist in making the consistency of a product suitable include carbomer, siliciumdioxide, magnesium and/or aluminum silicates, beeswax, stearic acid, stearyl alcohol polysaccharides and their derivatives such as xanthan gum, hydroxypropyl cellulose, polyacrylamides, acrylate crosspolymers preferably a carbomer, such as of type 980, 981, 1382, 2984, 5984 alone or mixtures thereof.
  • Suitable neutralizing agents which may be included in the cosmetic compositions of the present disclosure to neutralize components such as e.g.
  • an emulsifier or a foam builder/stabilizer include but are not limited to alkali hydroxides such as a sodium and potassium hydroxide; organic bases such as diethanolamine (DEA) , triethanolamine (TEA) , aminomethyl propanol, and mixtures thereof; amino acids such as arginine and lysine and any combination of any foregoing.
  • the neutralizing agent can be present in an amount of about 0.01 wt%to about 8 wt%in the cosmetic composition of the present disclosure, preferably, 1 wt%to about 5 wt%.
  • the addition of electrolytes into the cosmetic composition of the present disclosure may be suitable to change the behavior of a hydrophobic emulsifier.
  • the emulsions/microemulsions may contain preferably electrolytes of one or several salts including anions such as chloride, sulfates, carbonate, borate and aluminate, without being limited thereto.
  • Other suitable electrolytes can be on the basis of organic anions such as, but not limited to, lactate, acetate, benzoate, propionate, tartrate and citrate.
  • As cations preferably ammonium, alkylammonium, alkali-or alkaline earth metals, magnesium-, iron-or zinc-ions are selected.
  • Electrolytes can be present in an amount of about 0.01 wt%to about 8 wt%in the cosmetic compositions of the present disclosure.
  • the cosmetic compositions of the present disclosure are topical compositions in the form of a suspension or dispersion in solvents or fatty substances, or alternatively in the form of an emulsion or micro emulsion (in particular of O/W or W/O type, O/W/O or W/O/W-type) , PET-emulsions, multiple emulsions, bickering emulsions, hydrogels, alcoholic gels, lipogels, one or multiphase solutions or a vesicular dispersion and other usual compositions, which can also be applied by pens, as masks or as sprays.
  • the emulsions can also contain anionic, nonionic, cationic or amphoteric surfactant (s) .
  • Preferred compositions according to the present disclosure are skin care preparations, hair-care preparations, light protection preparations or functional preparations.
  • the cosmetic compositions of the present disclosure can be in the form of a liquid, a lotion, a thickened lotion, a gel, a cream, a milk, an ointment, a paste, a powder, a make-up, or a solid tube stick and can be optionally be packaged as an aerosol and can be provided in the form of a mousse such as an aerosol mousse, a foam or a spray foams, sprays, sticks, a gel, a plaster, a powder, a cleanser, a soap or aerosols or wipes.
  • a mousse such as an aerosol mousse, a foam or a spray foams, sprays, sticks, a gel, a plaster, a powder, a cleanser, a soap or aerosols or wipes.
  • the amount of the cosmetic composition according to the present disclosure, which is to be applied to the skin depends on the concentration of the active ingredients in the compositions and the desired cosmetic or pharmaceutical effect. For example, application can be such that a cream is applied to the skin. A cream is usually applied in an amount of 2 mg cream/cm 2 skin.
  • the amount of the composition which is applied to the skin is, however, not critical, and if with a certain amount of applied composition the desired effect cannot be achieved, a higher concentration of the active ingredients can be used e.g. by applying more of the composition or by applying compositions which contain more active ingredient.
  • the cosmetic composition according to the present disclosure is preferably applied at least once per day, e.g. twice or three times a day. Usually, it takes at least two weeks until the desired effect is achieved. However, it can take several weeks or even months until the desired effect is fully maximized.
  • the 5 ⁇ reductase test is often used to evaluate the efficacy of products designed to control sebum production in the skin.
  • the production of sebum is regulated by a number of factors, including hormones such as testosterone and dihydrotestosterone (DHT) .
  • DHT is produced from testosterone under the action of the 5 ⁇ reductase.
  • This enzyme is present in the skin and plays a key role in regulating sebum production. Therefore, determining the activity of 5 ⁇ reductase is a regular method to measure sebum control activity under this driven pathway.
  • the reacting components including buffer solution (Tris-HCl, pH7.4, Sigma T3253) , liver microsomes (Xenotech, H0610) , samples (10-HSA in an amount of 0.03125%, 0.0625%, 0.125%, 0.25%, or 0.5%) , testosterone (Sigma-Aldrich, T1500) , NADPH (Reduced nicotinamide adenine dinucleotide phosphate, Sigma 93205) were added to form a relative homogenous reacting system. After 30 mins, the reaction was terminated. The mixture was centrifuged. The supernatant was taken for further analysis.
  • buffer solution Tris-HCl, pH7.4, Sigma T3253
  • liver microsomes Xenotech, H0610
  • samples (10-HSA in an amount of 0.03125%, 0.0625%, 0.125%, 0.25%, or 0.5%)
  • testosterone Sigma-Aldrich, T1500
  • NADPH Reduced nic
  • UPLC-MS method (Q Exactive, ThermoFisher Scientific) was used to quantify the content of testosterone in the sample mixture, which reflected the enzyme activity by the consumption of the substrate testosterone. When the testosterone consumption in the test sample tube was lower than that in the reaction tube without an inhibitor, it was considered as having efficacy of inhibiting 5 ⁇ -reductase.
  • the inhibition ratio was calculated according to the formula:
  • Inhibition ratio (%) [ (B-Q) - (B-R) ] / (B-Q) ⁇ 100,
  • B represents the testosterone content in the blank control group
  • Q represents the testosterone content in the reaction group without an inhibitor
  • R represents the testosterone content in the reaction group with the tested inhibitor
  • Fig. 1 The results of 5 ⁇ reductase test are illustrated in Fig. 1. It shows that 10-HSA exhibits an effective inhibition on 5 ⁇ reductase activity at a concentration as low as 0.0625 wt%. And the inhibition efficacy is increased in a dose-dependent manner.
  • Human immortalized SZ95 sebocytes originated from human facial sebaceous glands (Zouboulis et al. 1999) , were cultured in Basal Medium (Sigma-Aldrich) supplemented with 10%fetal bovine serum (Corning) , 1 mM CaCl 2 , 5 ng/ml human recombinant epidermal growth factor (Pufei, China) , 1%Antibiotic-Antimycotic (Gibco TM , Thermo Fisher Scientific) at 37°C in a 5%CO 2 humidified incubator. The medium was changed every other day, and cells were sub-cultured at 60-80%confluence.
  • the cells were then detached with TrypLETM Express (Gibco) and transferred to 96-well black-well/clear-bottom plates (PE View plate) at a density of 10,000 cells/well.
  • the cells were maintained in supplemented human sebocyte growth medium (Sigma, FB205) overnight at 37°C and 5%CO 2 .
  • the cells were treated with 10-HSA sample (0.005%, 0.01%in DMSO and further diluted with supplemented human sebocyte growth medium) for 72h.
  • the lipid accumulation value % (Mean OD 520 active /Mean OD 520 control ) ⁇ 100%, relative IOD (Integral optical density) value was calculated in the table and figure to demonstrative the relative value normalized with control group.
  • Example 2 the inhibition effect of 10-HSA on the lipid accumulation under basal condition was investigated by using the Nile red staining method.
  • the procedure of cell culture and cell treatment in this example was conducted in the similar way as that in Example 2.
  • the relative lipid accumulation value % (Mean Flurorescent Intensity value active /Mean Flurorescent Intensity value control ) ⁇ 100%
  • Example 2 the effect of 10-HSA for inhibiting lipogenesis process induced by LA and DHT was investigated by using the Oil red staining method.
  • This example was conducted in the similar procedure as in Example 2, except that the cells were treated with LA and DHT (0.25 mM LA and 100 mM DHT in supplemented human sebocyte growth medium) together with 10-HSA at different concentrations.

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Abstract

L'invention concerne une nouvelle utilisation de compositions cosmétiques comprenant de l'acide 10-hydroxystéarique, un sel, un ester ou un amide de celui-ci, pour une application topique sur la peau afin de réguler l'équilibre lipidique dans les sébocytes, de réguler l'activité des sébocytes et/ou d'inhiber le processus de lipogenèse induit par un agent inducteur.
PCT/CN2023/111223 2023-08-04 2023-08-04 Nouvelle utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique Pending WO2025030260A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202380068264.8A CN119923246A (zh) 2023-08-04 2023-08-04 包含10-羟基硬脂酸的化妆品组合物的新用途
PCT/CN2023/111223 WO2025030260A1 (fr) 2023-08-04 2023-08-04 Nouvelle utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique
TW113129117A TWI909592B (zh) 2023-08-04 2024-08-05 包含10-羥基硬脂酸的化妝品組合物的新用途

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PCT/CN2023/111223 WO2025030260A1 (fr) 2023-08-04 2023-08-04 Nouvelle utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004069219A1 (fr) * 2003-01-08 2004-08-19 L'oreal Composition cosmetique pour le soin des peaux grasses, contenant un acide gras carboxylique ou l'un de ses derives
WO2016059169A1 (fr) * 2014-10-17 2016-04-21 Dsm Ip Assets B.V. Utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique
WO2017178236A1 (fr) * 2016-04-13 2017-10-19 Dsm Ip Assets B.V. Compositions d'acide 10-hydroxystéarique
WO2018153701A1 (fr) * 2017-02-24 2018-08-30 Dsm Ip Assets B.V. Composition topique à texture ferme
WO2020128071A1 (fr) * 2018-12-21 2020-06-25 L'oreal Utilisation cosmétique d'un acide gras à courte chaîne (scfa) pour prévenir et/ou traiter la peau sèche et/ou la peau âgée
WO2021138031A1 (fr) * 2019-12-30 2021-07-08 Rodan & Fields, Llc Complexe d'agoniste de ppar et procédés d'usage

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004069219A1 (fr) * 2003-01-08 2004-08-19 L'oreal Composition cosmetique pour le soin des peaux grasses, contenant un acide gras carboxylique ou l'un de ses derives
WO2016059169A1 (fr) * 2014-10-17 2016-04-21 Dsm Ip Assets B.V. Utilisation d'une composition cosmétique comprenant de l'acide 10-hydroxystéarique
WO2017178236A1 (fr) * 2016-04-13 2017-10-19 Dsm Ip Assets B.V. Compositions d'acide 10-hydroxystéarique
WO2018153701A1 (fr) * 2017-02-24 2018-08-30 Dsm Ip Assets B.V. Composition topique à texture ferme
WO2020128071A1 (fr) * 2018-12-21 2020-06-25 L'oreal Utilisation cosmétique d'un acide gras à courte chaîne (scfa) pour prévenir et/ou traiter la peau sèche et/ou la peau âgée
WO2021138031A1 (fr) * 2019-12-30 2021-07-08 Rodan & Fields, Llc Complexe d'agoniste de ppar et procédés d'usage

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