WO2021234005A1 - Composition de soins personnels - Google Patents

Composition de soins personnels Download PDF

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Publication number
WO2021234005A1
WO2021234005A1 PCT/EP2021/063304 EP2021063304W WO2021234005A1 WO 2021234005 A1 WO2021234005 A1 WO 2021234005A1 EP 2021063304 W EP2021063304 W EP 2021063304W WO 2021234005 A1 WO2021234005 A1 WO 2021234005A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
skin
resorcinol
dihydroxybiphenyl
butyl
Prior art date
Application number
PCT/EP2021/063304
Other languages
English (en)
Inventor
Shanthi APPAVOO
Maitreyee DUTTA
Nirmala Santosh NAIR
Morris Waskar
Original Assignee
Unilever Ip Holdings B.V.
Unilever Global Ip Limited
Conopco, Inc., D/B/A Unilever
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.)
Filing date
Publication date
Application filed by Unilever Ip Holdings B.V., Unilever Global Ip Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever Ip Holdings B.V.
Publication of WO2021234005A1 publication Critical patent/WO2021234005A1/fr

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Classifications

    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols

Definitions

  • the present invention relates to a personal care composition.
  • the present invention relates to a personal care composition that provides even skin tone e.g. that formed during melasma.
  • Skin is the outermost protective covering of living beings; and is the largest organ in the body. It acts as a barrier and protects the body from external factors e.g. dust, dirt, pollution and ultraviolet radiation contained in sunlight. Skin also helps prevent entry of harmful or potentially harmful microbes e.g. bacteria, fungi and viruses, from entering the body thereby preventing infection and/or other ill effects that may be caused.
  • harmful or potentially harmful microbes e.g. bacteria, fungi and viruses
  • skin is always exposed to one or more factors mentioned earlier.
  • skin is susceptible to developing one or more conditions e.g. dryness, wrinkles, loose/saggy skin, age spots, blotchy skin, melasma, freckle and increased pigmentation, which may lead to less preferred uneven skin tone.
  • compositions comprising one or more actives that deliver benefits e.g. moisturizing, anti-aging and skin glow with even tone, when applied on a surface of the human body e.g. skin.
  • US 2014256830 discloses methods and compositions comprising resorcinol derivatives for the use of treating, regulating or preventing a skin condition characterized by oxidative stress or a designative process. It also discloses methods of preventing, lightening or reducing the appearance of visible discontinuities of the skin resulting from skin pigmentation, skin aging or other disorder.
  • KR20030092645 discloses a compound comprising 4,4'-dihydroxybiphenyl showing improved tyrosinase inhibition activity compare to conventional hydroquinone based whitening agent.
  • the 4,4'-dihydroxybiphenyl compound is used as an active ingredient in a cosmetic composition for whitening skin by inhibiting the melanin generation and preventing the skin aging. Further, the compound is used in a pharmaceutical composition for treating skin diseases caused by the excessive generation of melanin such as freckles, liver spots, skin spots, hyperpigmentation or senile lentigo.
  • skin lightening agents e.g. 4-hexyl resorcinol (HR).
  • a personal care composition comprising a 2,2’- dihydroxybiphenyl substituted as described hereinafter, provides skin lightening. It has also been found that the skin lightening obtained is at par with that obtained using known skin lightening agents e.g. HR. Moreover, such comparable skin lightening is obtained using reduced amounts of the substituted 2,2’-dihydroxybiphenyl as compared to that of HR.
  • the present invention relates to a personal care composition
  • a personal care composition comprising from 0.001 to 10 wt% of a substituted 2,2’-dihydroxybiphenyl, wherein the substitution is linear or branched alkyl having carbon atoms from 1 to 10and mixtures thereof.
  • the present invention relates to a method of providing even tone on skin wherein, the method comprises: a. applying onto the skin a personal care composition according to the first aspect; and b. optionally, rinsing with water.
  • the present invention relates to use of the composition according to the first aspect for even skin tone.
  • the present invention relates to use of 3,3',5,5'-tetra-tert-butyl-2,2'- dihydroxybiphenyl for even skin tone.
  • the present invention relates to a personal care composition
  • a personal care composition comprising from 0.001 to 10 wt% of a substituted 2,2’-dihydroxybiphenyl, wherein the substitution is linear or branched alkyl having carbon atoms from 1 to 10, or cyclic alkyl having carbon atoms from 4 to 10, or linear or branched alkoxy having carbon atoms from 1 to 10; and mixtures thereof.
  • Substituted 2, 2’-dihydroxybiphenyl is a substance where an OH group is attached to binding sites 2 and 2’ in the general structure of 1,1 ’-biphenyl shown below; and any or all of the other binding sites are substituted with the same or different substitutions disclosed hereinbelow:
  • composition comprises 2,2’-dihydroxybiphenyl that is substituted with linear or branched alkyl having carbon atoms from 1 to 10, the same is preferably selected from the group consisting of methyl, ethyl, propyl (n-propyl and iso-propyl), butyl (n-butyl, sec-butyl, iso-butyl and tert-butyl), pentyl (n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl, sec-pentyl, 3-pentyl, sec- isopentyl), linear or branched hexyl, linear or branched heptyl, linear or branched octyl, linear or branched nonyl and linear or branched decyl groups.
  • the composition comprises a substituted 2,2’-dihydroxybiphenyl where the substitution is linear or branched alkyl having carbon atoms from 1 to 10 preferably 2 to 6 carbon atoms as disclosed above. More preferably, the composition comprises a substituted 2,2’-dihydroxybiphenyl that is substituted with linear alkyl having carbon atoms from 1 to 10 as disclosed above. In an alternate preferred aspect, the substituted 2,2’-dihydroxybiphenyl is tetra substituted with a linear or branched alkyl group having 1 to 10 carbon atoms.
  • the composition comprises a substituted 2,2’-dihydroxybiphenyl where the substitution is a branched or linear carbon chain having 4 carbon atoms i.e. a butyl group.
  • the present invention relates to a personal care composition comprising from 0.001 to 10 wt% substituted 2,2’-dihydroxybiphenyl, wherein the substitution is tetra substitution with linear or branched alkyl having carbon atoms from 1 to 10; and mixtures thereof.
  • the composition comprises butyl substitution at binding sites 3, 3’, 5 and 5’ on the structure of 2,2’-dihydroxybiphenyl so that the substance is 3,3’,5,5’-tetra-tert-butyl-2,2’-dihydroxybiphenyl (TTBDB; CAS 6390-69-8) that has the following structure: 3,3’,5,5’-tetra-tert-butyl-2,2’-dihvdroxybiphenyl
  • the composition comprises from 0.001 to 10 wt%, preferably from 0.005 to 9 wt%, more preferably from 0.01 to 8 wt%, even more preferably from 0.005 to 7 wt%, further more preferably from 0.1 to 6 wt%, still more preferably from 0.1 to 5 wt%, yet more preferably from 0.1 to 3 wt% and still further more preferably from 0.1 to 1 wt% substituted 2,2’-dihydroxybiphennyl.
  • the composition further comprises one or more skin lightening agents.
  • skin lightening agents may be selected from niacinamide, picolinamide, iso-nicotinamide, resorcinol, phenylethyl resorcinol, 4-alkyl resorcinol, vitamin B6, vitamin C, vitamin A, glutathione precursors, galardin, adapalene, ammonium lactate, arbutin, azelaic acid, butyl hydroxy anisole, butyl hydroxy toluene, citrate esters, deoxyarbutin, 1,3-diphenyl propane derivatives, 2,5-dihydroxybenzoic acid and its derivatives, 2-(4-acetoxyphenyl)-1,3-dithiane, 2-(4-hydroxyphenyl)-1,3- dithiane, ellagic acid, gluco pyranosyl-1 -ascorbate, gluconic acid, glycolic acid, 4- Hydr
  • 12-hydroxystearic acid is used as a skin lightening agent and not as a fatty acid.
  • the composition further comprise one or more additional skin lightening agent selected from the group consisting of niacinamide, picolinamide, isonicotinamide, 12-hydroxystearic acid, resorcinol, phenylethyl resorcinol, 4-alkyl resorcinol and galardin.
  • the composition comprise an additional skin lightening agent selected from niacinamide and 4-alkyl resorcinol; and mixtures thereof.
  • 4-alkyl substituted resorcinol examples include 4-methyl resorcinol, 4-ethyl resorcinol (ER), 4-propyl resorcinol, IPR, 4-butyl resorcinol (BR), 4-pentyl resorcinol, HR, 4-heptyl resorcinol, 4-octyl resorcinol and mixtures thereof.
  • Preferred 4-alkyl substituted resorcinol are ER, BR, HR and mixtures thereof. More preferred 4-alkyl substituted resorcinol are ER, HR and mixtures thereof.
  • the alkyl group in 4-alkyl substituted resorcinol can be straight chain alkyl or branched chain alkyl.
  • the alkyl group can be straight chain alkyl as in the case of 4-propyl resorcinol or it can be a branched chain alkyl like as in the case of 4-isopropyl resorcinol (IPR).
  • the composition comprises from 0.001 to 10 wt%, more preferably from 0.005 to 9 wt%, even more preferably from 0.01 to 8 wt%, further more preferably from 0.005 to 7 wt%, still more preferably from 0.1 to 6 wt%, yet more preferably from 0.1 to 5 wt%, still further more preferably from 0.1 to 3 wt% and yet further more preferably from 0.1 to 1 wt% additional skin lightening agent.
  • the composition further comprises a fatty acid selected from the group consisting of fatty acids having carbon atoms preferably in the range 10 to 22, more preferably 12 to 22, even more preferably 14 to 22, further more preferably 16 to 22, yet more preferably from 18 to 22.
  • fatty acids that may be used in the composition include lauric, myristic, palmitic, stearic, isostearic, oleic, linoleic, arachidic, behenic, erucic acid and mixtures thereof.
  • the fatty acid selected are from the group consisting of stearic acid, palmitic acid mixtures thereof.
  • the fatty acid is preferably hystric acid which is substantially (generally about 90 to 95%) a mixture of stearic acid and palmitic acid in a ratio of between 55:45 to 45:55.
  • the composition comprises from 4 to 25 wt%, more preferably from 6 to 20 wt%, even more preferably from 8 to 18 wt%, further more preferably from 10 to 18 wt%, still more preferably from 12 to 18 wt% and yet more preferably from 14 to 18 wt% fatty acid.
  • the composition further comprises from 0.1 to 10 wt%, more preferably from 0.1 to 8 wt%, even more preferably from 0.1 to 7 wt%, further more preferably from 1 to 5 wt% and still more preferably from 1 to 3 wt% soap.
  • the soap is preferably an alkali metal salt of fatty acids e.g. sodium or potassium salt, preferably potassium salt of the fatty acids.
  • the soap may be obtained in-situ by adding sodium hydroxide or potassium hydroxide, preferably potassium hydroxide in the composition that may comprises fatty acids.
  • inclusion of a fatty acid e.g. hystric acid and its soap prepared in-situ, is within the scope of the present invention.
  • the fatty acid together with soap provides a so-called vanishing cream, i.e. a composition, when applied on to the human skin, vanishes on the skin leaving behind no significant streaks of the composition.
  • the composition further comprises UVA organic sunscreens that absorbs UVA radiations and prevent them from reaching a surface e.g. skin of a user.
  • UVA organic sunscreens examples include dibenzoyl methane compound, bisdisulizole disodium (commercially available as Neo Heliopan® AP), diethylamino hydroxy benzoyl hexyl benzoate (commercially available as Uvinul® A Plus), Ecamsule (commercially available as Mexoryl SX) and Methyl anthranilate and also the class of water soluble sunscreens e. g. benzophenone Bisdisulizole disodium and disodium phenyl do benzimidazole tetrasulphonate
  • UVA organic sunscreen that may be used as UVA sunscreen in the composition is selected from a dibenzoylmethane compound.
  • UVA organic sunscreens may preferably be incorporated from 0.01 to 10 wt%, more preferably from 0.1 to 7 wt%, even more preferably from 1 to 5 wt%, further more preferably from 1 to 3.5 wt%, yet more preferably 1 to 3 wt%, still more preferably 1 to 2.5 wt% in the composition.
  • the composition further comprises UVB organic sunscreens that absorbs UVB radiations and prevent them from reaching a surface e.g. skin of a user.
  • UVB organic sunscreens that may be used in the composition include compounds from the class of cinnamic acid, salicylic acid, diphenyl acrylic acid and derivatives thereof.
  • Examples of such compounds include 2-ethylhexyl salicylate (commercially available as OctisalateTM), 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate (commercially available as HomosalateTM), Ethylhexyl Methoxycinnamate (commercially available as NeoHelipan® AV), 2-ethylhexyl 2-cyano-3,3- diphenylacrylate (OCR; commercially available as OctocryleneTM), 2-Hydroxy-4- methoxybenzophenone (commercially available as OxybenzoneTM), 2-ethyl-hexyl-4- methoxy cinnamate (MCX; commercially available as Parsol MCXTM) and mixtures thereof.
  • Examples of water soluble UVB organic sunscreens include phenyl benzimidazole sulphonic acid.
  • UVB organic sunscreens that may be used in the composition are selected from OCR, MCX and mixtures thereof.
  • UVB organic sunscreens may preferably be incorporated from 0.01 to 10 wt%, more preferably from 0.1 to 7 wt%, even more preferably from 1 to 5 wt%, further more preferably from 1 to 3.5 wt%, yet more preferably from 1 to 3 wt%, still more preferably 1 to 2.5 wt% in the composition.
  • the composition further comprises a nonionic surfactant having HLB value in the range 9 to 20, preferably 10 to 19, more preferably 12 to 18, even more preferably 13 to 17 and yet more preferably 15 to 17.
  • Typical values for various surfactants are given below: A value ⁇ 10 : Lipid soluble (water insoluble)
  • a value >10 Water soluble A value from 4 to 8 indicates an anti-foaming agent A value from 7 to 11 indicates a W/O (water in oil) emulsifier A value from 12 to 16 indicates oil in water emulsifier A value from 11 to 14 indicates a wetting agent A value from 12 to 15 is typical of detergents A value of 16 to 20 indicates a solubiliser or a hydrotrope.
  • the nonionic surfactant having HLB value in the range 9 to 20 is selected from fatty alcohol ethoxylates, alkyl phenol ethoxylates, polyoxyethylene sorbitan alkyl esters and mixtures thereof.
  • the nonionic surfactants are ones with at least 9 alkylene oxide groups preferably at least 9 ethylene oxide groups.
  • the nonionic surfactant having HLB value in the range 9 to 20 that may be present in the composition is fatty alcohol ethoxylate with saturated carbon chain having HLB higher than 15.5.
  • the composition comprises 0.5 to 5 wt%, more preferably 1 to 4 wt%, even more preferably from 2 to 3 wt% nonionic surfactant having HLB in the range 9 to 20. ll
  • the composition further comprises a polymer.
  • the polymer acts as thickener in the composition and improves sensorial properties of the composition.
  • the polymer is preferably selected from the following classes: acrylate / R-methacrylate copolymer e.g. acrylates/ steareth-20 methacrylate copolymer (commercially available as AculynTM 22) and acrylates/ beheneth-
  • acrylate copolymer commercially available as AculynTM 28
  • acrylate / R-methacrylate crosspolymer e.g. acrylates/steareth-20 methacrylate crosspolymer (commercially available as AculynTM 88), acrylates copolymer (commercially available as AculynTM 33), - acrylate/R-alkyl acrylate crosspolymer e.g.
  • acrylates/C 10-C30 alkyl acrylate crosspolymer (commercially available as PemulenTM TR-2), copolymer of ammonium acryloyldimethyltaurate with vinyl pyrrolidone (commercially available as Aristoflex® AVC), copolymer of sodium acryloyldimethyltaurate with vinyl pyrrolidone (commercially available as Aristoflex® AVS); and crosspolymer of acryloyldimethyltaurate with R-alkyl acrylate and methyacrylate e.g. Ammonium acryloyldimethyltaurate/ beheneth-25 methacrylate crosspolymer (commercially available as Aristoflex® HMB and Aristoflex®
  • the polymer is selected from acrylate / R-methacrylate copolymer, acrylates copolymer and mixtures thereof.
  • the composition comprises 0.1 to 5 wt%, more preferably 0.5 to 4.5 wt%, even more preferably 1 to 4 wt%, further more preferably from 1.5 to 3.5 wt%, still more preferably from 2 to 3 wt% polymer.
  • the composition further comprises emollients.
  • emollients that may be used in the composition include stearyl alcohol, glyceryl monoricinoleate, mink oil, cetyl alcohol, isopropyl isostearate, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone oils such as dimethylpolysiloxane, din-butyl sebacate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, cotton seed oil, olive oil, palm kernel oil, rape seed oil,
  • the composition further comprises solvents.
  • solvents that may be used in the composition include ethyl alcohol, isopropanol, acetone, ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether and mixtures thereof.
  • the composition further comprises preservatives to protect against the growth of potentially harmful microorganisms.
  • preservatives examples include alkyl esters of para hydroxybenzoic acid, hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • ingredients that may be used as preservative in the composition are sodium benzoate, iodopropynyl butyl carbamate, methylisothiazolinone, iodopropynylbutylcarbamate, phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate, ethylhexylglycerin, benzyl alcohol, alkane diols and mixtures thereof.
  • the alkane diols that are suitable for use as preservative are C6-C12 alkanes that are vicinally substituted with hydroxy groups.
  • Illustrative examples include 1,2-octane diol (caprylyl glycol), 2,3-octane diol, 1,2- nonane diol, 1,2-decane diol, 1,2-hexane diol, 3,4-octane diol, mixtures thereof or the like where caprylyl glycol is typically the most preferred.
  • preservatives are added preferably in an amount 0.001 to 5 wt%, more preferably 0.01 to 3 wt% and most preferably 0.02 to 2 wt%.
  • composition further comprises a range of other optional ingredients that include antioxidants, binders, buffering agents, colorants, astringents, fragrance, opacifying agents, conditioners, exfoliating agents, pH adjusters, skin soothing agents, skin healing agents and powders.
  • antioxidants binders, buffering agents, colorants, astringents, fragrance, opacifying agents, conditioners, exfoliating agents, pH adjusters, skin soothing agents, skin healing agents and powders.
  • the composition is preferably formulated in the form of a powder, flake, lotion, cream, gel or mousse. More preferably, the composition is formulated in the form of cream or lotion and most preferably in the form of cream.
  • the composition can be a leave-on or wash-off type of composition.
  • the composition is preferably a leave-on type of composition.
  • the packaging for the composition of this invention can be a patch, bottle, tube, roll-ball applicator, propellant driven aerosol device, squeeze container or lidded jar.
  • the present invention relates to a method of providing even tone on skin wherein, the method comprises: a. applying on to the skin a personal care composition according to the first aspect; and b. optionally, rinsing with water.
  • the composition according to the first aspect When the composition according to the first aspect is applied on to the skin, it provides even tone on skin with concomitant lightening.
  • the step of applying the composition may be optionally followed by rinsing with water. If rinsing is carried out, it is preferably carried out after 30 min, more preferably after 25 min, even more preferably after 20 min, further more preferably after 15 min, still more preferably after 10 min, yet more preferably after 5 min and most preferably after 1 min from applying it on to the skin.
  • the method is non-therapeutic.
  • the present invention relates to use of the composition according to the first aspect for skin lightening.
  • skin lightening is obtained.
  • the use is non-therapeutic.
  • the composition may also be used for providing even toned skin.
  • the use is non-therapeutic.
  • the composition may also be used for applying it selectively on unevenly pigmented spots for example, those formed during melasma, to obtain even toned skin.
  • One of the factors that is known to cause melasma is changing levels hormones such as estradiol, progesterone and a-MSH.
  • the composition may preferably be also used as a composition for spot correction.
  • the use is non-therapeutic.
  • the present invention relates to use of TTBDB for skin lightening. When TTBDB is applied on to the skin, skin lightening is obtained.
  • the use is non-therapeutic.
  • non-therapeutic as referred to in the second, the third and the fourth aspect, means a cosmetic improvement in skin appearance in healthy subjects, rather than treating any underlying medical disease or disorder.
  • HEMn-LP Lightly pigmenting human epidermal neonatal melanocytes
  • HEMn-LP were seeded at a density of 2.5 c 10 4 cells/well in a 24 well plate in Medium 254 + HMGS-2 for 72 h at 37°C under 5% CO2.
  • the cells were subjected to treatments as shown in table 1 , followed by incubation at 37°C under 5% CO2 for 1h post which, a mixture of hormones containing 25nM " ⁇ -Estradiol + 25nM Progesterone + 50nM NDP-MSH, was added.
  • DMSO Dimethyl sulfoxide

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition de soins personnels comprenant un 2,2'-dihydroxybiphényle substitué, la substitution étant une substitution tétra avec un alkyle linéaire ou ramifié ayant de 1 à 10 atomes de carbone, et des mélanges de ceux-ci.
PCT/EP2021/063304 2020-05-22 2021-05-19 Composition de soins personnels WO2021234005A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20175959 2020-05-22
EP20175959.4 2020-05-22

Publications (1)

Publication Number Publication Date
WO2021234005A1 true WO2021234005A1 (fr) 2021-11-25

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PCT/EP2021/063304 WO2021234005A1 (fr) 2020-05-22 2021-05-19 Composition de soins personnels

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WO (1) WO2021234005A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001091715A2 (fr) * 2000-06-02 2001-12-06 Pentapharm Ltd. Agent topique pour utilisation dermatologique
KR20030092645A (ko) 2002-05-30 2003-12-06 정해영 티로시나제 저해제용 4,4′-디하이드록시바이페닐 화합물
US20140256830A1 (en) 2013-03-08 2014-09-11 Ampere Life Sciences, Inc. Resorcinol compounds for dermatological use
EP2786741A1 (fr) * 2011-11-30 2014-10-08 Ajinomoto Co., Inc. Produit cosmétique de blanchiment de la peau

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001091715A2 (fr) * 2000-06-02 2001-12-06 Pentapharm Ltd. Agent topique pour utilisation dermatologique
KR20030092645A (ko) 2002-05-30 2003-12-06 정해영 티로시나제 저해제용 4,4′-디하이드록시바이페닐 화합물
EP2786741A1 (fr) * 2011-11-30 2014-10-08 Ajinomoto Co., Inc. Produit cosmétique de blanchiment de la peau
US20140256830A1 (en) 2013-03-08 2014-09-11 Ampere Life Sciences, Inc. Resorcinol compounds for dermatological use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RUZZA PAOLO ET AL: "Hydroxylated biphenyls as tyrosinase inhibitor: A spectrophotometric and electrochemical study", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 126, 13 December 2016 (2016-12-13), pages 1034 - 1038, XP029885688, ISSN: 0223-5234, DOI: 10.1016/J.EJMECH.2016.12.028 *

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