WO2010089754A1 - Agent cosmétique d'éclaircissement de la peau et sa composition - Google Patents

Agent cosmétique d'éclaircissement de la peau et sa composition Download PDF

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Publication number
WO2010089754A1
WO2010089754A1 PCT/IN2009/000085 IN2009000085W WO2010089754A1 WO 2010089754 A1 WO2010089754 A1 WO 2010089754A1 IN 2009000085 W IN2009000085 W IN 2009000085W WO 2010089754 A1 WO2010089754 A1 WO 2010089754A1
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WO
WIPO (PCT)
Prior art keywords
formula
skin lightening
lightening agent
skin
oreganol
Prior art date
Application number
PCT/IN2009/000085
Other languages
English (en)
Inventor
Gottumukkala Venkateswara Rao
Triptikumar Mukhopadhyay
Narayanaswamy Radhakrishnan
Original Assignee
Cavinkare Pvt. Ltd
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 Cavinkare Pvt. Ltd filed Critical Cavinkare Pvt. Ltd
Priority to PCT/IN2009/000085 priority Critical patent/WO2010089754A1/fr
Publication of WO2010089754A1 publication Critical patent/WO2010089754A1/fr

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]

Definitions

  • the present invention relates to an improved cosmetic skin lightening composition.
  • This invention particularly relates to an improved cosmetic skin lightening composition containing selective extracts of the plant Origanum vulgare.
  • the invention particularly relates to an improved cosmetic skin lightening composition involving glycosides of benzyl protocatechuate derivatives isolated from the plant Origanum vulgare.
  • the invention particularly relates to an improved cosmetic skin lightening composition containing glyocosides of benzyl protocatechuate derivatives of the Formula I given below
  • Ri and R 2 represent H or alkyl groups
  • R'n represents zero to two hydroxy or methoxy groups and at least one glycosyl hexose sugar group the pharmaceutically/ cosmetically acceptable salts, stereoisomers, enantiomers, polymorphs, pseudopolymorphs thereof, free from or mixed with other enantiomers or stereoisomers or polymorphs or pseudopolymorphs.
  • Skin lightening is an important contributor to skin care attribute of cosmetic preparation/ compositions, especially among darker skinned people including Asian population. Such a need includes a lightening of basal skin tone. Also it is desired by persons having spots, freckles or lesions which are hyperpigmented and thus need to be diminished. In other situations subjects may desire to reduce their natural skin colour or the skin darkening caused by exposure to intense sun rays.
  • 1,4- dihydroquinone can be considered to be a potent melanocyte cytotoxic agent and is also reported to induce mutations.
  • Kojic acid and arbutin are marginal tyrosinase inhibitors which are not very bio-available and have marginal efficacy.
  • a good protective agent is at the same time a skin lightening agent, and must have a high absorption capacity in the zone from 280 to 320 nm approximately, and also an optimal level of absorption capacity in the zone above 320 nm in order to offer the best condition for not counteracting the skin lightening effect of the compound.
  • free radicals particularly the reactive forms of oxygen (superoxide radical O 2 -, hydroxyl radical HO-, singlet oxygen O 2 1 , hydrogen peroxide H 2 O 2 ) act on a cellular scale, particularly damaging the membranous lipids with the formation of lipoperoxides, deterioration of proteins, blocking of enzyme systems and deterioration of the nuclear genetic capital.
  • Noxious effects are also produced in the fibroblastic macromolecules of the extracellular matrix of the dermis, namely in collagen, elastin and glycoaminoglycans, necessary for skin smoothness, firmness, and elasticity, thus contributing to the cause of wrinkles and aging.
  • antioxidants may help thwart environmental damage to the skin and are now recognizing the anti-aging benefits of topically applied antioxidants.
  • Some skin care products offer antioxidant benefits directly to the skin by including antioxidant-rich extracts and vitamins in their formulations.
  • antioxidant-rich extracts and vitamins in their formulations.
  • antioxidants There are hundreds of known antioxidants, many of which are plant derived. These natural antioxidant compounds, found in herbs, fruits and vegetables, are shown to act as radical scavengers and thus neutralize the negative effects of free radicals.
  • plant phenolic and polyphenols compounds are claimed to be useful antioxidants [see for example, S. Hsu, J. of the American Academy of Dermatology (2005), 52, 6, 1049-1059 ; J.
  • Oreganol A is described merely to be a radical scavenger and no indication has been made to its skin care property such as skin lightening via tyrosinase inhibition.
  • the recent trends in demands of the consumers for cosmetic preparations are directed to certain extent to demonstrated skin care effect by overcoming some deficiency, having improved performance as skin protection means and providing several properties simultaneously in the same product.
  • skin lightening it is found desirable to achieve skin lightening effects and also simultaneously serve as sunscreens to protect the skin from the deleterious effects of exposure to harmful radiations when exposed to intense sun rays.
  • Customers concern for such cosmetic preparation also calls for specific skin compatibilities and additions of natural products to derive the stated attributes.
  • the main objective of the present invention is to provide an improved cosmetic skin lightening composition which on one hand would be efficacious and would overcome the limitations and disadvantages observed in the existing tyrosinase inhibitors presently in use, with better consumers acceptance and on the other hand advantageously have conjoint attributes such as sunscreen and anti-aging thereby favouring- an improved performance spectrum of skin care.
  • Another objective of the present invention is to provide an improved cosmetic skin lightening composition containing the selective extract of the plant Origanum vulgare Linn.
  • Yet another objective of the present invention is to provide an improved cosmetic skin lightening composition containing selectively glycosides of benzyl protocatechuate derivatives isolated from the plant Origanum vulgare.
  • Still another objective of the present invention is to provide an improved cosmetic skin lightening composition comprising of selective glyocosides of benzyl protocatechuate derivatives of the Formula I as one of the skin lighetening agent/s.
  • Still another object of the invention is to provide an improved cosmetic skin lightening composition
  • an improved cosmetic skin lightening composition comprising of a selective Oreganol A of Formula II as at least one of the skin lightening agents.
  • Ri and R 2 represent H or alkyl groups
  • R'n represents zero to two hydroxy or methoxy groups and at least one glycosyl hexose sugar group the pharmaceutically/cosmetically acceptable salts, stereoisomers, enantiomers, polymorphs, pseudopolymorphs thereof, free from or mixed with other enantiomers or stereoisomers or polymorphs or pseudopolymorphs.
  • a skin lightening agent wherein said protocatechuic acid derivatives comprises as an active ingredient in effective amounts Oreganol A of Formula II
  • the skin lightening agent comprises said compound of Formula I or preferably Oreganol A of Formula II as extracts/concentrates from. plants preferably Origanum vulgare Linn., and most preferably methanol extract/concentrate or more preferably ethyl acetate " extract/concentrate and containing Oreganol A of Formula II as at least one ingredient in the concentrate.
  • the cosmetic composition for topical use comprises: a. 0.0001 wt% to 20 wt. % of said skin lightening agent, preferably 0.001 wt% to 10 wt% of said skin lightening agent and more preferably and 0.01 wt% to 5 wt% of said skin lightening agent as at least one ingredient. and b. a cosmetically acceptable vehicle with or without other skin benefit agents.
  • the said cosmetic composition for topical use comprises a leave-on or a wash-off product adapted for topical delivery in the form of creams, ointments, emulsions, gels, lotions, oils, sticks, sprays, soaps, packs, wraps, woven or nonwoven wipes, films or patches as a vehicle for topical application of the said skin lightening composition.
  • a cosmetic composition for topical use wherein said skin lightening agent comprises selectively pure compound of Formula I or preferably Oreganol A of Formula II, as a concentrate of an appropriate natural isolate comprising preferably compounds of Formula I/ or Oreganol A of Formula II an extract/concentrate of the natural source material comprising compound of Formula II or even a natural source material itself.
  • the said cosmetic composition for topical use includes skin lightening agent comprises extracts / concentrate from leaves of Origanum vulgare Linn., preferably methanol concentrate or more preferably ethyl acetate concentrate and containing Oreganol A of Formula II.
  • benzyl protocatechuate derivatives of the Formula I for use in the compositions of the invention are 4'-O-beta-D-glucopyranosyl-3',4'- dihyroxybenzyl protocatechuate, named as Oreganol A, and its O-methyl derivatives, which can be isolated from the plant Origanum vulgare.
  • the above discussed cosmetic composition for topical use can be a leave-on or a wash-off products wherein the delivery system comprises creams, ointments, emulsions, gels, lotions, oils, sticks, sprays, soaps, packs, wraps, woven or nonwoven wipes, films or patches as a vehicle for topical application of the said skin lightening composition.
  • Oreganol A of Formula II shows surprisingly good inhibition of mushroom tyrosinase indicating its role as. a skin lightening agent. It is further seen that Oreganol A of Formula II significantly reduces formation of melanin - the molecule responsible for skin pigmentation - in melanocytes which are the cells that synthesise melanin. Particularly noteworthy is that the skin lightening agent of this invention is more potent than some of the standard reference molecules such as Arbutin. Even more interesting finding is that Oreganol A of Formula II -even when present in an . extract form in a finished skin care product such as cream or lotion - continues to exhibit this melanin reduction property.
  • Oreganol A of Formula II showed skin lightening activity (tyrosinase inhibiting activity and reduction in melanin content in melanocytes) and which was known in the art to have merely displayed DPPH radical scavenging activity and further Oreganol A of Formula II is isolated from a source of the plant Origanum vulgare Linn.
  • composition according to the invention involving the above skin lightning agent is intended primarily as a product for topical application to skin- for ' the purpose of skin lightening.
  • a small quantity of the composition for example about 0.1 to about 5 ml, can be applied to exposed areas of the skin, from a suitable container or applicator and, if necessary, it is then spread over and/or rubbed into the skin using the hand or fingers or a suitable device for desired skin benefit activity.
  • ingredients essentially employed in such a composition are surfactants, emulsifiers emollients, silicones, thickeners, antioxidants, sunscreen agents, chelating agents, perfumes, opacifiers, colors, antimicrobial agents, herbal extract /compounds, pH adjusting agents and water to qs.
  • the composition may contain usually employed vehicle such as may be aqueous, anhydrous or an emulsion.
  • the compositions are aqueous or an emulsion, especially water-in-oil or oil-in-water emulsion, preferentially oil in water emulsion.
  • Water when present will be in amounts which may range from 5 to 99%, preferably from 20 to 85%, optimally between 40 and 80% by weight.
  • the cosmetic composition may contain other various other skin benefit agents, plasticizers, elastomers, calamine, pigments, antioxidants, chelating agents, and perfumes, as well as organic/inorganic sunscreens and including such sunscreens as UV diffusing/protection agents, typical of which is finely divided Titanium oxide and Zinc oxide.
  • the cosmetic composition of the present invention may optionally contain other adjunct minor components /ingredients such as including coloring agents, opacifiers, antimicrobial agents, pH adjusting agents and perfumes. Amounts of these other adjunct minor components may range anywhere from 0.0001% up to 20% by weight of the composition.
  • the composition may also contain suitable skin benefit agents include anti-aging, wrinkle- reducing, skin whitening, anti-acne, and sebum controlling / reducing agents.
  • suitable skin benefit agents include anti-aging, wrinkle- reducing, skin whitening, anti-acne, and sebum controlling / reducing agents.
  • alpha-hydroxy acids and esters beta-hydroxy acids and esters, polyhydroxy acids and esters, kojic acid and esters, ferulic acid and ferulate derivatives, vanillic acid and esters, dioic acids (such as sebacic and azeleic acids) and esters, retinol, retinal, retinyl esters, hydroquinone, t-butyl hydroquinone, mulberry extract, licorice extract, and glycosides of benzyl protocatechuate derivatives other than the derivatives discussed herein above.
  • Suitable cosmetic carriers are well known to one skilled in the art.
  • the cosmetic bases may be any bases which are ordinarily used for skin benefit agents and are not thus critical.
  • Cream bases are, for example, beeswax, cetyl alcohol, stearic acid, glycerine, propylene glycol, propylene glycol monostearate, polyoxyethylene cetyl ether and the like.
  • Lotion bases include, for example, oleyl alcohol, ethanol, propylene glycol, glycerine, lauryl ether, sorbitan monolaurate and the like.
  • the cosmetically acceptable vehicle may act as a diluant, dispersant or carrier for the skin benefit ingredients in the composition, so as to facilitate their distribution when the composition is applied to the skin.
  • relatively volatile solvents may also serve as carriers within compositions of the present invention.
  • monohydric Ci-C 3 alkanols include ethyl alcohol, methyl alcohol and isopropyl alcohol.
  • the amount of monohydric alkanol may range from 1 to 70%, preferably from 10 to 50%, optimally between 15 to 40% by weight.
  • Emollient materials may also serve as cosmetically acceptable carriers. These may be in the form of silicone oils and synthetic esters. Amounts of the emollients may range anywhere from 0.1 to 50%, preferably between 0.5 and 30% by weight.
  • Silicone oils may be divided into the volatile and non-volatile variety.
  • volatile refers to those materials which have a measurable vapor pressure at ambient temperature.
  • Volatile silicone oils are preferably chosen from cyclic or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
  • Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • the essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 1 to about 25 million centistokes at 25 0 C.
  • the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 10 to about 2,00,000 centistokes at 25. degree. C.
  • ester emollients are: (1) Alkenyl or alkyl esters of fatty acids having 10 to 20 carbon atoms. (2) Ether-esters such as fatty acid esters of ethoxylated fatty alcohols. (3)
  • Thickeners/ rheology modifiers may also be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention. Amounts of the thickener may range from 0.0001 to 10%, usually from 0.001 to 5%, by weight.
  • the water, solvents, silicones, esters, fatty acids, humectants and/or thickeners will constitute the cosmetically acceptable carrier in amounts from 1 to 99.9%, preferably from 80 to 99% by weight.
  • An oil or oily material may be present, together with an emulsifier to provide either a water- in-oil emulsion or an ' oil-in-water emulsion, depending largely on the average hydrophilic- lipophilic balance (HLB) of the emulsifier employed.
  • HLB hydrophilic- lipophilic balance
  • Surfactants may also be present in cosmetic compositions of the present invention.
  • total concentration of the surfactant will range from 0.1 to 40%, preferably from 1 to 20%, optimally from 1 to 15% by weight of the composition.
  • wash- off products such as cleansers and soap
  • total concentration of surfactant will range at about 1 to about 90%.
  • the surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives.
  • the inventive cosmetic compositions optionally contain a lathering surfactant.
  • a lathering surfactant is meanjt a surfactant which, when combined with water and mechanically agitated, generates a foam or lather.
  • the lathering surfactant should be mild, meaning that it must provide sufficient cleansing or detergent benefits but not overly dry the skin, and yet meet the lathering criteria described above.
  • the cosmetic compositions of the present invention may contain a lathering surfactant in a concentration of about 0.01% to about 50%.
  • compositions of the invention there may be added various other plasticizers, elastomers, calamine, pigments, antioxidants, chelating agents, and perfumes, as well as organic sunscreens and sunscreens such UV diffusing agents, typical of which is finely divided titanium oxide and zinc oxide.
  • adjunct minor components may also be incorporated into the cosmetic compositions. These ingredients may include coloring agents, opacifiers, and perfumes. Amounts of these other adjunct minor components may range anywhere from 0.001% up to 20% by weight of the composition.
  • the cosmetic skin composition of the present invention additionally may include organic UV- radiation protection agents to provide protection from the harmful effects of excessive exposure to sunlight.
  • Organic UV-radiation protection agents for purposes of the inventive compositions are organic UV-radiation protection agents having at least one chromophoric group absorbing within the ultraviolet range of from 280 to 400 nm.
  • Preferred organic sunscreens are either single UV-radiation protection agents or combinations of different UV- radiation protection agents so as to absorb the entire UV range.
  • the amount of the organic UV-radiation protection agents in the personal care composition is generally in the range of about 0.01% to about 20%, preferably in " the range of about 0.1% to about 10%.
  • the said organic UV-radiation protection agent is present in an amount of about 1 wt % to about 10 wt % of said cosmetic composition; and wherein the weight ratio of said organic UV-radiation protection agent to said glycosides of benzyl protocatechuate derivatives is about 10000:1 to about 1:10000.
  • the inorganic or physical sunscreens are in the range of 1-30% by weight of the composition.
  • Organic antioxidant in the composition of the invention suitable for use include amino acids and its derivatives, imidazoles and derivatives thereof, peptides, and derivatives thereof , carotenoids, carotenes or derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof, aurothioglucose, propylthiouracil and other thiols and salts thereof, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof and sulfoximine compounds and also (metal) chelating agents , alpha- hydroxy acids, humic acid, bile acid, bile extracts, bilirubin, biliverdin, boldin, boldo extract, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and derivatives thereof, folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives, to
  • UV light protection factors or antioxidants can be added in amounts of from 0.01 to 25% by weight, preferably 0.03 to 10% by weight and in particular 0.1 to 5% by weight, based on the total amount in the preparations.
  • a small quantity of the composition for example about 0.1 to about 10 ml, is required to be applied to exposed areas of the skin, from a suitable container or applicator and, if necessary, it is then spread over and/or rubbed into the skin using the hand or fingers or a suitable device.
  • Example 1 Extraction and isolation of Oreganol A from Origanum vulgare Linn.
  • the air-dried leaves of Origanum vulgare Linn., (550 g) was powdered, extracted with methanol through soxhlet apparatus for about 8 hrs.
  • the extract was concentrated under reduced pressure to get 88 g of crude methanolic concentrate.
  • the concentrate was dissolved in 100 ml of methanol and 300 ml of water was added to obtain a homogeneous solution.
  • aqueous extract was partitioned successively with hexane (500 ml X 4), chloroform (500 ml X 2), ethyl acetate (500 ml X 3) and saturated butanol solvents (200 ml X 3) to get fractions which upon concentrations gave concentrates of 15.66 g, 3.716 g, 22.07 g and 30.0 g respectively.
  • the crude concentrate (2Og) from ethyl acetate fraction was dissolved in ethyl acetate and methanol solvent mixture and adsorbed on silica gel (100-200 mesh).
  • 80 g of silica gel was packed in the glass column by using ethyl acetate: chloroform (3:1) as solvent and adsorbed silica gel was loaded on top of the column.
  • the column was eluted with solvent mixture of ethyl acetate: chloroform (3:1) and five fractions (each 150 ml) was collected. Later, the solvent polarity was changed to ethyl acetate and 13 fractions were collected. Based on TLC studies the abovesaid fractions were divided into five lots.
  • the Protocatechuic acid derivative of the invention displays the following characteristics. On thin layer chromatography using a pre-coated silica gel plate (Merck 1.05554.0001), the isolated substance provides a spot " with an R f value of 0.42 in EtOAc: MeOH 3: 1.
  • This example demonstrates the method of determining the skin lightening activity of the specially preferred concentrate/ compound/ formulations of the invention by mushroom tyrosinase inhibition method and cell culture method by estimating the melanin content of the cells.
  • Enzyme Mushroom Tyrosinase (ECl.14.18.1) was dissolved in 0.1 M Phosphate buffer (pH 6.8) to 500 U/ml stock solution. Aliquots were stored in vials at -70 0 C. 90 ⁇ l of this enzyme is used directly for the assay volume of 700 microliters.
  • inhibitor solutions were added and buffer volume adjusted accordingly.
  • the substrate, buffer and inhibitor solutions were added and incubated for 10 min at 25 0 C.
  • the enzyme was then added with an interval of one minute into each tube, incubated for 20 min at 25 0 C.
  • the orange-pink colour formed (Dopachrome) was measured as absorbance at 475 nm at the end of 20 min for each tube (T).
  • % inhibition B-(T-C)/B x 100.
  • Pellet contains melanin. Wash the pellet with 0.5 ml of ethanol :ether. Add 0.5 ml of ethanol .-ether to the pellet. With a 1 ml tip, pipette the pellet up and down several times to break the pellet.
  • Phase C material Disperse Phase C material and heat to 75 degree C on water bath. Add Phase B to C, then add Phase A to Phase X BC and stir for 5 minutes.

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Abstract

L'invention concerne des compositions cosmétiques améliorées pour éclaircir la couleur de la peau. Selon l'invention, l'ingrédient actif comprend un dérivé d'acide protocatéchique de formule I ou de préférence un dérivé d'acide protocatéchique, Oréganol A de formule II, en une quantité efficace, aux côtés de véhicules cosmétiquement acceptables, avec ou sans agents bénéfiques pour la peau. L'ingrédient actif est isolé sélectivement de parties de la plante Origanum vulgare Linn.
PCT/IN2009/000085 2009-02-06 2009-02-06 Agent cosmétique d'éclaircissement de la peau et sa composition WO2010089754A1 (fr)

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PCT/IN2009/000085 WO2010089754A1 (fr) 2009-02-06 2009-02-06 Agent cosmétique d'éclaircissement de la peau et sa composition

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PCT/IN2009/000085 WO2010089754A1 (fr) 2009-02-06 2009-02-06 Agent cosmétique d'éclaircissement de la peau et sa composition

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2802871C1 (ru) * 2022-11-16 2023-09-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный медицинский университет" Министерства здравоохранения Российской Федерации Применение ореганола а, обладающего нейротропной активностью

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006008555A (ja) * 2004-06-24 2006-01-12 Japan Science & Technology Agency オレガノ抽出物のα−グルコシダーゼ阻害剤およびその利用
US20080214669A1 (en) * 2005-01-14 2008-09-04 Lipo Chemicals Inc. Composition and Method For Treating Hyperpigmented Skin

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006008555A (ja) * 2004-06-24 2006-01-12 Japan Science & Technology Agency オレガノ抽出物のα−グルコシダーゼ阻害剤およびその利用
US20080214669A1 (en) * 2005-01-14 2008-09-04 Lipo Chemicals Inc. Composition and Method For Treating Hyperpigmented Skin

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2802871C1 (ru) * 2022-11-16 2023-09-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный медицинский университет" Министерства здравоохранения Российской Федерации Применение ореганола а, обладающего нейротропной активностью

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