WO2017057419A1 - Composition à usage externe - Google Patents

Composition à usage externe Download PDF

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Publication number
WO2017057419A1
WO2017057419A1 PCT/JP2016/078546 JP2016078546W WO2017057419A1 WO 2017057419 A1 WO2017057419 A1 WO 2017057419A1 JP 2016078546 W JP2016078546 W JP 2016078546W WO 2017057419 A1 WO2017057419 A1 WO 2017057419A1
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WO
WIPO (PCT)
Prior art keywords
extract
weight
composition
ascorbic acid
component
Prior art date
Application number
PCT/JP2016/078546
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English (en)
Japanese (ja)
Inventor
裕也 上原
希 伊藤
Original Assignee
小林製薬株式会社
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Filing date
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Publication of WO2017057419A1 publication Critical patent/WO2017057419A1/fr

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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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics 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
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K8/67—Vitamins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/57—Magnoliaceae (Magnolia family)
    • A61K36/575—Magnolia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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

Definitions

  • Patent Document 1 reports that a honoki extract has an action of inhibiting collagenase activity and is effective in preventing skin aging.
  • Patent Document 2 it is reported that the enzymatic degradation product of prune has an action of suppressing phagocytosis and exhibits a whitening effect by suppressing the movement of melanin to the body surface.
  • the cosmetic effect exhibited by the plant extract alone is slow, and there is a drawback that it cannot fully satisfy consumer needs.
  • the present inventor has intensively studied to solve the above-mentioned problems, and as a result, by using ascorbic acid and / or a derivative thereof together with an extract of a magnoliaceae magnolia plant, the production inhibitory effect of melanin is dramatically increased. It has been found that the whitening effect can be remarkably improved. Furthermore, it discovered that whitening effect improved further by combining the extract of a Rosaceae cherry tree genus plant with the said 2 component.
  • composition for external use of the present invention contains ascorbic acid and / or a derivative thereof.
  • Ascorbic acid and / or its derivatives are known components that have an antioxidant action and are known to have a whitening effect.
  • the magnoliaceae magnolia plant extract is obtained by extracting the plant part to be extracted as it is or after drying, chopping, crushing, pressing, enzyme treatment, boiling or fermentation treatment with the extraction solvent. Can be obtained.
  • solvent extraction treatment a commonly used extraction method of plant extracts can be employed. Specifically, immersion methods such as cold immersion and digestion; a method of stirring under heating; or a percolation method Etc.
  • the extract of the Rosaceae cherry genus plant only needs to be extracted from the flesh of the plant, but the plant part to be extracted includes fruit skin, seeds, etc., if necessary, in addition to the flesh. Also good.
  • Examples of the extraction solvent used in the solvent extraction treatment of Rosaceae are: water; lower alcohols having 1 to 5 carbon atoms such as methanol, ethanol, propanol, isopropyl alcohol, butanol and isobutanol; propylene glycol 1,3-butylene glycol, 1,2-butylene glycol, 1,4-butylene glycol, 1,5-pentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, And polyhydric alcohols such as 1,3,5-pentanetriol; phenoxyethanol, paraben, ethylparaben, methylparaben, propylparaben; and mixtures thereof.
  • lower alcohols having 1 to 5 carbon atoms such as methanol, ethanol, propanol, isopropyl alcohol, butanol and isobutanol
  • the extract of the Rosaceae cherry genus plant is the above extraction target plant part as it is or, if necessary, dried, shredded, crushed, pressed, enzymatically treated, boiled or fermented with the above extraction solvent. It is obtained by doing.
  • the Rosaceae genus plant to be subjected to the extraction treatment is subjected to an enzyme treatment in advance.
  • an enzyme-treated Rosaceae genus Sakura as an extraction raw material, it is possible to obtain an extract with an extremely high effect of improving the whitening effect.
  • the enzyme treatment conditions are not particularly limited, and may be set within the range of the working temperature and working pH of the enzyme to be used, and may be performed until the enzymatic reaction proceeds so as to obtain a desired effect. Examples include conditions of reacting at 20 to 45 ° C. for 3 to 24 hours. After carrying out the enzyme treatment to the Rosaceae cherry genus plant, the enzyme may be deactivated by heating or the like, if necessary, and subjected to the solvent extraction treatment.
  • the extract obtained by the solvent extraction treatment may be used in a liquid state, but may be used as a concentrate or a dried product by being subjected to a treatment such as concentration and drying, if necessary. Good. Further, after concentration or drying, the obtained concentrate or dried product may be purified by washing with a non-soluble solvent, or may be used by further dissolving or suspending it in a suitable solvent.
  • a commercially available product can be used as an extract of a Rosaceae genus Rosa or an enzyme-treated extract of a Rosaceae genus Sakura.
  • an extract of prunes that have been enzymatically decomposed “Cleaage” manufactured by Ichimaru Falcos Co., Ltd. can be mentioned.
  • the strong ruruboxy vinyl polymer is a water-soluble vinyl polymer having a carboxyl group, and specifically has a cross-linked structure with allyl sucrose, allyl ether of pentaerythritol, etc. with acrylic acid and / or metaglylic acid as the main chain. It is a polymer.
  • the alkyl-modified carboxyvinyl polymer is a polymer in which at least a part of the carboxyl group of the carboxyvinyl polymer is esterified with an alkyl group.
  • the alkyl group bonded by an ester bond may be either straight or branched.
  • the carbon number of the alkyl group is not particularly limited, and examples thereof include 8 to 35, preferably 8 to 30.
  • the molecular weight of the carboxyvinyl polymer and the alkyl-modified carboxyvinyl polymer is not particularly limited.
  • the viscosity at 20 ° C. of an aqueous solution (pH 6.5) dissolved so as to be 5% by weight is preferably 500 mPa ⁇ s or more. Can be 500 to 100,000 mPa ⁇ s.
  • rotor M3 (rotation speed: 20 rpm, time: 1 minute, unit: mPa ⁇ s) It is a value measured using.
  • water-soluble thickener commercially available ones can also be used.
  • commercially available products of carboxyvinyl polymer include “AQPEC HV-501E” and “AQUP EC HV-505E” manufactured by Sumitomo Seika Co., Ltd .; “Carbopol 940” and “Carbopole 941” manufactured by Lubrizol Advanced Materials.
  • Carbopol 980 “Hibiswaco 1103”, “Hibiswaco 1104”, “Hibiswaco 1105” manufactured by Wako Pure Chemical Industries, Ltd .; “Sintalen K”, “Sintalen L” manufactured by 3V Sigma, etc. It is done.
  • alkyl-modified carboxyvinyl polymer examples include “AQUPEC HV-501ER” manufactured by Sumitomo Seika Co., Ltd .; “Carpopol ultrez20”, “Carbopol ultrez21”, and “Carbopol 1342” manufactured by Lubrizol Advanced Materials. “Carbopol ETD2020”, “Pemlen TR-1”, “Pemlen TR-2” and the like.
  • the porous powder is not particularly limited as long as it is pharmaceutically or cosmetically acceptable.
  • Inorganic powders such as aluminum hydroxide, aluminum silicate, silicic anhydride, hydrous silicic acid, montmorillonite; polyester, polyethylene, polystyrene, methyl methacrylate resin, cellulose, nylon, copolymer of styrene and acrylic acid, polypropylene, Examples thereof include polymer powders such as vinyl chloride.
  • These porous powders may be used alone or in combination of two or more.
  • the average particle size of the porous powder is not particularly limited, and examples thereof include 1 to 25 ⁇ m, preferably 3 to 20 ⁇ m, and more preferably 3 to 15 ⁇ m.
  • the oil absorption amount of the porous powder is not particularly limited, and examples thereof include 50 to 500 ml / 100 g, preferably 50 to 300 ml / 100 g, and more preferably 50 to 200 ml / 100 g.
  • the specific surface area of porous powder is not particularly limited, for example, 30 ⁇ 1000m 2 / g, preferably 100 ⁇ 950m 2 / g, more preferably 200 ⁇ 800m 2 / g, more preferably 200 ⁇ 600 meters 2 / g.
  • the average particle diameter of the porous powder is an “arithmetic average value of particle diameters” defined in JIS Z 8901: 2006 “Test Powder and Test Particles”.
  • the oil absorption of the porous powder is a value measured according to JIS K5101-13-1.
  • the specific surface area of the porous powder is a BET specific surface area measured in accordance with JIS K6430 Appendix E.
  • Trimethylglycine is a component that is widely used as an amino acid-based moisturizing agent in plants of sea urchins, seaweeds, fish, and crustaceans.
  • the ratio of the component (D) to the component (F) is 0 (F) component per 1 part by weight of the component (D). Desirably, 1 to 6 parts by weight.
  • the ratio of the component (D) to the component (F) is as follows. The amount is preferably 1 to 4 parts by weight, more preferably 1.5 to 4 parts by weight.
  • the content of the component (E) in the composition for external use of the present invention may be appropriately set so that the ratio of the component (D) and the component (F) described above can be satisfied.
  • the content of the component (D) When the amount is 0.1 to 3% by weight, the content of component (E) is 0.01 to 18% by weight, preferably 0.1 to 12% by weight, more preferably 0.15 to 12%. % By weight.
  • composition for external use of the present invention may contain a polyhydric alcohol as necessary for the purpose of enhancing the moisturizing action.
  • the polyhydric alcohol is not particularly limited as long as it is pharmaceutically or cosmetically acceptable.
  • propylene glycol, ethylene glycol, 1,3-butylene glycol, isoprene glycol, diethylene glycol, dipropylene glycol examples include glycerin.
  • These polyhydric alcohols may be used individually by 1 type, and may be used in combination of 2 or more type. Among these polyhydric alcohols, 1,3-butylene glycol and glycerin are preferable.
  • the content when polyhydric alcohol is contained, the content may be appropriately set according to the type of polyhydric alcohol used, the formulation form of the composition for external use, etc. 0.01 to 30% by weight, preferably 0.1 to 20% by weight, and more preferably 1 to 20% by weight.
  • Composition for external use of the water present invention may contain water as a base.
  • water when the components (D) and (F) described above are included, it is desirable to include water as a base for dissolving these components.
  • the content of water is not particularly limited, and more specifically, for example, 10 to 99.5 wt%, preferably 10 to 98 wt% can be mentioned.
  • the water content is 25 to 95% by weight, preferably 35 to 95% by weight, and more preferably 45 to 95% by weight.
  • composition for external use of the present invention may contain other pharmacological components as necessary in addition to the components described above.
  • pharmacological components include antihistamines (diphenhydramine, diphenhydramine hydrochloride, chlorpheniramine maleate, etc.), local anesthetics (lidocaine, dibucaine, methyl aminobenzoate, procaine, tetracaine, bupipacaine, mepipacaine, chloroprocaine).
  • the external composition of the present invention may contain a base or an additive as necessary in order to obtain a desired formulation form.
  • bases and additives are not particularly limited as long as they are pharmaceutically acceptable, but for example, aqueous bases such as lower alcohols (ethanol, isopropanol, etc.); oils (olive oil, safflower oil) , Soybean oil, camellia oil, corn oil, rapeseed oil, sunflower oil, cottonseed oil, peanut oil, lard, squalane, fish oil, etc.), mineral oil (liquid paraffin, paraffin, gelled hydrocarbon, petroleum jelly, etc.), waxes and waxes (Beeswax, carnauba wax, candelilla wax, ceresin, rice wax, microcrystalline wax, etc.), ester oil (isopropyl myristate, isopropyl adipate, diethyl sebacate, isopropyl sebacate, isopropyl palmitate, cetyl palmitate,
  • composition for external use is a preparation form that can be applied transdermally
  • the formulation form is not particularly limited, and is liquid, solid, semi-solid (cream, gel, ointment, paste) Any of these may be used.
  • the composition for external use of the present invention may be a non-emulsifying preparation such as an aqueous preparation or an oily preparation, or an emulsion preparation such as an oil-in-water emulsion preparation or a water-in-oil emulsion preparation.
  • the liquid preparation or cream is preferable as the preparation form of the external composition.
  • composition for external use may be in any form of pharmaceutical preparation for external use of skin, cosmetics, skin cleansing agents, and the like.
  • Specific preparation forms of the external composition include liquids (including lotions, sprays, aerosols, and emulsions), water-soluble ointments, oily ointments, creams, foams, and gels. And skin external preparations such as patches; cosmetics such as ointments, creams, emulsions, lotions, lotions, packs and gels; and skin cleansing agents such as body shampoos, hair shampoos and rinses.
  • a skin external medicine more preferably a liquid or cream.
  • These preparation forms can be prepared by formulating with additives according to the preparation form according to a known method described in the 16th revised Japanese Pharmacopoeia General Rules for Preparations.
  • composition for external use of the present invention can suppress the production of melanin, and can prevent or improve skin spots, freckles, dullness, liver spots, senile pigment spots, darkening due to physical irritation, etc. It is suitably used as an external composition for whitening.
  • Test Example 1 Evaluation of melanin production inhibitory effect The melanin production inhibitory effect was evaluated using a three-dimensional cultured skin model (MEL-300-A, manufactured by MatTek). The specific test method is as follows.
  • UV irradiation was performed using a UVB lamp (manufactured by Toshiba Lighting & Technology Corp., fluorescent lamp for Toshiba health line) and a UV detector (manufactured by TOPCON, UV-1). Thereafter, the medium was changed and further cultured for 24 hours. Each time the medium was changed, 50 ⁇ l of a predetermined sample solution was added to the skin model cup. Furthermore, ultraviolet irradiation and medium exchange were repeated four times under the same conditions, so that ultraviolet irradiation was performed five times in total (total ultraviolet irradiation amount 30 mJ / cm 2 ), and medium replacement was performed five times in total. Thereafter, cell viability and melanin production were measured by the methods described below. As a control, an aqueous solution containing 0.5% by weight of 1,3-butylene glycol was used as a sample solution, and the test was performed under the same conditions as described above.
  • MTT test Specifically, 0.75 ml of MTT test drug and 8.25 ml of maintenance medium (EPI-100LLMM) were mixed and 300 ⁇ l per well was mixed. 1 was added. The skin model cup was transferred to the medium containing MTT prepared above and cultured in an incubator for exactly 3 hours. Thereafter, the bottom surface of the tissue was gently washed with PBS washing solution and transferred to a new plate. 0.04N HCl acidic isopropanol was added to the inside of the skin model cup in an amount of 1 ml, and blue formazan was extracted in an incubator overnight with a cover seal attached to the plate to prevent evaporation.
  • maintenance medium EPI-100LLMM
  • the isopropanol was mixed well and 200 ⁇ l was transferred to a 96-well plate.
  • the optical densities at 570 nm and 620 nm were measured with a microplate reader, and the difference between them was taken as the cell activity.
  • the amount of melanin produced per cell was determined by dividing the amount of melanin produced by the cell viability. Furthermore, assuming that the amount of melanin produced per cell of control was 100, the ratio of the amount of melanin produced per cell (melanin production ratio) when each sample solution was added was calculated.
  • Test Example 2 Evaluation of use feeling Skin cosmetics (solutions) having the compositions shown in Tables 3 and 4 were prepared. Specifically, the manufacturing procedure is as follows. A carboxyvinyl polymer and an alkyl-modified carboxyvinyl polymer were stirred and dissolved in purified water, and then glycerin was added and dissolved by stirring to obtain Preparation A. Separately, trimethylglycine and / or silica was added to 1,3-butylene glycol, and the mixture was stirred and homogenized to obtain Preparation B. Then, while stirring the preparation A, the preparation B was added, and the mixture was stirred with a homomixer and homogenized. Furthermore, after adjusting the pH to 6.5 by adding potassium hydroxide, L-ascorbic acid 2-glucoside, honoki extract, and prune extract are added and stirred to homogenize the skin cosmetic. Prepared.
  • Each of the obtained skin cosmetics was evaluated by the following methods for a firm application feeling at the time of application, a lack of stickiness and a refreshing feeling, a lack of powderiness after application, and a feeling of warmth.
  • Ten evaluation monitors apply about 0.5g of each skin cosmetic to the arm, and a firm application feeling at the time of application, no stickiness and refreshing feeling, and no powderiness after application and moisturizing The feeling was evaluated. Specifically, the evaluation was scored by conducting a questionnaire based on Visual Analogue Scale (hereinafter sometimes referred to as VAS) with “1” and “10” as follows. The questionnaire results were averaged, and the evaluation results were summarized by rounding off the first decimal place.
  • VAS Visual Analogue Scale
  • Formulation Examples 1-9 According to the formulation shown in Table 5, skin cosmetics were prepared by a conventional method (Prescription Examples 1 to 6 had a pH of 6.5 and Formulation Examples 7 to 9 had a pH of 4.5).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
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  • Mycology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
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  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

Le problème décrit par la présente invention est de fournir une composition à usage externe qui inhibe efficacement la mélanogenèse et, de ce fait, exerce un excellent effet de blanchiment. La solution selon l'invention porte sur une composition à usage externe comprenant de l'acide ascorbique et/ou un dérivé de celui-ci conjointement avec un extrait d'une plante appartenant au genre Magnolia de la famille des Magnoliacées. Grâce à l'utilisation combinée de ces ingrédients, un effet d'inhibition de la mélanogenèse est remarquablement amélioré et un effet de blanchiment nettement supérieur peut être obtenu.
PCT/JP2016/078546 2015-09-30 2016-09-27 Composition à usage externe WO2017057419A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-192887 2015-09-30
JP2015192887A JP6807636B2 (ja) 2015-09-30 2015-09-30 外用組成物

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WO2017057419A1 true WO2017057419A1 (fr) 2017-04-06

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Cited By (1)

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JP2021001126A (ja) * 2019-06-20 2021-01-07 小林製薬株式会社 ケラチノサイト内メラノソーム分解促進剤

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JP2007119430A (ja) * 2005-10-31 2007-05-17 Ichimaru Pharcos Co Ltd ペルオキシソーム増殖剤応答性受容体活性化剤
WO2007094312A1 (fr) * 2006-02-14 2007-08-23 Fancl Corporation Agent favorisant la production de transporteurs de vitamine c
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JP2004155702A (ja) * 2002-11-06 2004-06-03 Hidekazu Itaka 構造化濃縮深層水を用いた化粧品
JP2007119430A (ja) * 2005-10-31 2007-05-17 Ichimaru Pharcos Co Ltd ペルオキシソーム増殖剤応答性受容体活性化剤
WO2007094312A1 (fr) * 2006-02-14 2007-08-23 Fancl Corporation Agent favorisant la production de transporteurs de vitamine c
JP2014091717A (ja) * 2012-11-05 2014-05-19 Ichimaru Pharcos Co Ltd メラニン生成抑制剤、保湿剤、美白化粧料、美容飲食品

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NORIHISA KAWAI: "Atarashii Keshohin Genryo Mijikana Sozai kara Kaihatsu sareta Shinki Keshohin Genryo", OIL AND FAT, vol. 58, no. 8, 15 August 2005 (2005-08-15), pages 54 - 56 , 61 - 64 *
NORIHISA KAWAI: "The epoch-making ingredients for whitening", FRAGRANCE JOURNAL, June 2005 (2005-06-01), pages 39 - 43 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113811538A (zh) * 2019-06-20 2021-12-17 小林制药株式会社 外用组合物

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