JP5703313B2 - 3−ヒドロキシ−2−ピロンを含有する美白剤 - Google Patents
3−ヒドロキシ−2−ピロンを含有する美白剤 Download PDFInfo
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- JP5703313B2 JP5703313B2 JP2012553510A JP2012553510A JP5703313B2 JP 5703313 B2 JP5703313 B2 JP 5703313B2 JP 2012553510 A JP2012553510 A JP 2012553510A JP 2012553510 A JP2012553510 A JP 2012553510A JP 5703313 B2 JP5703313 B2 JP 5703313B2
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- pyrone
- hydroxy
- tyrosinase activity
- acid
- skin
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- LIPRKYKMVQPYPG-UHFFFAOYSA-N 3-Hydroxy-2H-pyran-2-one Chemical compound OC1=CC=COC1=O LIPRKYKMVQPYPG-UHFFFAOYSA-N 0.000 title claims description 95
- 230000002087 whitening effect Effects 0.000 title claims description 28
- 102000003425 Tyrosinase Human genes 0.000 claims description 54
- 108060008724 Tyrosinase Proteins 0.000 claims description 54
- 230000000694 effects Effects 0.000 claims description 48
- 230000008099 melanin synthesis Effects 0.000 claims description 29
- 239000003112 inhibitor Substances 0.000 claims description 10
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- 230000002401 inhibitory effect Effects 0.000 description 51
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 34
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 34
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 26
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- SBJKKFFYIZUCET-UHFFFAOYSA-N Dehydroascorbic acid Natural products OCC(O)C1OC(=O)C(=O)C1=O SBJKKFFYIZUCET-UHFFFAOYSA-N 0.000 description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
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- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 2
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- 240000003394 Malpighia glabra Species 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
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- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- PMOWTIHVNWZYFI-WAYWQWQTSA-N cis-2-coumaric acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1O PMOWTIHVNWZYFI-WAYWQWQTSA-N 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
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- 229930182470 glycoside Natural products 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 2
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- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 2
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- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LIVFBMFGLDWZSB-UHFFFAOYSA-N OC1=COC=CC1=O.OC1=COC=CC1=O Chemical compound OC1=COC=CC1=O.OC1=COC=CC1=O LIVFBMFGLDWZSB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical class O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
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- VJNCICVKUHKIIV-UHFFFAOYSA-N dopachrome Chemical compound O=C1C(=O)C=C2NC(C(=O)O)CC2=C1 VJNCICVKUHKIIV-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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Images
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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
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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)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
アスコルビン酸の酸化物であるデヒドロアスコルビン酸5.0268g (和光純薬工業株式会社製)に50mlの精製水を添加し、これを3時間、100℃で加熱することにより加熱処理液を得た。
チロシナーゼは、アミノ酸であるチロシンからメラニン色素が生成する過程で作用する重要な酵素として知られており、多くの美白作用成分はチロシナーゼ活性阻害作用を有する。そこで、コウジ酸、アスコルビン酸及び実験1で調製した3H2Pのチロシナーゼ活性阻害作用を測定した。
=(1−(サンプルの0分から3分の吸光度差)/(ブランクの0分から3分の吸光度差))x100
結果を図1に示す。この測定により、3H2Pは、コウジ酸よりやや弱いがアスコルビン酸と同等のチロシナーゼ活性阻害作用を有することが判明した。
実験2において3H2Pにチロシナーゼ活性阻害作用が確認されたため、更に、動物細胞に対するメラニン生成抑制試験を実施した。サンプルとして実験1で調製された3H2P、アルブチン及びコウジ酸を用いた。
3-ヒドロキシ-2-ピロンのチロシナーゼ活性阻害作用を、γ-ピロン化合物であるコウジ酸、α-ピロン化合物であるクマリン(coumalin)(α-ピロン)、クマリン酸と比較した。コウジ酸、クマリン及びクマリン酸は特許文献1でメラニン生成抑制作用があることが報告されている。
クマリン(α-ピロン、東京化成工業株式会社製)、クマリン酸(東京化成工業株式会社製)水溶液及び3H2Pのチロシナーゼ活性阻害作用について検討した。
=(1−(サンプルの0分から3分の吸光度差)/(ブランクの0分から3分の吸光度差))x100
各検体の終濃度を0.3%、0.1%、0.033%で試験を行い、チロシナーゼ活性阻害作用を比較した結果、明かにクマリン及びクマリン酸より3H2Pが強い阻害活性を有することが判明した。結果を図4に示す。
美白作用を有することなどが既に報告されている3-ヒドロキシ-4-ピロン(以下、3H4Pとする。別名:ピロメコン酸、ピロコメン酸、3-ハイドロキシ-4-ピロンなど)は、3H2Pと分子式が同一であるが、γ-ピロン類に分類される化合物である。尚、3H4Pは、MOLEKULA 社製の試薬を使用した。
=(1-(サンプルの0分から3分の吸光度差)/(ブランクの0分から3分の吸光度差))x100
測定の結果、γ-ピロン類のコウジ酸が最も強いチロシナーゼ活性阻害活性を示し、3H2Pと3H4Pは同等のチロシナーゼ活性阻害活性を示した(図5)。
3H4P、3H2Pおよびコウジ酸のメラニン生成抑制作用について比較検討を行った。3H4Pは、MOLEKULA社製を使用した。
Claims (3)
- 3-ヒドロキシ-2-ピロンを含有する美白剤。
- 3-ヒドロキシ-2-ピロンを含有するチロシナーゼ活性阻害剤。
- 3-ヒドロキシ-2-ピロンを含有するメラニン生成阻害剤。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2011/050986 WO2012098664A1 (ja) | 2011-01-20 | 2011-01-20 | 3-ヒドロキシ-2-ピロンを含有する美白剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2012098664A1 JPWO2012098664A1 (ja) | 2014-06-09 |
JP5703313B2 true JP5703313B2 (ja) | 2015-04-15 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2012553510A Expired - Fee Related JP5703313B2 (ja) | 2011-01-20 | 2011-01-20 | 3−ヒドロキシ−2−ピロンを含有する美白剤 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20130309187A1 (ja) |
EP (1) | EP2666460A4 (ja) |
JP (1) | JP5703313B2 (ja) |
CN (1) | CN103347486A (ja) |
WO (1) | WO2012098664A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6173440B2 (ja) * | 2013-04-23 | 2017-08-02 | 株式会社ニチレイバイオサイエンス | 新規美白剤 |
CN105903018A (zh) * | 2016-05-16 | 2016-08-31 | 上海俏佳人医疗美容门诊部股份有限公司 | 一种具有美白效果的针剂 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0347899A (ja) * | 1989-07-17 | 1991-02-28 | Ogawa Koryo Kk | 3―ヒドロキシピラン―2―オンを含有する香料組成物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS533538A (en) | 1976-06-28 | 1978-01-13 | Sansho Seiyaku Kk | Skin bleach cosmetics |
JPS6010005B2 (ja) * | 1982-08-20 | 1985-03-14 | 三省製薬株式会社 | 色白化粧料 |
JPH041188A (ja) * | 1990-04-18 | 1992-01-06 | Ogawa Koryo Kk | 3―ヒドロキシ―2□dh―ピラン―2―オンの製造方法 |
JPH042562A (ja) | 1990-04-19 | 1992-01-07 | Yamaha Motor Co Ltd | 移載装置の位置決めガイド装置 |
JP2007246475A (ja) | 2006-03-17 | 2007-09-27 | Univ Nihon | 血小板凝集抑制剤及び肝障害改善剤、並びに医薬用組成物及び機能性飲食品 |
US20080306144A1 (en) * | 2007-06-08 | 2008-12-11 | Stephanie Kay Clendennen | Hydroxybenzyl or hydroxypyranonemethyl esters as tyrosinase inhibitors |
-
2011
- 2011-01-20 CN CN2011800656284A patent/CN103347486A/zh active Pending
- 2011-01-20 JP JP2012553510A patent/JP5703313B2/ja not_active Expired - Fee Related
- 2011-01-20 EP EP11856236.2A patent/EP2666460A4/en not_active Withdrawn
- 2011-01-20 WO PCT/JP2011/050986 patent/WO2012098664A1/ja active Application Filing
- 2011-01-20 US US13/980,475 patent/US20130309187A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0347899A (ja) * | 1989-07-17 | 1991-02-28 | Ogawa Koryo Kk | 3―ヒドロキシピラン―2―オンを含有する香料組成物 |
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WO2012098664A1 (ja) | 2012-07-26 |
US20130309187A1 (en) | 2013-11-21 |
JPWO2012098664A1 (ja) | 2014-06-09 |
EP2666460A1 (en) | 2013-11-27 |
EP2666460A4 (en) | 2014-06-11 |
CN103347486A (zh) | 2013-10-09 |
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