DE69815750T2 - Verfahren zur Herstellung von Ascorbinsäurederivaten - Google Patents
Verfahren zur Herstellung von Ascorbinsäurederivaten Download PDFInfo
- Publication number
- DE69815750T2 DE69815750T2 DE69815750T DE69815750T DE69815750T2 DE 69815750 T2 DE69815750 T2 DE 69815750T2 DE 69815750 T DE69815750 T DE 69815750T DE 69815750 T DE69815750 T DE 69815750T DE 69815750 T2 DE69815750 T2 DE 69815750T2
- Authority
- DE
- Germany
- Prior art keywords
- ascorbic acid
- salt
- reaction
- ester
- acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 title claims 5
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- -1 fatty acid esters Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 2
- 229940048102 triphosphoric acid Drugs 0.000 claims description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 22
- 150000000996 L-ascorbic acids Chemical class 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 8
- 125000002252 acyl group Chemical group 0.000 abstract description 7
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 abstract description 3
- 229930003268 Vitamin C Natural products 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 3
- 235000019154 vitamin C Nutrition 0.000 abstract description 3
- 239000011718 vitamin C Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 230000004700 cellular uptake Effects 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- GDQHBHXCKVBPQE-FXAWDEMLSA-N [(2S)-2-hydroxy-2-[(2R)-3-hydroxy-5-oxo-4-phosphonooxy-2H-furan-2-yl]ethyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(OP(O)(O)=O)=C1O GDQHBHXCKVBPQE-FXAWDEMLSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011668 ascorbic acid Substances 0.000 description 9
- 229960005070 ascorbic acid Drugs 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000010323 ascorbic acid Nutrition 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- MIJPAVRNWPDMOR-ZAFYKAAXSA-N L-ascorbic acid 2-phosphate Chemical compound OC[C@H](O)[C@H]1OC(=O)C(OP(O)(O)=O)=C1O MIJPAVRNWPDMOR-ZAFYKAAXSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ACFGRWJEQJVZTM-LEJBHHMKSA-L Magnesium L-ascorbic acid-2-phosphate Chemical compound [Mg+2].OC[C@H](O)[C@H]1OC(=O)C(OP([O-])([O-])=O)=C1O ACFGRWJEQJVZTM-LEJBHHMKSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HYHGLHONPBPZGJ-YCWPWOODSA-L disodium;[(2r)-2-[(1s)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2h-furan-4-yl] phosphate Chemical compound [Na+].[Na+].OC[C@H](O)[C@H]1OC(=O)C(OP(O)([O-])=O)=C1[O-] HYHGLHONPBPZGJ-YCWPWOODSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- 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
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11309297 | 1997-04-30 | ||
| JP9113092A JPH10298174A (ja) | 1997-04-30 | 1997-04-30 | アスコルビン酸誘導体及びそれを含有するビタミンｃ剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69815750D1 DE69815750D1 (de) | 2003-07-31 |
| DE69815750T2 true DE69815750T2 (de) | 2004-04-29 |
Family
ID=14603288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69815750T Expired - Lifetime DE69815750T2 (de) | 1997-04-30 | 1998-04-29 | Verfahren zur Herstellung von Ascorbinsäurederivaten |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0875514B1 (enExample) |
| JP (1) | JPH10298174A (enExample) |
| AT (1) | ATE243702T1 (enExample) |
| DE (1) | DE69815750T2 (enExample) |
| ES (1) | ES2201368T3 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19933670A1 (de) * | 1999-07-17 | 2001-01-18 | Beiersdorf Ag | Verwendung von kosmetischen oder dermatologischen Zubereitungen zur Stabilisierung von Ascorbinsäure und/oder Ascorbylverbindungen |
| DE19936686A1 (de) * | 1999-08-04 | 2001-02-08 | Beiersdorf Ag | Verwendung von kosmetischen oder dermatologischen Zubereitungen zur Stabilisierung von Ascorbinsäure und/oder Ascorbylverbindungen |
| US20030035812A1 (en) | 2000-02-29 | 2003-02-20 | Shinobu Ito | Immune enhancement compositions and use thereof |
| CA2401352A1 (en) * | 2000-02-29 | 2001-09-07 | Shinobu Ito | Immune enhancement compositions and use thereof |
| FR2807320B1 (fr) * | 2000-04-10 | 2002-05-24 | Oreal | Utilisation de derives d'acide ascorbique pour augmenter la synthese des creramides epidermiques |
| GB0113348D0 (en) | 2001-06-01 | 2001-07-25 | Mars Uk Ltd | Skin diet |
| CN1314696C (zh) * | 2001-12-28 | 2007-05-09 | 三得利株式会社 | 2－O－(β－D－吡喃葡萄糖基)抗坏血酸、其生产方法以及包含含有它的组合物的食品和化妆品 |
| JP4111856B2 (ja) * | 2002-04-12 | 2008-07-02 | 昭和電工株式会社 | 安定化されたアスコルビン酸誘導体 |
| JP2005187465A (ja) * | 2003-12-04 | 2005-07-14 | Showa Denko Kk | アスコルビン酸−２−リン酸エステルの高級脂肪酸エステルの塩を含む乳化された皮膚外用剤、その製造方法、ならびに該エステル塩の安定化方法 |
| KR100719777B1 (ko) * | 2004-03-25 | 2007-05-18 | 도요 뷰티 가부시키가이샤 | 아스코르브산 유도체 및 미백 화장료 |
| RU2008110040A (ru) * | 2005-08-15 | 2009-09-27 | Юнилевер Н.В. (Nl) | Пищевой продукт и система для его обогащения |
| KR100691540B1 (ko) * | 2006-06-22 | 2007-03-12 | 주식회사 펩트론 | 펩타이드가 결합된 안정화된 비타민 ｃ 유도체, 이의제조방법 및 이를 함유하는 조성물 |
| JP2008007428A (ja) * | 2006-06-27 | 2008-01-17 | Showa Denko Kk | 皮膚外用シワ防止剤 |
| JP4495748B2 (ja) * | 2006-09-29 | 2010-07-07 | 株式会社ファンケル | Ｌ−アスコルビン酸−２−リン酸−６−脂肪酸凍結乾燥製剤及び化粧料 |
| NZ598544A (en) * | 2009-09-14 | 2012-12-21 | Univ Hokkaido Nat Univ Corp | Ascorbic acid derivatives as antiviral agents for treating viral conditions in plants |
| JP5552386B2 (ja) * | 2010-07-09 | 2014-07-16 | 株式会社ファンケル | Ｌ−アスコルビン酸−２−リン酸−６−脂肪酸凍結乾燥製剤及び化粧料 |
| JP5690208B2 (ja) | 2011-05-12 | 2015-03-25 | 昭和電工株式会社 | 皮膚外用剤およびその製造方法 |
| JP5856761B2 (ja) * | 2011-06-09 | 2016-02-10 | 昭和電工株式会社 | 皮膚外用剤およびその製造方法 |
| JP5856766B2 (ja) * | 2011-06-24 | 2016-02-10 | 昭和電工株式会社 | 皮膚外用剤およびその製造方法 |
| FR2978963A1 (fr) | 2011-08-11 | 2013-02-15 | Ascorbix | Nouveaux derives des furanones et composition pharmaceutique les contenant |
| JP5869296B2 (ja) * | 2011-10-26 | 2016-02-24 | 株式会社ファンケル | 油中水型乳化組成物 |
| JP2013091620A (ja) * | 2011-10-26 | 2013-05-16 | Fancl Corp | 油中水型乳化組成物 |
| WO2014013743A1 (ja) * | 2012-07-20 | 2014-01-23 | 日本曹達株式会社 | 植物へのストレスを軽減する薬剤組成物 |
| US9351915B2 (en) | 2012-12-20 | 2016-05-31 | Showa Denko K.K. | Ascorbic acid derivative composition and production method of the same, ascorbic acid derivative solution, and skin external preparation |
| JP6209855B2 (ja) * | 2013-05-16 | 2017-10-11 | 日油株式会社 | 皮膚化粧料 |
| GB2519972A (en) | 2013-11-01 | 2015-05-13 | Innospec Ltd | Detergent compositions |
| JP7376064B2 (ja) * | 2019-07-19 | 2023-11-08 | ピアス株式会社 | 表皮タンパク質のカルボニル化抑制剤 |
| CN113662882B (zh) * | 2021-10-09 | 2022-11-08 | 上海新高姿化妆品有限公司 | 一种美白淡斑紧致精华液及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58222078A (ja) * | 1982-06-17 | 1983-12-23 | Santen Pharmaceut Co Ltd | アスコルビン酸誘導体 |
| JPS61152613A (ja) * | 1984-12-26 | 1986-07-11 | Kanebo Ltd | 皮膚化粧料 |
| US4939128A (en) * | 1988-04-25 | 1990-07-03 | Takeda Chemical Industries, Ltd. | Ester of ascorbic acid 2-phosphate and pharmaceutical use |
| DE4000397A1 (de) * | 1990-01-09 | 1991-07-11 | Hoechst Ag | Lipidselektive antioxidantien sowie deren herstellung und verwendung |
-
1997
- 1997-04-30 JP JP9113092A patent/JPH10298174A/ja active Pending
-
1998
- 1998-04-29 EP EP98107843A patent/EP0875514B1/en not_active Expired - Lifetime
- 1998-04-29 AT AT98107843T patent/ATE243702T1/de not_active IP Right Cessation
- 1998-04-29 ES ES98107843T patent/ES2201368T3/es not_active Expired - Lifetime
- 1998-04-29 DE DE69815750T patent/DE69815750T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2201368T3 (es) | 2004-03-16 |
| ATE243702T1 (de) | 2003-07-15 |
| EP0875514A1 (en) | 1998-11-04 |
| EP0875514B1 (en) | 2003-06-25 |
| DE69815750D1 (de) | 2003-07-31 |
| JPH10298174A (ja) | 1998-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69815750T2 (de) | Verfahren zur Herstellung von Ascorbinsäurederivaten | |
| DE3707088A1 (de) | Faerbemittel fuer keratinfasern auf der basis von indolderivaten, neue indolderivate, anwendungsverfahren und vorrichtung zur durchfuehrung dieses verfahrens | |
| DE315540T1 (de) | Retinoesaeure-ester von makroliden, ihre verfahren zur herstellung und sie enthaltende pharmazeutische und kosmetische zusammensetzungen. | |
| EP0036583B1 (de) | Glycerin-3-phosphorsäurehalogenalkylester und Verfahren zu ihrer Herstellung und Weiterverarbeitung | |
| DE2258304A1 (de) | Neue 1,3-diphenyl-propanon-1 derivate und ihre salze beziehungsweise diese verbindungen enthaltende versuessungsmittel | |
| EP0344419B1 (de) | Verfahren zur Herstellung von Fettsäure- oder Hydroxyfettsäureestern von Isopropylidenderivaten eines Polyglycerins | |
| DE2050484B2 (de) | Verfahren zu deren Herstellung | |
| US6127409A (en) | Ascorbic acid derivative and vitamin C preparation containing the same | |
| EP0082542B1 (de) | Verfahren zur Herstellung von Chinolinsäure | |
| DE2616351A1 (de) | Halogenderivate | |
| DE69914560T2 (de) | Verfahren zur acylierung von aminoalcoholen | |
| DE2611788C2 (de) | Fluorprostaglandine, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel | |
| EP0359042B1 (de) | Verfahren zur Isolierung von 2-Keto-polyhydroxy-C6-carbonsäuren, insbesondere von 2-Keto-L-gulonsäure aus wässrigen Fermentationsausträgen | |
| EP0043967A1 (de) | 2,9-Dioxatricyclo(4,3,1,0(3,7))decane | |
| EP0523582A1 (de) | Verbessertes Verfahren zur Herstellung des Mononatriumsalzes von Riboflavin 5'-phosphat | |
| DE2345060C3 (de) | 1,2-Dialkylketonglycerin-3-phosphatide und Verfahren zu deren Herstellung | |
| DE2854353C3 (de) | Verfahren zur Herstellung von Erythorbinsäure- und Ascorbinsäure-6-fettsäureestern | |
| DE602004003315T2 (de) | Aluminium Salze phosphorylierter Glycerylether | |
| DE2728248A1 (de) | Nitroxolinderivate | |
| EP0007347A1 (de) | Lipidsenkende Alkylenglykolderivate und Verfahren zu ihrer Herstellung. | |
| DE2345057B2 (de) | Verfahren zur Herstellung von Propandiol (1,3)-phosphatiden | |
| DE2221123C2 (de) | Reserpsäurederivate, Verfahren zu deren Herstellung und Arzneimittel | |
| DE2625689C3 (de) | 1,3-Diphenoxypropanol-(2)-Derivate sowie Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE838140C (de) | Verfahren zur Herstellung von Amiino-aryl-pyridlyl-alkanolen und ihren Estern | |
| DE19633560A1 (de) | Chromanyl-ascorbinsäurederivate, deren Herstellung und Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |