JPH04117392A - アスコルビン酸リン脂質誘導体及びその製造方法 - Google Patents
アスコルビン酸リン脂質誘導体及びその製造方法Info
- Publication number
- JPH04117392A JPH04117392A JP23434890A JP23434890A JPH04117392A JP H04117392 A JPH04117392 A JP H04117392A JP 23434890 A JP23434890 A JP 23434890A JP 23434890 A JP23434890 A JP 23434890A JP H04117392 A JPH04117392 A JP H04117392A
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- phospholipid derivative
- phospholipid
- acid phospholipid
- derivative
- 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.)
- Granted
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims abstract description 86
- 229960005070 ascorbic acid Drugs 0.000 title claims abstract description 62
- 235000010323 ascorbic acid Nutrition 0.000 title claims abstract description 60
- 239000011668 ascorbic acid Substances 0.000 title claims abstract description 60
- -1 Ascorbic acid phospholipid Chemical class 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000004670 unsaturated fatty acids Chemical group 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 abstract description 15
- 102000011420 Phospholipase D Human genes 0.000 abstract description 12
- 108090000553 Phospholipase D Proteins 0.000 abstract description 12
- 235000013305 food Nutrition 0.000 abstract description 6
- 239000003963 antioxidant agent Substances 0.000 abstract description 4
- 235000006708 antioxidants Nutrition 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 150000003904 phospholipids Chemical class 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000012528 membrane Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000001095 phosphatidyl group Chemical group 0.000 description 4
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 3
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 3
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 3
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000002322 Egg Proteins Human genes 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 3
- 235000013345 egg yolk Nutrition 0.000 description 3
- 210000002969 egg yolk Anatomy 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- CSTRPYAGFNTOEQ-MGMRMFRLSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;octadecanoic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O.CCCCCCCCCCCCCCCCCC(O)=O CSTRPYAGFNTOEQ-MGMRMFRLSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000218483 Streptomyces lydicus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- RXKUYBRRTKRGME-UHFFFAOYSA-N butanimidamide Chemical compound CCCC(N)=N RXKUYBRRTKRGME-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940124447 delivery agent Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- MEUKEBNAABNAEX-UHFFFAOYSA-N hydroperoxymethane Chemical compound COO MEUKEBNAABNAEX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23434890A JPH04117392A (ja) | 1990-09-06 | 1990-09-06 | アスコルビン酸リン脂質誘導体及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23434890A JPH04117392A (ja) | 1990-09-06 | 1990-09-06 | アスコルビン酸リン脂質誘導体及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04117392A true JPH04117392A (ja) | 1992-04-17 |
| JPH05398B2 JPH05398B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-05 |
Family
ID=16969592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23434890A Granted JPH04117392A (ja) | 1990-09-06 | 1990-09-06 | アスコルビン酸リン脂質誘導体及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04117392A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364564A (en) * | 1993-02-04 | 1994-11-15 | Noda Institute For Scientific Research | Phosphatidyl chromanol derivative, the production method thereof, antioxidant and emulsifier |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03291289A (ja) * | 1990-04-10 | 1991-12-20 | Yakult Honsha Co Ltd | ホスファチジルアスコルベート、その製造方法、乳化剤、過酸化脂質抑制剤及び化粧料 |
| JPH0499724A (ja) * | 1990-08-15 | 1992-03-31 | Q P Corp | 皮膚外用剤 |
-
1990
- 1990-09-06 JP JP23434890A patent/JPH04117392A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03291289A (ja) * | 1990-04-10 | 1991-12-20 | Yakult Honsha Co Ltd | ホスファチジルアスコルベート、その製造方法、乳化剤、過酸化脂質抑制剤及び化粧料 |
| JPH0499724A (ja) * | 1990-08-15 | 1992-03-31 | Q P Corp | 皮膚外用剤 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364564A (en) * | 1993-02-04 | 1994-11-15 | Noda Institute For Scientific Research | Phosphatidyl chromanol derivative, the production method thereof, antioxidant and emulsifier |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05398B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2165115T5 (es) | Un procedimiento para la purificacion de fosfatidinilserina. | |
| DE69011739T2 (de) | Verfahren zur Herstellung von Phosphatidsäure. | |
| DE2820893C2 (de) | Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen | |
| EP0703954B1 (fr) | Compositions de derives de polyphenols et leur preparation | |
| EP0118316A2 (en) | Synthetic phospholipid compounds, their preparation and use | |
| WO1994010125A1 (en) | Glycerin derivatives and uses thereof | |
| Starodubtseva et al. | Design, synthesis, and biological activity of novel ammonium salts containing sterically hindered phenolic fragment and phosphoryl group | |
| EP1231213B1 (en) | Procedure for the preparation of pure phosphatides and their use in the cosmetic, pharmaceutical and alimentary fields | |
| US4254115A (en) | Phospholipid derivative with an antilipemic and antiarteriosclerotic effect | |
| JPH04117392A (ja) | アスコルビン酸リン脂質誘導体及びその製造方法 | |
| US6635456B2 (en) | Procedure for the preparation of pure phosphatides with phospholipase D | |
| US2317378A (en) | Antiseptic materials | |
| Lodyato et al. | Synthesis and properties of 11-(3, 5-Di-tert-butyl-2-hydroxyphenylcarbamoyl) undecanoic acid, a new amphiphilic antioxidant | |
| EP0400499B1 (de) | Neue Acylaminosäurederivate enthaltende Arzneimittel und Diätetika | |
| US5364564A (en) | Phosphatidyl chromanol derivative, the production method thereof, antioxidant and emulsifier | |
| FR2593505A1 (fr) | Ester phosphorique substitue par la serine et son procede de fabrication | |
| JPH07310023A (ja) | 青色系色素組成物 | |
| JP2942302B2 (ja) | ホスファチジルアスコルベート、その製造方法、乳化剤、過酸化脂質抑制剤及び化粧料 | |
| CA2904827C (en) | Natural lipids containing non-oxidizable fatty acids | |
| US5523429A (en) | N-acylphosphatidylethanolamines as anti-oxidants | |
| JPH10237081A (ja) | クロマノール誘導体およびその製造方法並びに抗酸化剤 | |
| JP3670609B2 (ja) | ダイズサポニン類誘導体を含有した抗酸化剤 | |
| JPS61129191A (ja) | ドコサヘキサエン酸含有グリセロリン脂質 | |
| KR20250118396A (ko) | 과산화수소 감응형 토코페롤 유도체 및 이의 용도 | |
| JPH0588718B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |