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
Authority: JP; Japan
Prior art keywords: ascorbic acid; phospholipid derivative; phospholipid; acid phospholipid; derivative
Prior art date: 1990-09-06
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

Application number

JP23434890A

Other languages

English (en)

Japanese (ja)

Other versions

JPH05398B2 (2

Inventor

Akihiko Nagao

昭彦長尾

Junji Terao

純二寺尾

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

National Food Research Institute

Original Assignee

National Food Research Institute

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.)

1990-09-06

Filing date

1990-09-06

Publication date

1992-04-17

1990-09-06 Application filed by National Food Research Institute filed Critical National Food Research Institute

1990-09-06 Priority to JP23434890A priority Critical patent/JPH04117392A/ja

1992-04-17 Publication of JPH04117392A publication Critical patent/JPH04117392A/ja

1993-01-05 Publication of JPH05398B2 publication Critical patent/JPH05398B2/ja

Status Granted legal-status Critical Current

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

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Preparation Of Compounds By Using Micro-Organisms (AREA)

JP23434890A 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 Granted JPH04117392A (ja)

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 (2)	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 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (2)	1993-01-05

Publication	Publication Date	Title
ES2165115T5 (es)	2010-03-25	Un procedimiento para la purificacion de fosfatidinilserina.
DE2820893C2 (de)	1986-02-20	Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen
EP0703954B1 (fr)	2001-12-19	Compositions de derives de polyphenols et leur preparation
JP2007259866A (ja)	2007-10-11	ホスファチドの製造と使用
JP3100783B2 (ja)	2000-10-23	ホスファチジルコリンおよびその製造方法
WO1994010125A1 (en)	1994-05-11	Glycerin derivatives and uses thereof
Starodubtseva et al.	2018	Design, synthesis, and biological activity of novel ammonium salts containing sterically hindered phenolic fragment and phosphoryl group
US6635456B2 (en)	2003-10-21	Procedure for the preparation of pure phosphatides with phospholipase D
EP0400499B1 (de)	1994-04-06	Neue Acylaminosäurederivate enthaltende Arzneimittel und Diätetika
US5364564A (en)	1994-11-15	Phosphatidyl chromanol derivative, the production method thereof, antioxidant and emulsifier
JPH05398B2 (2)	1993-01-05
US4751320A (en)	1988-06-14	Phosphoric ester and process for producing same
IE41597B1 (en)	1980-02-13	Synthetic phospholipids a process for their manufacture and their use
JPH07310023A (ja)	1995-11-28	青色系色素組成物
GB2051069A (en)	1981-01-14	Phospholipid Derivatives Useful in Therapy as Antilepaemics and Antiarteriosclerotics and Compositions Containing Them
JP2942302B2 (ja)	1999-08-30	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
KR102952112B1 (ko)	2026-04-13	과산화수소 감응형 토코페롤 유도체 및 이의 용도
US5523429A (en)	1996-06-04	N-acylphosphatidylethanolamines as anti-oxidants
CA2904827C (en)	2020-10-27	Natural lipids containing non-oxidizable fatty acids
JPH10237081A (ja)	1998-09-08	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)	2005-07-13	ダイズサポニン類誘導体を含有した抗酸化剤
JPS61129191A (ja)	1986-06-17	ドコサヘキサエン酸含有グリセロリン脂質
JPH0588718B2 (2)	1993-12-24
JP2010159383A (ja)	2010-07-22	複合脂質の分離法
JPS6236195A (ja)	1987-02-17	ホスファチジル基転位方法

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

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=16969592

Family Applications (1)

Country Status (1)

Cited By (1)

Citations (2)

Patent Citations (2)

Cited By (1)

Also Published As

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