NO312201B1 - Fremgangsmåte til fremstilling av konjugert linolsyre - Google Patents

Fremgangsmåte til fremstilling av konjugert linolsyre Download PDF

Info

Publication number: NO312201B1
Authority: NO; Norway
Prior art keywords: linoleic acid; oil; alkali; conjugated linoleic; conjugated
Prior art date: 1996-10-30

Application number

NO19974882A

Other languages

English (en)

Norwegian (no)

Other versions

NO974882L (no

NO974882D0 (no

Inventor

Toshio Iwata

Takeshi Kamegai

Yoshie Sato

Kazumasa Watanabe

Masaaki Kasai

Original Assignee

Rinoru Oil Mills Co Ltd

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.)

1996-10-30

Filing date

1997-10-23

Publication date

2002-04-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=17725721&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO312201(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-10-23 Application filed by Rinoru Oil Mills Co Ltd filed Critical Rinoru Oil Mills Co Ltd

1997-10-23 Publication of NO974882D0 publication Critical patent/NO974882D0/no

1998-05-04 Publication of NO974882L publication Critical patent/NO974882L/no

2002-04-08 Publication of NO312201B1 publication Critical patent/NO312201B1/no

Links

OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims description 37
238000000034 method Methods 0.000 title claims description 23
JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 title claims description 21
229940108924 conjugated linoleic acid Drugs 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 27
239000003921 oil Substances 0.000 claims description 18
235000019198 oils Nutrition 0.000 claims description 18
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 16
235000020778 linoleic acid Nutrition 0.000 claims description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
239000003513 alkali Substances 0.000 claims description 14
235000019197 fats Nutrition 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
238000006317 isomerization reaction Methods 0.000 claims description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
235000019485 Safflower oil Nutrition 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000003813 safflower oil Substances 0.000 claims description 6
235000005713 safflower oil Nutrition 0.000 claims description 6
235000019486 Sunflower oil Nutrition 0.000 claims description 3
239000002600 sunflower oil Substances 0.000 claims description 3
235000005687 corn oil Nutrition 0.000 claims description 2
239000002285 corn oil Substances 0.000 claims description 2
235000012343 cottonseed oil Nutrition 0.000 claims description 2
239000002385 cottonseed oil Substances 0.000 claims description 2
239000000944 linseed oil Substances 0.000 claims description 2
235000021388 linseed oil Nutrition 0.000 claims description 2
239000003549 soybean oil Substances 0.000 claims description 2
235000012424 soybean oil Nutrition 0.000 claims description 2
239000010497 wheat germ oil Substances 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
239000003925 fat Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BZVCUDFTTWZWPF-UHFFFAOYSA-M potassium;ethane-1,2-diol;hydroxide Chemical compound [OH-].[K+].OCCO BZVCUDFTTWZWPF-UHFFFAOYSA-M 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
DVWSXZIHSUZZKJ-UHFFFAOYSA-N 18:3n-3 Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OC DVWSXZIHSUZZKJ-UHFFFAOYSA-N 0.000 description 1
LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011810 insulating material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
DVWSXZIHSUZZKJ-YSTUJMKBSA-N methyl linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC DVWSXZIHSUZZKJ-YSTUJMKBSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
-1 tert-butyl alkoxide Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)

NO19974882A 1996-10-30 1997-10-23 Fremgangsmåte til fremstilling av konjugert linolsyre NO312201B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8288094A JP3017108B2 (ja)	1996-10-30	1996-10-30	共役リノール酸の製造方法

Publications (3)

Publication Number	Publication Date
NO974882D0 NO974882D0 (no)	1997-10-23
NO974882L NO974882L (no)	1998-05-04
NO312201B1 true NO312201B1 (no)	2002-04-08

Family

ID=17725721

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19974882A NO312201B1 (no)	1996-10-30	1997-10-23	Fremgangsmåte til fremstilling av konjugert linolsyre

Country Status (11)

Country	Link
US (1)	US5986116A (id)
EP (1)	EP0839897B1 (id)
JP (1)	JP3017108B2 (id)
KR (1)	KR100289205B1 (id)
AU (1)	AU722105B2 (id)
CA (1)	CA2219601C (id)
DE (1)	DE69704014T2 (id)
ID (1)	ID19188A (id)
MY (1)	MY116996A (id)
NO (1)	NO312201B1 (id)
TW (1)	TW393463B (id)

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DE69609196T3 (de)	1995-11-14	2006-01-26	Loders Croklaan B.V.	Verfahren zur Herstellung von Materialien mit hohem Gehalt an isomeren von konjugierter Linolsäure
CA2246085C (en) *	1997-09-12	2004-04-27	Krish Bhaggan	Production of materials rich in conjugated isomers of long chain polyunsaturated fatty acid residues
US7078051B1 (en)	1998-08-11	2006-07-18	Natural Asa	Conjugated linoleic acid alkyl esters in feedstuffs and food
EP0950410B1 (en)	1998-03-17	2007-01-03	Natural ASA	Conjugated linoleic acid compositions
US7776353B1 (en)	1998-03-17	2010-08-17	Aker Biomarine Asa	Conjugated linoleic acid compositions
US6015833A (en)	1998-03-17	2000-01-18	Conlinco., Inc.	Conjugated linoleic acid compositions
JP2003073269A (ja) *	1998-03-17	2003-03-12	Conlinco Inc	共役リノール酸組成物
US7101914B2 (en) *	1998-05-04	2006-09-05	Natural Asa	Isomer enriched conjugated linoleic acid compositions
US6060514A (en)	1998-05-04	2000-05-09	Conlin Co., Inc.	Isomer enriched conjugated linoleic acid compositions
US6696584B2 (en)	1998-05-04	2004-02-24	Natural Asa	Isomer enriched conjugated linoleic acid compositions
US6214372B1 (en)	1998-05-04	2001-04-10	Con Lin Co., Inc.	Method of using isomer enriched conjugated linoleic acid compositions
WO1999056780A1 (en)	1998-05-04	1999-11-11	Conlinco, Inc.	Isomer enriched conjugated linoleic acid compositions
ITMI991894A1 (it) *	1999-09-09	2001-03-09	Carlo Ghisalberti	Acido linoleico coniugato e trigliceride nuovi metodi di sintesi e d'uso
US7947737B1 (en)	1999-09-30	2011-05-24	Aker Biomarine Asa	Method of treating hypertension and reducing serum lipase activity
CA2393391C (en) *	2000-01-12	2009-10-27	Martin J. T. Reaney	Method for commercial preparation of preferred isomeric forms of ester free conjugated fatty acids with solvent systems containing polyether alcohol solvents
CA2404799C (en)	2000-04-06	2007-08-07	Conlinco, Inc.	Conjugated linoleic acid compositions
US20030149288A1 (en) *	2000-04-18	2003-08-07	Natural Asa	Conjugated linoleic acid powder
US6756405B2 (en)	2000-04-18	2004-06-29	Natural Asa	Conjugated linoleic acid powder
US6380409B1 (en) *	2000-04-24	2002-04-30	Conlin Co., Inc.	Methods for preparing CLA isomers
US6927239B1 (en) *	2000-08-02	2005-08-09	Pharmanutrients	Methods and compositions for the attenuation and/or prevention of stress/catabolic responses
EP1357977B1 (en)	2000-09-21	2004-07-21	Nutrition 21, Inc.	Chromium containing compositions for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity and reduction of hyperglycemia and hypercholesteremia
DE10102050A1 (de)	2001-01-17	2002-07-18	Basf Ag	Zubereitung zur Verbesserung der Nahrungsverwertung
US6479683B1 (en)	2001-03-06	2002-11-12	Ag Processing Inc	Process for conjugating fatty acid esters
AU2002257714B2 (en)	2001-03-29	2007-06-28	Basf Aktiengesellschaft	Conjugated unsaturated glyceride mixtures and a method for producing the same
WO2002095783A1 (fr) *	2001-05-21	2002-11-28	Matsushita Electric Industrial Co., Ltd.	Fusible thermique
US6677470B2 (en)	2001-11-20	2004-01-13	Natural Asa	Functional acylglycerides
US6409649B1 (en) *	2001-11-27	2002-06-25	Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture & Agri-Food Canada	Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst
US6414171B1 (en) *	2001-11-27	2002-07-02	Her Majesty In Right Of Canada, As Represented By The Minister Of Agriculture & Agri-Food Canada	Method for commercial preparation of conjugated linoleic acid from by-products of vegetable oil refining
US6743931B2 (en)	2002-09-24	2004-06-01	Natural Asa	Conjugated linoleic acid compositions
US7193096B2 (en)	2003-07-01	2007-03-20	Loders Croklaan Usa Llc	Process for producing a conjugated di- or poly-unsaturated fatty acid of 12 to 24 carbon atoms or salt or ester thereof
CA2436650A1 (en) *	2003-08-06	2005-02-06	Naturia Inc.	Conjugated linolenic acid (clnatm) compositions: synthesis, purification and uses
US20050069593A1 (en) *	2003-09-29	2005-03-31	Life Time Fitness, Inc.	Nutritional supplement containing 7-Keto-DHEA and conjugated linoleic acid
DE10349455A1 (de) *	2003-10-23	2005-05-25	Bioghurt Biogarde Gmbh & Co. Kg	Verfahren zur Herstellung konjugierter, mehrfach ungesättigter Fettsäureester
US7666447B2 (en) *	2004-10-08	2010-02-23	Pharmanutrients	Compositions including Krill extracts and conjugated linoleic acid and methods of using same
US20070049763A1 (en) *	2005-08-23	2007-03-01	Reaney Martin J	Methods for preparation and use of strong base catalysts
CN100369881C (zh) *	2006-01-13	2008-02-20	国家***第一海洋研究所	高含量9,11共轭亚油酸的组合物及其制备方法
DK2498617T3 (da) *	2009-11-10	2014-09-15	Cognis Ip Man Gmbh	Sammensætning, der omfatter et lipid, der er egnet til human indtagelse
CN102229527B (zh)	2009-12-14	2016-05-04	脂质营养品有限公司	工艺方法
CN104725216A (zh) *	2015-02-12	2015-06-24	湖北华龙生物制药有限公司	一种从乌桕梓油中纯化分离高纯度α-亚麻酸、亚油酸的方法

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US3984444A (en) *	1971-11-10	1976-10-05	Hoechst Aktiengesellschaft	Isomerization process of a higher fatty acid ester having isolated double bonds
US4164505A (en) *	1977-07-08	1979-08-14	Sylvachem Corporation	Flow process for conjugating unconjugated unsaturation of fatty acids
JPS5495502A (en) *	1978-01-10	1979-07-28	Japan Synthetic Rubber Co Ltd	Preparation of 3-methyl-2-buten-1-ol
US5208356A (en) *	1989-02-17	1993-05-04	Wisconsin Alumni Research Foundation	Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions
US5208358A (en) *	1992-07-13	1993-05-04	Dow Corning Corporation	Process for preparation of silyl ketene acetals
EP0779033B1 (en) *	1995-11-14	2001-09-26	Unilever N.V.	Edible fat-spread
DE19546028C2 (de) *	1995-12-09	2000-04-27	Fresenius Ag	Bilanzierdisposable zum Bilanzieren von Flüssigkeiten für eine medizinische Behandlungsvorrichtung sowie eine medizinische Behandlungsvorrichtung mit einem Systemeinschub zur Aufnahme eines derartigen Bilanzierdisposables

1996
- 1996-10-30 JP JP8288094A patent/JP3017108B2/ja not_active Expired - Lifetime
1997
- 1997-10-23 AU AU42784/97A patent/AU722105B2/en not_active Expired
- 1997-10-23 DE DE69704014T patent/DE69704014T2/de not_active Revoked
- 1997-10-23 EP EP97118467A patent/EP0839897B1/en not_active Revoked
- 1997-10-23 NO NO19974882A patent/NO312201B1/no not_active IP Right Cessation
- 1997-10-24 US US08/957,774 patent/US5986116A/en not_active Expired - Lifetime
- 1997-10-24 MY MYPI97005010A patent/MY116996A/en unknown
- 1997-10-27 TW TW086115866A patent/TW393463B/zh not_active IP Right Cessation
- 1997-10-29 KR KR1019970055819A patent/KR100289205B1/ko not_active IP Right Cessation
- 1997-10-29 CA CA002219601A patent/CA2219601C/en not_active Expired - Lifetime
- 1997-10-30 ID IDP973555A patent/ID19188A/id unknown

Also Published As

Publication number	Publication date
KR19980033256A (ko)	1998-07-25
ID19188A (id)	1998-06-28
CA2219601A1 (en)	1998-04-30
CA2219601C (en)	2002-03-19
EP0839897A1 (en)	1998-05-06
TW393463B (en)	2000-06-11
DE69704014T2 (de)	2001-06-21
NO974882L (no)	1998-05-04
NO974882D0 (no)	1997-10-23
JPH10130199A (ja)	1998-05-19
DE69704014D1 (de)	2001-03-08
KR100289205B1 (ko)	2001-05-02
AU4278497A (en)	1998-05-07
AU722105B2 (en)	2000-07-20
US5986116A (en)	1999-11-16
MY116996A (en)	2004-04-30
EP0839897B1 (en)	2001-01-31
JP3017108B2 (ja)	2000-03-06

Legal Events

Date	Code	Title	Description
2017-11-13	MK1K	Patent expired

Publication	Publication Date	Title
NO312201B1 (no)	2002-04-08	Fremgangsmåte til fremstilling av konjugert linolsyre
WO2001018161A2 (en)	2001-03-15	Process for the preparation of conjugated linoleic acid (cla)
KR100719860B1 (ko)	2007-05-21	클로로-1-부탄을 사용하여 식물유로부터 비사포닌화물질을 추출하는 방법, 상기 비사포닌화 물질을 포함하는조성물
US6815551B2 (en)	2004-11-09	Processes for concentrating tocopherols and/or sterols
US20090118379A1 (en)	2009-05-07	Process for the manufacture of a composition containing at least one xanthophyll
Bagby et al.	1966	Stereochemistry of α-parinaric acid from Impatiens edgeworthii seed oil
Nakanishi et al.	1976	Water-participation in the crystalline-state photodimerization of cinnamic acid derivatives. A new type of organic photoreaction.
Young	1986	Formation of sodium bisulfite addition products with trichothecenones and alkaline hydrolysis of deoxynivalenol and its sulfonate
US4776983A (en)	1988-10-11	Polymerization of fatty acids
WO1991018874A1 (de)	1991-12-12	VERFAHREN ZUR HERSTELLUNG VON HELLFARBIGEN α-SULFOFETTSÄUREALKYLESTER-ALKALIMETALLSALZPASTEN
NO900741L (no)	1990-08-17	Fremgangsmaate for syntetisering av tris-hydroxymethyl-lavere-alkanestere som fettimitasjoner.
US20220251289A1 (en)	2022-08-11	Method for preparing an elastomer from a hydroxylated fatty acid and elastomer obtained by such a method
US8674124B2 (en)	2014-03-18	Preparation of an active intermediate
KR20070034061A (ko)	2007-03-27	4-케토루테인의 제조 및 식품 첨가제로서의 용도
EP1625105B1 (en)	2008-11-19	Method of making alkyl esters using pressure
EP0349138B1 (en)	1994-08-24	Recovery of carotenoids
JPS6323837A (ja)	1988-02-01	Ｈｌｂの高いポリグリセリン脂肪酸エステルの製造法
US8742148B1 (en)	2014-06-03	Oligomerization of jojoba oil in super-critical CO2 for different applications
US3356699A (en)	1967-12-05	Alkali isomerization of crepenynic acid to 8, 10, 12-octadecatrienoic acid
Daloze et al.	1998	(13E, 15E, 18Z, 20Z)-1-Hydroxypentacosa-13, 15, 18, 20-tetraen-11-yn-4-one 1-acetate, from the venom of a Brazilian Crematogaster ant
US6552207B2 (en)	2003-04-22	Process for the preparation of amphoglycinates from vegetable oils and butters and the use thereof
Nag et al.	1995	In search of a new vegetable oil
US20080015374A1 (en)	2008-01-17	Method for the synthesis and isolation of phytosterol esters
SU522202A1 (ru)	1976-07-25	Способ получени алкидной смолы
GB2209750A (en)	1989-05-24	Manufacture of higher fatty monoglyceride monosulphate detergents