公开(公告)号：WO2016025312A1

公开(公告)日：2016-02-18

申请号：PCT/US2015/044194

申请日：2015-08-07

Applicant: STEPAN COMPANY

Inventor： DRAGAN, Vladimir ,  GALANTE, Jenifer Heydinger ,  HEIMERIKX, Jos

IPC: C12P7/64 ,  C11C3/00 ,  C07C57/00

CPC classification number: C12P7/6427 ,  A23K20/158 ,  A23L33/12 ,  A23V2002/00 ,  A61K31/201 ,  C11C1/045 ,  C11C1/10 ,  A23V2200/304 ,  A23V2200/328 ,  A23V2200/332 ,  A23V2250/1866

Abstract: A process for preparing a conjugated linoleic acid (CLA) material that is enriched in the cis 9, trans 11 (rumenic acid) CLA isomer. The process involves subjecting a material containing at least 75 weight % CLA moieties to an enzymatic conversion, wherein the enzyme has the ability to discriminate between the cis 9, trans 11 and trans 10, cis 12 isomers. The enzyme is advantageously a lipase derived from Candida rugosa . The resulting CLA product stream is distilled to separate the free fatty acid fraction from the glyceride fraction. The recovered free fatty acid fraction contains about 55 weight % to about 70 weight % of the cis 9, trans 11 isomer (rumenic acid), and has a weight ratio of cis 9, trans 11 isomer to trans 10, cis 12 isomer of at least 3.5:1. The material enriched in rumenic acid may be used in foods, particularly infant formulas, or in food supplements or in pharmaceutical compositions.

Abstract translation: 制备富含顺式9，反式11（rumenic acid）CLA异构体的共轭亚油酸（CLA）材料的方法。 该方法包括使含有至少75重量％CLA部分的材料经酶促转化，其中该酶具有区分顺式9，反式11和反式10顺式12异构体的能力。 该酶有利地是衍生自假丝酵母（Candida rugosa）的脂肪酶。 将所得CLA产物流蒸馏以从游离脂肪酸部分与甘油酯部分分离。 回收的游离脂肪酸馏分含有约55重量％至约70重量％的顺式9，反式11异构体（瘤黄酸），并且具有顺式9，反式11异构体与反式10的重量比， 至少3.5：1。 丰富的鲁米酸的物质可以用于食品，特别是婴儿配方食品，或食品添加剂或药物组合物中。

公开(公告)号：WO2005081669A2

公开(公告)日：2005-09-09

申请号：PCT/US2004/002511

申请日：2004-01-29

Applicant: STEPAN COMPANY ,  GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  SCHULTZ, Alfred K.

Inventor： GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  SCHULTZ, Alfred K.

CPC classification number: C12P7/6472 ,  C12P7/6454

Abstract: A process for enzymatic production of glyceride compositions, specifically industrially practicable production of triglycerides, including conjugated linoleic and linolenic acid triglycerides, and the compositions produced by such process. An enzymatic reaction zone is first utilized, in which a mixture of glycerol and fatty acids or fatty acid derivatives is reacted in the presence of an enzymatic catalyst to form 1,3 diglycerides. The mixture is then circulated through a second thermal rearrangement zone, maintained at a higher temperature, to promote rearrangement of the 1,3 diglycerides to 1,2 diglycerides. Triglycerides are produced by re-circulating the mixture through the enzymatic production zone.

Abstract translation: 用于酶促生产甘油酯组合物的方法，特别是在工业上可行地生产甘油三酯，包括共轭亚油酸和亚麻酸甘油三酸酯，以及通过该方法制备的组合物。 首先使用酶反应区，其中甘油和脂肪酸或脂肪酸衍生物的混合物在酶催化剂的存在下反应以形成1,3-甘油二酯。 然后将混合物循环通过维持在较高温度的第二热重排区，以促进1,3-甘油二酯重新配置为1,2-甘油二酯。 通过将混合物再循环通过酶促生产区来产生甘油三酸酯。

公开(公告)号：WO2004101719A2

公开(公告)日：2004-11-25

申请号：PCT/US2004/012387

申请日：2004-04-21

Applicant: STEPAN COMPANY ,  RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  XAYARIBOUN, Phouvieng

Inventor： RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  XAYARIBOUN, Phouvieng

IPC: C11C

CPC classification number: C07C51/09 ,  C07C57/12

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials including conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material, such as sunflower oil or safflower oil, to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, optionally followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

Abstract translation: 包含共轭亚油酸盐和酸的共轭亚油酸（CLA）材料的制备方法，其富含希望的顺式-9，反式-11-和反式-10，顺式-12-CLA异构体，并且在某些不需要的异构体中是低的 。 该方法通常需要含亚油酸的材料的烷基酯如向日葵油或红花油的异构化，以实现双键的缀合，然后将所得的含CLA脂肪酸酯皂化以产生CLA- 任选地随后用酸源中和含CLA的脂肪酸盐以产生含CLA的脂肪酸。

公开(公告)号：EP1620384B1

公开(公告)日：2009-07-15

申请号：EP04760826.0

申请日：2004-04-21

Applicant: STEPAN COMPANY

Inventor： RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  XAYARIBOUN, Phouvieng

IPC: C07C51/347

CPC classification number: C07C51/09 ,  C07C57/12

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials including conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material, such as sunflower oil or safflower oil, to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, optionally followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

公开(公告)号：EP3180439A1

公开(公告)日：2017-06-21

申请号：EP15832205.7

申请日：2015-08-07

Applicant: Stepan Company

Inventor： DRAGAN, Vladimir ,  GALANTE, Jenifer Heydinger ,  HEIMERIKX, Jos

IPC: C12P7/64 ,  C11C3/00 ,  C07C57/00

CPC classification number: C12P7/6427 ,  A23K20/158 ,  A23L33/12 ,  A23V2002/00 ,  A61K31/201 ,  C11C1/045 ,  C11C1/10 ,  A23V2200/304 ,  A23V2200/328 ,  A23V2200/332 ,  A23V2250/1866

Abstract: A process for preparing a conjugated linoleic acid (CLA) material that is enriched in the cis 9, trans 11 (rumenic acid) CLA isomer. The process involves subjecting a material containing at least 75 weight % CLA moieties to an enzymatic conversion, wherein the enzyme has the ability to discriminate between the cis 9, trans 11 and trans 10, cis 12 isomers. The enzyme is advantageously a lipase derived from Candida rugosa. The resulting CLA product stream is distilled to separate the free fatty acid fraction from the glyceride fraction. The recovered free fatty acid fraction contains about 55 weight % to about 70 weight % of the cis 9, trans 11 isomer (rumenic acid), and has a weight ratio of cis 9, trans 11 isomer to trans 10, cis 12 isomer of at least 3.5:1. The material enriched in rumenic acid may be used in foods, particularly infant formulas, or in food supplements or in pharmaceutical compositions.

Abstract translation: 制备富含顺式9，反式11（瘤胃酸）CLA异构体的共轭亚油酸（CLA）物质的方法。 该方法涉及使含有至少75重量％CLA部分的物质经历酶促转化，其中所述酶具有区分顺式9，反式11和反式10，顺式12异构体的能力。 该酶有利地是来源于皱褶假丝酵母的脂肪酶。 将所得的CLA产物流蒸馏以将游离脂肪酸馏分与甘油酯馏分分离。 回收的游离脂肪酸部分含有约55重量％至约70重量％的顺式9，反式11异构体（瘤胃酸），并且其重量比为顺式9，反式11异构体至反式10，顺式12异构体 至少3.5：1。 富含瘤胃酸的物质可用于食物，特别是婴儿配方食品，或用于食物补充剂或药物组合物中。

公开(公告)号：EP1749099B1

公开(公告)日：2016-09-07

申请号：EP04706513.1

申请日：2004-01-29

Applicant: STEPAN COMPANY

Inventor： GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  SCHULTZ, Alfred K.

IPC: C12P7/00 ,  C12P7/64

CPC classification number: C12P7/6472 ,  C12P7/6454

公开(公告)号：EP1957063B1

公开(公告)日：2010-08-25

申请号：EP06847505.2

申请日：2006-12-05

Applicant: STEPAN COMPANY

Inventor： RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  BERNHARDT, Randal J.

IPC: C07C69/587 ,  C07C57/12 ,  C07C51/09 ,  C07C51/353 ,  C07C51/377 ,  C07C67/03 ,  C07C67/08 ,  C07C67/327 ,  C07C69/73 ,  A23K1/16 ,  A23L1/30

CPC classification number: C07C51/09 ,  A23K20/158 ,  A23L33/12 ,  C07C51/353 ,  C07C51/377 ,  C07C67/03 ,  C07C67/08 ,  C07C67/327 ,  C07C57/12 ,  C07C69/73 ,  C07C69/587

Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.

公开(公告)号：EP1749099A2

公开(公告)日：2007-02-07

申请号：EP04706513.1

申请日：2004-01-29

Applicant: STEPAN COMPANY

Inventor： GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  SCHULTZ, Alfred K.

IPC: C12P20060101

CPC classification number: C12P7/6472 ,  C12P7/6454

Abstract: A process for enzymatic production of glyceride compositions, specifically industrially practicable production of triglycerides, including conjugated linoleic and linolenic acid triglycerides, and the compositions produced by such process. An enzymatic reaction zone is first utilized, in which a mixture of glycerol and fatty acids or fatty acid derivatives is reacted in the presence of an enzymatic catalyst to form 1,3 diglycerides. The mixture is then circulated through a second thermal rearrangement zone, maintained at a higher temperature, to promote rearrangement of the 1,3 diglycerides to 1,2 diglycerides. Triglycerides are produced by re-circulating the mixture through the enzymatic production zone.

公开(公告)号：EP1957063A2

公开(公告)日：2008-08-20

申请号：EP06847505.2

申请日：2006-12-05

Applicant: STEPAN COMPANY

Inventor： RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  BERNHARDT, Randal J.

IPC: A61K31/225 ,  C07C51/347

CPC classification number: C07C51/09 ,  A23K20/158 ,  A23L33/12 ,  C07C51/353 ,  C07C51/377 ,  C07C67/03 ,  C07C67/08 ,  C07C67/327 ,  C07C57/12 ,  C07C69/73 ,  C07C69/587

Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.

公开(公告)号：EP1620384A2

公开(公告)日：2006-02-01

申请号：EP04760826.0

申请日：2004-04-21

Applicant: STEPAN COMPANY

Inventor： RONGIONE, Joseph C. ,  GALANTE, Jenifer Heydinger ,  CLAUSS, Steven L. ,  BERNHARDT, Randal J. ,  XAYARIBOUN, Phouvieng

IPC: C07C51/347

CPC classification number: C07C51/09 ,  C07C57/12

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials including conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material, such as sunflower oil or safflower oil, to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, optionally followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

Abstract translation: 一种生产共轭亚油酸（CLA）的材料的方法，所述共轭亚油酸包含共轭亚油酸盐和富含所需顺式-9，反式11和反式10，顺式-12-CLA异构体并且某些不希望的异构体 。 该方法通常需要使含有亚油酸的物质如葵花油或红花油的烷基酯异构化以实现双键的共轭，接着皂化所得的含CLA的脂肪酸酯以产生CLA- 随后用酸源中和含CLA的脂肪酸盐以产生含CLA的脂肪酸。