10-hydroxy-12-trans-octadecenoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10-hydroxy-12-trans-octadecenoic acid
• 英文别名: 10-Hydroxy-12-octadecenoic acid；(E)-10-hydroxyoctadec-12-enoic acid
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: WVYIZGMCLSGZGG-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 苯磺酰胺 、 Lactobacillus plantarum AKU 1009a 作用下， 以 phosphate buffer 为溶剂， 反应 96.0h， 生成 共轭亚油酸 、 共轭亚油酸 、 (9E,11Z)-Octadeca-9,11-dienoic acid 、 10-hydroxy-12-trans-octadecenoic acid
  参考文献：
  名称：

  乳酸菌从亚油酸中共轭亚油酸生产

  摘要：

  AbstractAfter screening 14 genera of lactic acid bacteria, Lactobacillus plantarum AKU 1009a was selected as a potential strain for CLA production from linoleic acid. Washed cells of L. plantarum with high levels of CLA production were obtained by cultivation in a nutrient medium with 0.06% (wt/vol) linoleic acid (cis‐9,cis‐12‐octadecadienoic acid). Under the optimal reaction conditions with the free form of linoleic acid as the substrate, washed cells of L. plantarum produced 40 mg CLA/mL reaction mixture (33% molar yield) from 12% (wt/vol) linoleic acid in 108 h. The resulting CLA was a mixture of two CLA isomers, cis‐9,trans‐11 (or trans‐9,cis‐11)‐octadecadienoic acid (CLA1, 38% of total CLA) and trans‐9,trans‐11‐octadecadienoic acid (CLA2, 62% of total CLA), and accounted for 50% of the total FA obtained. A higher yield (80% molar yield to linoleic acid) was attained with 2.6% (wt/vol) linoleic acid as the substrate in 96 h, resulting in CLA production of 20 mg/mL reaction mixture [consisting of CLA1 (2%) and CLA2 (98%)] and accounting for 80% of total FA obtained. Most of the CLA produced was associated with the cells (ca. 380 mg CLA/g dry cells), mainly as FFA.

  DOI：

  10.1007/s11746-002-0451-4

文献信息

• Verfahren zur Hydratisierung ungesättigter Carbonsäuren
  申请人：FORSCHUNGSZENTRUM JÜLICH GMBH

  公开号：EP0230043A2

  公开（公告）日：1987-07-29

  Die Addition von Wasser an eine C9C10-Doppelbindung von ein- oder mehrfach ungesättigten längerkettigen Carbonsäuren gelingt biotechnologisch mit Hilfe eines Mikroorganismus der Species Acetobacterium woodii. Besonders geeignet sind Acetobacterium woodii ATCC 29683 sowie dessen Mutanten oder Varianten gleicher Wirkungsrichtung. Dieses Verfahren eignet sich insb. zur Umsetzung mehrfach ungesättigter Carbonsäuren mit 12-24 Kohlenstoffatomen, insb. von Linolsäure und/oder Linolensäure.

  单链或多链不饱和长链羧酸的 C9C10 双键加水是通过生物技术，借助木醋杆菌（Acetobacterium woodii）微生物实现的。木醋杆菌 ATCC 29683 及其具有相同作用模式的突变体或变种尤其适用。这种工艺尤其适用于 12-24 个碳原子的多不饱和羧酸，特别是亚油酸和/或亚麻酸的转化。
• Fermentation process for preparing 10-hydroxy-C18-carboxylic acid and gamma-dodecalactone derivatives
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0578388A2

  公开（公告）日：1994-01-12

  Described is a fermentation process for preparing 10-hydroxy-C18-carboxylic acid derivative containing compositions containing compounds defined according to the structure : and gamma-dodecalactone derivative-containing compositions containing compounds defined according to the structure : wherein the dashed lines represent the same or different carbon-carbon bonds; with each of the dashed lines representing a carbon-carbon single bond or a carbon-carbon double bond, products produced thereby and organoleptic uses thereof including uses for augmenting, enhancing or imparting aromas or flavors to or in consumable materials including but not limited to perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, beverages, toothpastes, hair preparations, tobacco compositions and smoking tobacco articles.

  所描述的是一种发酵工艺，用于制备含有 10-羟基-C18-羧酸衍生物的组合物，该组合物含有根据......结构定义的化合物： 和含有γ-十二内酯衍生物的组合物，其中含有根据结构......定义的化合物： 其中虚线代表相同或不同的碳-碳键；每条虚线代表一个碳-碳单键或一个碳-碳双键，由此生产的产品及其感官用途，包括用于增加、提高或赋予消费品的香气或味道，消费品包括但不限于香水组合物、古龙水、香水制品、食品、口香糖、饮料、牙膏、头发制剂、烟草组合物和烟草制品。
• Process for preparing sebacic acid
  申请人：BASF SE

  公开号：EP2706117A1

  公开（公告）日：2014-03-12

  A process for preparing sebacic acid by reacting in a first step (i) linoleic acid with water catalyzed by an oleate hydratase to form10- hydroxy-12-octadecenoic acid, in a second step (ii) pyrolysing the 10-hydroxy-12-octadecenoic acid to 1-octene and 10-oxo-decanoic acid and in a third step(iii) oxidizing the 10-oxo-decanoic acid to sebacic acid.

  一种制备癸二酸的工艺，第一步(i)亚油酸在油酸水解酶催化下与水反应生成10-羟基-12-十八烯酸，第二步(ii)将10-羟基-12-十八烯酸热解为1-辛烯和10-氧代癸酸，第三步(iii)将10-氧代癸酸氧化为癸二酸。
• INTESTINAL TRACT-PROTECTING AGENT CONTAINING HYDROXYLATED FATTY ACID
  申请人：Kyoto University

  公开号：EP2959897A1

  公开（公告）日：2015-12-30

  The present invention provides an intestinal tract-protecting agent, an agent for the prophylaxis or improvement of a disease caused by damage in intestinal tract barrier function, which contains hydroxylated fatty acid, particularly hydroxylated unsaturated fatty acid, having a hydroxyl group at the 10-position and/or the 12-position, which is an intermediate of the metabolism of unsaturated fatty acid by lactobacillus.

  本发明提供了一种肠道保护剂，一种用于预防或改善因肠道屏障功能受损而引起的疾病的药物，它含有羟基化脂肪酸，特别是羟基化不饱和脂肪酸，在 10 位和/或 12 位具有羟基，它是乳酸杆菌代谢不饱和脂肪酸的中间产物。
• ANTI-INFLAMMATORY AGENT CONTAINING RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3097910A1

  公开（公告）日：2016-11-30

  The present invention provides an anti-inflammatory agent containing a rare fatty acid such as hydroxylated fatty acid, oxo fatty acid and the like, and further, food, pharmaceutical product and the like containing the anti-inflammatory agent.

  本发明提供了一种含有稀有脂肪酸（如羟化脂肪酸、氧代脂肪酸等）的消炎剂，以及含有该消炎剂的食品、药品等。