13-hydroxy-cis-9-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: 13-hydroxy-cis-9-octadecenoic acid
• 英文别名: 13-Hydroxy-cis-9-octadecenoic acid；(Z)-13-hydroxyoctadec-9-enoic acid
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: QVAVREIGSFJSOU-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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

• 作为反应物：
  描述：

  13-hydroxy-cis-9-octadecenoic acid 在 linoleate C-9 double bond hydratases of Lacto bacillus acidophilus NBRC 13951 、 水 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 6.0h， 以54%的产率得到12-hydroxydodec-9(Z)-enoic acid
  参考文献：
  名称：

  亚油酸双键水合酶为关键酶，将亚油酸生物转化为羟基脂肪酸和羧酸

  摘要：

  AbstractHydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C‐9 or the C‐12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13‐hydroxy‐cis‐9‐octadecenoic acid and 10‐hydroxy‐cis‐12‐octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12‐hydroxy‐cis‐9‐dodecenoic acid, α,ω‐tridec‐9‐enedioic acid) and lactones (i.e., δ‐decalactone, γ‐dodecelactone) via whole‐cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.magnified image

  DOI：

  10.1002/adsc.201400893
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 linoleate C-12 double bond hydratases of Lacto bacillus acidophilus NBRC 13951 、 水 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 6.0h， 以61%的产率得到13-hydroxy-cis-9-octadecenoic acid
  参考文献：
  名称：

  亚油酸双键水合酶为关键酶，将亚油酸生物转化为羟基脂肪酸和羧酸

  摘要：

  AbstractHydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C‐9 or the C‐12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13‐hydroxy‐cis‐9‐octadecenoic acid and 10‐hydroxy‐cis‐12‐octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12‐hydroxy‐cis‐9‐dodecenoic acid, α,ω‐tridec‐9‐enedioic acid) and lactones (i.e., δ‐decalactone, γ‐dodecelactone) via whole‐cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.magnified image

  DOI：

  10.1002/adsc.201400893

文献信息

• Rational Engineering of Hydratase from <i>Lactobacillus acidophilus</i> Reveals Critical Residues Directing Substrate Specificity and Regioselectivity
  作者：Bekir Engin Eser、Michal Poborsky、Rongrong Dai、Shigenobu Kishino、Anita Ljubic、Michiki Takeuchi、Charlotte Jacobsen、Jun Ogawa、Peter Kristensen、Zheng Guo

  DOI：10.1002/cbic.201900389

  日期：2020.2.17

  Lactobacillus acidophilus were compared: FA-HY2 has a narrow substrate scope and strict regioselectivity, whereas FA-HY1 utilizes longer chain substrates and hydrates various double-bond positions. It is revealed that three active-site residues play a remarkable role in directing substrate specificity and regioselectivity of hydration. If these residues on FA-HY2 are mutated to the corresponding ones in FA-HY1

  脂肪酸水合酶（FAHs）对脂肪酸（FAs）的酶促转化为生产高价值的羟基脂肪酸（HFA）提供了一条绿色而有效的途径。然而，迄今为止，关于链长和羟基位置，HFA之间实现了有限的多样性。在这项研究中，比较了嗜酸乳杆菌的两种高度相似的FAH：FA-HY2具有较窄的底物范围和严格的区域选择性，而FA-HY1利用较长的链底物并水合了各种双键位置。揭示了三个活性位点残基在指导底物特异性和水合区域选择性方面起着显著作用。如果将FA-HY2上的这些残基突变为FA-HY1中的相应残基，观察到底物范围的显着扩展和双键向FAs的ω端水合的明显增强。FA-HY2（TM-FA-HY2）的三残基突变体显示出对亚油酸的区域选择性的令人印象深刻的逆转，使HFA区域异构体的比例（10-OH / 13-OH）从99：1变为12:88 。对于花生四烯酸和C18多不饱和脂肪酸底物，还观察到区域选择性的显着变化。另外，TM-FA-H
• EXTREME-PRESSURE ADDITIVE, PROCESS FOR PRODUCING THE SAME, CUTTING FLUID, AND GRINDING FLUID
  申请人：DAINIPPON INK AND CHEMICALS, INC.

  公开号：EP1116782A1

  公开（公告）日：2001-07-18

  The present invention provides a sulfur-based extreme-pressure additive that is completely soluble in water without using a surfactant, and has satisfactory odor and hue. In addition, the present invention provides a cutting liquid and grinding liquid having superior defoaming property and rust preventive characteristics, while also having high load resistance and lubrication performance comparable to cutting oils and grinding oils of the prior art. The above objects are achieved by an extreme-pressure additive comprising the salt of a condensation product of a sulfurized hydroxy-unsaturated fatty acid, the condensation product having a sulfur content of 8 to 15% by weight (mass), color of 6 or less, and acid value of 80 to 200, and a grinding liquid comprising that extreme-pressure additive and water.

  本发明提供了一种硫基极压添加剂，无需使用表面活性剂即可完全溶于水，并且具有令人满意的气味和色调。此外，本发明还提供了一种切削液和研磨液，它具有优异的消泡性和防锈特性，同时还具有与现有技术中的切削油和研磨油相当的高抗负荷性和润滑性能。上述目的是通过一种极压添加剂和一种由该极压添加剂和水组成的研磨液来实现的，极压添加剂包括硫化羟基不饱和脂肪酸缩合产物的盐，该缩合产物的硫含量为 8 至 15%（重量），色度为 6 或更低，酸值为 80 至 200。
• 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。
• METABOLISM-IMPROVING AGENT COMPRISING RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3097911A1

  公开（公告）日：2016-11-30

  The present invention provides a metabolism improving 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 metabolism improving 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）的新陈代谢促进剂，以及含有该新陈代谢促进剂的食品、药品等。
• METHOD FOR PRODUCING RARE FATTY ACID USING NOVEL ENZYME, AND NOVEL RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3098313A1

  公开（公告）日：2016-11-30

  The present invention provides production of hydroxylated fatty acid by a hydration reaction using a novel enzyme derived from lactobacillus and using fatty acid as a substrate, and further, a production method of oxo fatty acid by an enzyme reaction or chemical oxidation reaction using the hydroxylated fatty acid as a substrate. In addition, a valuable novel rare fatty acid obtained by such production method is also provided.

  本发明提供了一种以脂肪酸为底物，使用源自乳酸杆菌的新型酶，通过水合反应生产羟基化脂肪酸的方法，并进一步提供了一种以羟基化脂肪酸为底物，通过酶反应或化学氧化反应生产氧化脂肪酸的方法。此外，还提供了通过这种生产方法获得的有价值的新型稀有脂肪酸。