10-hydroxy-8E-octadecenoic acid | 91999-06-3

• 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-8E-octadecenoic acid
• 英文别名: (E)-10-hydroxyoctadec-8-enoic acid；10-Hydroxy-8-octadecenoic acid
• CAS: 91999-06-3
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: RXBFKZNLXJKTLQ-NTCAYCPXSA-N

物化性质

• 沸点：
  445.4±28.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 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：

  10-hydroxy-8E-octadecenoic acid 在 吡啶 作用下， 反应 18.0h， 生成
  参考文献：
  名称：

  A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids

  摘要：

  A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenyl methyl ester (IAP) derivatives. The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.

  DOI：

  10.1016/0009-3084(94)90056-6
• 作为产物：
  描述：

  1-十一烯 在 吡啶 、 叔丁基过氧化氢 、 sodium periodate 、 四氧化锇 、 selenium(IV) oxide 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 10-hydroxy-8E-octadecenoic acid
  参考文献：
  名称：

  Stereoselective synthesis of unsaturated C-18 hydroxy fatty acids the self defensive substances

  摘要：

  DOI：

  10.1016/s0040-4020(01)90314-x

文献信息

• Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity
  作者：Shijiao Zha、Kazuyoshi Kuwano、Tomohiro Shibahara、Fumito Ishibashi

  DOI：10.1016/j.fitote.2020.104639

  日期：2020.9

  Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR

  通过监测针对赤潮浮游植物沙门氏菌的拟南芥活性，生物测定指导的济州毛Tri甲醇提取物的分离导致分离出由四种异构体组成的活性部分。活性化合物鉴定为（E）-9-羟基十八碳烯-10 （1），（E）-10-羟基十八碳烯-8（2），（E）-11-羟基-12-12烯酸（3）和（E）-12-羟基十八烷基-10-烯酸（4NMR，IR和质谱数据）。结构通过与那些真实样品的NMR和MS数据的比较确认1 - 4由明确的合成而获得。合成的羟基酸1 - 4和相关化合物进行了评估针对杀藻活性C.蝇并且发现的所有1 - 4具有高的活性（> 80％的死亡率在第24小时）在20微克/ mL的浓度。使用11种相关化合物进行的结构-活性关系研究表明，羟基的存在对于活性很重要，双键可能被三键取代。
• Isomerization of epoxides to allylic alcohols using methylmagnesium N-cyclohexylisopropylamide
  作者：Paul Mosset、Sukumar Manna、Jacques Viala、J.R. Falck

  DOI：10.1016/s0040-4039(00)84001-0

  日期：1986.1

  The scope of methylmagnesium N-cyclohexylisopropylamide promoted isomerizations of epoxides to allylic alcohols Is described.

  描述了甲基镁N-环己基异丙酰胺促进环氧化物异构化为烯丙基醇的范围。
• Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids
  作者：Rosanna Cardillo、Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Andrea Mele、Domenica Pizzi、Gianna Allegrone、Massimo Barbeni、Antonella Pisciotta

  DOI：10.1021/jo00018a001

  日期：1991.8

  (S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.
• Preparation of fatty acid cholesterol ester hydroperoxides by photosensitized oxidation
  作者：M El Hafidi、F Michel、J Bascoul、A Crastes de Paulet

  DOI：10.1016/s0009-3084(99)00049-3

  日期：1999.7

  Preparation of fatty acid cholesterol ester hydroperoxides was undertaken with the purpose of evaluating their biological effects on cell growth. Cholesterol stearate, oleate, linoleate and alpha-linolenate were oxidized using methylene blue as a photosensitizer. The structures of all compounds were established by mass spectrometry and by nuclear magnetic resonance. The photosensitized oxidation of cholesterol oleate gave two hydroperoxide isomers: 9-hydroperoxy-trans-10-octadecenoate, and 10-hydroperoxy-trans-8-octadecenoate. In the case of the cholesterol linoleate, hydroperoxide isomers formed were: 9-hydroperoxy-trans-10, cis-12-octadecadienoate; 10-hydroperoxy-trans-8, cis-12-octadecadienoate; 12-hydroperoxy-cis-9, trans-13-octadecadienoate; 13-hydroperoxy-cis-9, trans-11-octadecadienoate. The oxidation of the cholesterol alpha-linolenate gave a mixture of six hydroperoxide isomers, at positions 9, 10, 12, 13, 15 and 16 of the fatty acid chain. The photosensitized oxidation of cholesterol stearate produced a formation of hydroperoxide at position 5 alpha of cholesterol. The same hydroperoxide isomers on the fatty acid chain were obtained as described in the literature for the fatty acid methyl esters. (C) 1999 Published by Elsevier Science ireland Ltd. All rights reserved.
• Natural estolides produced by<i>Pseudomonas</i>sp. 42A2 grown on oleic acid: Production and characterization
  作者：M. Peláez、C. Orellana、A. Marqués、M. Busquets、A. Guerrero、A. Manresa

  DOI：10.1007/s11746-003-0786-x

  日期：2003.9

  AbstractEstolides are a group of FA polyesters resulting from ester bond formation between a hydroxyl or olefinic group of one FA and the terminal carboxyl group of a second FA. These products are commonly found in trace amounts, forming tetraglycerides in several oil seed plants, and have been produced by acid clay and enzymatic catalysis in vitro. In this study, natural estolides produced by a bacterial culture are presented for the first time. Pseudomonas sp. 42A2 produced (E)‐10‐hydroxy‐8‐octadecenoic acid and (E)‐7,10‐dihydroxy‐8‐octadecenoic acid when grown on oleic acid. It is suggested that these FA were polymerized in culture by a lipase produced by the bacterial strain, resulting in a mixture of estolides. These compounds amounted to 3.8 g/L after 72 h of incubation. LC‐MS analysis indicated that the types of estolides formed were dimers (m/z 560–610), trimers (m/z 845–906), tetramers (m/z 1122–1202), pentamers (m/z 1328–1424), and hexamers (m/z 1554–1788), with a relative abundance of 27.5, 19.4, 15, 9.7, and 11%, respectively. This is the first report in which hexamers were detected in a bacterial culture.