methyl (E)-9-hydroxyoctadec-10-enoate | 10075-09-9

• 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: methyl (E)-9-hydroxyoctadec-10-enoate
• 英文别名: methyl 9R,S-hydroxy-10E-octadecenoate；methyl ester of (E)-9-hydroxy-10-octadecenoic acid；methyl 9-hydroxyoctadec-trans-10-enoate；(E)-methyl 9-hydroxyoctadec-10-enoate；9-Hydroxy-trans-10-octadecensaeuremethylester
• CAS: 10075-09-9
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: BXSXGBHYOADYAM-NTCAYCPXSA-N

物化性质

• 沸点：
  406.1±33.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-9-hydroxyoctadec-10-enoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 9-hydroxy-10E-octadecenoic acid
  参考文献：
  名称：

  赤藻Tricleocarpa jejuensis的杀藻羟基化的C18不饱和脂肪酸：鉴定，合成和生物学活性。

  摘要：

  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。

  DOI：

  10.1016/j.fitote.2020.104639
• 作为产物：
  描述：

  trans-9-hydroperoxyoctadec-10-enoic acid 在 sodium tetrahydroborate 作用下， 生成 methyl (E)-9-hydroxyoctadec-10-enoate
  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

文献信息

• Bascetta, Emanuele; Gunstone, Frank D., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2207 - 2216
  作者：Bascetta, Emanuele、Gunstone, Frank D.

  DOI：——

  日期：——
• A Mechanistic Study of Oleate Autoxidation: Competing Peroxyl H-Atom Abstraction and Rearrangement
  作者：Ned A. Porter、Karen A. Mills、Randall L. Carter

  DOI：10.1021/ja00094a026

  日期：1994.7

  The mechanism of methyl oleate autoxidation was investigated. HPLC techniques were developed to analyze the products of autoxidation (hydroperoxides and the corresponding alcohols). The alcohols could be completely resolved by normal-phase chromatography, six products being characterized having oxygen substitution and double position as follows: 11-OOH-trans-Delta(9-10), 11-OOH-cis-Delta(9-10), 10-OOH-trans-Delta(8-9), 9-OOH-trans-Delta(10-11), 8-OOH-trans-Delta(9-10), 8-OOH-cis-Delta(9-10) As the hydrogen atom donor concentration of the medium of autoxidation is increased, increased 11-cis, 8-cis, 9-trans, and 10-trans hydroperoxides and decreased 11-trans and 8-trans hydroperoxides were obtained, consistent with a mechanism in which peroxyl H-atom abstraction and [2,3] allylperoxyl rearrangement are in competition. An iterative computer kinetic analysis was developed which modeled the oleate autoxidation mechanism, and rearrangement rate constants were determined. Allylperoxyl radicals undergo rearrangement with different rates depending on the geometry of the allylperoxyl.
• Frankel, Edwin N.; Garwood, Robert F.; Khambay, Bhupinder P. S., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2233 - 2240
  作者：Frankel, Edwin N.、Garwood, Robert F.、Khambay, Bhupinder P. S.、Moss, Gerard P.、Weedon, Basil C. L.

  DOI：——

  日期：——
• Identification of (<i>e</i>)-11-hydroxy-9-octadecenoic acid and (<i>E</i>)-9-hydroxy-10-octadecenoic acid by biotransformation of oleic acid by<i>Pseudomonas</i>sp. 32T3
  作者：E. Rodríguez、M. J. Espuny、A. Manresa、A. Guerrero

  DOI：10.1007/s11746-001-0310-3

  日期：2001.6

  AbstractPseudomonas sp. 32T3, a newly identified strain originally isolated from a vegetable oil‐contaminated soil, produces three monohydroxy acids—(E)‐11‐hydroxy‐9‐octadecenoic acid, (E)‐10‐hydroxy‐8‐octadecenoic acid, and (E)‐9‐hydroxy‐10‐octadecenoic acid—as bioconversion products of oleic acid. The bacterial cells were grown in a mineral medium containing oleic acid as the main carbon substrate. The compounds were identified as the corresponding methyl esters on the basis of their chromatographic and spectroscopic (1H and 13C nuclear magnetic resonance and gas chromatography‐mass spectrometry) features.
• CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631
  作者：CAPELLA, P.、CABONI, M. F.、BONAGA, G.、LERCKER, G.

  DOI：——

  日期：——