12,13-Epoxylinoleic acid | 32381-42-3

• 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: 12,13-Epoxylinoleic acid
• 英文别名: (-)-vernolic acid；(-)-leukotoxin B；vernolic acid；(-)-12(R),13(S)-vernolic acid；(-)-Vernolsaeure；(Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoic acid
• CAS: 32381-42-3
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: CCPPLLJZDQAOHD-BEBBCNLGSA-N

物化性质

• 熔点：
  30-31°
• 比旋光度：
  D -8°

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12,13-Epoxylinoleic acid 在 methylmagnesium derivative of N-cyclohexylisopropylamine 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 13(s)-羟基-9z,11e-十八二烯酸
  参考文献：
  名称：

  Synthesis of 12(R),13(S)-oxido-9-octadecenoic (vernolic) and 13(S)-hydroxy-9, 11-octadecadienoic (coriolic) acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)84002-2
• 作为产物：
  描述：

  (9Z)-11-[(2S,3R)-3-戊基-2-环氧乙烷基]-9-十一碳烯酸甲酯 在 三乙烯二胺 、 aluminum oxide 、 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 二丁醚 、 水 、 乙腈 为溶剂， 反应 68.0h， 生成 12,13-Epoxylinoleic acid
  参考文献：
  名称：

  Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

  摘要：

  Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S), 15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(01)00694-3

文献信息

• AN OXYGENATED FATTY ACID FROM THE SEED OIL OF HIBISCUS ESCULENTUS
  作者：Mary J. Chisholm、C. Y. Hopkins

  DOI：10.1139/v57-053

  日期：1957.4.1

  The fatty acids of okra seed oil (Hibiscusesculentus L.) were examined. Acetylation of the oil, followed by saponification and separation of the acids, gave 12,13-dihydroxyoleic acid. From this and other evidence it is concluded that 12,13-epoxyoleic acid is present as a constituent of the glycerides. An oxygenated acid has not been identified previously in seed oils of this plant family (Malvaceae)

  检查了秋葵籽油 (Hibiscusesculentus L.) 的脂肪酸。油的乙酰化，然后皂化和酸的分离，得到12,13-二羟基油酸。从这个和其他证据得出结论，12,13-环氧油酸作为甘油酯的成分存在。先前尚未在该植物科（锦葵科）的种子油中发现含氧酸。还发现了 9-十六碳烯酸。总脂肪酸组成通过甲酯的蒸馏和蒸馏馏分的分析来确定。确定的酸的百分比估计如下：9-十六烯酸0.6、棕榈酸29、亚油酸39、油酸23、硬脂酸2、12,13-环氧油酸3、花生酸<1。未检测到肉豆蔻酸、二十碳烯酸和三烯酸，如果存在，
• Compositions of matter that reduce pain, shock, and inflammation by blocking linoleic acid metabolites and uses thereof
  申请人：Board of Regents of the University of Texas System

  公开号：US10100317B2

  公开（公告）日：2018-10-16

  A method for treating and/or diagnosing pain and the source or type of pain, shock, and/or inflammatory conditions in a subject. A method of using a therapeutically effective amount of a DNA or RNA aptamer that shows high affinity for OLAMs to at least partially treat pain, shock, and/or inflammatory conditions in a subject. The DNA or RNA aptamer that shows high affinity for OLAMs may be coupled to a plasma protein binding compound or a pharmacologically active agent. A method of treating and or diagnosing pain, shock, and/or inflammatory conditions in a subject may include inactivating or preventing at least one linoleic acid metabolite to treat certain conditions (e.g., pain, shock, and/or inflammation) using a DNA or RNA aptamer that shows high affinity for OLAMs.

  一种治疗和/或诊断受试者疼痛以及疼痛、休克和/或炎症的来源或类型的方法。一种使用对 OLAMs 具有高亲和力的治疗有效量的 DNA 或 RNA 合体来至少部分治疗受试者的疼痛、休克和/或炎症的方法。对 OLAMs 具有高亲和力的 DNA 或 RNA 合体可与血浆蛋白结合化合物或药理活性剂偶联。治疗和或诊断受试者疼痛、休克和/或炎症的方法可包括使用对 OLAMs 表现出高亲和力的 DNA 或 RNA 合酶灭活或阻止至少一种亚油酸代谢物，以治疗某些病症（如疼痛、休克和/或炎症）。
• Hopkins; Chisholm, Journal of the American Oil Chemists' Society, 1960, vol. 37, p. 682
  作者：Hopkins、Chisholm

  DOI：——

  日期：——
• Metabolomics-Based Identification of Disease-Causing Agents
  申请人：Skolnick Jeffrey

  公开号：US20110246081A1

  公开（公告）日：2011-10-06

  A method, computer-readable medium, and system for identifying one or more metabolites associated with a disease, comprising: comparing gene expression data from diseased cells to gene expression data from control cells in order to deduce genes that are differentially-regulated in the diseased cells relative to the control cells; based on enzyme function and pathway data for all human metabolites that utilize the genes that are differentially-regulated in the disease cells, identifying one or more metabolites whose intracellular levels are higher or lower in diseased cells than in control cells, and thereby associating the one or more metabolites with the disease.
• COMPOSITIONS OF MATTER THAT REDUCE PAIN, SHOCK, AND INFLAMMATION BY BLOCKING LINOLEIC ACID METABOLITES AND USES THEREOF
  申请人：Board of Regents of the University of Texas System

  公开号：US20140128588A1

  公开（公告）日：2014-05-08

  A method for treating and/or diagnosing pain and the source or type of pain, shock, and/or inflammatory conditions in a subject. A method of using a therapeutically effective amount of a DNA or RNA aptamer that shows high affinity for OLAMs to at least partially treat pain, shock, and/or inflammatory conditions in a subject. The DNA or RNA aptamer that shows high affinity for OLAMs may be coupled to a plasma protein binding compound or a pharmacologically active agent. A method of treating and or diagnosing pain, shock, and/or inflammatory conditions in a subject may include inactivating or preventing at least one linoleic acid metabolite to treat certain conditions (e.g., pain, shock, and/or inflammation) using a DNA or RNA aptamer that shows high affinity for OLAMs.