(+/-)-cis-9,10-epoxy-12(Z)-octadecenoic acid | 16833-56-0

• 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: (+/-)-cis-9,10-epoxy-12(Z)-octadecenoic acid
• 英文别名: cis-9,10-epoxy-12(Z)-octadecenoic acid；(9,10Z)-epoxyoctadec-(12Z)-enoic acid；leukotoxin；ltx；cis-9,10-Epoxy-cis-12-octadecen-saeure, Coronarsaeure；9(10)-EpOME；8-[(2S,3R)-3-[(Z)-oct-2-enyl]oxiran-2-yl]octanoic acid
• CAS: 16833-56-0；61949-82-4；65167-83-1；110658-06-5；113972-57-9；126639-25-6；132201-82-2；135094-09-6；146987-78-2
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: FBUKMFOXMZRGRB-XKJZPFPASA-N

物化性质

• 沸点：
  422.6±18.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 peroxygenase from tomato yeast extract 、 双氧水 作用下， 以 aq. acetate buffer 为溶剂， 反应 1.0h， 生成 (+/-)-顺式-12,13-环氧-9(Z)-十八碳烯酸 、 (+/-)-cis-9,10-epoxy-12(Z)-octadecenoic acid
  参考文献：
  名称：

  Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana

  摘要：

  Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (V-max) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid With V-max of 3.83 mu mol min mg(-1) but NbEH1.1 could not hydrolyze cis-9,10-epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.02.020

文献信息

• TREATING PULMONARY DISEASES MEDIATED BY POLYUNSATURATED LIPID METABOLITES AND ASSAYS FOR EPOXIDE HYDROLASE INHIBITORS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0926951B1

  公开（公告）日：2004-04-21
• US5955496A
  申请人：——

  公开号：US5955496A

  公开（公告）日：1999-09-21
• US6174695B1
  申请人：——

  公开号：US6174695B1

  公开（公告）日：2001-01-16
• Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana
  作者：Fong-Chin Huang、Wilfried Schwab

  DOI：10.1016/j.phytochem.2013.02.020

  日期：2013.6

  Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (V-max) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid With V-max of 3.83 mu mol min mg(-1) but NbEH1.1 could not hydrolyze cis-9,10-epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants. (C) 2013 Elsevier Ltd. All rights reserved.