methyl colnelenate | 52077-22-2

• 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 colnelenate
• 英文别名: methyl (E)-9-[(1E,3Z,6Z)-nona-1,3,6-trienoxy]non-8-enoate
• CAS: 52077-22-2
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: ZHADMZSKNJUERU-BWLZIVRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl colnelenate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 反-2-,顺-6-壬二烯醛 、 9-氧代壬酸甲酯
  参考文献：
  名称：

  An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes

  摘要：

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.

  DOI：

  10.1039/p19910000567
• 作为产物：
  描述：

  重氮甲烷 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 氧气 作用下， 生成 (8E,1'E,3'Z)-9-(1',3'-nonadienyloxy)-8-nonenoic acid methyl ester 、 methyl colnelenate
  参考文献：
  名称：

  An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes

  摘要：

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.

  DOI：

  10.1039/p19910000567

文献信息

• An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes
  作者：Leslie Crombie、David O. Morgan、Elisabeth H. Smith

  DOI：10.1039/p19910000567

  日期：——

  Contrary to earlier reports, the divinyl 9-ether oxygen of coloneleic acid is shown by experiment with O-18(2) to originate from oxygen, not water. Using [9,10,12,13-H-2(4)]-9(S)-hydroperoxyoctadeca-10(E), 12(Z)-dienoic acid, made enzymically from synthetic [9,10,12,13-H-2(4)]linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneleic acid formed by potato enzyme, is consistent with the intervention of an epoxycarbonium ion intermediate. Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.