(+)-(10R,7Z,11E,13Z,16Z,19Z)-methyl 10-hydroxy-7,11,13,16,19-docosapentaenoate | 117333-03-6

• 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: (+)-(10R,7Z,11E,13Z,16Z,19Z)-methyl 10-hydroxy-7,11,13,16,19-docosapentaenoate
• 英文别名: methyl (7Z,10R,11E,13Z,16Z,19Z)-10-hydroxydocosa-7,11,13,16,19-pentaenoate
• CAS: 117333-03-6
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: ASDVBLDKFHDZRJ-VCNSIJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  (S)-(-)-1-苯乙基异氰酸酯 、 (+)-(10R,7Z,11E,13Z,16Z,19Z)-methyl 10-hydroxy-7,11,13,16,19-docosapentaenoate 以 甲苯 为溶剂， 反应 13.0h， 生成 (10R,7Z,11E,13Z,16Z,19Z)-methyl 10-<(S)-(1-phenylethyl)carbamoyloxy>-7,11,13,16,19-docosapentaenoate
  参考文献：
  名称：

  Leiopathic Acid（一种新型的光学活性羟基二十二碳五烯酸）及其相关化合物，来自黑珊瑚Leiopathes sp.。圣保罗岛（南印度洋）

  摘要：

  此处显示，在圣保罗岛附近收集的抗病性Leiopathes sp。含有相对较高的含量的新型脂肪酸Leiopathic acid（=（+）-（10 R，7 Z，11 E，13 Z，16 Z，19 Z）-10-羟基-7,11,13,16,19-二十二碳五烯酸;（+）- 1），除了（+）-（8 R，5 Z，9 E，11 Z，14 Z， 17 Z）-8-羟基-5,9,11,14,17-二十碳五烯酸（（+）- 11）和（+）-（8 R，5 Z，9 E，11 Z，14 Z，）-8-羟基-05,9,11,14-二十碳四烯酸（（+）- 16）及其乙酯（+）- 2，（+）- 12和（+）- 17。

  DOI：

  10.1002/hlca.19880710523
• 作为产物：
  描述：

  leiopathic acid 生成 (+)-(10R,7Z,11E,13Z,16Z,19Z)-methyl 10-hydroxy-7,11,13,16,19-docosapentaenoate
  参考文献：
  名称：

  GUERRIERO, ANTONIO;DAMBROSIO, MICHELE;PIETRA, FRANCESCO, HELV. CHIM. ACTA, 71,(1988) C. 1094-1100

  摘要：

  DOI：

文献信息

• Novel 10-Hydroxydocosapolyenoic Acids from Deep-Water Scleractinian Corals
  作者：Ines Mancini、Antonio Guerriero、Graziano Guella、Torkild Bakken、Helmut Zibrowius、Francesco Pietra

  DOI：10.1002/(sici)1522-2675(19990505)82:5<677::aid-hlca677>3.0.co;2-0

  日期：1999.5.5

  The new 10-hydroxydocosapolyenoic acids (10R,7Z,11E,13E,16Z,19Z)-10-hydroxydocosa-7,11,13,16,19-pentaenoic acid (1a) and (10R*,4Z,7Z,11E,13Z,16Z,19Z)-10-hydroxydocosa-4,7,11,13,16,19-hexaenoic acid (2a) were isolated as methyl esters 1b and 2b, respectively, following CH2N2 treatment of the EtOH extract of the scleractinian coral Madrepora oculata from deep-water of the southern Indian Ocean. From the same species from the Norwegian Sea, 1b and the methyl ester 3b of the new (10R,7Z,11E,13Z,16Z)-10-hydroxydocosa-7, 11,13,16-tetraenoic acid (3a) were analogously isolated, while from the untreated extract, the free acid 3a itself could be isolated. The absolute configuration of 1a and 3a was established by the chiral exciton coupling of the C(10) benzoate esters 1c and 3c. Other known 10-hydroxydocosapolyenoic acids and 8-hydroxyeicosapolyenoic acid were also isolated from M. oculata from both locations. These results imply the intervention of a rare lipooxygenase with high omega 13 specificity. In an examination of several other deep-water scleractinians, hydroxypolyenoic acids were found only in Lophelia pertusa from the northeastern Atlantic Ocean.