8(R)-hydroxyeicosatetraenoic acid methyl ester | 100896-77-3

• 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: 8(R)-hydroxyeicosatetraenoic acid methyl ester
• 英文别名: methyl (5Z,8R,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoate
• CAS: 100896-77-3
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: FEVDXZUVWOIUKK-MIFXIWNASA-N

物化性质

• 沸点：
  447.7±45.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  8(R)-hydroxyeicosatetraenoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (5Z,8R,9E,11Z,14Z)-8-羟基-5,9,11,14-二十碳四烯酸
  参考文献：
  名称：

  对映体全合成8和12-羟基二十碳四烯酸

  摘要：

  从辛酸二甲酯衍生的前体合成了8和12个羟基二十碳四烯酸（8和12-HETE）的R和S异构体。

  DOI：

  10.1016/s0040-4039(00)85392-7
• 作为产物：
  描述：

  (5Z,9E,11Z,14Z)-(R)-8-Hydroperoxy-icosa-5,9,11,14-tetraenoic acid methyl ester 在 三甲氧基磷 作用下， 以 苯 为溶剂， 反应 0.17h， 生成 8(R)-hydroxyeicosatetraenoic acid methyl ester
  参考文献：
  名称：

  Intermediacy of 8-(R)-HPETE in the conversion of arachidonic acid to pre-clavulone a by Clavularia viridis. Implications for the biosynthesis of marine prostanoids

  摘要：

  DOI：

  10.1021/ja00235a053

文献信息

• Leiopathic Acid, a Novel Optically Active Hydroxydocosapentaenoic Acid, and related compounds, from the black coralLeiopathes sp. of Saint Paul Island (S. Indian Ocean)
  作者：Antonio Guerriero、Michele D'Ambrosio、Francesco Peitra

  DOI：10.1002/hlca.19880710523

  日期：1988.8.10

  Leiopathes sp., collected around Saint Paul Island, is shown here to contain, in relatively high amounts, the novel fatty acid leiopathic acid ( = (+)-(10R,7Z,11E,13Z,16Z,19Z)-10-hydroxy-7,11,13,16,19-docosapentaenoic acid; (+)-1), besides (+)-(8R,5Z,9E,11Z,14Z,17Z)-8-hydroxy-5,9,11,14,17-icosapentaenoic acid ((+)-11) and (+)-(8R,5Z,9E,11Z,14Z,)-8-hydroxy-05,9,11,14-icosatetraenoic acid ((+)-16) and

  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。
• 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.