(S)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid

• 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: (S)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid
• 英文别名: (9S,12Z,15Z)-9-hydroxy-10-oxo-12,15-octadecadienoic acid；9-hydroxy-10-oxo-12Z,15Z-octadecadienoic acid；9-hydroxy-10-keto-12Z,15Z-octadecadienoic acid；(S)-KODA；(S,12z,15z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid；(9S,12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: NJAYHLDXCVDTEV-BGZLHHJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid 在 1,4-dithio-D,L-threitol 、 acyl-CoA oxidase 、 2-enoylacyl-CoA hydratase 、 3-hydroxyacyl-CoA dehydrogenase 、 3-ketoacyl-CoA thiolase 、 acyl-CoA synthetase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 (5S,6S,8Z,11Z)-5,6-dihydroxytetradeca-8,11-dienoic acid 、 (7S,8S,10Z,13Z)-7,8-dihydroxyhexadeca-10,13-dienoic acid
  参考文献：
  名称：

  Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

  摘要：

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.077
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 乙二胺四乙酸 作用下， 生成 (S)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid 、 9R-hydroperoxy-10E,12Z,15Z-octadecatrienoic acid 、 5,8-dihydroxy-9Z,12Z,15Z-octadecatrienoic acid 、 (R)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid
  参考文献：
  名称：

  Lasiodiplodia theobromae 的亚麻酸 9R-双加氧酶和丙二烯氧化合酶活性。

  摘要：

  茉莉酸 (JA) 是由亚麻酸 (18:3n-3) 通过 13-脂肪氧化酶、丙二烯氧化合酶 (AOS) 和丙二烯氧化环化酶的顺序作用合成的。真菌 Lasiodiplodia theobromae 可产生大量 JA，最近据报道可形成 JA 前体 12-氧代植物二烯酸。我们研究的目的是表征这种真菌的脂肪酸双加氧酶活性。两株低 JA 分泌的 L. theobromae 菌株（~0.2 mg/L 培养基）将 18:3n-3 氧化为 5,8-二羟基-9Z,12Z,15Z-十八碳三烯酸以及 9R-氢过氧-10E,12Z， 15Z-十八碳三烯酸，通过 AOS 活性代谢为 9-羟基-10-氧代-12Z,15Z-十八碳二烯酸。用亚油酸 (18:2n-6) 观察到类似的转化。使用 [11S-(2)H]18 的研究：图 2n-6 揭示了推定的 9R-双加氧酶催化了 11R 氢的立体特异性去除，然后是 C-9 处双氧的表面攻击。来自这些

  DOI：

  10.1007/s11745-011-3622-5

文献信息

• Linolenate 9 <i>R</i> ‐Dioxygenase and Allene Oxide Synthase Activities of <i>Lasiodiplodia theobromae</i>
  作者：Fredrik Jernerén、Felipe Eng、Mats Hamberg、Ernst H. Oliw

  DOI：10.1007/s11745-011-3622-5

  日期：2012.1

  sequential action of 13-lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase. The fungus Lasiodiplodia theobromae can produce large amounts of JA and was recently reported to form the JA precursor 12-oxophytodienoic acid. The objective of our study was to characterize the fatty acid dioxygenase activities of this fungus. Two strains of L. theobromae with low JA secretion (~0.2 mg/L medium)

  茉莉酸 (JA) 是由亚麻酸 (18:3n-3) 通过 13-脂肪氧化酶、丙二烯氧化合酶 (AOS) 和丙二烯氧化环化酶的顺序作用合成的。真菌 Lasiodiplodia theobromae 可产生大量 JA，最近据报道可形成 JA 前体 12-氧代植物二烯酸。我们研究的目的是表征这种真菌的脂肪酸双加氧酶活性。两株低 JA 分泌的 L. theobromae 菌株（~0.2 mg/L 培养基）将 18:3n-3 氧化为 5,8-二羟基-9Z,12Z,15Z-十八碳三烯酸以及 9R-氢过氧-10E,12Z， 15Z-十八碳三烯酸，通过 AOS 活性代谢为 9-羟基-10-氧代-12Z,15Z-十八碳二烯酸。用亚油酸 (18:2n-6) 观察到类似的转化。使用 [11S-(2)H]18 的研究：图 2n-6 揭示了推定的 9R-双加氧酶催化了 11R 氢的立体特异性去除，然后是 C-9 处双氧的表面攻击。来自这些
• Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet
  作者：Ariaki Murata、Kenji Kai、Ken Tsutsui、Jun Takeuchi、Yasushi Todoroki、Kazuo Furihata、Mineyuki Yokoyama、Susanne Baldermann、Naoharu Watanabe

  DOI：10.1016/j.tet.2012.04.077

  日期：2012.7

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.