(12Z,15Z)-methyl 10-hydroxyoctadeca-12,15-dienoate | 34932-15-5

• 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: (12Z,15Z)-methyl 10-hydroxyoctadeca-12,15-dienoate
• 英文别名: methyl (12Z,15Z)-10-hydroxyoctadeca-12,15-dienoate
• CAS: 34932-15-5
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: CFOOYFLUSNACLH-XJJAZQAQSA-N

物化性质

• 沸点：
  408.1±25.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  (12Z,15Z)-methyl 10-hydroxyoctadeca-12,15-dienoate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(12Z,15Z)-methyl 10-oxooctadeca-12,15-dienoate
  参考文献：
  名称：

  Structure–activity relationship study of flowering-inducer FN against Lemna paucicostata

  摘要：

  FN1 (1) and FN2 (2), cycloadducts of alpha-ketol octaclecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.115
• 作为产物：
  描述：

  (S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid 在 conjugated linoleic acid dehydrogenase 、 nicotinamide adenine dinucleotide 、 还原型辅酶Ⅰ 、 bovine serum albumin 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 (12Z,15Z)-methyl 10-hydroxyoctadeca-12,15-dienoate
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020

文献信息

• A Bi‐Enzymatic Cascade Pathway towards Optically Pure FAHFAs**
  作者：Yan Zhang、Bekir Engin Eser、Zheng Guo

  DOI：10.1002/cbic.202100070

  日期：2021.6.15

  Full enzymatic synthesis of FAHFAs: Various hydroxy fatty acids with different −OH positions can be synthesized from renewable fatty acids by wild-type and engineered fatty acid hydratases, which can be cascaded with lipase to prepare value-added FAHFAs with potential medical value.

  FAHFA 的全酶法合成：可以通过野生型和工程化脂肪酸水合酶从可再生脂肪酸合成具有不同 -OH 位置的各种羟基脂肪酸，这些水合酶可以与脂肪酶级联以制备具有潜在医疗价值的增值 FAHFA。
• Sakata, Kazuhiko; Takizawa, Naoya; Sankawa, Ushio, Agricultural and Biological Chemistry, 1986, vol. 50, # 4, p. 1077 - 1080
  作者：Sakata, Kazuhiko、Takizawa, Naoya、Sankawa, Ushio、Ebizuka, Yutaka、Noguchi, Hiroshi

  DOI：——

  日期：——
• Structure–activity relationship study of flowering-inducer FN against Lemna paucicostata
  作者：Kenji Kai、Jun Takeuchi、Taichi Kataoka、Mineyuki Yokoyama、Naoharu Watanabe

  DOI：10.1016/j.tet.2008.04.115

  日期：2008.7

  FN1 (1) and FN2 (2), cycloadducts of alpha-ketol octaclecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity. (C) 2008 Elsevier Ltd. All rights reserved.
• Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a
  作者：Michiki Takeuchi、Shigenobu Kishino、Si-Bum Park、Nahoko Kitamura、Jun Ogawa

  DOI：10.1016/j.molcatb.2015.03.020

  日期：2015.7

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.