(Z)-9-hydroxy-10-oxooctadec-12-enoic 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: (Z)-9-hydroxy-10-oxooctadec-12-enoic acid
• 英文别名: (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid；9-Hydroxy-10-oxo-cis-12-octadecensaeure；10-Oxo-9-hydroxy-cis-12-octadecensaeure；9-hydroxy-10-oxo-12Z-octadecenoic acid
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: KUSHOISAFGTTRU-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (Z)-9-hydroxy-10-oxooctadec-12-enoic acid 、 去甲肾上腺素 在 Tris-HCl buffer 、 氧气 作用下， 以 水 为溶剂， 反应 15.0h， 以18%的产率得到11-((3R,3aS,4S,5S,7R)-3,7-dihydroxy-8-oxo-4-pentyl-2,3,4,5,7,8-hexahydro-1H-3a,7-methanooxocino[5,4-b]pyrrol-5-yl)-9-hydroxy-10-oxoundecanoic acid
  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：

  (Z)-methyl 9-hydroxy-10-oxooctadec-12-enoate 在 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 (Z)-9-hydroxy-10-oxooctadec-12-enoic acid
  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

文献信息

• Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins
  作者：Alexander N. Grechkin、Anna V. Ogorodnikova、Alevtina M. Egorova、Fakhima K. Mukhitova、Tatiana M. Ilyina、Bulat I. Khairutdinov

  DOI：10.1002/open.201800045

  日期：2018.5

  (9‐HPOD), and (9S,10E,12Z,15Z)‐9‐hydroperoxy‐10,12,15‐octadecatrienoic acid, respectively, via the corresponding allene oxides and cyclopropanones. The data indicate that conversion of the allene oxide into the cyclopropanone is controlled by soluble cyclase. The short‐lived cyclopropanones are hydrolyzed to products 1–3. The collective name “graminoxins” has been ascribed to oxylipins 1–3.

  小麦，大麦和高粱的年轻根以及茉莉酸甲酯预处理的水稻幼苗，经历了针对以前未知的磷脂1到3的空前的氧化烯合酶途径。这些Favorskii类制品，（4 Ž）-2-戊基-4-十三烯-1,13-二酸（1），（2' Ž）-2-（2'-辛烯基） -癸烷1,10-二酸（2），和（2' ž，5' ž）-2-（2'，5'-辛二烯） -癸烷-1,10-二酸（3），具有在侧链羧基功能，由他们的MS和NMR光谱数据揭示。化合物1 - 3是检测到的主要磷脂，以及相关的α-酮醇。产品13从（9生物合成Ž，11 ê，13小号）-13-氢过氧基9,11-十八碳二烯酸，（9小号，10 ê，12 Ž）-9-氧化氢-10,12-十八碳二烯酸（9‐HPOD）和（9 S，10 E，12 Z，15 Z）‐9‐氢过氧‐10,12,15‐十八碳三烯酸，分别通过相应的丙二烯氧化物和环丙烷酮。数据表明氧化烯到环氧丙烷的转化是由可溶性环化酶控制的。寿命短的环丙烷酮水解成产物1
• 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
• ANTI-INFLAMMATORY AGENT CONTAINING RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3097910A1

  公开（公告）日：2016-11-30

  The present invention provides an anti-inflammatory agent containing a rare fatty acid such as hydroxylated fatty acid, oxo fatty acid and the like, and further, food, pharmaceutical product and the like containing the anti-inflammatory agent.

  本发明提供了一种含有稀有脂肪酸（如羟化脂肪酸、氧代脂肪酸等）的消炎剂，以及含有该消炎剂的食品、药品等。
• Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots
  作者：Anna V. Ogorodnikova、Larisa R. Latypova、Fahima K. Mukhitova、Lucia S. Mukhtarova、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2008.09.011

  日期：2008.11

  Incubations of linoleic acid with cell-free preparations from Lily-of-the-Valley (Convallaria majalis L, Ruscaceae) roots revealed the presence of 13-lipoxygenase and divinyl ether synthase (DES) activities. Exogenous linoleic acid was metabolized predominantly into (9Z,11E,1'E)-12-(1'-hexenyloxy)-9,11-dodecadienoic (etheroleic) acid. Its identification was confirmed by the data of ultraviolet spectroscopy, mass spectra, H-1 NMR, COSY, catalytic hydrogenation. The isomeric divinyl ether (8E,1'E,3'Z)-1 2-(1',3'-nonadienyloxy)-8-nonenoic (colneleic) acid was detected as a minor product. Incubations with linoleic acid hydroperoxides revealed that 13-hydroperoxide was a preferential substrate, while the 9-hydroperoxide was utilized with lesser efficiency. (C) 2008 Elsevier Ltd. All rights reserved.
• US6174712B1
  申请人：——

  公开号：US6174712B1

  公开（公告）日：2001-01-16