(12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid | 51146-89-5

• 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)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid
• CAS: 51146-89-5
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: NJAYHLDXCVDTEV-ZJSQCTGTSA-N

物化性质

• 沸点：
  500.5±50.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

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：

  (12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以100%的产率得到(12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic 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：

  sodium linolenate 在 lipoxygenase from rice 、 环氧化物酶 水 、 氧气 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 (12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid
  参考文献：
  名称：

  WO2006/57446

  摘要：

  公开号：

文献信息

• Insight into the chemistry of cycloaddition between α-ketol oxylipin and epinephrine: isolation and structure elucidation of a new reaction product
  作者：Kenji Kai、Yukie Oba、Ryota Akaike、Ariaki Murata、Toshio Nishikawa、Naoharu Watanabe

  DOI：10.1016/j.tetlet.2013.02.062

  日期：2013.5

  flowering in Lemna paucicostata. Here we isolate compound 5 from the reaction mixture and identify it as a Michael-type adduct of 1 with adrenochrome (6), an oxidized form of 2. Compound 5 was gradually converted into KEs in aqueous solution, suggesting that the compound is an intermediate of KEs. From these results, we newly propose the reaction mechanism of the cycloaddition between 1 and 2.

  α-酮酚脂（12 Z，15 Z）-9-羟基-10-氧辛基十八烷基-12,15-二烯酸（1）与肾上腺素（2）反应生成独特的环加合物KE1（3）和KE2（4） ，两者都强烈诱导了Lemna paucicostata的开花。在这里，我们分离化合物5从反应混合物中并且将其识别为的Michael型加成物1与肾上腺色素（6），的氧化形式2。化合物5在水溶液中逐渐被转化为KEs，表明该化合物是KEs的中间体。从这些结果，我们新提出了1和2之间的环加成反应的机理。
• Structure and biological activity of novel FN analogs as flowering inducers
  作者：Kenji Kai、Jun Takeuchi、Taichi Kataoka、Mineyuki Yokoyama、Naoharu Watanabe

  DOI：10.1016/j.bmc.2008.10.014

  日期：2008.12

  (12Z, 15Z)-9-Hydroxy-10-oxooctadeca-12,15-dienoic acid (1) and norepinephrine (2) undergo cycloaddition to afford FN1 (3) and FN2 (4), both of which induce flowering in Lemna paucicostata. Although the derivatives of 1 were suggested to also yield FN-like compounds after reacting with 2, their structures have not been elucidated. In this report, we investigated the structure and stereochemistry of seven novel FN analogs. These analogs were shown to be formed in the same regio- and stereocontrolled manner as FNs. Moreover, the activity of FN analogs on flowering induction was investigated, and we determined that all analogs, except for compound 8, were effective flowering inducers for L. paucicostata. (c) 2008 Elsevier Ltd. All rights reserved.

  (12Z, 15Z)-9-羟基-10-氧基-顺式-12,15-十八碳二烯酸(1)和去甲肾上腺素(2)通过环加成反应生成FN1(3)和FN2(4)。这两种产物都能诱导Lemna paucicostata开花。尽管1的衍生物与2反应后被认为也能生成类似的FN化合物，但它们的具体结构尚未明确。本研究调查了七种新型FN类似物的结构和立体化学特性。研究显示，这些类似物与FNs在相同的区域和立体控制方式下形成。此外，我们评估了FN类似物在诱导开花方面的活性，结果表明除化合物8外，所有类似物均为L. paucicostata的有效开花诱导剂。版权 © 2008 Elsevier Ltd. 保留所有权利。
• Total Synthesis of α-Ketol Derivative of Linolenic Acid (KODA), a Flower-inducing Factor in<i>Lemna paucicostata</i>
  作者：Yoshihiro Yokokawa、Kouji Kobayashi、Mineyuki Yokoyama、Shosuke Yamamura

  DOI：10.1246/cl.2003.844

  日期：2003.9

  Racemic 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid [(±)-KODA] was synthesized via a coupling reaction between a diyne and an epoxide derived from methyl oleate as a key step. An optically active 9R-KODA was also synthesized by enantioselective lipase-catalyzed esterification of an allyl alcohol. Both synthetic (±)-KODA and 9R-KODA showed remarkable flower-inducing activity in Pharbitis nil.

  作为关键步骤，外消旋 9-羟基-10-氧代-12(Z),15(Z)-十八碳二烯酸 [(±)-KODA] 是通过二炔和衍生自油酸甲酯的环氧化物之间的偶联反应合成的。还通过对映选择性脂肪酶催化的烯丙醇酯化合成了光学活性 9R-KODA。合成的 (±)-KODA 和 9R-KODA 在 Pharbitis nil 中均显示出显着的花诱导活性。
• Synthetic method of ketol unsaturated fatty acids
  申请人：——

  公开号：US20020156304A1

  公开（公告）日：2002-10-24

  The present invention provides an efficient synthetic method of &agr;-ketol unsaturated fatty acid having a double bond at a &bgr;-position to the ketone group thereof. It comprises the steps of: preparing compound (4) by reacting monosubstituted acetylene (2) with epoxide (3); and preparing &agr;-ketol unsaturated fatty acid (1) from said compound (4) as shown in Reaction Formula 1: 1 wherein R 1 represents an alkyl group of 1-18 carbon atoms or an aliphatic hydrocarbon group of 2-18 carbon atoms having 1-5 double or triple bonds at given positions; R 2 represents a protecting group for a hydroxyl group; R 3 represents a protecting group for a carboxyl group; R is identical to R 1 or, when R 1 has one or more triple bonds, represents an aliphatic hydrocarbon group in which each triple bond of R 1 is converted to a double bond; and A represents an alkylene group of 1-18 carbon atoms.

  本发明提供了一种高效的合成方法，用于具有双键位于其β-位置的α-酮烯酸。它包括以下步骤：通过将单取代乙炔（2）与环氧化物（3）反应制备化合物（4）；并从所述化合物（4）制备α-酮烯酸（1），如反应式1所示：其中R1表示碳原子数为1-18的烷基基团或碳原子数为2-18的脂肪烃基团，在给定位置具有1-5个双键或三键；R2表示羟基的保护基团；R3表示羧基的保护基团；R与R1相同，或者当R1具有一个或多个三键时，表示将R1的每个三键转化为双键的脂肪烃基团；A表示碳原子数为1-18的亚烯基团。
• Isomeric Product Detection in the Heterogeneous Reaction of Hydroxyl Radicals with Aerosol Composed of Branched and Linear Unsaturated Organic Molecules
  作者：Theodora Nah、Haofei Zhang、David R. Worton、Christopher R. Ruehl、Benjamin B. Kirk、Allen H. Goldstein、Stephen R. Leone、Kevin R. Wilson

  DOI：10.1021/jp508378z

  日期：2014.12.11

  hydroxyalkyl radical. In addition, allylic alkyl radicals, formed from H atom abstraction reactions by hydroxyalkyl or OH radicals play important roles in the chemistry of product formation. Functionalization products dominate the squalene reaction at ∼1% [O2], with the total abundance of observed functionalization products being approximately equal to the fragmentation products at 10% [O2]. The large

  研究了不饱和有机气溶胶非均相氧化过程中分子结构（支链或线性）对产物形成的影响。由角鲨烯（C 30 H 50，具有六个C═C双键的支链烯烃）和亚麻酸（C 18 H 30 O 2，具有三个C═C双键的线性羧酸）反应形成的颗粒相产物异构体使用二维气相色谱-质谱法鉴定和定量带有OH自由基的化合物。在低和高[O 2 ]时测量反应（〜1％对10％[O 2]）了解羟烷基和羟过氧自由基中间体在产物形成中的作用。关键的反应步骤是将OH加成C═C双键以形成羟烷基基团。另外，由H原子抽象反应通过羟烷基或OH自由基形成的烯丙基烷基自由基在产物形成的化学中起重要作用。官能化产物以约1％[O 2 ]占主导地位，在角鲨烯反应中，观察到的官能化产物的总丰度大约等于10％[O 2 ]时的裂解产物。10％[O 2时，大量的角鲨烯裂解产物]归因于叔羟基烷氧基自由基中间体的形成和离解。对于亚麻酸气溶胶，官能化产物的形成在1％和10％[O