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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-methyl 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienate	282091-45-6	C19H32O4	324.461
  Γ-十八碳三烯酸	(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid	463-40-1	C18H30O2	278.435

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(7R,8S,10Z,13Z)-7,8-dihydroxyhexadeca-10,13-dienoic acid	1400693-76-6	C16H28O4	284.396
  ——	(7R,8R,10Z,13Z)-7,8-dihydroxyhexadeca-10,13-dienoic acid	1400693-75-5	C16H28O4	284.396
  ——	(inverted exclamation markA)9,10-DiHODE	1400693-71-1	C18H32O4	312.45
  ——	(9R,10S,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid	1400693-72-2	C18H32O4	312.45
  ——	(5R,6S,8Z,11Z)-5,6-dihydroxytetradeca-8,11-dienoic acid	1400693-80-2	C14H24O4	256.342
  ——	(5R,6R,8Z,11Z)-5,6-dihydroxytetradeca-8,11-dienoic acid	1400693-79-9	C14H24O4	256.342

反应信息

• 作为反应物：
  描述：

  (R)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid 在 1,4-dithio-D,L-threitol 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  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：

  (R)-methyl 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienate 在 Lipase PS 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 生成 (R)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid
  参考文献：
  名称：

  亚麻酸 (KODA) 的 α-酮醇衍生物的全合成，亚麻酸的花诱导因子

  摘要：

  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。

  DOI：

  10.1246/cl.2003.844

文献信息

• 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。
• 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
• METHOD OF SYNTHESIZING ALPHA-KETOL UNSATURATED FATTY ACID
  申请人：Shiseido Co., Ltd.

  公开号：EP1357106A1

  公开（公告）日：2003-10-29

  The present invention provides an efficient synthetic method of α-ketol unsaturated fatty acid having a double bond at a β-position to the ketone group thereof. It comprises the steps of: preparing compound (4) by reacting monosubstituted acetylene (2) with epoxide (3); and preparing α -ketol unsaturated fatty acid (1) from said compound (4) as shown in Reaction Formula 1: wherein R1 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; R2 represents a protecting group for a hydroxyl group; R3 represents a protecting group for a carboxyl group; R is identical to R1 or, when R1 has one or more triple bonds, represents an aliphatic hydrocarbon group in which each triple bond of R1 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α-酮醇不饱和脂肪酸的高效合成方法，该脂肪酸的酮基在β位有双键。它包括以下步骤：通过单取代炔（2）与环氧化物（3）反应制备化合物（4）；以及从所述化合物（4）制备如反应式 1 所示的 α-酮醇不饱和脂肪酸（1）： 其中 R1 代表 1-18 个碳原子的烷基或 2-18 个碳原子的脂肪族烃基，在给定位置上有 1-5 个双键或三键；R2 代表羟基的保护基团；R3 代表羧基的保护基团；R 与 R1 相同，或者当 R1 有一个或多个三键时，代表脂肪族烃基，其中 R1 的每个三键转化为双键；以及 A 代表 1-18 个碳原子的亚烷基。
• US6605741B2
  申请人：——

  公开号：US6605741B2

  公开（公告）日：2003-08-12
• 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。