12-hydroxydodec-9(Z)-enoic acid | 79894-09-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 12-hydroxydodec-9(Z)-enoic acid
• 英文别名: 12-hydroxy-9(Z)-dodecenoic acid；12-hydroxydodeca-9-enoic acid；(9Z)-12-hydroxy-9-dodecenoic acid；(Z)-12-hydroxydodec-9-enoic acid
• CAS: 79894-09-0
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: AWMQDOYIFAMZEM-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 linoleate C-12 double bond hydratases of Lacto bacillus acidophilus NBRC 13951 、 linoleate C-9 double bond hydratases of Lacto bacillus acidophilus NBRC 13951 、 水 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 12.0h， 生成 12-hydroxydodec-9(Z)-enoic acid
  参考文献：
  名称：

  亚油酸双键水合酶为关键酶，将亚油酸生物转化为羟基脂肪酸和羧酸

  摘要：

  AbstractHydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C‐9 or the C‐12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13‐hydroxy‐cis‐9‐octadecenoic acid and 10‐hydroxy‐cis‐12‐octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12‐hydroxy‐cis‐9‐dodecenoic acid, α,ω‐tridec‐9‐enedioic acid) and lactones (i.e., δ‐decalactone, γ‐dodecelactone) via whole‐cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.magnified image

  DOI：

  10.1002/adsc.201400893

文献信息

• Alkylaluminum Chloride Catalyzed Ene Reactions of Formaldehyde with Unsaturated Carboxylic Acids, Esters and Alcohols
  作者：Jürgen O. Metzger、Ursula Biermann

  DOI：10.1055/s-1992-26137

  日期：——

  Dimethylaluminum chloride and ethylaluminum sesquichloride catalyze the ene reactions of formaldehyde with the C,C-double bond of unsaturated carboxylic acids, for example oleic acid and 10-undecenoic acid, and of the respective alcohols. Ethylaluminum dichloride catalyzes the ene reactions of formaldehyde with the respective carboxylic acid esters.

  二甲基氯化铝和乙基倍半氯化铝催化甲醛与不饱和羧酸（例如油酸和10-十一碳烯酸）及其相应醇的C,C双键进行ene反应。乙基二氯化铝催化甲醛与相应的羧酸酯进行ene反应。
• The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
  作者：Yana Y. Toporkova、Elena O. Smirnova、Tatiana M. Iljina、Lucia S. Mukhtarova、Svetlana S. Gorina、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2020.112512

  日期：2020.11

  The CYP74 family of cytochromes P450 includes four enzymes of fatty acid hydroperoxide metabolism: allene oxide synthase (AOS), hydroperoxide lyase (HPL), divinyl ether synthase (DES), and epoxyalcohol synthase (EAS). The present work is concerned with catalytic specificities of three recombinant DESs, namely, the 9-DES (LeDES, CYP74D1) of tomato (Solanum lycopersicum), 9-DES (NtDES, CYP74D3) of tobacco

  CYP74 细胞色素 P450 家族包括四种脂肪酸氢过氧化物代谢酶：丙二烯氧化合酶 (AOS)、氢过氧化物裂解酶 (HPL)、二乙烯基醚合酶 (DES) 和环氧醇合酶 (EAS)。目前的工作涉及三种重组 DES 的催化特异性，即番茄 (Solanum lycopersicum) 的 9-DES (LeDES, CYP74D1)、烟草 (Nicotiana tabacum) 的 9-DES (NtDES, CYP74D3) 和 13-DES (LuDES, CYP74B16) 亚麻 (Linum usitatissimum)，以及它们对定点诱变的改变。LeDES 和 NtDES 都将亚油酸和 α-亚麻酸的 9-氢过氧化物转化为二乙烯基醚 colleneic 和 colnelenic 酸（分别），只有少数 HPL 和 EAS 产物。相比之下，LeDES 和 NtDES 对亚油酸 13-过氧化氢
• Kuchin, A. V.; Tolstikov, A. G.; Gorobets, E. V., Doklady Chemistry, 1989, vol. 308, # 1-3, p. 261 - 263
  作者：Kuchin, A. V.、Tolstikov, A. G.、Gorobets, E. V.、Odinokov, V. N.、Grechkin, A. N.、Tolstikov, G. A.

  DOI：——

  日期：——
• Biotransformation of Linoleic Acid into Hydroxy Fatty Acids and Carboxylic Acids Using a Linoleate Double Bond Hydratase as Key Enzyme
  作者：Hye-Jin Oh、Sae-Um Kim、Ji-Won Song、Jung-Hoo Lee、Woo-Ri Kang、Ye-Seul Jo、Kyoung-Rok Kim、Uwe T. Bornscheuer、Deok-Kun Oh、Jin-Byung Park

  DOI：10.1002/adsc.201400893

  日期：2015.2.9

  AbstractHydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C‐9 or the C‐12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13‐hydroxy‐cis‐9‐octadecenoic acid and 10‐hydroxy‐cis‐12‐octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12‐hydroxy‐cis‐9‐dodecenoic acid, α,ω‐tridec‐9‐enedioic acid) and lactones (i.e., δ‐decalactone, γ‐dodecelactone) via whole‐cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.magnified image