(9Z,13E,15Z)-12-hydroxy-9,13,15-octadecatrienoic acid | 81325-64-6

• 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: (9Z,13E,15Z)-12-hydroxy-9,13,15-octadecatrienoic acid
• 英文别名: 12-hydroxy-cis,trans,cis-9,13,15-octadecatrienoic acid；(9Z,13E,15Z)-12-hydroxyoctadeca-9,13,15-trienoic acid
• CAS: 81325-64-6
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: WOZLPPGKSWZLBI-YMVUBCEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  Γ-十八碳三烯酸 在 air 、 recombinant E_. coli ER₂₅₆₆ cells expressing 9S-lipoxygenase and epoxide hydrolase from Myxococcus xanthus 作用下， 以 aq. buffer 为溶剂， 反应 1.5h， 以62.6%的产率得到12,13,14-trihydroxy-9,15-octadecadienoic acid
  参考文献：
  名称：

  从C18多不饱和脂肪酸微生物合成亚油酸酯9 S-脂氧合酶衍生的植物C18氧化脂

  摘要：

  由C18多不饱和脂肪酸（PUFA）生物合成的植物羟基磷脂，包括羟基脂肪酸，环氧羟基脂肪酸和三羟基脂肪酸，参与了针对真菌感染的病原体特异性防御​​机制。然而，尚未报道它们通过植物酶的定量生物转化。少数细菌会产生C18三羟基脂肪酸，但尚未报道与细菌中植物脂蛋白生物合成有关的酶和途径。在这项研究中，我们首先通过表达亚油酸9报告C18多不饱和脂肪酸的生物转化成植物C18氧脂素小号脂肪氧合酶与不从变形菌环氧化物水解酶粘细菌在重组大肠杆菌。在九个类型的植物氧脂素，12,13-环氧-14-羟基的顺式，顺式-9,15十八碳二烯酸，鉴定为通过NMR分析的新化合物，以及9,10,11羟基顺式，顺式通过LC-MS / MS分析，建议将-6,12-十八碳二烯酸和12,13,14-三羟基顺式，顺式-9,15-十八碳二烯酸作为新化合物。这项研究表明，具有生物活性的植物脂蛋白可以通过微生物酶产生。

  DOI：

  10.1021/acs.jafc.8b05857

文献信息

• UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE
  作者：Tadahiro Kato、Yoshihiro Yamaguchi、Takumi Hirano、Toshiro Yokoyama、Tadao Uyehara、Tsuneo Namai、Susumu Yamanaka、Nobuyuki Harada

  DOI：10.1246/cl.1984.409

  日期：1984.3.5

  In addition to the previously described epoxy fatty acids, five hydroxy fatty acids were characterized as self defensive substances produced in the rice plant against rice blast disease.

  除了之前描述的环氧脂肪酸外，还鉴定出五种羟基脂肪酸作为水稻植物对抗稻瘟病的自我防御物质。
• REDUCED SODIUM FOOD PRODUCT
  申请人：GENERAL MILLS, INC.

  公开号：EP3466930A1

  公开（公告）日：2019-04-10

  The present invention relates to the use of a compound according to Formula B3: where: R1 and R2 are each independently OH or C1-C3 alkoxy, and R3 is selected from the group consisting of (i) C10-C20 unsubstituted straight or branched chain alkenyl with one or more double bonds; and (ii) where X, Y and Z are independently CH, CH2, CO or CHOR5 where R5 is H or C1-C3 alkyl, provided that if one of X or Y are CH then Z is also CH, and where R4 is C1-C8 straight or branched chain unsubstituted alkyl or where n is 1-5, provided that if R4 is C1-C8 straight or branched chain alkyl, then Y is CHOR5 where R5 is C1-C3 alkyl; for substituting sodium chloride in food products.

  本发明涉及根据式 B3 所述化合物的用途： 其中 R1 和 R2 各自独立地为 OH 或 C1-C3 烷氧基，以及 R3 选自以下组别 (i) 具有一个或多个双键的 C10-C20 未取代直链或支链烯基；和 (ii) 其中 X、Y 和 Z 独立地为 CH、CH2、CO 或 CHOR5，其中 R5 为 H 或 C1-C3 烷基，但如果 X 或 Y 之一为 CH，则 Z 也为 CH，且其中 R4 为 C1-C8 未取代的直链或支链烷基，或 其中 n 为 1-5，但如果 R4 为 C1-C8 直链或支链烷基，则 Y 为 CHOR5，其中 R5 为 C1-C3 烷基； 用于替代食品中的氯化钠。
• Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
  作者：Aldwin Anterola、Cornelia Göbel、Ellen Hornung、George Sellhorn、Ivo Feussner、Howard Grimes

  DOI：10.1016/j.phytochem.2008.11.012

  日期：2009.1

  Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 alpha-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering plants. To identify the fatty acid substrates used by moss lipoxygenases, eight lipoxygenase genes from Physcomitrella patens were heterologously expressed in Escherichia coli, and then analyzed for lipoxygenase activity using linoleic, alpha-linolenic and arachidonic acids as substrates. Among the eight moss lipoxygenases, only seven were found to be enzymatically active in vitro, two of which selectively used arachidonic acid as the substrate, while the other five preferred alpha-linolenic acid. Based on enzyme assays using a Clark-type oxygen electrode, all of the active lipoxygenases had an optimum pH at 7.0, except for one with highest activity at pH 5.0. HPLC analyses indicated that the two arachidonic acid lipoxygenases form (12S)-hydroperoxy eicosatetraenoic acid as the main product, while the other five lipoxygenases produce mainly (13S)-hydroperoxy octadecatrienoic acid from alpha-linolenic acid. These results suggest that mosses may have both C20 and C18 based oxylipin pathways. Published by Elsevier Ltd.
• REDUCED SODIUM FOOD PRODUCTS
  申请人：GENERAL MILLS, INC.

  公开号：EP2954037B1

  公开（公告）日：2018-04-11
• [EN] REDUCED SODIUM FOOD PRODUCTS<br/>[FR] PRODUITS ALIMENTAIRES PAUVRES EN SODIUM
  申请人：GEN MILLS INC

  公开号：WO2014124193A1

  公开（公告）日：2014-08-14

  Naturally-derived compounds having various structures elicit the perception of salty taste, enhance the perception of salty taste of a salt, or act at one or more sodium channels. Food products may include such naturally-derived compounds, which may be used to reduce the sodium content, while imparting a similar level of saltiness.