14,15-(trans)-arachidonic acid | 171235-57-7

• 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: 14,15-(trans)-arachidonic acid
• 英文别名: eicosa-cis-5,8,11-trans-14-tetraenoic acid；arachidonic acid；(5Z,8Z,11Z,14E)-Icosa-5,8,11,14-tetraenoic acid
• CAS: 171235-57-7
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: YZXBAPSDXZZRGB-QGDKPUJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  14,15-(trans)-arachidonic acid 在 Bacillus megaterium cytochrome P₄₅₀BM₃ 、 sodium potassium phosphate buffer 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 二甲基亚砜 为溶剂， 生成 18-hydroxyarachidonic acid 、 cis-14,15-epoxyeicosatrienoic acid
  参考文献：
  名称：

  Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450BM3 from Bacillus megaterium

  摘要：

  来自大肠杆菌的细胞色素P450BM3催化亚油酸1的环氧化反应，生成15,16-环氧油酸2，具有完全的区域选择性和适度的对映选择性（60% ee）。产品的绝对构型暂时被指认为15(R),16(S)-。该反应的米哈利斯-门腾参数kcat和Km分别为3126 ± 226 min−1和24 ± 6 μM。

  DOI：

  10.1039/b506155e
• 作为产物：
  描述：

  Methyl 14,15-epoxyeicosa-cis-5,8,11-trienoate 在 溶剂黄146 、 锌 作用下， 生成 14,15-(trans)-arachidonic acid
  参考文献：
  名称：

  Synthesis of arachidonic acid metabolites produced by purified kidney cortex microsomal cytochrome P-450

  摘要：

  DOI：

  10.1016/s0040-4039(00)81319-2

文献信息

• Stereospecific synthesis of trans-arachidonic acids
  作者：U.Murali Krishna、M.Muralidhar Reddy、Jianing Xia、J.R. Falck、Michael Balazy

  DOI：10.1016/s0960-894x(01)00442-5

  日期：2001.9

  An effective synthesis is described for the preparation of all four mono trans isomers of arachidonic acid via deoxidation of epoxide precursors with lithium diphenylphosphide and quaternization with methyl iodide.

  描述了一种有效的合成方法，该方法用于通过用二苯基磷化锂使环氧化物前体脱氧并用甲基碘进行季铵化来制备花生四烯酸的所有四个单反式异构体。
• MICROBIAL OIL, METHOD FOR MANUFACTURING MICROBIAL OIL, CONCENTRATED MICROBIAL OIL, AND METHOD FOR MANUFACTURING CONCENTRATED MICROBIAL OIL
  申请人：Nippon Suisan Kaisha, Ltd.

  公开号：EP3101138A1

  公开（公告）日：2016-12-07

  A microbial oil comprising: a specific amount of at least one polyunsaturated fatty acid having at least 20 carbon atoms in fatty acid alkyl ester form and/or in free fatty acid form; and specific amount of thermally-produced fatty acid having from 16 to 22 carbon atoms in a fatty acid alkyl ester form and/or a free fatty acid form. A production method thereof comprising: providing a starting oil containing at least one polyunsaturated fatty acid having at least 20 carbon atoms in an alkyl ester form and/or a free fatty acid form obtained from microbial biomass; performing a rectification of the starting oil under specific conditions; and obtaining the aforementioned microbial oil. A concentrated microbial oil obtained using the production method described above, and a production method thereof. An agent for treating or preventing an inflammatory disease comprising the microbial oil or the concentrated microbial oil.

  一种微生物油，包含：一定量的以脂肪酸烷基酯形式和/或以游离脂肪酸形式存在的至少一种多不饱和脂肪酸，其碳原子数至少为 20；以及一定量的以脂肪酸烷基酯形式和/或以游离脂肪酸形式存在的热产脂肪酸，其碳原子数为 16 至 22。一种生产方法，包括：提供含有至少一种多不饱和脂肪酸的起始油，该脂肪酸以烷基酯和/或游离脂肪酸的形式至少具有 20 个碳原子，该脂肪酸从微生物生物质中获得；在特定条件下对起始油进行精馏；获得上述微生物油。利用上述生产方法获得的浓缩微生物油及其生产方法。一种用于治疗或预防炎症性疾病的制剂，包含上述微生物油或浓缩微生物油。
• MICROBIAL OIL, PRODUCTION METHOD FOR MICROBIAL OIL, CONCENTRATED MICROBIAL OIL, AND PRODUCTION METHOD FOR CONCENTRATED MICROBIAL OIL
  申请人：NIPPON SUISAN KAISHA, LTD.

  公开号：EP3900543A1

  公开（公告）日：2021-10-27

  A microbial oil comprises dihomo-γ-linolenic acid in fatty acid alkyl ester form and/or in free fatty acid form at a content of at least 50% by weight of the total weight of fatty acids in the oil. The content of thermally-produced fatty acid having from 16 to 22 carbon atoms, generated by heat associated with distillation in the production method, is from 0.0001% by weight to 3.0% by weight of the total weight of fatty acids in the microbial oil. A production method thereof comprises providing a starting oil containing dihomo-γ-linolenic acid in alkyl ester form and/or a free fatty acid form, obtained from microbial biomass; performing rectification of the starting oil under specific conditions; and obtaining the aforementioned microbial oil. Other aspects are a concentrated microbial oil, and use of the described oils as an agent for treating or preventing inflammatory disease.

  一种微生物油包含脂肪酸烷基酯形式和/或游离脂肪酸形式的二氢-γ-亚麻酸，其含量至少占油中脂肪酸总重量的 50%（按重量计）。在生产方法中，通过蒸馏产生的热量产生的具有 16 至 22 个碳原子的脂肪酸的含量占微生物油中脂肪酸总重量的 0.0001%（按重量计）至 3.0%（按重量计）。其生产方法包括提供从微生物生物质中获得的含有烷基酯形式和/或游离脂肪酸形式的二氢-γ-亚麻酸的起始油；在特定条件下对起始油进行精馏；获得上述微生物油。其他方面是浓缩微生物油，以及将所述油用作治疗或预防炎症疾病的制剂。
• Microbial oil, production method for microbial oil, concentrated microbial oil, and production method for concentrated microbial oil
  申请人：NIPPON SUISAN KAISHA, LTD.

  公开号：US11330817B2

  公开（公告）日：2022-05-17

  A microbial oil comprising: a specific amount of at least one polyunsaturated fatty acid having at least 20 carbon atoms in fatty acid alkyl ester form and/or in free fatty acid form; and specific amount of thermally-produced fatty acid having from 16 to 22 carbon atoms in a fatty acid alkyl ester form and/or a free fatty acid form. A production method thereof comprising: providing a starting oil containing at least one polyunsaturated fatty acid having at least 20 carbon atoms in an alkyl ester form and/or a free fatty acid form obtained from microbial biomass; performing a rectification of the starting oil under specific conditions; and obtaining the aforementioned microbial oil. A concentrated microbial oil obtained using the production method described above, and a production method thereof. An agent for treating or preventing an inflammatory disease comprising the microbial oil or the concentrated microbial oil.

  一种微生物油，包含：一定量的以脂肪酸烷基酯形式和/或以游离脂肪酸形式存在的至少一种多不饱和脂肪酸，其碳原子数至少为 20；以及一定量的以脂肪酸烷基酯形式和/或以游离脂肪酸形式存在的热产脂肪酸，其碳原子数为 16 至 22。一种生产方法，包括：提供含有至少一种多不饱和脂肪酸的起始油，该脂肪酸以烷基酯和/或游离脂肪酸的形式至少具有 20 个碳原子，该脂肪酸从微生物生物质中获得；在特定条件下对起始油进行精馏；获得上述微生物油。利用上述生产方法获得的浓缩微生物油及其生产方法。一种用于治疗或预防炎症性疾病的制剂，包含上述微生物油或浓缩微生物油。
• PRODUCTS FOR OXIDATIVELY CHANGING THE COLOR OF KERATIN FIBERS, IN A DISPENSER
  申请人：Henkel AG & Co. KGaA

  公开号：US20160158125A1

  公开（公告）日：2016-06-09

  A product for oxidatively coloring and/or lightening keratinic fibers includes (1) a dispenser, which has two chambers (A) and (B) separate from one another; an outlet opening (C) communicating with chamber (A) and with chamber (B); (2) a preparation (a) in chamber (A), which preparation includes one or more thickening polymers in a total amount by weight (G1) of 0.1 to 20%, based on preparation (a); one or more fatty components in a total amount by weight (G2) of 0.1 to 20%, based on preparation (a); and (3) a preparation (b) in chamber (B), which preparation includes one or more thickening polymers in a total amount by weight (G3) of 0.1 to 20%, based on preparation (b), and one or more fatty components in a total amount by weight (G4) of 0.1 to 20%, based on the total weight of the preparation (b). The weight ratio of G1/G3 has a value of 0.5 to 2.0 and the weight ratio of G2/G4 has a value of 0.5 to 2.0.