9,11-Octadecadienoic acid, 13-hydroxy-, (E,Z)-(R)-

• 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: 9,11-Octadecadienoic acid, 13-hydroxy-, (E,Z)-(R)-
• 英文别名: (9E,11Z,13R)-13-hydroxyoctadeca-9,11-dienoic acid
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.4
• InChiKey: HNICUWMFWZBIFP-PXBBSODISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

文献信息

• Process for the synthesis of unsaturated alcohols
  申请人：Maughon R. Bob

  公开号：US20050080301A1

  公开（公告）日：2005-04-14

  A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

  一种制备不饱和醇（烯醇）的过程，例如，保护羟基取代的不饱和脂肪酸或脂肪酸酯，例如来自种子油的甲基蓖麻油酸甲酯，形成羟基保护的不饱和脂肪酸或脂肪酸酯; 同型交换或交叉交换羟基保护的不饱和脂肪酸或脂肪酸酯，以产生含有羟基保护的不饱和交换产物的产物混合物; 并在足以制备不饱和醇的条件下去除羟基保护的不饱和交换产物。优选地，通过交叉或同型交换将甲基蓖麻油酸甲酯转化为同型烯丙基单醇1-癸烯-4-醇或同型烯丙基多醇9-十八烯-7,12-二醇。
• Process for producing hydroxylated fatty acids and delta-lactones
  申请人：——

  公开号：US20040197882A1

  公开（公告）日：2004-10-07

  The process which comprises causing cells or a culture of a microorganism having the activity to introduce hydroxy into the [n-5]-position (n is an even number of 10 or more) and hydrogen into the [n-6]-position of a straight-chain fatty acid having n carbon atoms wherein at least the [n-6]-position is a double bond to make the [n-6]-position a single bond or a treated matter thereof to act on a straight-chain fatty acid having n carbon atoms wherein at least the [n-6]-position is a double bond or a composition containing the fatty acid to form an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond, causing cells or a culture of a microorganism having the activity to &bgr;-oxidize an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond or a treated matter thereof to act on the formed [n-5]-hydroxy fatty acid, and recovering the formed &dgr;-lactones.

  该过程包括使用具有将羟基引入n-5位置（n为10或更多的偶数）和氢引入n-6位置的微生物细胞或培养基的活性，作用于直链脂肪酸（其中至少n-6位置为双键），使n-6位置成为单键或处理后的物质，作用于直链脂肪酸（其中至少n-6位置为双键）或含有脂肪酸的组合物，以形成n-5羟基脂肪酸，其中n-6位置为单键，使用具有β-氧化活性的微生物细胞或培养基作用于n-5羟基脂肪酸（其中n-6位置为单键）或处理后的物质，以回收形成的δ-内酯。
• PROCESS FOR PRODUCING HYDROXYLATED FATTY ACID AND DELTA-LACTONE
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1197560A1

  公开（公告）日：2002-04-17

  The process which comprises causing cells or a culture of a microorganism having the activity to introduce hydroxy into the [n-5]-position (n is an even number of 10 or more) and hydrogen into the [n-6)-position of a straight-chain fatty acid having n carbon atoms wherein at least the [n-6]-position is a double bond to make the [n-6]-position a single bond or a treated matter thereof to act on a straight-chain fatty acid having n carbon atoms wherein at least the [n-6]-position is a double bond or a composition containing the fatty acid to form an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond, causing cells or a culture of a microorganism having the activity to β-oxidize an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond or a treated matter thereof to act on the formed [n-5]-hydroxy fatty acid, and recovering the formed δ-lactones.

  本发明的工艺包括使具有活性的细胞或微生物培养物将羟基引入具有 n 个碳原子的直链脂肪酸的[n-5]位(n 为 10 个或更多的偶数)，并将氢引入具有 n 个碳原子的直链脂肪酸的[n-6]位，其中至少[n-6]位是双键，以使[n-6]位成为单键或其处理物作用于具有 n 个碳原子的直链脂肪酸，其中至少[n-6]位是双键。位为双键，使[n-6]-位成为单键或其处理物作用于具有 n 个碳原子的直链脂肪酸（其中至少[n-6]-位为双键）或含有该脂肪酸的组合物，以形成[n-5]-羟基脂肪酸（其中[n-6]-位为单键）、使具有β-氧化[n-5]-羟基脂肪酸（其中[n-6]-位为单键）活性的细胞或微生物培养物或其处理物作用于形成的[n-5]-羟基脂肪酸，并回收形成的δ-内酯。
• Process for the production of delta 5-unsaturated fatty acids in transgenic organisms
  申请人：BASF Plant Science GmbH

  公开号：EP1790731A2

  公开（公告）日：2007-05-30

  A process for the production of Δ5-unsaturated fatty acids in transgenic organisms comprises transforming an organism with nucleic acid encoding a Δ5-desaturase.

  一种在转基因生物体中生产Δ5-不饱和脂肪酸的工艺，包括用编码Δ5-去饱和酶的核酸转化生物体。
• Process for the production of arachidonic acid and/or eicosapentaenoic acid
  申请人：BASF Plant Science GmbH

  公开号：EP2450434A2

  公开（公告）日：2012-05-09

  The present invention relates to a new process for the production of arachidonic acid and/or eicosapentaenoic acid in plants through the co-expression of a Δ-12-/Δ-15-desaturase, Δ-9-elongase, Δ-8-desaturase and a Δ-5-desaturase and a process for the production of lipids or oils having an increased content of unsaturated fatty acids, in particular ω-3 and w-6 fatty acids having at least two double bonds and a 18 or 20 carbon atom chain length. Preferably the arachidonic acid and eicosapentaenoic acid are produced in at least a 1:2 ratio. The invention furthermore relates to the production of a transgenic plants, preferably a transgenic crop plant, having an increased content of arachidonic acid and/or eicosapentaenoic acid, oils or lipids containing C18- or C20- fatty acids with a double bond in position Δ□□5. 8, 9, 11, 12, 14, 15 or 17 of the fatty acid produced, respectively due to the expression of the Δ-12-/Δ-15-desaturase, of the Δ-9-elongase, of the Δ-8-desaturase and of the Δ-5-desaturase in the plant. The expression of the inventive Δ-12-/Δ-15-desaturase leads preferably to linoleic acid and linolenic acid as products having a double bond in the position Δ□□ 9, 12 and 15 of the fatty acid. The invention additionally relates to specific nucleic acid sequences encoding for proteins with Δ-12-/Δ-15-desaturase-, Δ-9-elongase-, A-8-desaturase- or Δ-5-desaturase-activity, nucleic acid constructs, vectors and transgenic plants containing said nucleic acid sequences.

  本发明涉及一种通过共同表达Δ-12-/Δ-15-去饱和酶、Δ-9-elongase、Δ-8-去饱和酶和Δ-5-去饱和酶，以及生产不饱和脂肪酸含量增加的脂类或油类的工艺，特别是具有至少两个双键和18或20个碳原子链长的ω-3和w-6脂肪酸。花生四烯酸和二十碳五烯酸的生产比例最好至少为 1:2。 本发明还涉及转基因植物，最好是转基因作物植物的生产，其花生四烯酸和/或二十碳五烯酸、油或脂类的含量增加，这些油或脂类含有在 Δ□□5 位有双键的 C18- 或 C20- 脂肪酸。由于植物中表达了Δ-12-/Δ-15-去饱和酶、Δ-9-延长酶、Δ-8-去饱和酶和Δ-5-去饱和酶，产生的脂肪酸分别为Δ-12-/Δ-15-去饱和脂肪酸的8、9、11、12、14、15或17。本发明的Δ-12-/Δ-15-去饱和酶的表达优选导致亚油酸和亚麻酸作为在脂肪酸的Δ□□9、12 和 15 位上具有双键的产物。 本发明还涉及编码具有Δ-12-/Δ-15-去饱和酶、Δ-9-长效酶、A-8-去饱和酶或Δ-5-去饱和酶活性的蛋白质的特异性核酸序列、核酸构建体、载体和含有所述核酸序列的转基因植物。