(6Z,9Z,11E,13S)-13-氢过氧基-6,9,11-十八碳三烯酸 | 121107-97-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (6Z,9Z,11E,13S)-13-氢过氧基-6,9,11-十八碳三烯酸
• 英文名称: 13S-hydroperoxy-6Z,9Z,11E-octadecatrienoic acid
• 英文别名: 13(S)-HpOTrE(gamma)；(6Z,9Z,11E,13S)-13-hydroperoxyoctadeca-6,9,11-trienoic acid
• CAS: 121107-97-9
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: LYFGXCQTRBQQMX-KYLWABQHSA-N

物化性质

• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50 mg/ml； DMSO：50 mg/ml；乙醇：50 mg/ml； PBS pH 7.2：1 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6Z,9Z,11E,13S)-13-氢过氧基-6,9,11-十八碳三烯酸 在 sodium tetrahydroborate 作用下， 生成 (6Z,9Z,11E,13S)-13-羟基十八碳-6,9,11-三烯酸
  参考文献：
  名称：

  Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogs

  摘要：

  The structural requirements for inhibition of RBL-1 (rat basophilic leukemia) 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15-HETE, 1) were studied by systematic chemical modifications of the molecule at the hydroxyl and carboxyl groups, the double bonds, and the carboxylate and omega side chains. The most potent inhibitors were analogues that contained a 5,8-cis,cis-diene system and acted as alternate substrates for the enzyme. However, several analogues in which the 5,8-diene had been reduced were also found to inhibit the enzyme. Inhibition of 5-lipoxygenase by 15-hydroxyeicosa-11,13-dienoic acid (15-HEDE) analogues was optimal in compounds that generally contained a free carboxyl group, a carboxylate side chain of nine carbons, an omega side chain of five or six carbons, a cis,trans- or trans,cis-11,13-diene or 11,13-diyne system, and a 15-hydroxyl group. Conversion of 15-HEDE to its 16-membered lactone reduced but did not eliminate 5-lipoxygenase inhibitory activity. In contrast, a 3- to 10-fold enhancement of activity occurred when 5,15-diHETE (58) or 5-HETE (56) were cyclized to their respective delta-lactones. Molecular modeling of 15-HEDE analogues, modified in the C11-C15 region, showed that inactive analogues protrude into regions in space not occupied by active analogues. These structural studies indicate that multiple regions are important for 5-lipoxygenase inhibition by both 15-HETE and 15-HEDE analogues and that no single region plays a predominant role in inhibition.

  DOI：

  10.1021/jm00385a005
• 作为产物：
  描述：

  γ-亚麻酸 在 4-羟乙基哌嗪丙磺酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (6Z,9Z,11E,13S)-13-氢过氧基-6,9,11-十八碳三烯酸
  参考文献：
  名称：

  大肠杆菌共表达脂氧合酶和环氧化物水解酶将植物油高效氧化为C18三羟基脂肪酸

  摘要：

  C18 三羟基脂肪酸 (THFA)、植物氧脂素被用作抗真菌剂和疫苗佐剂。THFAs的化学合成有几个缺点，包括产量低和环境污染。微生物和植物也在体内产生四氢呋喃；但是，生产率很低。在这里，我们报道了一种重组大肠杆菌共表达具有高异构化活性的细菌亚油酸 (LA) 13-脂氧合酶和可转化 200 mM 多不饱和脂肪酸，包括 LA、α-亚麻酸和 γ-亚麻酸 (GLA) 的环氧化物水解酶。 )，在烧瓶中通过环氧羟基脂肪酸以高转化率 (>60%) 转化为 THFA。其中GLA衍生的12 S ,13 S -epoxy-11R-羟基十八碳二烯酸和 11 R ,12 R ,13 S-三羟基十八碳二烯酸是新化合物。为了将红花油有效地生物转化为 THFA，通过在红花油中添加含有脂肪酶的吸附树脂来增加红花油水解物中的 LA 含量。树脂结合不饱和脂肪酸，从而去除未结合的杂质，例如棕榈酸和甘油。在一个 3 L 的生物反

  DOI：

  10.1039/d1gc04113d

文献信息

• Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogs
  作者：Fortuna Haviv、James D. Ratajczyk、Robert W. DeNet、Yvonne C. Martin、Richard D. Dyer、George W. Carter

  DOI：10.1021/jm00385a005

  日期：1987.2

  The structural requirements for inhibition of RBL-1 (rat basophilic leukemia) 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15-HETE, 1) were studied by systematic chemical modifications of the molecule at the hydroxyl and carboxyl groups, the double bonds, and the carboxylate and omega side chains. The most potent inhibitors were analogues that contained a 5,8-cis,cis-diene system and acted as alternate substrates for the enzyme. However, several analogues in which the 5,8-diene had been reduced were also found to inhibit the enzyme. Inhibition of 5-lipoxygenase by 15-hydroxyeicosa-11,13-dienoic acid (15-HEDE) analogues was optimal in compounds that generally contained a free carboxyl group, a carboxylate side chain of nine carbons, an omega side chain of five or six carbons, a cis,trans- or trans,cis-11,13-diene or 11,13-diyne system, and a 15-hydroxyl group. Conversion of 15-HEDE to its 16-membered lactone reduced but did not eliminate 5-lipoxygenase inhibitory activity. In contrast, a 3- to 10-fold enhancement of activity occurred when 5,15-diHETE (58) or 5-HETE (56) were cyclized to their respective delta-lactones. Molecular modeling of 15-HEDE analogues, modified in the C11-C15 region, showed that inactive analogues protrude into regions in space not occupied by active analogues. These structural studies indicate that multiple regions are important for 5-lipoxygenase inhibition by both 15-HETE and 15-HEDE analogues and that no single region plays a predominant role in inhibition.
• Highly efficient oxidation of plant oils to C18 trihydroxy fatty acids by <i>Escherichia coli</i> co-expressing lipoxygenase and epoxide hydrolase
  作者：Jin Lee、Tae-Hun Kim、Yoon-Joo Ko、Jin-Byung Park、Deok-Kun Oh

  DOI：10.1039/d1gc04113d

  日期：——

  polyunsaturated fatty acids, including LA, α-linolenic acid, and γ-linolenic acid (GLA), into THFAs via epoxy hydroxy fatty acids with high conversion yields (>60%) in a flask. Among the products, GLA-derived 12S,13S-epoxy-11R-hydroxyoctadecadienoic acid and 11R,12R,13S-trihydroxyoctadecadienoic acid were new compounds. For the efficient biotransformation of safflower oil into THFA, the LA content in the

  C18 三羟基脂肪酸 (THFA)、植物氧脂素被用作抗真菌剂和疫苗佐剂。THFAs的化学合成有几个缺点，包括产量低和环境污染。微生物和植物也在体内产生四氢呋喃；但是，生产率很低。在这里，我们报道了一种重组大肠杆菌共表达具有高异构化活性的细菌亚油酸 (LA) 13-脂氧合酶和可转化 200 mM 多不饱和脂肪酸，包括 LA、α-亚麻酸和 γ-亚麻酸 (GLA) 的环氧化物水解酶。 )，在烧瓶中通过环氧羟基脂肪酸以高转化率 (>60%) 转化为 THFA。其中GLA衍生的12 S ,13 S -epoxy-11R-羟基十八碳二烯酸和 11 R ,12 R ,13 S-三羟基十八碳二烯酸是新化合物。为了将红花油有效地生物转化为 THFA，通过在红花油中添加含有脂肪酶的吸附树脂来增加红花油水解物中的 LA 含量。树脂结合不饱和脂肪酸，从而去除未结合的杂质，例如棕榈酸和甘油。在一个 3 L 的生物反