(9Z,11E,13S)-13-(acetoxy)-9,11-octadecadienoic acid | 252910-06-8

• 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,11E,13S)-13-(acetoxy)-9,11-octadecadienoic acid
• 英文别名: (9Z,11E,13S)-13-acetyloxyoctadeca-9,11-dienoic acid
• CAS: 252910-06-8
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: IZWDXHOINXOUIB-GXLICYTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9Z,11E,13S)-13-(acetoxy)-9,11-octadecadienoic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 tert-butyl (9Z,11E,13S)-13-(acetoxy)-9,11-octadecadienoate
  参考文献：
  名称：

  Reactivity of Lysine Moieties toward an Epoxyhydroxylinoleic Acid Derivative:  Aminolysis versus Hydrolysis

  摘要：

  Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of tert-butyl (9R*,10S*,11E,13S)-9,10-epoxy-13-hydroxy-11-octadecenoate (11a,b) toward lysine moieties is investigated, employing N-2-acetyllysine 4-methylcoumar-7-ylamide (12) as a model for protein-bound lysine. The prefixes R* and S* denote the relative configuration at the respective stereogenic centers. Independent synthesis and unequivocal structural characterization are reported for 11a,b, its precursors, and tert-butyl (9R*,10R*,11E,13S)-10-({5-(acetylamino)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)amino]-6-oxohexyl}amino)-9,13-dihydroxy-11-octadecenoate (13a-d). Reactions of 11a,b and 12 in 1-methyl-2-pyrrolidone (MP) and MP/water mixtures at pH 7.4 and 37 degrees C for 56 days show formation of the aminols 13a-d to be favored by an increased water content. The same trend is observed for hydrolytic cleavage of 11a,b to tert-butyl (E)-9,10,13-trihydroxy-11-octadecenoate (14) and tert-butyl (E)-9,12,13-trihydroxy-10-octadecenoate (15). Under the given conditions, aminolysis proceeds via an S(N)2 substitution, in contrast with the S(N)1 process for hydrolysis. In the MP/water (8:2) incubation, 15.8% of 12 has been transformed to 13a-d and 10.5% of 11a,b hydrolyzed to the regioisomers 14 and 15 after 8 weeks, respectively. Aminolysis of alpha,beta-unsaturated epoxides by lysine moieties therefore is expected to be an important mode of interaction between proteins and lipid oxidation products.

  DOI：

  10.1021/jf990383o
• 作为产物：
  描述：

  13(S)--过氧羟基-9,11-十八碳二烯酸 在 吡啶 、 sodium tetrahydroborate 作用下， 反应 18.0h， 生成 (9Z,11E,13S)-13-(acetoxy)-9,11-octadecadienoic acid
  参考文献：
  名称：

  Reactivity of Lysine Moieties toward an Epoxyhydroxylinoleic Acid Derivative:  Aminolysis versus Hydrolysis

  摘要：

  Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of tert-butyl (9R*,10S*,11E,13S)-9,10-epoxy-13-hydroxy-11-octadecenoate (11a,b) toward lysine moieties is investigated, employing N-2-acetyllysine 4-methylcoumar-7-ylamide (12) as a model for protein-bound lysine. The prefixes R* and S* denote the relative configuration at the respective stereogenic centers. Independent synthesis and unequivocal structural characterization are reported for 11a,b, its precursors, and tert-butyl (9R*,10R*,11E,13S)-10-({5-(acetylamino)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)amino]-6-oxohexyl}amino)-9,13-dihydroxy-11-octadecenoate (13a-d). Reactions of 11a,b and 12 in 1-methyl-2-pyrrolidone (MP) and MP/water mixtures at pH 7.4 and 37 degrees C for 56 days show formation of the aminols 13a-d to be favored by an increased water content. The same trend is observed for hydrolytic cleavage of 11a,b to tert-butyl (E)-9,10,13-trihydroxy-11-octadecenoate (14) and tert-butyl (E)-9,12,13-trihydroxy-10-octadecenoate (15). Under the given conditions, aminolysis proceeds via an S(N)2 substitution, in contrast with the S(N)1 process for hydrolysis. In the MP/water (8:2) incubation, 15.8% of 12 has been transformed to 13a-d and 10.5% of 11a,b hydrolyzed to the regioisomers 14 and 15 after 8 weeks, respectively. Aminolysis of alpha,beta-unsaturated epoxides by lysine moieties therefore is expected to be an important mode of interaction between proteins and lipid oxidation products.

  DOI：

  10.1021/jf990383o