(8Z,12E,14Z)-eicosa-8,12,14-trienoic acid | 26322-26-9

• 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: (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid
• 英文别名: 8-cis,12-trans,14-cis-eicosantriensaeure；8Z,12E,14Z-eicosatrienoic acid；(8Z,12E,14Z)-icosa-8,12,14-trienoic acid
• CAS: 26322-26-9
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: ZSWYXLJIFJJAFJ-FQMWOSCKSA-N

物化性质

• 沸点：
  441.8±24.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  甲醇 、 (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid 在 三氟化硼 作用下， 反应 0.17h， 生成 methyl (8Z,12E,14Z)-eicosa-8,12,14-trienoate
  参考文献：
  名称：

  Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs

  摘要：

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00049-5
• 作为产物：
  描述：

  (E)-dodec-4-en-6-ynal 在 正丁基锂 、 二(3-甲基丁烷-2-基)硼烷 、 lithium 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.25h， 生成 (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid
  参考文献：
  名称：

  Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs

  摘要：

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00049-5

文献信息

• Beerthuis,R.K. et al., Recueil des Travaux Chimiques des Pays-Bas, 1971, vol. 90, p. 943 - 960
  作者：Beerthuis,R.K. et al.

  DOI：——

  日期：——
• Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs
  作者：O Loreau、J.M Chardigny、J.L Sébédio、J.P Noël

  DOI：10.1016/s0009-3084(03)00049-5

  日期：2003.7

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.