(6Z,10E,12Z)-octadeca-6,10,12-trienoic acid | 109241-60-3

• 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: (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid
• 英文别名: 6Z,10E,12Z-C18:3
• CAS: 109241-60-3
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: JVXOCQRVBGITPW-FQMWOSCKSA-N

物化性质

• 沸点：
  379.3±11.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 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 、 (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid 在 三氟化硼 作用下， 反应 0.17h， 生成 methyl (6Z,10E,12Z)-octadeca-6,10,12-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：

  1-庚炔 在 哌啶 、 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 iron(III)-acetylacetonate 、 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 、 N-甲基吡咯烷酮 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.75h， 生成 (6Z,10E,12Z)-octadeca-6,10,12-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

• [EN] NEW CONJUGATED LINOLENIC ACIDS AND METHODS FOR COMMERCIAL PREPARATION AND PURIFICATION<br/>[FR] NOUVEAUX ACIDES LINOLENIQUES CONJUGUES ET PROCEDES DE PREPARATION ET DE PURIFICATION A DES FINS COMMERCIALES
  申请人：UNIV LAVAL

  公开号：WO2004013078A1

  公开（公告）日：2004-02-12

  A method for the preparation and purification of conjugated linolenic acids is described. The method comprises blending a mixture of vegetable oils and or fats including various concentrations of alpha or gamma and or both linolenic acids with a base. The method transforms approximately over two thirds of α-linolenic acid (9Z,12Z,15Z-octadecatrienoic acid) into 9Z,11E,15Z-octadecatrienoic acid and 9Z,13E,15Z-octadecatrienoic acid. The method also transforms gamma-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid) into 6Z,8E,15Z-octadeccatrienoic acid and 6Z,10E,12Z-octadecatrienoic acid. In all cases, geometrical isomers and fully conjugated isomers are also produced.

  描述了一种制备和纯化共轭亚麻酸的方法。该方法包括混合一种包括各种浓度的α或γ或两者亚麻酸的植物油和/或脂肪的混合物与一种碱。该方法将大约三分之二的α-亚麻酸（9Z,12Z,15Z-八十八碳三烯酸）转化为9Z,11E,15Z-八十八碳三烯酸和9Z,13E,15Z-八十八碳三烯酸。该方法还将γ-亚麻酸（6Z,9Z,12Z-八十八碳三烯酸）转化为6Z,8E,15Z-八十八碳三烯酸和6Z,10E,12Z-八十八碳三烯酸。在所有情况下，还会产生几何异构体和完全共轭异构体。
• Conjugated fatty acids and related compounds
  申请人：Natural ASA

  公开号：US20010023259A1

  公开（公告）日：2001-09-20

  It has been demonstrated that conjugated linoleic acid isomers with the first double bond in position 9 (cis) or 10 (trans), added exogenously, can be desaturated in position 6 by the cyanobacterium Spirulina platensis . The metabolites, 6-cis, 9-cis, 11-trans-octadecatrienoic and 6-cis,10-trans,12-cis-octadecatrienoic acids, which have not previously been characterized, were isolated by a combination of chromatographic techniques and the structures were confirmed by gas chromatography-mass spectrometry in the form of picolinyl ester and dimethyloxazoline derivatives.

  研究表明，外源添加的共轭亚油酸异构体的第一个双键位于第 9 位（顺式）或第 10 位（反式），可以通过蓝藻的作用使第 6 位脱饱和 蓝藻 .这些代谢物，即 6-顺式、9-顺式、11-反式-十八碳三烯酸和 6-顺式、10-反式、12-顺式-十八碳三烯酸，以前从未被表征过，它们通过色谱技术的组合被分离出来，并以吡啶酯和二甲基噁唑啉衍生物的形式通过气相色谱-质谱法确认了其结构。
• NEW CONJUGATED LINOLENIC ACIDS AND METHODS FOR COMMERCIAL PREPARATION AND PURIFICATION
  申请人：Université Laval

  公开号：EP1546082A1

  公开（公告）日：2005-06-29
• Conjugated linolenic acids and methods for commerical preparation and purification
  申请人：Angers Paul

  公开号：US20060281814A1

  公开（公告）日：2006-12-14

  A method for the preparation and purification of conjugated linolenic acids is described. The method comprises blending a mixture of vegetable oils and or fats including various concentrations of alpha or gamma and or both linolenic acids with a base. The method transforms approximately over two thirds of α-linolenic acid (9Z,12Z,15Z-octadecatrienoic acid) into 9Z,11E,15Z-octadecatrienoic acid and 9Z,13E,15Z-octadecatrienoic acid. The method also transforms gamma-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid) into 6Z,8E,15Z-octadeccatrienoic acid and 6Z,10E,12Z-octadecatrienoic acid. In all cases, geometrical isomers and fully conjugated isomers are also produced.
• 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.