(E,E,E)-2,4,7-undecatrienoate | 76896-86-1

• 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: (E,E,E)-2,4,7-undecatrienoate
• 英文别名: ethyl (E,E,E)-2,4,7-undecatrienoate；ethyl (2E,4E,7E)-undeca-2,4,7-trienoate
• CAS: 76896-86-1
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: OBTDXZCTHSIWPN-NRSJTBBXSA-N

物化性质

• 沸点：
  298.8±19.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,E,E)-2,4,7-undecatrienoate 在 lithium aluminium tetrahydride 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 4-((2E,4E,7E)-undeca-2,4,7-trienylamino)benzoic acid
  参考文献：
  名称：

  Novel triacsin C analogs as potential antivirals against rotavirus infections

  摘要：

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.010
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 lithium aluminium tetrahydride 、 乙基溴化镁 、 copper(l) cyanide 、 草酸 、 三溴化磷 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 36.5h， 生成 (E,E,E)-2,4,7-undecatrienoate
  参考文献：
  名称：

  Novel triacsin C analogs as potential antivirals against rotavirus infections

  摘要：

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.010

文献信息

• E2, E4,Z8-undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP2112135A2

  公开（公告）日：2009-10-28

  Described is a genus of undecatrienoic acid derivatives useful in imparting, augmenting and/or enhancing flavors, aromas and somatosensory effects in or to consumable materials such as foods, beverages, skin care products, oral care products, medicinal products and the like. Also described is a synthesis process for producing such derivatives.

  描述的是一种十一碳三烯酸衍生物，可用于赋予、增强和/或提高食品、饮料、护肤品、口腔护理产品、医药产品等消费品的风味、香气和体感效果。此外，还描述了生产此类衍生物的合成工艺。
• Structure and synthesis of a new hypotensive vasodilator isolated from
  作者：Hirokazu Tanaka、Keizo Yoshida、Yoshikuni Itoh、Hiroshi Imanaka

  DOI：10.1016/s0040-4039(01)81921-3

  日期：1981.1
• E2, E4,Z8-Undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP1496042B1

  公开（公告）日：2009-11-11
• YOSHIDA, KEIZO;TANAKA, HIROKAZU;OKAMOTO, MASANORI;IGUCHI, EIKO;KOHSAKA, M+
  作者：YOSHIDA, KEIZO、TANAKA, HIROKAZU、OKAMOTO, MASANORI、IGUCHI, EIKO、KOHSAKA, M+

  DOI：——

  日期：——
• Novel triacsin C analogs as potential antivirals against rotavirus infections
  作者：Yunjeong Kim、David George、Allan M. Prior、Keshar Prasain、Shuanghong Hao、Duy D. Le、Duy H. Hua、Kyeong-Ok Chang

  DOI：10.1016/j.ejmech.2012.02.010

  日期：2012.4

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.