12-hexadecenol, E | 72698-35-2

• 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: 12-hexadecenol, E
• 英文别名: (E)-hexadec-12-en-1-ol
• CAS: 72698-35-2
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: QTZQYQLPKOVNSX-SNAWJCMRSA-N

物化性质

• 沸点：
  309.0±10.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)
• 保留指数：
  1877

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  12-hexadecenol, E 在 jones reagent 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以243 mg的产率得到(E)-12-hexadecenoic acid
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100
• 作为产物：
  描述：

  11-溴-1-十一醇 在 盐酸 、 正丁基锂 、 氨 、 sodium 、 lithium 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 33.08h， 生成 12-hexadecenol, E
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100

文献信息

• [EN] ISOLATION AND STRUCTURE OF TURBOSTATINS 1-4<br/>[FR] ISOLEMENT ET STRUCTURE DES TURBOSTATINES 1 A 4
  申请人：UNIV ARIZONA STATE

  公开号：WO2006122296A1

  公开（公告）日：2006-11-16

  [EN] Described herein are novel cerebroside compounds, designated as Turbostatin 1, Turbostatin 2, Turbostatin 3, and Turbostatin 4. These compounds were extracted and isolated from the marine mollusk Turbo stenogyrus, and their structures elucidated. The new compounds exhibit significant cancer cell growth inhibition activity against a variety of murine and human cancer cell lines, and as such appear will be useful in the treatment of various forms of neoplastic disease.
  [FR] L'invention concerne de nouveaux composes cérébrosides, appelés Turbostatine 1, Turbostatine 2, Turbostatine 3, et Turbostatine 4. Ces composés sont extraits et isolés à partir du mollusque marin Turbo stenogyrus, et leur structure a été élucidée. Les nouveaux composés montrent une activité d'inhibition significative de la croissance des cellules cancéreuses contre diverses lignées cellulaires cancéreuses chez la souris et l'humain, et en tant que tels apparaissent comme étant utiles dans le traitement de diverses formes de maladies néoplasiques.
• Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes
  作者：Gemma Villorbina、Lidia Roura、Francisco Camps、Jesús Joglar、Gemma Fabriàs

  DOI：10.1021/jo0267100

  日期：2003.4.1

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.