methyl vaccenate | 17257-41-9

• 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: methyl vaccenate
• 英文别名: methyl (Z)-octadec-8-enoate
• CAS: 17257-41-9
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: KXOOHHMDCDXCBV-QXMHVHEDSA-N

物化性质

• 沸点：
  370.9±21.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  methyl vaccenate 在 lithium hydroxide 作用下， 以67%的产率得到顺式8-十八碳烯酸
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345
• 作为产物：
  描述：

  十八碳-8-炔酸 在 硫酸 、 氢气 、 乙二胺 作用下， 以 乙醇 、 水 为溶剂， 生成 methyl vaccenate
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912

文献信息

• Selective catalytic hydrogenation of 1,4-dienes to cis-monoenes using (naphthalene)(tricarbonyl)chromium
  作者：James R. Tucker、Dennis P. Riley

  DOI：10.1016/0022-328x(85)87006-6

  日期：1985.1

  subsequent reduction of the conjugated dienes to the isomeric cis-monoene products. The active metal fragment appears to be selective in the isomerization of 1,4 to 1,3 dienes and inert toward cis to trans geometrical isomerization of the monoene products. The results of kinetic studies using methyl cis,cis-9,12-octadecadienoate (methyl linoleate) as a substrate for the hydrogenation reactions are discussed

  亚甲基间断的二烯在H 2下与（萘）（三羰基）铬反应，生成位置异构的顺-单烯产物的混合物。异构体分布，与拟议的有机中间体的反应以及动力学研究表明，该机理包括以下方面：（1）金属片段中的芳烃损失；（2）1,4二烯异构化为1,3共轭二烯；以及（ 3）随后将共轭二烯还原为异构体顺-单烯产物。活性金属片段在1,4至1,3二烯的异构化中似乎具有选择性，并且对顺式至单烯产物的反式几何异构化呈惰性。使用甲基的动力学研究结果讨论了顺式，顺式-9,12-十八碳二烯酸酯（亚油酸甲酯）作为氢化反应的底物。
• An active site mutant of Escherichia coli cyclopropane fatty acid synthase forms new non-natural fatty acids providing insights on the mechanism of the enzymatic reaction
  作者：Guangqi E、Thierry Drujon、Isabelle Correia、Olivier Ploux、Dominique Guianvarc'h

  DOI：10.1016/j.biochi.2013.08.007

  日期：2013.12

  After extraction of phospholipids and conversion into the corresponding fatty acid methyl esters (FAMEs), we observed the formation of cyclopropanated FAMEs suggesting that the mutant retained some of the normal activity in vivo. However, we also observed the formation of new C17 methyl-branched unsaturated FAMEs whose structures were determined using GC/MS and NMR analyses. The double bond was located

  我们已经通过用谷氨酸残基（对应于同源霉菌酸甲基转移酶Hma的E146）取代了谷氨酸残基来替代环丙烷合成酶中严格保守的G236，从而生产并纯化了大肠杆菌环丙烷脂肪酸合酶（CFAS）的活性位点突变体，从而产生了羟甲基霉菌酸。G236E CFAS突变体的野生型酶的体外活性不到1％。我们在大肠杆菌（DE3）菌株中表达了G236E CFAS突变体，其中的染色体cfa基因已被删除。提取磷脂并将其转化为相应的脂肪酸甲酯（FAME）后，我们观察到环丙烷化FAME的形成，表明该突变体在体内保留了一些正常的活性。然而，我们还观察到了新的C17甲基支链不饱和FAME的形成，其结构使用GC / MS和NMR分析确定。双键位于8、9或10的不同位置，甲基位于10或9的不同位置。因此，这种新的FAME可能是由G236E CFAS转化的磷脂的16：1酰基链产生的体内突变体。因此，由该G236E CFAS突变体催化的反应
• Biologically Active Substances of Japanese Inedible Mushrooms
  作者：Yoshinori Asakawa、Toshihiro Hashimoto

  DOI：10.3987/rev-97-sr(n)6

  日期：——
• Structure Determination of an Endogenous Sleep-Inducing Lipid, <i>cis</i>-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product
  作者：Benjamin F. Cravatt、Richard A. Lerner、Dale L. Boger

  DOI：10.1021/ja9532345

  日期：1996.1.1

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
• Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins
  作者：Qinghai Zhang、Yu Fu、Yue Weng、Wen-Xu Hong

  DOI：10.1055/s-0030-1259912

  日期：2011.4

  A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization.

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。