1-Decanoic-1-14C acid | 94033-36-0

• 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: 1-Decanoic-1-14C acid
• 英文别名: [1-C14]capric acid；(114C)decanoic acid
• CAS: 94033-36-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 174.257
• InChiKey: GHVNFZFCNZKVNT-HRVHXUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 2910 7

反应信息

• 作为反应物：
  描述：

  1-Decanoic-1-14C acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-Decanol-1-14C
  参考文献：
  名称：

  Pyrolysis of Alkyl Acetates. A Radical Pathway for the Formation of Minor Products

  摘要：

  Decyl acetate and decene pyrolysis under the same reaction conditions show that the formation of the minor products during the pyrolysis of esters occurs by a parallel, and not a secondary, reaction. The radioactivity observed in the CO2 and CO produced during the pyrolysis of 1-hexyl acetate-1-C-14 and the radioactivity in the methane from the pyrolysis of 1-hexyl acetate-2-C-14 strongly suggested a radical reaction pathway for the formation of the minor products. Considering the above results together with the radioactivity data of gas samples from the pyrolysis of 1-decyl-1-C-14 acetate, 1-hexyl-1 -C-14 acetate, and 1-heptadecyl-1-C-14 acetate leads to the conclusion that the mechanism of pyrolysis of esters may be viewed as a cyclo-D(E)D(N)A(N) mechanism for the formation of the major alkene product and a radical mechanism for the formation of minor products. A useful synthetic procedure for the preparation of high carbon number alkenes (>10) also results from this study.

  DOI：

  10.1021/jo00083a028
• 作为产物：
  描述：

  1-溴壬烷 、 二氧化碳-14C 在 magnesium 作用下， 生成 1-Decanoic-1-14C acid
  参考文献：
  名称：

  Pyrolysis of Alkyl Acetates. A Radical Pathway for the Formation of Minor Products

  摘要：

  Decyl acetate and decene pyrolysis under the same reaction conditions show that the formation of the minor products during the pyrolysis of esters occurs by a parallel, and not a secondary, reaction. The radioactivity observed in the CO2 and CO produced during the pyrolysis of 1-hexyl acetate-1-C-14 and the radioactivity in the methane from the pyrolysis of 1-hexyl acetate-2-C-14 strongly suggested a radical reaction pathway for the formation of the minor products. Considering the above results together with the radioactivity data of gas samples from the pyrolysis of 1-decyl-1-C-14 acetate, 1-hexyl-1 -C-14 acetate, and 1-heptadecyl-1-C-14 acetate leads to the conclusion that the mechanism of pyrolysis of esters may be viewed as a cyclo-D(E)D(N)A(N) mechanism for the formation of the major alkene product and a radical mechanism for the formation of minor products. A useful synthetic procedure for the preparation of high carbon number alkenes (>10) also results from this study.

  DOI：

  10.1021/jo00083a028

文献信息

• Molecular Cloning of CYP76B9, a Cytochrome P450 from<i>Petunia hybrida</i>, Catalyzing the ω-Hydroxylation of Capric Acid and Lauric Acid
  作者：Hiromasa IMAISHI、Mariana PETKOVA-ANDONOVA

  DOI：10.1271/bbb.60396

  日期：2007.1.23

  A cDNA encoding a cytochrome P450 (CYP76B9) was isolated from Petunia hybrida. Northern blot analysis revealed preferential expression of the gene in flowers and leaves. The recombinant yeast microsomes expressing CYP76B9 was allowed to react with capric acid and lauric acid as substrates. One major metabolite was produced from each fatty acid after incubation with yeast microsomes expressing CYP76B9. The metabolites were identified by gas chromatography–mass spectrometry (GC–MS) as ω-hydroxy capric acid and ω-hydroxy lauric acid. The kinetic parameters of the reactions were K  m=9.4 μm and V  max=13.6 mol min−1 per mol of P450 for capric acid, and K  m=5.7 μm and V  max=19.1 mol min−1 per mol of P450 for lauric acid. We found that the ω-hydroxy metabolites of capric acid and lauric acid can affect the plant growth of Arabidopsis thaliana. Plants grown in the presence of ω-hydroxy fatty acids exhibited shorter root length than control plants with the corresponding non-hydroxylated fatty acids.

  从杂交牵牛花（Petunia hybrida）中分离出了一种编码细胞色素P450（CYP76B9）的cDNA。北方印迹分析显示该基因在花朵和叶子中有优先表达。表达CYP76B9的重组酵母微粒体与癸酸和月桂酸作为底物反应。经过与表达CYP76B9的酵母微粒体孵育后，从每种脂肪酸中产生了一种主要代谢产物。通过气相色谱-质谱联用（GC-MS），这些代谢产物被鉴定为ω-羟基癸酸和ω-羟基月桂酸。反应的动力学参数为：癸酸的K_m=9.4 μm，V_max=每摩尔P450 13.6 mol min−1；月桂酸的K_m=5.7 μm，V_max=每摩尔P450 19.1 mol min−1。我们发现癸酸和月桂酸的ω-羟基代谢产物会影响阿拉伯芥（Arabidopsis thaliana）的植物生长。在存在ω-羟基脂肪酸的条件下生长的植物，其根长度比对照组（使用相应的非羟基化脂肪酸）短。