methyl 11-oxohexadecanoate | 54527-12-7

• 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 11-oxohexadecanoate
• 英文别名: Methyl-11-oxo-hexadecanoat；Methyl-11-oxopalmitat
• CAS: 54527-12-7
• 化学式: C₁₇H₃₂O₃
• 分子量: 284.439
• InChiKey: SFQLDWUVQAHQCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 11-oxohexadecanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以145 mg的产率得到甲基11-羟基十六烷酸酯
  参考文献：
  名称：

  Resin Glycosides. XVIII. Determination by Mosher's Method of the Absolute Configurations of Mono- and Dihydroxyfatty Acids Originated from Resin Glycosides.

  摘要：

  通过酸水解各种树脂糖苷，四种羟基脂肪酸（墨西哥胡椒酸、旋花酸、伊普罗酸和3,11-二羟基十六烷酸）的绝对构型分别被确定为11S、11S、3S、11S和3S、11S，通过莫舍尔法测定。因此，先前由霍罗法定义的墨西哥胡椒酸的R构型被修改为S。

  DOI：

  10.1248/cpb.41.1023
• 作为产物：
  描述：

  10-十一烯-1-醇 在 jones reagent 、 dimethyl sulfide borane 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 25.58h， 生成 methyl 11-oxohexadecanoate
  参考文献：
  名称：

  Products of Cytochrome P450_BioI (CYP107H1)-Catalyzed Oxidation of Fatty Acids

  摘要：

  [GRAPHICS]Oxidation of tetradecanoic and hexadecanoic acids by cytochrome P450(Biol) (CYP107H1) produces mainly the 11-, 12-, and 13-hydroxy C-14 fatty acids and the 11- to 15-hydroxy C-16 fatty acids, respectively. In contrast to previous reports, terminal hydroxylation is not observed. The enantiospecificity of fatty acid hydroxylation by P450(Biol) was also determined, and the enzyme was shown to be moderately selective for production of the (R)-alcohols.

  DOI：

  10.1021/ol035254e

文献信息

• GULACAR, FAZIL O.;BUCHS, ARMAND;SUSINI, ALBERTO, J. CHROMATOGR., 479,(1989) N, C. 61-72
  作者：GULACAR, FAZIL O.、BUCHS, ARMAND、SUSINI, ALBERTO

  DOI：——

  日期：——
• YUSUFOGLU, A.;OEZERIS, S., CHIM. ACTA TURC., 1982, 10, N 3, 217-224
  作者：YUSUFOGLU, A.、OEZERIS, S.

  DOI：——

  日期：——
• Products of Cytochrome P450_BioI (CYP107H1)-Catalyzed Oxidation of Fatty Acids
  作者：Max J. Cryle、Nick J. Matovic、James J. De Voss

  DOI：10.1021/ol035254e

  日期：2003.9.1

  [GRAPHICS]Oxidation of tetradecanoic and hexadecanoic acids by cytochrome P450(Biol) (CYP107H1) produces mainly the 11-, 12-, and 13-hydroxy C-14 fatty acids and the 11- to 15-hydroxy C-16 fatty acids, respectively. In contrast to previous reports, terminal hydroxylation is not observed. The enantiospecificity of fatty acid hydroxylation by P450(Biol) was also determined, and the enzyme was shown to be moderately selective for production of the (R)-alcohols.
• Resin Glycosides. XVIII. Determination by Mosher's Method of the Absolute Configurations of Mono- and Dihydroxyfatty Acids Originated from Resin Glycosides.
  作者：Masateru ONO、Fumiko YAMADA、Naoki NODA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.41.1023

  日期：——

  The absolute configurations of four hydroxyfatty acids, jalapinolic acid, convolvulinolic acid, ipurolic acid and 3, 11-dihydroxyhexadecanoic acid, obtained by acid hydrolysis of various resin glycosides, have been determined to be 11S, 11S, 3S, 11S, and 3S, 11S, respectively, by Mosher's method. The R-configuration of jalapinolic acid previously defined by Horeau's method was therefore revised to S.

  通过酸水解各种树脂糖苷，四种羟基脂肪酸（墨西哥胡椒酸、旋花酸、伊普罗酸和3,11-二羟基十六烷酸）的绝对构型分别被确定为11S、11S、3S、11S和3S、11S，通过莫舍尔法测定。因此，先前由霍罗法定义的墨西哥胡椒酸的R构型被修改为S。