(+)-(S)-13-Hydroxytetradecansaeure-methylester | 133447-69-5

• 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: (+)-(S)-13-Hydroxytetradecansaeure-methylester
• 英文别名: S-13-hydroxytetradecanoic acid methyl ester；methyl 13-hydroxy tetradecanoate；Methyl-13-L-hydroxy-tetradecanoat；methyl (13S)-13-hydroxytetradecanoate
• CAS: 133447-69-5
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: YRNFMRNZKAELNA-AWEZNQCLSA-N

物化性质

• 熔点：
  47.2-47.7 °C
• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(S)-13-Hydroxytetradecansaeure-methylester 在 盐酸 作用下， 生成 13-hydroxy tetradecanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of monohydroxy tetradecanoic acids and their methyl esters

  摘要：

  Methyl 3-, 6- and 13-oxo tetradecanoates were reduced by NaBH4 in the presence of 1,2:5,6-di-O-isopropylidene-Dglucofuranose (DIPGH) and (-)-menthol together with isovaleric and pivalic acids in THF solution. The highest enantiomeric purity was found for the 13-hydroxy ester isomer of 96%, ee. Enantiomeric excess (ee, %) was determined by chiral HPLC and H-1 NNIR with shift reagent, EU(tfc)(3). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.020
• 作为产物：
  描述：

  十四烷 生成 (+)-(S)-13-Hydroxytetradecansaeure-methylester
  参考文献：
  名称：

  Tulloch,A.P.; Spencer,J.F.T., Canadian Journal of Chemistry, 1968, vol. 46, p. 1523 - 1528

  摘要：

  DOI：

文献信息

• 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.
• Kuechler, Birgit; Voss, Gundula; Gerlach, Hans, Liebigs Annalen der Chemie, 1991, # 6, p. 545 - 552
  作者：Kuechler, Birgit、Voss, Gundula、Gerlach, Hans

  DOI：——

  日期：——
• KUCHLER, BIRGIT;VOSS. , GUNDULA;GERLACH, HANS, LIEBIGS ANN. CHEM.,(1991) N, C. 545-552
  作者：KUCHLER, BIRGIT、VOSS. , GUNDULA、GERLACH, HANS

  DOI：——

  日期：——
• Tulloch,A.P.; Spencer,J.F.T., Canadian Journal of Chemistry, 1968, vol. 46, p. 1523 - 1528
  作者：Tulloch,A.P.、Spencer,J.F.T.

  DOI：——

  日期：——
• Asymmetric synthesis of monohydroxy tetradecanoic acids and their methyl esters
  作者：Belma Hasdemir、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2003.10.020

  日期：2004.1

  Methyl 3-, 6- and 13-oxo tetradecanoates were reduced by NaBH4 in the presence of 1,2:5,6-di-O-isopropylidene-Dglucofuranose (DIPGH) and (-)-menthol together with isovaleric and pivalic acids in THF solution. The highest enantiomeric purity was found for the 13-hydroxy ester isomer of 96%, ee. Enantiomeric excess (ee, %) was determined by chiral HPLC and H-1 NNIR with shift reagent, EU(tfc)(3). (C) 2003 Elsevier Ltd. All rights reserved.