Methyl 9-Hydroxy-trans-10,trans-12,cis-15-octadecatrienoat | 65179-57-9

• 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 9-Hydroxy-trans-10,trans-12,cis-15-octadecatrienoat
• 英文别名: methyl (10E,12E,15Z)-9-hydroxyoctadeca-10,12,15-trienoate
• CAS: 65179-57-9
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: MTOOOXVLHAITCG-KISNLZSESA-N

物化性质

• 沸点：
  421.4±45.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (10E,12E,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid 、 重氮甲烷 生成 Methyl 9-Hydroxy-trans-10,trans-12,cis-15-octadecatrienoat
  参考文献：
  名称：

  ZDERO, C.;BOHLMANN, F.;MUNGAI, G. M., PHYTOCHEMISTRY, 29,(1990) N, C. 2247-2252

  摘要：

  DOI：

文献信息

• Soybean lipoxygenase: Substrate structure and product selectivity
  作者：Gerhard Scheller、Elke Jaeger、Bettina Hoffmann、Marko Schmitt、Peter Schreier

  DOI：10.1021/jf00055a005

  日期：1995.7

  To study the influence of structural properties of the substrate on the selectivity of the dioxygenation catalyzed by soybean lipoxygenase (LOX), a number of synthesized (Z,Z)-3,6-dienyl 1-adipates with various distal residues were used and the kinetic parameters, the regioselectivity, and the enantioselectivity of product formation determined. Product analysis comprised the reduction of hydroperoxides, derivatization to their methyl esters, purification by silica gel chromatography, and subsequent HPLC separation of (Z,E)-1,3-hydroxydiene methyl esters using both achiral and chiral phases. Enantioseparations were performed by HPLC on chiral phases employing both underivatized products and naphthoylate derivatives. The calculation of the hydrophobicity difference between the distal and the proximal residues of the substrate was confirmed to be a quantitative parameter to predict the positional specificity of the enzymic catalysis. enantiomeric excess was observed only for 7-oxygenated products; 3-oxygenated products were found to be racemic.
• ZDERO, C.;BOHLMANN, F.;MUNGAI, G. M., PHYTOCHEMISTRY, 29,(1990) N, C. 2247-2252
  作者：ZDERO, C.、BOHLMANN, F.、MUNGAI, G. M.

  DOI：——

  日期：——