methyl 9-hydroxylinelonate | 64265-95-8

• 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-hydroxylinelonate
• 英文别名: Methyl 9-Hydroxy-trans-10,cis-12,cis-15-octadecatrienoat；(10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid methyl ester；methyl (10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoate
• CAS: 64265-95-8
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: MTOOOXVLHAITCG-RUDXKNGCSA-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

• 作为反应物：
  描述：

  methyl 9-hydroxylinelonate 、 苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (10E,12Z,15Z)-9-benzoyloxy octadecatrienoate
  参考文献：
  名称：

  Production of Hydroxy Unsaturated Fatty Acids Using Crude Lipoxygenase Obtained from Infected Rice Plants

  摘要：

  为了探索从感染的水稻植物中获得的脂氧化酶（LOX）的氧化模式，通过LOX和氧气处理了典型的不饱和脂肪酸（3—8）。观察到在异源ω-6（4和5）和ω-3（7和8）系列的不饱和脂肪酸中，主要在ω-10和ω-6位发生氧化。而在内源性脂肪酸（3和6）的情况下，ω-6位的氧化占主导地位。通过用NaBH4还原氧化产物获得的所有烯丙醇均具有S构型。

  DOI：

  10.1246/bcsj.69.1663
• 作为产物：
  描述：

  12-epoxylinolenic acid 在 lithium diisopropyl amide 作用下， 生成 methyl 9-hydroxylinelonate
  参考文献：
  名称：

  UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE

  摘要：

  除了之前描述的环氧脂肪酸外，还鉴定出五种羟基脂肪酸作为水稻植物对抗稻瘟病的自我防御物质。

  DOI：

  10.1246/cl.1984.409

文献信息

• Tallman, Keri A.; Rector, Christopher L.; Porter, Ned A., Journal of the American Chemical Society, 2009, vol. 131, p. 5635 - 5641
  作者：Tallman, Keri A.、Rector, Christopher L.、Porter, Ned A.

  DOI：——

  日期：——
• Kato, Tadahiro; Yamaguchi, Yoshihiro; Namai, Tsuneo, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 2, p. 283 - 287
  作者：Kato, Tadahiro、Yamaguchi, Yoshihiro、Namai, Tsuneo、Hirukawa, Toshifumi

  DOI：——

  日期：——
• 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.
• RAO, A. V. RAMA;REDDY, E. RAJARATHNAM;PURANDARE, A. V.;VARAPRASAD, CH. V.+, TETRAHEDRON, 43,(1987) N 19, 4385-4394
  作者：RAO, A. V. RAMA、REDDY, E. RAJARATHNAM、PURANDARE, A. V.、VARAPRASAD, CH. V.+

  DOI：——

  日期：——
• UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE
  作者：Tadahiro Kato、Yoshihiro Yamaguchi、Takumi Hirano、Toshiro Yokoyama、Tadao Uyehara、Tsuneo Namai、Susumu Yamanaka、Nobuyuki Harada

  DOI：10.1246/cl.1984.409

  日期：1984.3.5

  In addition to the previously described epoxy fatty acids, five hydroxy fatty acids were characterized as self defensive substances produced in the rice plant against rice blast disease.

  除了之前描述的环氧脂肪酸外，还鉴定出五种羟基脂肪酸作为水稻植物对抗稻瘟病的自我防御物质。