9-((1R,2S)-2-Butyl-cyclopentyl)-nonanoic acid methyl ester | 108708-61-8

• 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: 9-((1R,2S)-2-Butyl-cyclopentyl)-nonanoic acid methyl ester
• 英文别名: Methyl cis-9-(2-butylcyclopentyl)nonanoate；methyl 9-[(1R,2S)-2-butylcyclopentyl]nonanoate
• CAS: 108708-61-8
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: LFIBOCIUNNYIJD-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 1,3-dihexadecanoyl-2-(9,12,15-octadecatrienoyl)glycerol 在 platinum(IV) oxide 三氟化硼 、 氢气 作用下， 生成 10-((1R,2R)-2-Propyl-cyclopentyl)-decanoic acid methyl ester 、 10-((1R,2S)-2-Propyl-cyclopentyl)-decanoic acid methyl ester 、 9-((1R,2R)-2-Propyl-cyclohexyl)-nonanoic acid methyl ester 、 9-((1R,2S)-2-Propyl-cyclohexyl)-nonanoic acid methyl ester 、 9-((1R,2R)-2-Butyl-cyclopentyl)-nonanoic acid methyl ester 、 9-((1R,2S)-2-Butyl-cyclopentyl)-nonanoic acid methyl ester
  参考文献：
  名称：

  脂肪酸位置分布和三酰基甘油组成对热处理过程中脂质副产物形成的影响：III-环状脂肪酸单体研究

  摘要：

  AbstractThe influence of isomeric triacylglycerols (TG) containing 18:3n‐3 and 18:2n‐6 on the formation of cyclic fatty acid monomers (CFAM) after heat treatment was assessed. Diacid TG, containing linoleic acid (L) or linolenic acid (α‐Ln) along with palmitic acid (P), and positioned either in the central position (PLP and PLnP, respectively), or in one of the two outer positions (PPL and PPLn, respectively) were synthesized. Monoacid TG of trilinolein and trilinolenin mixed with tripalmitin were also prepared. The CFAM formed after heating were analyzed after total hydrogenation. The results obtained with the model TG were compared to another model consisting of a canola oil and its randomized counterpart. In diacid TG, the location of α‐Ln in the central position of the TG molecule (PLnP) greatly enhanced the formation of the CFAM upon heating at temperatures below 240°C. On the other hand, 18:3n‐3 in monoacid TG (LnLnLn) was highly resistant to CFAM formation within the same range of temperatures (180–220°C). The TG structure, more than the TG composition, seemed to explain the differences in the CFAM formation between the original canola oil and its interesterified counterpart. Like α‐Ln, 18:2n‐6 was more prone to cyclization when attached at the central position of the model TG. Conversely, the influence of the TG composition on the cyclization rate was less important for L than for α‐Ln. It was concluded that positioning the C18 polyunsaturated fatty acid in the central position of TG rendered the oils much more sensitive to the cyclization reaction upon heat treatment.

  DOI：

  10.1007/s11746-998-0318-y