ximenynic acid methyl ester | 34724-42-0

• 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: ximenynic acid methyl ester
• 英文别名: methyl santalbate；Methyl octadeca-9-yn-11-trans-enoate；methyl (E)-octadec-11-en-9-ynoate
• CAS: 34724-42-0
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: QMZUILXAAOEXNR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ximenynic acid methyl ester 生成 西门木炔酸
  参考文献：
  名称：

  毛白僵菌种子油中的乙炔脂肪酸

  摘要：

  耻节菌种子油包含十八烷基反式-11,17-dien-9-ynoic，8-羟基十八烷基反式-11,17-dien-9-ynoic，ximenynic，油酸和其他酸。估计了油的总脂肪酸组成。苏式-10,11- Dihydroxyheptadec -8-炔和苏-11,12-dihydroxyoctadec -9-炔酸已经制备。

  DOI：

  10.1039/j39680002462
• 作为产物：
  描述：

  12-chloro-octadec-9-ynoic acid methyl ester 在 喹啉 作用下， 生成 ximenynic acid methyl ester
  参考文献：
  名称：

  脂质。第二部分 蓖麻油酸的全合成

  摘要：

  DOI：

  10.1039/jr9550001740

文献信息

• Separation and identification of ximenynic acid isomers in the seed oil of<i>Santalum spicatum</i> R.Br. as their 4,4‐dimethyloxazoline derivatives
  作者：Yandi D. Liu、Robert B. Longmore、John E. D. Fox

  DOI：10.1007/bf02517979

  日期：1996.12

  The seed oil ofSantalum spicatum contains a significant amount of ximenynic acid,trans‐11‐octadecen‐9‐ynoic acid, a long‐chain acetylenic fatty acid, as a major component (34%). The identity oftrans‐ximenynic acid was confirmed after isolation by ultraviolet, infrared, and nuclear magnetic resonance (NMR) (¹H‐ and¹³C‐) spectroscopy and by gas chromatography/mass spectrometry (GC/MS). Thecis isomer of ximenynic acid was also found (<1%) in some samples. Thecis andtrans isomers were characterized by GC/MS comparison of their methyl esters and 4,4‐dimethyloxazoline derivatives.

  摘要刺五加的种子油中含有大量的西门宁酸（反式-11-十八烯-9-炔酸），这是一种长链乙炔脂肪酸，是其主要成分（34%）。经紫外线、红外线和核磁共振（NMR）（1H- 和 13C-）光谱以及气相色谱/质谱法（GC/MS）分离后，确认了反式-西门宁酸的身份。在一些样品中还发现了西门酸的顺式异构体（<1%）。通过对其甲酯和 4,4-二甲基噁唑啉衍生物进行气相色谱/质谱比较，确定了顺式和反式异构体的特征。
• Grigor et al., Journal of the Chemical Society, 1955, p. 1069
  作者：Grigor et al.

  DOI：——

  日期：——
• Hatt; Szumer, Chemistry and industry, 1954, p. 962
  作者：Hatt、Szumer

  DOI：——

  日期：——
• The lindlar-catalyzed reduction of methyl santalbate: a facile preparation of methyl 9-<i>cis</i> ,11-<i>trans</i> -Octadecadienoate-9,10-d₂
  作者：Richard O. Adlof

  DOI：10.1007/s11746-999-0235-8

  日期：1999.3

  AbstractConjugated linoleic acid (CLA) has been associated with the reduction of chemically induced cancers in mice and rats and the suppression of atherosclerosis in rats. We have found seed oils to be a valuable source of precursors for the rapid preparation of gram quantities of deuterium‐labeled fats. Methyl santalbate (methyl 11‐trans‐octadecen‐9‐ynoate), obtained from Santalum album (Linn.) seed, was reduced with Lindlar catalyst, quinoline, and deuterium gas to produce, in yields of 65–75%, the gram quantities of methyl 9‐cis,11‐trans‐octadecadienoate‐9,10‐d2 (CLA‐d2) we required for metabolism and oxidation studies. Unlike monoacetylenic and methylene‐interrupted polyacetylenic fatty acid methyl esters, the conjugated system was reduced with no noticeable break in the rate of deuterium uptake. The quantity of poison (quinoline) present did influence the amount of CLA‐d2 produced, but the production of overreduced fatty acid methyl esters (perhaps because of the conjugated system) could not be prevented. Fractionation of the reaction mixture by silver resin chromatography resulted in the isolation of >99% chemically pure CLA‐d2 in yields of 60–70%.
• Ligthelm et al., Journal of the Chemical Society, 1952, p. 1088,1091
  作者：Ligthelm et al.

  DOI：——

  日期：——