methyl (E)-8-hydroperoxyoctadec-9-enoate | 26194-98-9

• 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 (E)-8-hydroperoxyoctadec-9-enoate
• CAS: 26194-98-9
• 化学式: C₁₉H₃₆O₄
• 分子量: 328.492
• InChiKey: HAMWHUVAVRLDJS-NTCAYCPXSA-N

物化性质

• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-8-hydroperoxyoctadec-9-enoate 生成 methyl (E)-8-hydroxyoctadec-9-enoate
  参考文献：
  名称：

  CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631

  摘要：

  DOI：
• 作为产物：
  描述：

  反-9-十八碳烯酸甲酯 生成 methyl (E)-8-hydroperoxyoctadec-9-enoate
  参考文献：
  名称：

  CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631

  摘要：

  DOI：

文献信息

• Conversion of allylic hydroxy oleate to conjugated linoleic acid and methoxy oleate by acid‐catalyzed methylation procedures
  作者：Martin P. Yurawecz、Jennifer K. Hood、John A. G. Roach、Magdi M. Mossoba、Daniel H. Daniels、Yuoh Ku、Michael W. Pariza、Sou F. Chin

  DOI：10.1007/bf02675911

  日期：1994.10

  Conjugated linoleic acid (CLA), a term describing a group of conjugated octadecadienoic acids that are both naturally occurring and formed during food processing, is the subject of considerable current research because of the recently reported antioxidant and anticarcinogenic properties of these compounds. Allylic hydroxy oleates (AHOs), secondary products of lipid autoxidation, have also been found in foods. By means of high‐performance liquid chromatography with ultraviolet detection, gas chromatography/mass spectrometry and gas chromatography/matrix isolation/Fourier transform infrared spectroscopy, we determined that currently used acid‐catalyzed methylation procedures convert AHOs to CLA and other products that potentially yield high values in determination of CLA in foods. A mixture of AHOs, containing mainly (8‐ and 11‐)hydroxy‐9‐octadecadecenoates, was synthesized and tested by methylation procedures with the following catalysts: BF₃, HCl, NaOMe and tetramethylguanidine. Both the BF₃ and the HCl procedures converted AHOs to CLA. The base‐catalyzed procedures did not convert AHOs to CLA.

  摘要共轭亚油酸（CLA）是一组共轭十八碳二烯酸的总称，既有天然存在的，也有在食品加工过程中形成的。食品中还发现了烯丙基羟基油酸酯（AHOs），这是脂质自氧化的次级产物。通过紫外检测高效液相色谱法、气相色谱/质谱法和气相色谱/基质分离/傅立叶变换红外光谱法，我们确定了目前使用的酸催化甲基化程序可将 AHOs 转化为 CLA 和其他产物，这些产物有可能为食品中 CLA 的测定提供高值。我们合成了一种主要含有（8-和 11-）羟基-9-十八碳烯酸酯的 AHOs 混合物，并使用以下催化剂通过甲基化程序进行了测试：BF3、HCl、NaOMe 和四甲基胍。BF3 和 HCl 程序都能将 AHO 转化为 CLA。碱催化程序没有将 AHOs 转化为 CLA。
• A Mechanistic Study of Oleate Autoxidation: Competing Peroxyl H-Atom Abstraction and Rearrangement
  作者：Ned A. Porter、Karen A. Mills、Randall L. Carter

  DOI：10.1021/ja00094a026

  日期：1994.7

  The mechanism of methyl oleate autoxidation was investigated. HPLC techniques were developed to analyze the products of autoxidation (hydroperoxides and the corresponding alcohols). The alcohols could be completely resolved by normal-phase chromatography, six products being characterized having oxygen substitution and double position as follows: 11-OOH-trans-Delta(9-10), 11-OOH-cis-Delta(9-10), 10-OOH-trans-Delta(8-9), 9-OOH-trans-Delta(10-11), 8-OOH-trans-Delta(9-10), 8-OOH-cis-Delta(9-10) As the hydrogen atom donor concentration of the medium of autoxidation is increased, increased 11-cis, 8-cis, 9-trans, and 10-trans hydroperoxides and decreased 11-trans and 8-trans hydroperoxides were obtained, consistent with a mechanism in which peroxyl H-atom abstraction and [2,3] allylperoxyl rearrangement are in competition. An iterative computer kinetic analysis was developed which modeled the oleate autoxidation mechanism, and rearrangement rate constants were determined. Allylperoxyl radicals undergo rearrangement with different rates depending on the geometry of the allylperoxyl.
• Frankel, Edwin N.; Garwood, Robert F.; Khambay, Bhupinder P. S., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2233 - 2240
  作者：Frankel, Edwin N.、Garwood, Robert F.、Khambay, Bhupinder P. S.、Moss, Gerard P.、Weedon, Basil C. L.

  DOI：——

  日期：——
• CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631
  作者：CAPELLA, P.、CABONI, M. F.、BONAGA, G.、LERCKER, G.

  DOI：——

  日期：——
• Porter Ned A., Mills Karen A., Carter Randall L., J. Amer. Chem. Soc, 116 (1994) N 15, S 6690-6696
  作者：Porter Ned A., Mills Karen A., Carter Randall L.

  DOI：——

  日期：——