(4R)-Ethyl 4-methyloctanoate | 16177-10-9

• 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: (4R)-Ethyl 4-methyloctanoate
• 英文别名: (R)-4-methyloctanoic acid ethyl ester；(-)(R)-4-methyl-caprylic acid ethyl ester；(-)(R)-4-Methyl-caprylsaeure-aethylester；(4r)-Ethyl-4-methyloctanoate；ethyl (4R)-4-methyloctanoate
• CAS: 16177-10-9
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: GXARNRCIGKRBAP-SNVBAGLBSA-N

物化性质

• 沸点：
  214.2±8.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (4R)-Ethyl 4-methyloctanoate 生成 (-)(R)-2.5-dimethyl-nonane
  参考文献：
  名称：

  Levene; Marker, Journal of Biological Chemistry, 1932, vol. 95, p. 15

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)-β-香茅醇 在 吡啶 、 4-二甲氨基吡啶 、 potassium permanganate 、 2,3-二巯基丁二酸 、 臭氧 作用下， 生成 (4R)-Ethyl 4-methyloctanoate
  参考文献：
  名称：

  Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

  摘要：

  Male coconut minoceros beetles, Oryctes rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl-4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pheromone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps significantly enhanced attraction. With increasing dose, captures of O. rhinoceros increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.

  DOI：

  10.1007/bf02035152

文献信息

• Substrate sorption into the polymer matrix of Novozym 435® and its effect on the enantiomeric ratio determination
  作者：Nicole W.J.T. Heinsman、Carin G.P.H. Schroën、Albert van der Padt、Maurice C.R. Franssen、Remko M. Boom、Klaas van‘t Riet

  DOI：10.1016/s0957-4166(03)00577-9

  日期：2003.9

  In the enantioselective esterification of 4-methyloctanoic acid with ethanol by immobilised Candida antarctica lipase B (Novozym 435(R)), the enantiomeric excesses determined during the Course of the reaction deviated strongly from the theoretical values, leading to unacceptably large confidence intervals for the enantiomeric ratio (E value). This observation was in contrast to our previous findings for transesterification and hydrolysis reactions with this enzyme. Herein, the three reactions are compared; the anomalous results in the esterification reaction appear to be caused by adsorption of 4-methyloctanoic acid inside the enzyme beads. We found that on average 1.19 g of 4-methyloctanoic acid was incorporated per g of Novozym 435(R). if the concentration of this substrate was adjusted accordingly in the calculations, the resulting E values showed acceptable confidence intervals. In previous research on transesterification reactions in excess apolar solvent (comparable affinity for the beads), sorption does not play an important role because only small amounts of substrate were lost. For hydrolysis reactions, sorption takes place but the acid is released from the beads upon titration and no effect on the E value is found. However, for esterification reactions, sorption should not be neglected since there is no driving force to release the acid from the beads. (C) 2003 Elsevier Ltd. All rights reserved.
• Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)
  作者：Rebecca H. Hallett、Alice L. Perez、Gerhard Gries、Regine Gries、Harold D. Pierce、Junming Yue、A. Cameron Oehlschlager、Lilliana M. Gonzalez、John H. Borden

  DOI：10.1007/bf02035152

  日期：1995.10

  Male coconut minoceros beetles, Oryctes rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl-4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pheromone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps significantly enhanced attraction. With increasing dose, captures of O. rhinoceros increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.
• Levene; Marker, Journal of Biological Chemistry, 1932, vol. 95, p. 15
  作者：Levene、Marker

  DOI：——

  日期：——