p-menth-1-en-3-(2-methyl-1,3-butadienyl)-8-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: p-menth-1-en-3-(2-methyl-1,3-butadienyl)-8-ol
• 英文别名: p-Menth-1-en-3-[2-methyl-1,3-butadienyl]-8-ol；2-[4-methyl-2-[(1E)-2-methylbuta-1,3-dienyl]cyclohex-3-en-1-yl]propan-2-ol
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: DVYSNYGZMYYMJK-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-menth-1-en-3-(2-methyl-1,3-butadienyl)-8-ol 、 N,O-双(三甲基硅烷基)三氟乙酰胺 以 乙醚 、 正戊烷 为溶剂， 生成
  参考文献：
  名称：

  Odor-Active Alcohols from the Fungal Transformation of α-Farnesene

  摘要：

  Submerged microbial cultures were screened for their potential to oxifunctionalize R-farnesene. The major oxidation product in all transforming cultures, 3,7,11-trimethyldodeca-1,3(E),5(E)10-tetraen-7-ol, showed a pleasant citrus-like odor and peak concentrations of 170 mg L-1. An Aspergillus niger isolate from mango generated another two terpene alcohols identified as diastereomeric menth-1-en-3-[2-methyl-1,3-butadienyl]-8-ol, a new natural compound with an apricot-like odor. The regiospecifity of the oxygen attack with concurrent lack of stereoselectivity suggested that the initial step of the bioconversion resembled the chemical autoxidation starting with the generation of an intermediate resonance-stabilized carbon-centered radical or carbocation.

  DOI：

  10.1021/jf062089j

文献信息

• Odor-Active Alcohols from the Fungal Transformation of α-Farnesene
  作者：Ulrich Krings、Björn Hardebusch、Dieter Albert、Ralf G. Berger、Mario Maróstica,、Glaucia M. Pastore

  DOI：10.1021/jf062089j

  日期：2006.11.1

  Submerged microbial cultures were screened for their potential to oxifunctionalize R-farnesene. The major oxidation product in all transforming cultures, 3,7,11-trimethyldodeca-1,3(E),5(E)10-tetraen-7-ol, showed a pleasant citrus-like odor and peak concentrations of 170 mg L-1. An Aspergillus niger isolate from mango generated another two terpene alcohols identified as diastereomeric menth-1-en-3-[2-methyl-1,3-butadienyl]-8-ol, a new natural compound with an apricot-like odor. The regiospecifity of the oxygen attack with concurrent lack of stereoselectivity suggested that the initial step of the bioconversion resembled the chemical autoxidation starting with the generation of an intermediate resonance-stabilized carbon-centered radical or carbocation.