p-menth-1,8-dien-10-oic acid | 177479-01-5

• 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-1,8-dien-10-oic acid
• 英文别名: iso-perillic acid；(+/-)-p-menthadien-(1.8)-oic acid-(10)；p-mentha-1,8(10)-dien-9-oic acid；(+/-)-p-Menthadien-(1.8)-saeure-(10)；p-Mentha-1,8(10)-dien-9-saeure；2-(4-Methylcyclohex-3-en-1-yl)prop-2-enoic acid
• CAS: 177479-01-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ZUCQJOQBPVWZQK-UHFFFAOYSA-N

物化性质

• 沸点：
  300.6±21.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-menth-1,8-dien-10-oic acid 在 lithium aluminium tetrahydride 、 mercury(II) diacetate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 乙醚 、 二甲基亚砜 、 苯 为溶剂， 生成 β-bisabolene
  参考文献：
  名称：

  Vig,O.P. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 475 - 478

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-3-环己烯-1-酮 在 palladium on activated charcoal potassium fluoride 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙二醇 为溶剂， 生成 p-menth-1,8-dien-10-oic acid
  参考文献：
  名称：

  Vig,O.P. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 475 - 478

  摘要：

  DOI：

文献信息

• Inhibition of protein prenylation by metabolites of limonene
  作者：IanR Hardcastle、MartinG Rowlands、Amelia Moreno Barber、RachelM Grimshaw、MukeshK Mohan、BernardP Nutley、Michael Jarman

  DOI：10.1016/s0006-2952(98)00349-9

  日期：1999.4

  The monoterpenes limonene and perillyl alcohol are undergoing clinical evaluation in cancer patients. In this paper, we report the chemical synthesis, characterisation, and quantitation in patients' plasma of a novel human metabolite of limonene, which is identified as an isomer of perillic acid. The synthesis of R-perillic acid is also described, because previous reports on the activity of perillic acid against isoprenylation enzymes refer to the S-enantiomer, although it is the R-enantiomer which is the metabolite of R-limonene. The above monoterpenes, with several related compounds, were assayed for inhibitory activity towards the isoprenylation enzymes in rat brain cytosol. Although R- and S-limonene are only weak inhibitors of the isoprenylation enzymes, their major metabolites, perillic acid and perillyl alcohol, are more potent inhibitors, with IC50 values in the low mM range. The metabolites possess greater activity towards the geranylgeranyltransferase type I enzyme than farnesyltransferase, while the novel metabolite displays IC50 values similar to those of perillic acid suggesting that it may contribute to the in vivo activity of limonene. (C) 1999 Elsevier Science Inc.
• Wallach; Schmitz, Justus Liebigs Annalen der Chemie, 1906, vol. 345, p. 128
  作者：Wallach、Schmitz

  DOI：——

  日期：——
• Vig,O.P. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 475 - 478
  作者：Vig,O.P. et al.

  DOI：——

  日期：——