α-terpenyl Δ⁹-tetrahydrocannabinolate | 1006605-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: α-terpenyl Δ⁹-tetrahydrocannabinolate
• 英文别名: alpha-Terpenyl delta9-Tetrahydrocannabinolate；2-(4-methylcyclohex-3-en-1-yl)propan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylate
• CAS: 1006605-92-0
• 化学式: C₃₂H₄₆O₄
• 分子量: 494.715
• InChiKey: QFWADGLXGUFMMG-OPWSDZRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 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：

  α-terpenyl Δ⁹-tetrahydrocannabinolate 、 N,O-bis(trimethylsilyl)trifluoroacetamide 在 吡啶 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Cannabinoid Ester Constituents from High-Potency Cannabis sativa

  摘要：

  Eleven new cannabinoid esters, together with three known cannabinoid acids and Delta(9)-tetrahydrocannabinol (Delta(9)-THC), were isolated from a high-potency variety of Cannabis sativa. The structures were determined by extensive spectroscopic analyses to be beta-fenchyl Delta(9)-tetrahydrocannabinolate (1), epi-bornyl Delta(9)-tetrahydrocannabinolate (2), alpha-terpenyl Delta(9)-tetrahydrocannabinolate (3), 4-terpenyl Delta(9)-tetrahydrocannabinolate (4), alpha-cadinyl Delta(9)-tetrahydrocannabinolate (5), gamma-eudesmyl Delta(9)-tetrahydrocannabinol ate (6), gamma-eudesmyl cannabigerolate (7), 4-terpenyl cannabinolate (8), bomyl Delta(9)-tetrahydrocannabinol ate (9), cc-fenchyl Delta(9)-tetrahydrocannabinolate (10), alpha-cadinyl cannabigerolate (11), Delta(9)-tetrahydrocannabinol (Delta(9)-THC), Delta(9)-tetrahydrocannabinolic acid A (Delta(9)-THCA), cannabinolic acid A (CBNA), and cannabigerolic acid (CBGA). Compound 8 showed moderate antimicrobial activity against Candida albicans ATCC 90028 with an IC50 value of 8.5 mu g/mL. CB-1 receptor assay indicated that the esters, as well as the parent acids, are not active.

  DOI：

  10.1021/np070454a