(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylic acid

• ChemBase编号: 153450
• 分子式: C21H28O4
• 平均质量: 344.44462
• 单一同位素质量: 344.19875938
• SMILES: CCCCCc1cc(c2c(c1)OC([C@H]1[C@H]2C=C(CC1)C(=O)O)(C)C)O
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(CC1)C(=O)O)(C)C
• InChI: InChI=1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24)/t15-,16-/m1/s1
• InChIKey: YOVRGSHRZRJTLZ-HZPDHXFCSA-N

名称和登记号

名称

• IUPAC标准名: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylic acid
• IUPAC传统名: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylic acid
• 别名: (6aR,10aR)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid; (6aR-trans)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid; (-)-11-Nor-9-carboxy-9-THC; 11-Nor-9-carboxy-9-tetrahydrocannabinol; 1-Tetrahydrocannabinol-7-oic Acid; (-)-11-Nor-Δ9-Tetrahydro Cannabinol-9-carboxylic Acid; Δ1-Tetrahydrocannabinol-7-oic acid; 9-Carboxy-11-nor-Δ9-tetrahydrocannabinol; 11-Nor-Δ9-tetrahydrocannabinol-9-carboxylic acid

登记号

• CAS号: 56354-06-4
• MDL号: MFCD00079485
• PubChem SID: 162247589
• PubChem CID: 108207

理论计算性质

• Acid pKa: 4.207634
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.8243272
• LogD (pH = 7.4): 2.1027062
• Log P: 5.1358495
• 摩尔折射率: 98.4507 cm^3
• 极化性: 37.96242 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: vacuum-dried powder

安全信息

• 德国WGK号: 3
• 毒品管制信息: USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: -20°C

产品相关信息

• Empirical Formula (Hill Notation): C21H28O4

详细说明

Sigma Aldrich - N3142

Application
Standard for identification of THC metabolites
Biochem/physiol Actions
Major metabolite of Δ9-tetrahydrocannabinol; has antinociceptive properties

Toronto Research Chemicals - N826250

A metabolite of Tetrahydrocannabinol (T293200). Controlled substance.

参考文献

• Fellermeier, M., et al.: Eur. J. Biochem., 268, 1596 (2001)
• Rohrich, J., et al.: J. Anal. Toxicol., 34, 196 (2001)