(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid

• ChemBase ID: 129791
• Molecular Formular: C22H30O4
• Molecular Mass: 358.4712
• Monoisotopic Mass: 358.21440944
• SMILES: CCCCCc1cc2c([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)c(c1C(=O)O)O
• Canonical SMILES: CCCCCc1cc2OC(C)(C)[C@H]3[C@H](c2c(c1C(=O)O)O)C=C(CC3)C
• InChI: InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1
• InChIKey: UCONUSSAWGCZMV-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid
• IUPAC Traditional name: (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid
• Synonyms: THCA-A; Δ9-Tetrahydrocannabinolic acid A; Tetrahydrocannabinolic acid; Δ9-四氢大麻酚酸 A

Database IDs

• CAS Number: 23978-85-0
• MDL Number: MFCD20133805
• PubChem SID: 162224079
• PubChem CID: 98523
• Wikipedia Title: Tetrahydrocannabinolic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.8862457
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6866982
• LogD (pH = 7.4): 2.7650998
• Log P: 6.25174
• Molar Refractivity: 103.9897 cm^3
• Polarizability: 39.77692 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule I; Home Office Schedule 1; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Grade: analytical standard, for drug analysis
• Suitability: corresponds for H-NMR
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H30O4