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

• ChemBase ID: 105249
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: CCCCCc1cc2c(C3CC(=CCC3C(C)(C)O2)C(=O)O)c(O)c1
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC(C1C2CC(=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/h8,10-11,15-16,22H,4-7,9,12H2,1-3H3,(H,23,24)
• InChIKey: OGXXAQFMAFTSRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• IUPAC Traditional name: 1-hydroxy-6,6-dimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• Synonyms: 11-nor-8-Tetrahydrocannabinol-9-carboxylic acid; TETRAHYDROCANNABINOL-7-OIC ACID

Database IDs

• CAS Number: 39690-06-7
• PubChem SID: 162093333
• PubChem CID: 1411

CALCULATED PROPERTIES

• Acid pKa: 4.2535286
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.867675
• LogD (pH = 7.4): 2.1385074
• Log P: 5.1358495
• Molar Refractivity: 98.4507 cm^3
• Polarizability: 37.888184 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02159199

Purity: 98%
A tetrahydrocannabinol metabolite with bronchodilatory, anti-inflammatory and analgesic properties. Acts as a platelet activating factor antagonist and blocks leukocyte adhesion.

REFERENCES

• Burstein, S., et al., FASEB J. , 2 : 3024, (1988).
• Burstein, S., et al., J. Pharmacol. Exp. Ther. , 251 : 531, (1989).
• Burstein, S., et al., Biochem. Pharmacol. , 35 : 2553, (1986).