Cannabidiol
Title: Cannabidiol
CAS Registry Number: 13956-29-1
CAS Name: 2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
Additional Names: trans-(-)-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol
Molecular Formula: C21H30O2
Molecular Weight: 314.46
Percent Composition: C 80.21%, H 9.62%, O 10.18%
Literature References: Major nonpsychoactive constituent of cannabis, q.v. (Cannabis sativa L., Cannabinaceae). Exhibits multiple bioactivities including anticonvulsant, anxiolytic and anti-inflammatory effects. Isoln from wild hemp: R. Adams et al., J. Am. Chem. Soc. 62, 196, 2194 (1940); from hashish: A. Jacob, A. R. Todd, J. Chem. Soc. 1940, 649. Structure: R. Mechoulam, Y. Shvo, Tetrahedron 19, 2073 (1963). Crystal and molecular structure: T. Ottersen et al., Acta Chem. Scand. B 31, 807 (1977). Abs config: Y. Gaoni, R. Mechoulam, J. Am. Chem. Soc. 93, 217 (1971). Synthesis of (±)-form: eidem, ibid. 87, 3273 (1965); of (-)-form: T. Petrzilka et al., Helv. Chim. Acta 52, 1102 (1969); H. J. Kurth et al., Z. Naturforsch. 36B, 275 (1981). LC-IT-MS determn in cannabis products: A. A. M. Stolker et al., J. Chromatogr. A 1058, 143 (2004). Review of isoln, chemistry and metabolism: R. Mechoulam, L. Hanus, Chem. Phys. Lipids 121, 35-43 (2002); of pharmacology and bioactivity: R. Mechoulam et al., J. Clin. Pharmacol. 42, 11S-19S (2002).
Properties: Pale yellow resin or crystals, mp 66-67°. bp2 187-190° (bath temp 220°). bp0.001 130°. d440 1.040. nD20 1.5404. [a]D27 -125° (0.066 g in 5 ml 95% ethanol). [a]D18 -129° (c = 0.45 in ethanol). uv max (ethanol): 282, 274 nm (log e 3.10, 3.12). Practically insol in water or 10% NaOH. Sol in ethanol, methanol, ether, benzene, chloroform, petr ether.
Melting point: mp 66-67°
Boiling point: bp2 187-190° (bath temp 220°); bp0.001 130°
Optical Rotation: [a]D27 -125° (0.066 g in 5 ml 95% ethanol); [a]D18 -129° (c = 0.45 in ethanol)
Index of refraction: nD20 1.5404
Absorption maximum: uv max (ethanol): 282, 274 nm (log e 3.10, 3.12)
Density: d440 1.040

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