Title: Boldine
CAS Registry Number: 476-70-0
CAS Name: 5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol
Additional Names: 1,10-dimethoxy-6aa-aporphine-2,9-diol; 1,10-dimethoxy-2,9-dihydroxyaporphine; 2,6-dihydroxy-3,5-dimethoxyaporphine
Molecular Formula: C19H21NO4
Molecular Weight: 327.37
Percent Composition: C 69.71%, H 6.47%, N 4.28%, O 19.55%
Literature References: Isoln from boldo (Peumus boldus Molina, Monimiaceae): Bourgoin, Verne, J. Pharm. Chim. 16, 191 (1872); from Laurelia novaezelandiae A. Cunn.: Bernauer, Helv. Chim. Acta 50, 1583 (1967). Structure: Warnat, Ber. 58, 2768; 59, 85 (1926); Späth, Tharrer, ibid. 66, 904 (1933); Schlittler, ibid. 988. Synthesis of dl-form: S. M. Kupchan et al., Chem. Commun. 1976, 91. Biosynthetic study: D. S. Bhakuni et al., J. Chem. Soc. Perkin Trans. 1 1977, 706. Detailed description of the boldo brush, its ingredients and pharmacological properties: H. Schindler, Arzneim.-Forsch. 7, 747 (1957).
Derivative Type: d-Form
Properties: Crystals from ether. mp 162-164°. [a]D25 +127° (c = 0.1 in alcohol). Very slightly sol in water or ether; sol in alcohol, chloroform, dil acids.
Melting point: mp 162-164°
Optical Rotation: [a]D25 +127° (c = 0.1 in alcohol)
Derivative Type: d-Form hydrochloride
Properties: Crystals from methanol-ether and methanol, mp 212-220°.
Melting point: mp 212-220°
Derivative Type: dl-Form
Properties: mp 159-162°.
Melting point: mp 159-162°
Derivative Type: Dimethyl ether see Glaucine
NOTE: Boldine is used as an ingredient in choleretics and laxatives. The total alkaloids from boldo are also marketed as a grayish-white to grayish-yellow, bitter powder; almost insol in water. Sol in alc, chloroform, slightly in ether. |