1325. Boldine

Nomenclature

CAS number: 476-70-0
5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol; 1,10-dimethoxy-6aα-aporphine-2,9-diol; 1,10-dimethoxy-2,9-dihydroxyaporphine; 2,6-dihydroxy-3,5-dimethoxyaporphine.
C19H21NO4; mol wt 327.37.
C 69.71%, H 6.47%, N 4.28%, O 19.55%.

Description and 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); Sp"ath, 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).

Chemical structure

Derivative

d-Form.

Properties

Crystals from ether. mp 162-164°. [α]D25 +127° (c = 0.1 in alcohol). Very slightly sol in water or ether; sol in alcohol, chloroform, dil acids.

Derivative

d-Form hydrochloride.

Properties

Crystals from methanol-ether and methanol, mp 212-220°.

Derivative

dl-Form.

Properties

mp 159-162°.

Derivative

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.