5929. Metaphanine
Nomenclature
CAS number: 1805-86-3
(8β,10β)-8,10-Epoxy-8-hydroxy-3,4-dimethoxy-17-methylhasubanan-7-one. C19H23NO5; mol wt 345.39.
C 66.07%, H 6.71%, N 4.06%, O 23.16%.
Description and references
A member of the hasubanan alkaloids; also possesses an intramolecular hemiketal ring. Isolated from stems of Stephania japonica Miers, Menispermaceae from which the alkaloids stephanine and protostephanine, q.v. are also obtained: Kondo, Sanada, J. Pharm. Soc. Jpn. 514, 5 (1924); Yakugaku Zasshi 44, 5, 1034 (1924); 48, 177, 930 (1927); Kondo, Watanabe, ibid. 58, 268 (1938). Structure and stereochemistry: Tomita et al., Tetrahedron Lett. 1964, 3605; Chem. Pharm. Bull. 13, 695 (1965). Synthesis of dl-form: Ibuka et al., Tetrahedron Lett. 1972, 1393; eidem, Chem. Pharm. Bull. 22, 907 (1974).
Properties
Needles, mp 232°. Also reported as colorless prisms, mp 205-206° for the dl-form (Ibuka). pKa 6.03. Sol in water, alcohol.Derivative
Dihydrometaphanine.C19H25NO5; mol wt 347.41.
C 65.69%, H 7.25%, N 4.03%, O 23.03%.