Metaphanine
Title: Metaphanine
CAS Registry Number: 1805-86-3
CAS Name: (8b,10b)-8,10-Epoxy-8-hydroxy-3,4-dimethoxy-17-methylhasubanan-7-one
Molecular Formula: C19H23NO5
Molecular Weight: 345.39
Percent Composition: C 66.07%, H 6.71%, N 4.06%, O 23.16%
Literature 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.
Melting point: mp 232°; mp 205-206° for the dl-form (Ibuka)
pKa: pKa 6.03
 
Derivative Type: Dihydrometaphanine
Molecular Formula: C19H25NO5
Molecular Weight: 347.41
Percent Composition: C 65.69%, H 7.25%, N 4.03%, O 23.03%
Properties: Cryst, mp 211°. [a]D20 +72° (in chloroform). pKa 6.76.
Melting point: mp 211°
pKa: pKa 6.76
Optical Rotation: [a]D20 +72° (in chloroform)

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