Title: Matrine
CAS Registry Number: 519-02-8
CAS Name: Matridin-15-one
Additional Names: sophocarpidine
Molecular Formula: C15H24N2O
Molecular Weight: 248.36
Percent Composition: C 72.54%, H 9.74%, N 11.28%, O 6.44%
Literature References: Occurs naturally as the (+)-form in the Chinese drug Kuh Seng or the Japanese Shinkyogan, the dried roots of Sophora angustifolia Sieb. & Zucc., S. flavescens Ait. and other Sophora spp., Leguminosae. Isomeric with lupanine, q.v. Isoln: Kondo, Arch. Pharm. 266, 1 (1928); Winterfeld, Knener, Ber. 64, 150 (1931); Orechov, Proskurnina, Ber. 67, 77 (1934); Briggs, Ricketts, J. Chem. Soc. 1937, 1795. Identity with sophocarpidine: Orechov et al., Ber. 68, 429 (1935). Alternate method of isoln: F. Bohlmann et al., Ber. 91, 2189 (1958). Structure: Tsuda, Murakami, Ber. 69, 429 (1936). Configuration: Bohlmann et al., Ber. 91, 2176 (1958). Absolute configuration: Okuda et al., Chem. Pharm. Bull. 14, 314 (1966); Cervinka, Z. Chem. 7, 190 (1967). Synthetic studies: Tsuda et al., J. Org. Chem. 21, 1481 (1956); 23, 1179 (1958). Synthesis of matridine (deoxymatrine): Mandell, Singh, J. Am. Chem. Soc. 83, 1766 (1961). Total synthesis of (±)-matrine: Mandell et al., ibid. 87, 5234 (1965); J. Chen et al., Chem. Commun. 12, 905 (1986). Synthesis of (+)-matrine: Okuda et al., Chem. Pharm. Bull. 14, 275 (1966). Biosynthesis: Schütte et al., Arch. Pharm. 295, 34 (1962).
Properties: Has been obtained in four forms: a-Form: needles or flat prisms, mp 76°. b-Form: orthorhombic prisms, mp 87°, [a]D20 +38° (alc). g-Form: liquid, bp6 223°, d420 1.088, nD85 1.5287. d-Form: prisms, mp 84°. Sol in water, benzene, chloroform, ether, carbon disulfide; slightly sol in petr ether.
Melting point: mp 76°; mp 87°; mp 84°
Boiling point: bp6 223°
Optical Rotation: [a]D20 +38° (alc)
Index of refraction: nD85 1.5287
Density: d420 1.088 |