Title: 3-Methylcholanthrene
CAS Registry Number: 56-49-5
CAS Name: 1,2-Dihydro-3-methylbenz[j]aceanthrylene
Additional Names: 20-methylcholanthrene; 3-MECA; 3-MC
Molecular Formula: C21H16
Molecular Weight: 268.35
Percent Composition: C 93.99%, H 6.01%
Literature References: From desoxycholic acid: Wieland, Schlichting, Z. Physiol. Chem. 150, 267 (1925); Wieland, Wiedersheim, ibid. 186, 229 (1930); Wieland, Dane, ibid. 219, 240 (1933). From cholic acid: Cook, Haslewood, J. Chem. Soc. 1934, 428; Fieser, Seligman; J. Am. Chem. Soc. 58, 2482 (1936); cf. Bachmann, J. Org. Chem. 1, 347 (1936). Methylcholanthrene has been produced also by an unusual pyrolytic degradation of cholesterol derivatives. Total synthesis: Buchta, Güllich, Angew. Chem. 70, 190 (1958); P. W. Tang, C. A. Maggiulli, J. Org. Chem. 46, 3429 (1981); S. A. Jacobs, R. G. Harvey, Tetrahedron Lett. 22, 1093 (1981). Review: E. Clar, Polycyclic Hydrocarbons Vol. 1 & 2 (Academic Press, 1964).
Properties: Pale yellow, slender prisms from benzene + ether, mp 179-180°. bp80 280°; d20 1.28. Absorption spectrum: Fieser, Hershberg, J. Am. Chem. Soc. 60, 940 (1938). Sol in benzene, xylene, toluene; slightly sol in amyl alcohol. Insol in water.
Melting point: mp 179-180°
Boiling point: bp80 280°
Density: d20 1.28
Use: Exptlly in cancer research. |