6044. 3-Methylcholanthrene
Nomenclature
CAS number: 56-49-5
1,2-Dihydro-3-methylbenz[j]aceanthrylene; 20-methylcholanthrene; 3-MECA; 3-MC. C21H16; mol wt 268.35.
C 93.99%, H 6.01%.
Description and 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).
