12-00964. Bacimethrin [Archived]

Nomenclature

CAS number: 3690-12-8
4-Amino-2-methoxy-5-pyrimidinemethanol; 4-amino-5-hydroxymethyl-2-methoxypyrimidine.
C6H9N3O2; mol wt 155.15.
C 46.45%, H 5.85%, N 27.08%, O 20.62%.

Description and references

Antibiotic substance produced by Bacillus megatherium from Japanese soil. Isoln and structure: F. Tanaka et al., J. Antibiot. 14A, 161 (1961); 15A, 191, 197 (1962). Prepn: GB 884772 (1961 to Merck & Co.); Koppel et al., J. Org. Chem. 27, 1492, 3614 (1962). Biological studies: T. Nishimura, N. Tanaka, J. Antibiot. 16A, 179 (1963).

Chemical structure

Properties

Needles from methanol, or ethanol + ether, mp 174°. uv max (water): 227, 271 nm (ε 7600, 7300); (0.1N HCl): 229, 261 nm (ε 8400, 9500). Sol in water, methanol, acetic acid. Mod sol in ethanol, pyridine. Practically insol in other organic solvents. LD50 in mice (mg/kg): 300 i.v., 300 i.p (Tanaka, p 191).

Status

This monograph has been retired and is no longer subject to revision or update.