841. Aspergillic Acid

Nomenclature

CAS number: 490-02-8
(+)--6-(1-methylpropyl)-3-(2-methylpropyl)pyrazinol 1-oxide; 1-hydroxy-6-(1-methylpropyl)-3-(2-methylpropyl)-2(1H)-pyrazinone; 6-sec-butyl-1-hydroxy-3-isobutyl-2(1H)-pyrazinone; 6-sec-butyl-3-isobutylpyrazinol 1-oxide; 2-hydroxy-3-isobutyl-6-(1-methylpropyl)pyrazine 1-oxide; 3-isobutyl-6-sec-butyl-2-hydroxypyrazine 1-oxide.
C12H20N2O2; mol wt 224.30.
C 64.26%, H 8.99%, N 12.49%, O 14.27%.

Description and references

Antibiotic substance produced by Aspergillus flavus: White, Hill, J. Bacteriol. 45, 433 (1943); Dunn et al., J. Chem. Soc. 1949, Suppl. S126. Extraction and purification: Dutcher, J. Biol. Chem. 171, 321 (1947). Structure: idem, ibid. 232. 785 (1958). Biosynthesis: MacDonald, ibid. 236, 512 (1961), 237, 1977 (1962). Synthesis of racemate: Chigira et al., Bull. Chem. Soc. Jpn. 39, 632 (1966); Masaki et al., J. Org. Chem. 31, 4143 (1966); Ohta, Fujii, Chem. Pharm. Bull. 17, 851 (1969). Industrial prepn: Omata, Ueno, JP 65 13794 (1965 to Dainippon), C.A. 63, 11589b (1965). Proposed as a hypotensive: Jones, Martin, US 3720768 (1973 to Abbott). Reviews: MacDonald, “Aspergillic Acid and Related Compounds” in Antibiotics vol. II, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 43-51; Wilson, “Miscellaneous Aspergillus Toxins” in Microbial Toxins vol. VI, A. Ciegler et al., Eds. (Academic Press, New York, 1971) pp 207-235.

Chemical structure

Properties

Pale yellow needles having odor similar to black walnuts, mp 97-99° (methanol). pK′a 5.5. [α]D18 +13.3° (c = 3.9 in ethanol). uv max (water pH 8): 328, 235 nm (ε 8500, 10500). Slightly sol in cold water; sol in dil acids and alkalies, alcohol, ether, acetone, benzene, chloroform, pyridine.