Title: Aspergillic Acid
CAS Registry Number: 490-02-8
CAS Name: 1-Hydroxy-6-(1-methylpropyl)-3-(2-methylpropyl)-2(1H)-pyrazinone
Additional Names: 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
Molecular Formula: C12H20N2O2
Molecular Weight: 224.30
Percent Composition: C 64.26%, H 8.99%, N 12.49%, O 14.27%
Literature 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.
Properties: Pale yellow needles having odor similar to black walnuts, mp 97-99° (methanol). pK¢a 5.5. [a]D18 +13.3° (c = 3.9 in ethanol). uv max (water pH 8): 328, 235 nm (e 8500, 10500). Slightly sol in cold water; sol in dil acids and alkalies, alcohol, ether, acetone, benzene, chloroform, pyridine.
Melting point: mp 97-99° (methanol)
pKa: pK¢a 5.5
Optical Rotation: [a]D18 +13.3° (c = 3.9 in ethanol)
Absorption maximum: uv max (water pH 8): 328, 235 nm (e 8500, 10500) |