Title: Patulin
CAS Registry Number: 149-29-1
CAS Name: 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Additional Names: clavacin; clavatin; claviformin; expansine; mycoin C3; penicidin
Molecular Formula: C7H6O4
Molecular Weight: 154.12
Percent Composition: C 54.55%, H 3.92%, O 41.52%
Literature References: An antibiotic derived from the metabolites of a number of fungi, e.g., Aspergillus clavatus, A. claviforme, A. giganteus, A. terreus, Penicillium patulum, P. expansum, P. melinii, P. leucopus, P. urticae and Gymnoascus spp. Isoln and antibacterial activity: Birkinshaw et al., Lancet 245, 625 (1943); Birkinshaw, Michael, US 2417584 (1947 to Therap. Res. Corp. of Great Britain); cf. Waksman et al., Science 96, 202 (1942); Brack, Helv. Chim. Acta 30, 1 (1947); Norstadt, McCalla, Appl. Microbiol. 17, 193 (1969). Structure: Birkinshaw, loc. cit.; Bergel et al., J. Chem. Soc. 1944, 415; Woodward, Singh, J. Am. Chem. Soc. 71, 758 (1949); Shemyakin, Khokhlov, Dokl. Akad. Nauk SSSR 75, 47 (1950). Synthesis: Woodward, Singh, J. Am. Chem. Soc. 72, 1428 (1950). Biosynthesis: Bu'Lock, Ryan, Proc. Chem. Soc. London 1958, 222; Tanenbaum, Bassett, J. Biol. Chem. 234, 1861 (1959). Inhibition of K+ ion uptake in erythrocytes: Kahn, J. Pharmacol. Exp. Ther. 121, 234 (1957). Physicochemical data: A. E. Pohland et al., Pure Appl. Chem. 54, 2219 (1982). Has carcinogenic activity attributable to a,b-unsaturation together with an external conjugated double bond attached to 4 position of the g-lactone ring: Dickens, Br. Med. Bull. 20, 96 (1964). Toxicity: R. Kinosita, T. Shikata, "On Toxic Moldy Rice" in Mycotoxins in Foodstuffs, G. N. Wogan, Ed. (The M.I.T. Press, Cambridge, 1965) pp 117-119. Review and evaluation of studies of carcinogenic action in laboratory animals: IARC Monographs 10, 205-210 (1976). Review: Ciegler et al., "Patulin, Penicillic Acid and Other Carcinogenic Lactones" in Microbial Toxins vol. VI, A. Ciegler et al., Eds. (Academic Press, New York, 1971) p 409-414.
Properties: Compact prisms or thick plates from ether or chloroform, mp 111.0°; also reported as 105-108° (Pohland). [a]D21 -6.2° (chloroform). uv max: 276.5 nm (Bergel). Sol in water and the common organic solvents except petr ether; very sol in ethyl or amyl acetate. Unstable in alkali with loss of biological activity. LD50 s.c. in mice: 10-15 mg/kg (Kinosita, Shikata).
Melting point: mp 111.0°
Optical Rotation: [a]D21 -6.2° (chloroform)
Absorption maximum: uv max: 276.5 nm (Bergel)
Toxicity data: LD50 s.c. in mice: 10-15 mg/kg (Kinosita, Shikata)
Derivative Type: Acetylpatulin
Molecular Formula: C9H8O5
Molecular Weight: 196.16
Percent Composition: C 55.11%, H 4.11%, O 40.78%
Properties: Prisms from 50% alcohol, mp 118-120°.
Melting point: mp 118-120°
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