Title: Aflatoxins G
Literature References: Toxic metabolites of fungi Aspergillus flavus Link ex Fries and Aspergillus parasiticus. Total synthesis of G1: Büchi, Weinreb, J. Am. Chem. Soc. 93, 746 (1971). Physical and chemical data: Hartley et al., Nature 198, 1056 (1963); Asao, J. Am. Chem. Soc. 87, 882 (1965). Toxicity data: R. B. A. Carnaghan et al., Nature 200, 1101 (1963). For general refs see Aflatoxins B.
Derivative Type: Aflatoxin G1
CAS Registry Number: 1165-39-5
CAS Name: (7aR,10aS)-3,4,7a,10a-Tetrahydro-5-methoxy-1H,12H-furo[3¢,2¢:4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione
Molecular Formula: C17H12O7
Molecular Weight: 328.27
Percent Composition: C 62.20%, H 3.68%, O 34.12%
Properties: Crystals, mp 244-246°. Exhibits green fluorescence. [a]D -556° (chloroform). uv max (ethanol): 243, 257, 264, 362 nm (e 11500, 9900, 10000, 16100). LD50 orally in day old duckling: 39.2 mg/50 gm body wt (Carnaghan).
Melting point: mp 244-246°
Optical Rotation: [a]D -556° (chloroform)
Absorption maximum: uv max (ethanol): 243, 257, 264, 362 nm (e 11500, 9900, 10000, 16100)
Toxicity data: LD50 orally in day old duckling: 39.2 mg/50 gm body wt (Carnaghan)
Derivative Type: Aflatoxin G2
CAS Registry Number: 7241-98-7
CAS Name: (7aR,10aS)-3,4,7a,9,10,10a-Hexahydro-5-methoxy-1H,12H-furo[3¢,2¢:4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione
Molecular Formula: C17H14O7
Molecular Weight: 330.29
Percent Composition: C 61.82%, H 4.27%, O 33.91%
Literature References: The 9,10-dihydro deriv of aflatoxin G1.
Properties: Crystals, mp 237-240°. Exhibits green-blue fluorescence. [a]D -473° (c = 0.084 in chloroform). uv max (ethanol): 265, 363 nm (e 9700, 21000). LD50 orally in day old duckling: 172.5 mg/50 gm body wt (Carnaghan).
Melting point: mp 237-240°
Optical Rotation: [a]D -473° (c = 0.084 in chloroform)
Absorption maximum: uv max (ethanol): 265, 363 nm (e 9700, 21000)
Toxicity data: LD50 orally in day old duckling: 172.5 mg/50 gm body wt (Carnaghan)
CAUTION: The aflatoxins are listed as known human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-8. |