Title: Aflatoxins M
Literature References: Highly toxic 4-hydroxylated aflatoxin B derivs found in the milk of cows fed toxic meal. Initial reports: Allcroft, Carnaghan, Vet. Rec. 75, 259 (1963). Isoln: De Iongh et al., Nature 202, 466 (1964); Allcroft et al., ibid. 209, 154 (1966). Isoln and structure of M1 and M2: C. W. Holzapfel, P. S. Steyn, Tetrahedron Lett. 1966, 2799. Total synthesis of M1: Büchi, Weinreb, J. Am. Chem. Soc. 91, 5408 (1969); 93, 746 (1971); G. Büchi et al., ibid. 103, 3497 (1981). Carcinogenicity studies: Wogan, Paglialunga, Food Cosmet. Toxicol. 12, 381 (1974). For general refs see Aflatoxins B.
Derivative Type: Aflatoxin M1
CAS Registry Number: 6795-23-9
CAS Name: (6aR,9aR)-2,3,6a,9a-Tetrahydro-9a-hydroxy-4-methoxycyclopenta[c]furo[3¢,2¢:4,5]furo[2,3-h][1]benzopyran-1,11-dione
Additional Names: 4-hydroxyaflatoxin B1
Molecular Formula: C17H12O7
Molecular Weight: 328.27
Percent Composition: C 62.20%, H 3.68%, O 34.12%
Properties: Crystals from methanol, mp 299° (dec). Exhibits blue-violet fluorescence. [a]D -280° (c = 0.1 in DMF). uv max (ethanol): 226, 265, 357 nm (e 23100, 11600, 19000). LD50 orally in day old Pekin ducklings: 16.6 mg/duckling (Holzapfel, Steyn).
Melting point: mp 299° (dec)
Optical Rotation: [a]D -280° (c = 0.1 in DMF)
Absorption maximum: uv max (ethanol): 226, 265, 357 nm (e 23100, 11600, 19000)
Toxicity data: LD50 orally in day old Pekin ducklings: 16.6 mg/duckling (Holzapfel, Steyn)
Derivative Type: Aflatoxin M2
CAS Registry Number: 6885-57-0
CAS Name: 2,3,6a,8,9,9a-Hexahydro-9a-hydroxy-4-methoxycyclopenta[c]furo[3¢,2¢:4,5]furo[2,3-h][1]benzopyran-1,11-dione
Additional Names: 4-hydroxyaflatoxin B2
Molecular Formula: C17H14O7
Molecular Weight: 330.29
Percent Composition: C 61.82%, H 4.27%, O 33.91%
Literature References: The 8,9-dihydro deriv of aflatoxin M1.
Properties: Exhibits violet fluorescence. Crystals from methanol-chloroform, mp 293° (dec). uv max (ethanol): 221, 264, 357 nm (e 20000, 10900, 21000). LD50 orally in day old Pekin ducklings: 62 mg/duckling (Holzapfel, Steyn).
Melting point: mp 293° (dec)
Absorption maximum: uv max (ethanol): 221, 264, 357 nm (e 20000, 10900, 21000)
Toxicity data: LD50 orally in day old Pekin ducklings: 62 mg/duckling (Holzapfel, Steyn)
CAUTION: The aflatoxins are listed as known human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-8. |