Flavoglaucin

ID 2: 181

Toxin: n

Trivial name:

Benzaldehyde, 2-​heptyl-​3,​6-​dihydroxy-​5-​(3-​methyl-​2-​butenyl)​- (9CI); Gentisaldehyde, 6-​heptyl-​3-​(3-​methyl-​2-​butenyl)​- (6CI,​7CI,​8CI); Flavoglaucin; Flavoglaucine

Systematic name:

Benzaldehyde, 2-heptyl-3,6-dihydroxy-5-(3-methyl-2-butenyl)-

Molecular formulae: 

C19H28O3

Molecular weight: 304.42

Chemical abstract number: 523-73-9

Literature reference:

  • The biochemistry of micro-organisms. XL. The crystalline pigments of species in the Aspergillus glaucus series. Gould, Bernard S.; Raistrick, Harold. Biochemical Journal (1934), 28, 1640-56.
    Chemical investigations of Aspergillus echinulatus. IV. Some unsaturated ketonic derivatives of hydroquinone with structures similar to flavoglaucin. Quilico, A.; Cardani, C.; Panizzi, L. Gazzetta Chimica Italiana (1950), 80, 325-46.
    Growth and pigmentation of Aspergillus umbrosus. Carbone, Louis J.; Johnson, G. T. Mycologia (1964), 56, 185-95.
    New metabolic products of Aspergillus flavus. II. Asperflavin, anhydroasperflavin, an 5,​7-​dihydroxy-​4-​methylphthalide. Grove, John Frederick. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1972), (19), 2406-11.
    Isoprene-​containing metabolites of Aspergillus amstelodami. Allen, Charles M., Jr. Canadian Journal of Microbiology (1972), 18(8), 1275-82.
    Synthesis of aromatic compounds by Eurotium echinulatum. Saiz-Jimenez, C.; Haider, K. Anales de Edafologia y Agrobiologia (1975), 34(11-12), 931-41
    Isolation and structures of two new metabolites from Aspergillus ruber. Hamasaki, Takashi; Fukunaga, Mamoru; Kimura, Yasuo; Hatsuda, Yuichi. Agricultural and Biological Chemistry (1980), 44(7), 1685-7.
    Structure of a new metabolite, dihydroauroglaucin, produced by Aspergillus chevalieri. Hamasaki, Takashi; Kimura, Yasuo; Hatsuda, Yuichi; Nagao, Minako. Agricultural and Biological Chemistry (1981), 45(1), 313-14.
    Flavoglaucin, a metabolite of Eurotium chevalieri, its antioxidation and synergism with tocopherol. Ishikawa, Yukihiro; Morimoto, Kyozo; Hamasaki, Takashi. JAOCS, J. Am. Oil Chem. Soc. (1984), 61(12), 1864-8.
    Antioxidants produced by Eurotium herbariorum of filamentous fungi used for the manufacture of karebushi, dried bonito (Katsuobushi). Miyake, Yoshiaki; Ito, Chihiro; Itoigawa, Masataka; Osawa, Toshihiko. Bioscience, Biotechnology, and Biochemistry (2009), 73(6), 1323-1327

References URL: 

Aspergillus Species known to produce this metabolite:

Structure image:  

flavoglaucinweb

Date uploaded: 2008-07-07 16:08:30

Mycotoxin & Metabolites

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