Patulin

ID 2: 536

Toxin: y

Trivial name:

Patulin (6CI); 4-​Hydroxy-​4H-​furo[3,​2-​c]​pyran-​2(6H)​-​one; Acetic acid, (2,​4-​dihydroxy-​2H-​pyran-​3(6H)​-​ylidene)​-​, 3,​4-​lactone; Clairformin; Clavacin; Clavatin; Claviformin; DL-​Patulin; Expansin; Expansin (antibiotic); Expansine; Gigantin; Leucopin; Mycoin; Mycoin C; Mycoin C3; NSC 32951; NSC 8120; Patuline; Penicidin; Terinin

Systematic name:

4H-​Furo[3,​2-​c]​pyran-​2(6H)​-​one, 4-​hydroxy-

Molecular formulae: 

C₇H₆O₄

Molecular weight: 154.12

Chemical abstract number: 149-29-1

Chemical type: Hydroxyfuropyranone

Literature reference:

• Production of two antibacterial substances, fumigacin and clavacin. Waksman, Selman A.; Horning, Elizabeth S.; Spencer, Ernest L. Science (Washington, DC, United States) (1942), 96, 202-3.
  Mycotoxin production and evolutionary relationships among species of Aspergillus section Clavati. Varga, Janos; Rigo, Krisztina; Molnar, Janos; Toth, Beata; Szencz, Szilvia; Teren, Jozsef; Kozakiewicz, Zofia. Antonie van Leeuwenhoek (2003), 83(2), 191-200
  Antibiotics from Moulds. J. KENT & N. G. HEATLEY. Nature 156, 295-296 (08 September 1945)
  Production of patulin by Micromycetes. Steiman R., Seiglle-Murandi F., Sage L. and Krivobok S. 1989. Mycopathologia 105: 129–133.
  Scott P.M. 1974. Patulin. In: Purchase I.F.H. (ed.), Mycotodins. Elsevier, Amsterdam, pp. 383–403
  

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/4696
• http://www.sciencemag.org/content/96/2487/202
• http://www.nature.com/nature/journal/v156/n3958/pdf/156295b0.pdf
• http://link.springer.com/article/10.1023/A:1023355707646
• http://download.springer.com/static/pdf/964/art%253A10.1007%252FBF00437244.pdf?auth66=1407085414_5c62dd6756b6e1b3c983d1a59508f24a&ext=.pdf

Aspergillus Species known to produce this metabolite:

• /species/clavatus
• /species/a-terreus
• /species/a-giganteus
• /species/longivesica
• /species/candidus
• /species/a-amstelodami
• /species/a-echinulatus
• /species/a-fumigatus
• /species/a-parasiticus
• /species/a-repens
• /species/a-variecolor
• /species/a-versicolor
• /species/a-carneus
• /species/a-niveus
• /species/a-pallidus

Toxicity:

The oral LD50 in rats and mice is 30-35 mg/kg body-weight causing liver, spleen and kidney damage with oedema and haemorrhaging. It has been suspected as carcinogenic for many years and recent assessments of chronic toxicity have not conclusively removed this possibility.

Date uploaded: 2008-01-25 00:58:40

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Mycotoxin & Metabolites

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Aspergillus species produce a large number of secondary metabolites, sometimes referred to as extrolites. We attempt to list them all here and we also collect published papers.

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