Citrinine

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Structural formula
Structural formula of citrinine
General
Surname Citrinine
other names
  • (3 R , 4 S ) -4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3 H -2-benzopyran-7-carboxylic acid
  • Antimycin
Molecular formula C 13 H 14 O 5
Brief description

lemon yellow crystals

External identifiers / databases
CAS number 518-75-2
EC number 208-257-2
ECHA InfoCard 100,007,508
PubChem 219203
ChemSpider 10222475
Wikidata Q420354
properties
Molar mass 250.24 g mol −1
Physical state

firmly

Melting point

179 ° C

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health

danger

H and P phrases H: 301-311-331-351
P: 261-280-301 + 310-311
Toxicological data

112 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Citrinin is a mycotoxin (mold toxin) that is mainly produced by molds of the genus Penicillium and some species of Aspergillus . It is also produced in the leaves of Crotalaria crispata , a plant from the legume family . Chemically Citrinin one of the benzopyran - carboxylic acids .

Occurrence

Citrinine occurs naturally in countries with a temperate climate because the Penicillium species that produce it prefer lower temperatures. The mold toxin can be found in barley , oats , rye , wheat , corn flour , flaxseed meal , peanuts and the products made from them. Citrinine is often associated with ochratoxin .

Biological and toxic effects

Citrinin is a carcinogenic and mutation- causing substance as well as a potent kidney , liver and cell poison . It also has an antibiotic effect .

Individual evidence

  1. ↑ G. Haese: About Antimycin . In: Archives of Pharmacy . tape 296 , no. 4 , 1963, pp. 227 , doi : 10.1002 / ardp.19632960405 ( PDF ).
  2. ↑ a b entry on citrinine. In: Römpp Online . Georg Thieme Verlag, accessed on October 9, 2016.
  3. ↑ a b Citrinine data sheet from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
  4. ↑ Entry on citrinine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  5. ↑ U. Kück, M. Nowrousian, B. Hoff, I. Engh, J. Reiss: Molds: way of life, benefit, harm, control. 3rd edition, Springer, 2009, ISBN 978-3-540-88716-4 , pp. 166-167.

literature

  • Jürgen Reiss (editor): Mycotoxins in food . Gustav Fischer Verlag, Stuttgart, New York 1981.