Citrinin

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Citrinin[1]
Skeletal formula of citrinin
Space-filling model of the citrinin molecule
Names
IUPAC name
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
Other names
Antimycin
Identifiers
518-75-2 YesY
ChEMBL ChEMBL510139 N
ChemSpider 10222475 N
Jmol 3D model Interactive image
KEGG C16765 N
PubChem 54680783
UNII 3S697X6SNZ N
  • InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1 N
    Key: CQIUKKVOEOPUDV-IYSWYEEDSA-N N
  • InChI=1/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
    Key: CQIUKKVOEOPUDV-IYSWYEEDBV
  • O=C2C(C(O)=O)=C(O)C1=CO[C@H](C)[C@@H](C)C1=C2C
Properties
C13H14O5
Molar mass 250.24
Appearance Lemon-yellow needles
Melting point 175 °C (347 °F; 448 K) (decomposes)
Insoluble
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Citrinin is a mycotoxin originally isolated in 1931 by Hetherington and Raistrick from a culture of Penicillium citrinum.[2] It has since been found to be produced by a variety of other fungi that are found or used in the production of human foods, such as grain, cheese, sake, and red pigments. Citrinin has also been found in commercial red yeast rice supplements.[3]

Toxicity

Citrinin acts as a nephrotoxin in all species in which it has been tested, but its acute toxicity varies.[4] It causes mycotoxic nephropathy in livestock and has been implicated as a cause of Balkan nephropathy and a form of cardiac beriberi (often referred to as "yellow rice disease" or "shoshin-kakke") in humans.[5][6]

Citrinin is used as a reagent in biological research. It induces mitochondrial permeability pore opening and inhibits respiration by interfering with complex III of the respiratory chain.

Citrinin can permeate through the human skin.[7] Although no significant health risk is expected after dermal contact in agricultural or residential environments, dermal exposure should nevertheless be limited.

Citrinin producers

Citrinin is produced by a variety of fungi, including:

References

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  1. ↑ Merck Index, 11th Edition, 2329.
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