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Skeletal formula of citrinin
Space-filling model of the citrinin molecule
IUPAC name
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
Other names
518-75-2 YesY
ChemSpider 10222475 N
Jmol interactive 3D Image
KEGG C16765 N
PubChem 54680783
Molar mass 250.24
Appearance Lemon-yellow needles
Melting point 175 °C (347 °F; 448 K) (decomposes)
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 mold rice supplements.[3]


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[edit]

Citrinin is produced by a variety of fungi, including:


  1. ^ Merck Index, 11th Edition, 2329.
  2. ^ Hetherington, A. C.; Raistrick, H. (1931). "On the Production and Chemical Constitution of a New Yellow Colouring Matter, Citrinin, Produced from Glucose by Penicillium citrinum Thom". Philosophical Transactions of the Royal Society B: Biological Sciences 220 (468–473): 269–95. doi:10.1098/rstb.1931.0025. ISSN 0962-8436. 
  3. ^ Gordon, R. Y.; Cooperman, T.; Obermeyer, W.; Becker, D. J. (2010). "Marked Variability of Monacolin Levels in Commercial Red Mold Rice Products: Buyer Beware!". Archives of Internal Medicine 170 (19): 1722–7. doi:10.1001/archinternmed.2010.382. PMID 20975018. 
  4. ^ Bennett, J. W.; Klich, M. (2003). "Mycotoxins". Clinical Microbiology Reviews 16 (3): 497–516. doi:10.1128/CMR.16.3.497-516.2003. PMC 164220. PMID 12857779. 
  5. ^ Peraica, M.; Radic, B.; Lucic, A.; Pavlovic, M. (1999). "Toxic Effects of Mycotoxins in Humans". Bulletins of the World Health Organization 77 (9): 754-766. 
  6. ^ Kushiro, Masayo (2015). "Historical review of researches on yellow rice and mycotoxigenic fungi adherent to rice in Japan". Mycotoxins 65 (1): 19–23. doi:10.2520/myco.65.19. 
  7. ^ Boonen, J.; Malysheva, S. V.; Taevernier, L.; Diana di Mavungu, J.; de Saeger, S.; de Spiegeleer, B. (2012). "Human skin penetration of selected model mycotoxins". Toxicology 301 (1–3): 21–32. doi:10.1016/j.tox.2012.06.012. PMID 22749975. 
  8. ^ "Citrinin". Fermentek.