Citrinin

Citrinin[1]
IUPAC name (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
Other names Antimycin
Identifiers
CAS number	518-75-2 Y
PubChem	54680783
ChemSpider	10222475 N
UNII	3S697X6SNZ N
KEGG	C16765 N
ChEMBL	CHEMBL510139 N
Jmol-3D images	{{#if:O=C2C(C(O)=O)=C(O)C1=CO[C@H](C)[C@@H](C)C1=C2C|Image 1
SMILES O=C2C(C(O)=O)=C(O)C1=CO[C@H](C)[C@@H](C)C1=C2C
InChI 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
Properties
Molecular formula	C13H14O5
Molar mass	250.25 g mol−1
Appearance	Lemon-yellow needles
Melting point	175 °C (decomp.)
Solubility in water	Insoluble
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 yellow rice fever in humans.

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.^[5] 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:

• Aspergillus niveus
• Aspergillus ochraceus
• Aspergillus oryzae
• Aspergillus terreus
• Monascus ruber
• Monascus purpureus
• Penicillium citrinum^[6]
• Penicillium camemberti

References

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): 269–295. 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 Yeast Rice Products: Buyer Beware!". Archives of Internal Medicine 170 (19): 1722–1727. 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. ↑ Boonen, Jente; Malysheva, Svetlana V.; Taevernier, Lien; Diana Di Mavungu, José; De Saeger, Sarah; De Spiegeleer, Bart (2012). "Human skin penetration of selected model mycotoxins". Toxicology 301 (1–3): 21–32. doi:10.1016/j.tox.2012.06.012. PMID 22749975. 
6. ↑ citrinin product page from Fermentek