1.02010-04-08 22:06:50 UTC2019-11-26 03:00:45 UTCFDB005766Citrinin Citrinin is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Citrinin can be found in barley and common wheat, which makes citrinin a potential biomarker for the consumption of these food products. Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminate long-stored food and it causes different toxic effects, like nephrotoxic, hepatotoxic and cytotoxic effects. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products .(-)-CitrininAntimycinCitriainCitrininFintrolC13H14O5250.2473250.084123558(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-6,8-dione642-15-9C[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1CInChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1JLWQFKMKUKQXMW-FSPLSTOPSA-N belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.BenzopyransOrganic compoundsOrganoheterocyclic compoundsBenzopyransAliphatic heteropolycyclic compoundsCyclohexenonesHydrocarbon derivativesKetene acetalsO-quinomethanesOrganic oxidesOxacyclic compoundsVinylogous acidsVinylogous estersAliphatic heteropolycyclic compoundBenzopyranCarbonyl groupCyclic ketoneCyclohexenoneHydrocarbon derivativeKetene acetal or derivativesKetoneO-quinomethaneOrganic oxideOrganic oxygen compoundOrganooxygen compoundOxacycleQuinomethaneVinylogous acidVinylogous esterlogp1.04logs-2.42solubility9.61e-01 g/lmelting_point178.5 oClogp1.88pka_strongest_acidic-1.2pka_strongest_basic-4.8iupac(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dioneaverage_mass250.2473mono_mass250.084123558smilesC[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1CformulaC13H14O5inchiInChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1inchikeyJLWQFKMKUKQXMW-FSPLSTOPSA-Npolar_surface_area83.83refractivity74.57polarizability24.53rotatable_bond_count0acceptor_count5donor_count2physiological_charge-2formal_charge0Specdb::MsMs1246936Specdb::MsMs1246937Specdb::MsMs1246938Specdb::MsMs1362271Specdb::MsMs1362272Specdb::MsMs136227348708BarleyType 1specificHordeum vulgare4513Common wheatType 1specificTriticum aestivum4565aldose reductase inhibitor40An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.