1.0 2010-04-08 22:11:36 UTC 2019-11-26 03:11:06 UTC FDB015009 Deoxynivalenol Production by Fusarium graminearum and Fusarium roseum, responsible for headblight in cereals Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpeneoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and maize, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum (Gibberella zeae) and F. culmorum, both of which are important plant pathogens which cause Fusarium head blight in wheat and Gibberella ear rot in maize. A direct relationship between the incidence of Fusarium head blight and contamination of wheat with deoxynivalenol has been established. The incidence of Fusarium head blight is strongly associated with moisture at the time of flowering (anthesis), and the timing of rainfall, rather than the amount, is the most critical factor. Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use. Deoxynivalenol is found in cereals and cereal products. Deoxynivalenol Rd toxin Vomitoxin C15H20O6 296.3157 296.125988372 3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one 3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one 51481-10-8 CC1=CC2OC3C(O)CC(C)(C33CO3)C2(CO)C(O)C1=O InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3 LINOMUASTDIRTM-UHFFFAOYSA-N belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Trichothecenes Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic heteropolycyclic compounds Cyclic alcohols and derivatives Cyclohexenones Dialkyl ethers Epoxides Hydrocarbon derivatives Organic oxides Oxacyclic compounds Oxanes Oxepanes Primary alcohols Secondary alcohols Alcohol Aliphatic heteropolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Dialkyl ether Ether Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxepane Oxirane Primary alcohol Secondary alcohol Trichothecene skeleton logp -0.76 ALOGPS logs -0.92 ALOGPS solubility 3.60e+01 g/l ALOGPS melting_point Mp 151-153° logp -0.97 ChemAxon pka_strongest_acidic 12.68 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one ChemAxon average_mass 296.3157 ChemAxon mono_mass 296.125988372 ChemAxon smiles CC1=CC2OC3C(O)CC(C)(C33CO3)C2(CO)C(O)C1=O ChemAxon formula C15H20O6 ChemAxon inchi InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3 ChemAxon inchikey LINOMUASTDIRTM-UHFFFAOYSA-N ChemAxon polar_surface_area 99.52 ChemAxon refractivity 71.62 ChemAxon polarizability 29.3 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16872 Specdb::CMs 44755 Specdb::CMs 118701 Specdb::CMs 129190 Specdb::CMs 147015 Specdb::CMs 147017 Specdb::CMs 147019 Specdb::CMs 147021 Specdb::CMs 147023 Specdb::CMs 147024 Specdb::CMs 147026 Specdb::CMs 166619 Specdb::CMs 279570 Specdb::CMs 817342 Specdb::CMs 817343 Specdb::CMs 817344 Specdb::CMs 817345 Specdb::CMs 817346 Specdb::CMs 817347 Specdb::CMs 817348 Specdb::CMs 817349 Specdb::CMs 817350 Specdb::CMs 817351 Specdb::CMs 817352 Specdb::CMs 817353 Specdb::NmrOneD 133978 Specdb::NmrOneD 133979 Specdb::NmrOneD 133980 Specdb::NmrOneD 133981 Specdb::NmrOneD 133982 Specdb::NmrOneD 133983 Specdb::NmrOneD 133984 Specdb::NmrOneD 133985 Specdb::NmrOneD 133986 Specdb::NmrOneD 133987 Specdb::NmrOneD 133988 Specdb::NmrOneD 133989 Specdb::NmrOneD 133990 Specdb::NmrOneD 133991 Specdb::NmrOneD 133992 Specdb::NmrOneD 133993 Specdb::NmrOneD 133994 Specdb::NmrOneD 133995 Specdb::NmrOneD 133996 Specdb::NmrOneD 133997 Specdb::MsMs 11714 Specdb::MsMs 11715 Specdb::MsMs 11716 Specdb::MsMs 18386 Specdb::MsMs 18387 Specdb::MsMs 18388 Specdb::MsMs 2226445 Specdb::MsMs 2228768 Specdb::MsMs 2231096 Specdb::MsMs 2233128 Specdb::MsMs 2233487 Specdb::MsMs 2235429 Specdb::MsMs 2717907 Specdb::MsMs 2717908 Specdb::MsMs 2717909 Specdb::MsMs 2964045 Specdb::MsMs 2964046 Specdb::MsMs 2964047 HMDB36156 #<Reference:0x000055ce30a7aae0> Breakfast cereal Type 2 specific Cereals and cereal products Unknown generic