Vomitoxin information

Vomitoxin
Names
	IUPAC name 3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
	Systematic IUPAC name (2R,2′S,3R,5R,5aR,6S,9aR)-3,8-Dihydroxy-5a-(hydroxymethyl)-5,6-dimethylspiro[[2,5]methano[1]benzoxepine-10,2′-oxiran]-7(6H)-one
	Other names ; Deoxynivalenol (DON); Vomitoxin
Identifiers
CAS Number	51481-10-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10022;
ChEMBL	ChEMBL513300 ;
ChemSpider	36584 ;
ECHA InfoCard	100.129.971
KEGG	C09747 ;
PubChem CID	40024;
UNII	JT37HYP23V ;
CompTox Dashboard (EPA)	DTXSID3020382 ;
	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/t8-,9-,11-,12-,13-,14-,15+/m1/s1 Key: LINOMUASTDIRTM-QGRHZQQGSA-N ; InChI=1/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/t8-,9-,11-,12-,13-,14-,15+/m1/s1 Key: LINOMUASTDIRTM-QGRHZQQGBF;
	SMILES CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@]([C@]2([C@H](O)C1=O)CO)([C@]13OC1)C;
Properties
Chemical formula	C15H20O6
Molar mass	296.319 g·mol−1
Related compounds
Related compounds	nivalenol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, 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 or fusarium ear blight in corn. 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. However, increased amount of moisture towards harvest time has been associated with lower amount of vomitoxin in wheat grain due to leaching of toxins.^[1] Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use.^[2] It occurs abundantly in grains in Norway due to heavy rainfall.^[3]

F. graminearum grows optimally at a temperature of 25 °C and at a water activity above 0.88. F. culmorum grows optimally at 21 °C and at a water activity above 0.87. The geographical distribution of the two species appears to be related to temperature, F. graminearum being the more common species occurring in warmer climates. Deoxynivalenol has been implicated in incidents of mycotoxicoses in both humans and farm animals.

^ Gautam, P. and Dill-Macky, R. 2012. Impact of moisture, host genetics and Fusarium graminearum isolates on Fusarium head blight development and trichothecene accumulation in spring wheat. Mycotoxin Research 28 (1) doi:10.1007/s12550-011-0115-6 [1]
^ Beyer M, Klix MB, Klink H, Verreet J-A (2006): Quantifying the effects of previous crop, tillage, cultivar and triazole fungicides on the deoxynivalenol content of wheat grain – a review. Journal of Plant Diseases and Protection 113: 241–246. [2]
^ "Archived copy" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2015-03-29.{{cite web}}: CS1 maint: archived copy as title (link)

[1] Gautam, P. and Dill-Macky, R. 2012. Impact of moisture, host genetics and Fusarium graminearum isolates on Fusarium head blight development and trichothecene accumulation in spring wheat. Mycotoxin Research 28 (1) doi:10.1007/s12550-011-0115-6 [1]

[2] Beyer M, Klix MB, Klink H, Verreet J-A (2006): Quantifying the effects of previous crop, tillage, cultivar and triazole fungicides on the deoxynivalenol content of wheat grain – a review. Journal of Plant Diseases and Protection 113: 241–246. [2]

[3] "Archived copy" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2015-03-29.{{cite web}}: CS1 maint: archived copy as title (link)

Vomitoxin information

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Names

IUPAC name 3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
Systematic IUPAC name (2R,2′S,3R,5R,5aR,6S,9aR)-3,8-Dihydroxy-5a-(hydroxymethyl)-5,6-dimethylspiro[[2,5]methano[1]benzoxepine-10,2′-oxiran]-7(6H)-one
Other names Deoxynivalenol (DON) Vomitoxin
Identifiers
CAS Number	51481-10-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10022
ChEMBL	ChEMBL513300^Y
ChemSpider	36584^Y
ECHA InfoCard	100.129.971
KEGG	C09747^N
PubChem CID	40024
UNII	JT37HYP23V^N
CompTox Dashboard (EPA)	DTXSID3020382
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/t8-,9-,11-,12-,13-,14-,15+/m1/s1^Y Key: LINOMUASTDIRTM-QGRHZQQGSA-N^Y InChI=1/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/t8-,9-,11-,12-,13-,14-,15+/m1/s1 Key: LINOMUASTDIRTM-QGRHZQQGBF
SMILES CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@]([C@]2([C@H](O)C1=O)CO)([C@]13OC1)C
Properties
Chemical formula	C₁₅H₂₀O₆
Molar mass	296.319 g·mol⁻¹
Related compounds
Related compounds	nivalenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references