3-Acetyldeoxynivalenol
Basic information
- CAS
50722-38-8- Standard SMILES
CC(=O)O[C@@H]1C[C@]2(C)[C@@]3(CO)[C@H](O)C(=O)C(C)=C[C@H]3O[C@H]1[C@@]21CO1- InChIKey
ADFIQZBYNGPCGY-HTJQZXIKSA-N- Molecular formula
- C17H22O7
- Average molar mass
- 338.4 g/mol
- Monoisotopic mass
- 338.13655304
Overview
3-acetyldeoxynivalenol is a trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-3. A skin and eye irritant, along with its 15-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants. It has a role as a mycotoxin and an epitope. It is functionally related to a deoxynivalenol.
Names & identifiers
- Preferred name
- 3-Acetyldeoxynivalenol
- IUPAC
- [(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate
- English name
- 3-Acetyldeoxynivalenol
- Molecular formula
- C17H22O7
- Molecular weight
- 338.35
Names & synonyms
3-Acetyldeoxynivalenol50722-38-83-Acetyl dondeoxynivalenol 3-acetateDeoxynivalenol monoacetate3-ADONDehydronivalenol monoacetateDTXSID60891850CHEBI:146195838JJ2425YNSC-267036acetylDON
Show more names
3-ACDON3-olNSC 2670363-acetyldonDON-3-acetate3α-Acetylvomitoxinreference material3ALPHA-ACETYLVOMITOXIN
[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate((1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-10-yl) acetateRefChem:92824DTXCID3010312713-Acetyl Deoxynivalenol3-Acetyl-deoxynivalenol3-acetyl-DON7alpha,15-dihydroxy-8-oxo-12,13-epoxytrichothec-9-en-3alpha-yl acetate
Database identifiers
- CAS
50722-38-8
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 657
Experimental & physicochemical properties
Collision Cross Section
196 Ų [M+H3C2O2]- [CCS Type: TW; Method: calibrated with polyalanine]
183.83 Ų [M+Na]+
Physicochemical properties
- Melting point
- 185.75 °C · 185.75°C
- Boiling point
- 394.5 °C · 394.5°C (rough estimate)
- Density
- 1.2179 · 1.2179 (rough estimate)
- refractive index
- 1.479 · 1.4790 (estimate)
- Flash point
- 2 °C · 2 °C
- storage temp.
- -20 °C · -20°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
- pka
- 11.84 · 11.84±0.70(Predicted)
- form
- powder
- biological source
- Fusarium roseum
- Major Application
- cleaning productscosmeticsfood and beveragespersonal care
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Toxicology
Treatment
There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Administer charcoal as a slurry in case of acute oral exposure. In case of inhalation: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (A704)
Health Effects
Trichothecenes have multiorgan effects including anoerxia and weight loss, growth retardation, nervous disorders, cardiovascular alterations, immunodepression, hemostatic derangements, skin toxicity, decreased reproductive capacity, bone marrow damage, and alimentary toxic aleukia. (L1948, L1949, A2964)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Trichothecenes are lipophilic and thus easily absorbed through the skin, gut, and pulmonary mucosa. They are metabolized mainly by cytochrome P-450 and trichothecene-specific carboxylesterase activity in the liver, although other tissues such as the kidney, spleen, and intestine also show some metabolic activity. Trichothecenes are metabolically transformed to less toxic metabolites by such reactions as hydrolysis, hydroxylation, de-epoxidation, and glucuronidation. Metabolites are excreted in the urine and feces. (L1910, L1949)
Uses & manufacturing
Uses
Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948)
Applications
Uses3-Acetyldeoxynivalenol solution may be used as an analytical reference standard for the quantification of the analyte in bovine milk using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS).
Uses3-Acetyldeoxynivalenol is a trichothecene mycotoxin that is produced in a plant-pathogenic fungus, Fusarium graminearum Schwabe.
General Description3-Acetyldeoxynivalenol is a trichothecene mycotoxin, secreted by Fusarium species. It stimulates the activation of c-Jun N-terminal kinase (JNK)/ p38 mitogen-activated protein kinases and prevents protein synthesis. 3-Acetyldeoxynivalenol is a weak inducer of apoptosis.
Additional notes
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…