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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:41:35 UTC
Update Date2019-07-23 06:31:37 UTC
HMDB IDHMDB0040148
Secondary Accession Numbers
  • HMDB40148
Metabolite Identification
Common NameTrimethyloxazole
DescriptionTrimethyloxazole belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole. Trimethyloxazole is a moderately basic compound (based on its pKa). Trimethyloxazole is a mustard, nut skin, and nutty tasting compound. Outside of the human body, trimethyloxazole is found, on average, in the highest concentration in kohlrabis. trimethyloxazole has also been detected, but not quantified in, nuts and potato. This could make trimethyloxazole a potential biomarker for the consumption of these foods.
Structure
Data?1563863497
Synonyms
ValueSource
2,4,5-TrimethyloxazoleHMDB
Oxazole, 2,4,5-trimethylHMDB
Trimethyl-oxazoleHMDB
Chemical FormulaC6H9NO
Average Molecular Weight111.1418
Monoisotopic Molecular Weight111.068413915
IUPAC Nametrimethyl-1,3-oxazole
Traditional Nametrimethyl-1,3-oxazole
CAS Registry Number20662-84-4
SMILES
CC1=NC(C)=C(C)O1
InChI Identifier
InChI=1S/C6H9NO/c1-4-5(2)8-6(3)7-4/h1-3H3
InChI KeyZRLDBDZSLLGDOX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassOxazoles
Direct Parent2,4,5-trisubstituted oxazoles
Alternative Parents
Substituents
  • 2,4,5-trisubstituted 1,3-oxazole
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.4 g/LALOGPS
logP1.7ALOGPS
logP0.37ChemAxon
logS-0.89ALOGPS
pKa (Strongest Basic)1.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.95 m³·mol⁻¹ChemAxon
Polarizability12.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bf-9200000000-5af4aca2a8967058030bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bf-9200000000-5af4aca2a8967058030bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9500000000-501b01fa8963c7b2bba9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-757ba2ec4dde5ee4e284Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-ab9e137a6ff7a4ec62f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-742760726cabe09e3506Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-5900000000-92dd184d1d0a526dc409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-547692a7594c458abb27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-593d1a50051824d0258cSpectrum
MSMass Spectrum (Electron Ionization)splash10-03dl-9400000000-cd08a3e93a88886c9226Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019845
KNApSAcK IDNot Available
Chemspider ID28060
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound30215
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marchand S, Almy J, de Revel G: The cysteine reaction with diacetyl under wine-like conditions: proposed mechanisms for mixed origins of 2-methylthiazole, 2-methyl-3-thiazoline, 2-methylthiazolidine, and 2,4,5-trimethyloxazole. J Food Sci. 2011 Aug;76(6):C861-8. doi: 10.1111/j.1750-3841.2011.02261.x. Epub 2011 Jul 15. [PubMed:21762161 ]
  2. Marchand S, de Revel G, Bertrand A: Approaches to wine aroma: release of aroma compounds from reactions between cysteine and carbonyl compounds in wine. J Agric Food Chem. 2000 Oct;48(10):4890-5. [PubMed:11052750 ]
  3. Xi J, Huang TC, Ho CT: Characterization of volatile compounds from the reaction of 3-hydroxy-2-butanone and ammonium sulfide model system. J Agric Food Chem. 1999 Jan;47(1):245-8. [PubMed:10563879 ]
  4. Pripis-Nicolau L, de Revel G, Bertrand A, Maujean A: Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions. J Agric Food Chem. 2000 Sep;48(9):3761-6. [PubMed:10995267 ]
  5. Keim H, de Revel G, Marchand S, Bertrand A: Method for determining nitrogenous heterocycle compounds in wine. J Agric Food Chem. 2002 Oct 9;50(21):5803-7. [PubMed:12358442 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .