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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:41:35 UTC
Update Date2022-03-07 02:56:29 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 mustard, nut skin, and nutty tasting compound. trimethyloxazole is found, on average, in the highest concentration in kohlrabis. Trimethyloxazole has also been detected, but not quantified, in nuts and potato.
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

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point133.00 to 134.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2801 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.206 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.58131661259
DarkChem[M-H]-120.37931661259
DeepCCS[M+H]+132.14330932474
DeepCCS[M-H]-129.93530932474
DeepCCS[M-2H]-165.8630932474
DeepCCS[M+Na]+140.72530932474
AllCCS[M+H]+123.032859911
AllCCS[M+H-H2O]+118.232859911
AllCCS[M+NH4]+127.532859911
AllCCS[M+Na]+128.832859911
AllCCS[M-H]-121.632859911
AllCCS[M+Na-2H]-124.232859911
AllCCS[M+HCOO]-127.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimethyloxazoleCC1=NC(C)=C(C)O11173.5Standard polar33892256
TrimethyloxazoleCC1=NC(C)=C(C)O1819.0Standard non polar33892256
TrimethyloxazoleCC1=NC(C)=C(C)O1841.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Trimethyloxazole EI-B (Non-derivatized)splash10-07bf-9200000000-5af4aca2a8967058030b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimethyloxazole EI-B (Non-derivatized)splash10-07bf-9200000000-5af4aca2a8967058030b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9500000000-501b01fa8963c7b2bba92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03dl-9400000000-cd08a3e93a88886c92262015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Positive-QTOFsplash10-03di-0900000000-757ba2ec4dde5ee4e2842016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Positive-QTOFsplash10-03di-5900000000-ab9e137a6ff7a4ec62f82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Positive-QTOFsplash10-0udi-9000000000-742760726cabe09e35062016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Negative-QTOFsplash10-03xr-5900000000-92dd184d1d0a526dc4092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Negative-QTOFsplash10-02t9-9400000000-547692a7594c458abb272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Negative-QTOFsplash10-0006-9000000000-593d1a50051824d0258c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Negative-QTOFsplash10-03di-4900000000-7a3b553b5edff96467a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Negative-QTOFsplash10-0006-9200000000-07741d829f4be9e8c5122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Negative-QTOFsplash10-0006-9000000000-4fe36503d6ea48cb98ee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Positive-QTOFsplash10-03di-3900000000-725f385ddea6912f6e6d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Positive-QTOFsplash10-0i6u-9200000000-9f7b7c9aa2c2a5b8cf802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Positive-QTOFsplash10-0uxu-9000000000-256dd4c427a78407aa8d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1051411
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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.. .