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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:41:35 UTC

Update Date

2023-02-21 17:27:46 UTC

HMDB ID

HMDB0040148

Secondary Accession Numbers

HMDB40148

Metabolite Identification

Common Name

Trimethyloxazole

Description

Trimethyloxazole 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4,5-Trimethyloxazole	HMDB
Oxazole, 2,4,5-trimethyl	HMDB
Trimethyl-oxazole	HMDB

Chemical Formula

C₆H₉NO

Average Molecular Weight

111.1418

Monoisotopic Molecular Weight

111.068413915

IUPAC Name

trimethyl-1,3-oxazole

Traditional Name

trimethyl-1,3-oxazole

CAS Registry Number

20662-84-4

SMILES

CC1=NC(C)=C(C)O1

InChI Identifier

InChI=1S/C6H9NO/c1-4-5(2)8-6(3)7-4/h1-3H3

InChI Key

ZRLDBDZSLLGDOX-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

2,4,5-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0040148)
Cytoplasm (HMDB: HMDB0040148)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040148)

Source

Exogenous

Food

Food (HMDB: HMDB0040148)

Vegetable

Root vegetable

Kohlrabi (FooDB: FOOD00033)

Tuber

Potato (FooDB: FOOD00175)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0040148)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040148)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	133.00 to 134.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2801 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.206 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.4 g/L	ALOGPS
logP	1.7	ALOGPS
logP	0.37	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.95 m³·mol⁻¹	ChemAxon
Polarizability	12.63 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	122.581	31661259
DarkChem	[M-H]-	120.379	31661259
DeepCCS	[M+H]+	132.143	30932474
DeepCCS	[M-H]-	129.935	30932474
DeepCCS	[M-2H]-	165.86	30932474
DeepCCS	[M+Na]+	140.725	30932474
AllCCS	[M+H]+	123.0	32859911
AllCCS	[M+H-H2O]+	118.2	32859911
AllCCS	[M+NH4]+	127.5	32859911
AllCCS	[M+Na]+	128.8	32859911
AllCCS	[M-H]-	121.6	32859911
AllCCS	[M+Na-2H]-	124.2	32859911
AllCCS	[M+HCOO]-	127.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethyloxazole	CC1=NC(C)=C(C)O1	1173.5	Standard polar	33892256
Trimethyloxazole	CC1=NC(C)=C(C)O1	819.0	Standard non polar	33892256
Trimethyloxazole	CC1=NC(C)=C(C)O1	841.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trimethyloxazole EI-B (Non-derivatized)	splash10-07bf-9200000000-5af4aca2a8967058030b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimethyloxazole EI-B (Non-derivatized)	splash10-07bf-9200000000-5af4aca2a8967058030b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9500000000-501b01fa8963c7b2bba9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03dl-9400000000-cd08a3e93a88886c9226	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Positive-QTOF	splash10-03di-0900000000-757ba2ec4dde5ee4e284	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Positive-QTOF	splash10-03di-5900000000-ab9e137a6ff7a4ec62f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Positive-QTOF	splash10-0udi-9000000000-742760726cabe09e3506	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Negative-QTOF	splash10-03xr-5900000000-92dd184d1d0a526dc409	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Negative-QTOF	splash10-02t9-9400000000-547692a7594c458abb27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-593d1a50051824d0258c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Negative-QTOF	splash10-03di-4900000000-7a3b553b5edff96467a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Negative-QTOF	splash10-0006-9200000000-07741d829f4be9e8c512	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-4fe36503d6ea48cb98ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 10V, Positive-QTOF	splash10-03di-3900000000-725f385ddea6912f6e6d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 20V, Positive-QTOF	splash10-0i6u-9200000000-9f7b7c9aa2c2a5b8cf80	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyloxazole 40V, Positive-QTOF	splash10-0uxu-9000000000-256dd4c427a78407aa8d	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019845

KNApSAcK ID

Not Available

Chemspider ID

28060

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

30215

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1051411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Trimethyloxazole (HMDB0040148)

MOL for HMDB0040148 (Trimethyloxazole)

3D MOL for HMDB0040148 (Trimethyloxazole)

3D SDF for HMDB0040148 (Trimethyloxazole)

3D-SDF for HMDB0040148 (Trimethyloxazole)

PDB for HMDB0040148 (Trimethyloxazole)

3D PDB for HMDB0040148 (Trimethyloxazole)

SMILES for HMDB0040148 (Trimethyloxazole)

INCHI for HMDB0040148 (Trimethyloxazole)

Structure for HMDB0040148 (Trimethyloxazole)

3D Structure for HMDB0040148 (Trimethyloxazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra