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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:07:19 UTC

Update Date

2023-02-21 17:26:08 UTC

HMDB ID

HMDB0037865

Secondary Accession Numbers

HMDB37865

Metabolite Identification

Common Name

2-Ethyl-4,5-dimethyloxazole

Description

2-Ethyl-4,5-dimethyloxazole 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. 2-Ethyl-4,5-dimethyloxazole is a creamy, earthy, and green tasting compound. 2-Ethyl-4,5-dimethyloxazole has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, potatos (Solanum tuberosum), and robusta coffees (Coffea canephora). This could make 2-ethyl-4,5-dimethyloxazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Ethyl-4,5-dimethyloxazole.

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-Ethyl-4,5-dimethyl oxazole	HMDB
2-Ethyl-4,5-dimethyl-1,3-oxazole	HMDB
2-Ethyl-4,5-dimethyl-oxazole	HMDB
4,5-Dimethyl-2-ethyloxazole	HMDB
FEMA 3672	HMDB

Chemical Formula

C₇H₁₁NO

Average Molecular Weight

125.1683

Monoisotopic Molecular Weight

125.084063979

IUPAC Name

2-ethyl-4,5-dimethyl-1,3-oxazole

Traditional Name

2-ethyl-4,5-dimethyl-1,3-oxazole

CAS Registry Number

53833-30-0

SMILES

CCC1=NC(C)=C(C)O1

InChI Identifier

InChI=1S/C7H11NO/c1-4-7-8-5(2)6(3)9-7/h4H2,1-3H3

InChI Key

LCYOFVYHDBWYSI-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: HMDB0037865)
Cytoplasm (HMDB: HMDB0037865)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037865)

Source

Exogenous

Exogenous (HMDB: HMDB0037865)

Food

Food (HMDB: HMDB0037865)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Plant (HMDB: HMDB0037865)
Coffea (HMDB: HMDB0037865)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037865)

Biological role

Nutrient (HMDB: HMDB0037865)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	60.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	949.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.715 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.89 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.07	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.83	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	1	ChemAxon
Refractivity	35.58 m³·mol⁻¹	ChemAxon
Polarizability	14.63 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]+	127.2	31661259
DarkChem	[M-H]-	125.327	31661259
DeepCCS	[M+H]+	135.301	30932474
DeepCCS	[M-H]-	132.751	30932474
DeepCCS	[M-2H]-	169.254	30932474
DeepCCS	[M+Na]+	144.274	30932474
AllCCS	[M+H]+	126.5	32859911
AllCCS	[M+H-H2O]+	121.8	32859911
AllCCS	[M+NH4]+	130.8	32859911
AllCCS	[M+Na]+	132.0	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.18 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1648 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1181.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	480.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	300.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	411.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	563.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1004.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1187.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	479.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	46.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-4,5-dimethyloxazole	CCC1=NC(C)=C(C)O1	1236.2	Standard polar	33892256
2-Ethyl-4,5-dimethyloxazole	CCC1=NC(C)=C(C)O1	910.2	Standard non polar	33892256
2-Ethyl-4,5-dimethyloxazole	CCC1=NC(C)=C(C)O1	909.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Ethyl-4,5-dimethyloxazole EI-B (Non-derivatized)	splash10-0706-9500000000-fb0d7c2217cb671cbeea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Ethyl-4,5-dimethyloxazole EI-B (Non-derivatized)	splash10-0706-9500000000-fb0d7c2217cb671cbeea	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-4,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-9600000000-38719fbd86e323cc4159	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-4,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01r6-9600000000-1dec1c13983334178eef	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 - 2-Ethyl-4,5-dimethyloxazole 10V, Positive-QTOF	splash10-004i-0900000000-916eee99ba4e485eb38b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 20V, Positive-QTOF	splash10-004i-6900000000-7a411f5abbe3146770dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 40V, Positive-QTOF	splash10-0udi-9000000000-92a3385d1157b866561d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 10V, Negative-QTOF	splash10-00di-3900000000-57a0dc105551d2b1c1fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 20V, Negative-QTOF	splash10-0089-9300000000-8190f2b532708d169487	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-f5da892dd1038d150b7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 10V, Positive-QTOF	splash10-004i-2900000000-54e19a17e5b306ed4b51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 20V, Positive-QTOF	splash10-0059-9300000000-14cb0c94b66f21cdb3f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 40V, Positive-QTOF	splash10-0pc0-9000000000-66fbc9e4d25c8e4657e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 10V, Negative-QTOF	splash10-00di-2900000000-b6419ab3133503750ef1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 20V, Negative-QTOF	splash10-0fl3-9300000000-1d6b86125828d4c8f787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-4,5-dimethyloxazole 40V, Negative-QTOF	splash10-0udl-9000000000-7eae5ac1d4fe6ce7d43b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

FDB017018

KNApSAcK ID

Not Available

Chemspider ID

55906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62069

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037371

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 2-Ethyl-4,5-dimethyloxazole (HMDB0037865)

MOL for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

3D MOL for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

3D SDF for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

3D-SDF for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

PDB for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

3D PDB for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

SMILES for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

INCHI for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

Structure for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

3D Structure for HMDB0037865 (2-Ethyl-4,5-dimethyloxazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra