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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:34 UTC

Update Date

2022-03-07 02:52:52 UTC

HMDB ID

HMDB0031199

Secondary Accession Numbers

HMDB31199

Metabolite Identification

Common Name

2,5-Dihydro-2,4,5-trimethyloxazole

Description

2,5-Dihydro-2,4,5-trimethyloxazole belongs to the class of organic compounds known as oxazolines. These are organic compounds containing 1,3-oxazoline, a five-membered ring with a nitrogen and an oxygen atoms at the 1- and 3-position, respectively. Additionally, it contains two double bonds. 2,5-Dihydro-2,4,5-trimethyloxazole is a caramel, green, and musty tasting compound. 2,5-Dihydro-2,4,5-trimethyloxazole has been detected, but not quantified in, nuts. This could make 2,5-dihydro-2,4,5-trimethyloxazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,5-Dihydro-2,4,5-trimethyloxazole.

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-Trimethyl-2,5-dihydrooxazole	HMDB
2,4,5-Trimethyl-3-oxazoline	HMDB
2,4,5-Trimethyl-3-oxazoline, 8ci	HMDB
2,4,5-Trimethyl-delta-3-oxazoline	HMDB
2,5-dihydro-2,4,5-Trimethl-oxazole	HMDB
2,5-dihydro-2,4,5-Trimethyl-oxazole	HMDB
FEMA 3525	HMDB

Chemical Formula

C₆H₁₁NO

Average Molecular Weight

113.1576

Monoisotopic Molecular Weight

113.084063979

IUPAC Name

2,4,5-trimethyl-2,5-dihydro-1,3-oxazole

Traditional Name

3-oxazoline, 2,4,5-trimethyl-

CAS Registry Number

22694-96-8

SMILES

CC1OC(C)C(C)=N1

InChI Identifier

InChI=1S/C6H11NO/c1-4-5(2)8-6(3)7-4/h5-6H,1-3H3

InChI Key

YFSGRMONVCFYTC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolines. These are organic compounds containing 1,3-oxazoline, a five-membered ring with a nitrogen and an oxygen atoms at the 1- and 3-position, respectively. Additionally, it contains two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Oxazolines

Direct Parent

Oxazolines

Alternative Parents

Substituents

Oxazoline
Ketimine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031199)
Cytoplasm (HMDB: HMDB0031199)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031199)

Source

Endogenous

Endogenous (HMDB: HMDB0031199)

Plant

Plant (HMDB: HMDB0031199)

Exogenous

Food

Food (HMDB: HMDB0031199)

Nut

Nuts (FooDB: FOOD00869)

Exogenous (HMDB: HMDB0031199)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	125.00 to 127.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.683 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.16 g/L	ALOGPS
logP	0.54	ALOGPS
logP	0.91	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.78 m³·mol⁻¹	ChemAxon
Polarizability	12.72 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]+	125.247	31661259
DarkChem	[M-H]-	119.537	31661259
DeepCCS	[M+H]+	126.796	30932474
DeepCCS	[M-H]-	123.925	30932474
DeepCCS	[M-2H]-	160.529	30932474
DeepCCS	[M+Na]+	135.402	30932474
AllCCS	[M+H]+	125.1	32859911
AllCCS	[M+H-H2O]+	120.4	32859911
AllCCS	[M+NH4]+	129.6	32859911
AllCCS	[M+Na]+	130.8	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	127.5	32859911
AllCCS	[M+HCOO]-	130.5	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.	2.02 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2362 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1651.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	408.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	389.0 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	502.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	189.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	844.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	353.1 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	1137.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	357.4 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	70.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dihydro-2,4,5-trimethyloxazole	CC1OC(C)C(C)=N1	1116.1	Standard polar	33892256
2,5-Dihydro-2,4,5-trimethyloxazole	CC1OC(C)C(C)=N1	759.7	Standard non polar	33892256
2,5-Dihydro-2,4,5-trimethyloxazole	CC1OC(C)C(C)=N1	799.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-18ea57e22dccc94baf0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 10V, Positive-QTOF	splash10-03di-2900000000-b5e01a3e58f4e654a685	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 20V, Positive-QTOF	splash10-03di-6900000000-3f16324a7f9b1ecfc060	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 40V, Positive-QTOF	splash10-0pb9-9000000000-13c01c05c2534e106369	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 10V, Negative-QTOF	splash10-03di-0900000000-9ada6691af320522a61e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 20V, Negative-QTOF	splash10-03di-4900000000-36b5a2e411b35fb7090c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 40V, Negative-QTOF	splash10-00kf-9000000000-65c822f709c4dcb8b281	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 10V, Positive-QTOF	splash10-03k9-7900000000-791a04df27ac61761dd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 20V, Positive-QTOF	splash10-05fu-9100000000-9b037f7bf22e5494120f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 40V, Positive-QTOF	splash10-0006-9000000000-b745aa03053145ac1de3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 10V, Negative-QTOF	splash10-01q9-9400000000-7b0896de8be2baef413e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 20V, Negative-QTOF	splash10-0006-9100000000-c94541b065241ea671af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dihydro-2,4,5-trimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-6053bdef9684a7e6ea07	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart 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

FDB003220

KNApSAcK ID

Not Available

Chemspider ID

29208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31492

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1009461

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 2,5-Dihydro-2,4,5-trimethyloxazole (HMDB0031199)

MOL for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

3D MOL for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

3D SDF for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

3D-SDF for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

PDB for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

3D PDB for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

SMILES for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

INCHI for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

Structure for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

3D Structure for HMDB0031199 (2,5-Dihydro-2,4,5-trimethyloxazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra