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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:08:03 UTC

Update Date

2023-02-21 17:26:13 UTC

HMDB ID

HMDB0037880

Secondary Accession Numbers

HMDB37880

Metabolite Identification

Common Name

2-Isobutyl-4,5-dimethyloxazole

Description

2-Isobutyl-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-Isobutyl-4,5-dimethyloxazole is a burnt and roasted tasting compound. 2-Isobutyl-4,5-dimethyloxazole has been detected, but not quantified in, potatos (Solanum tuberosum). This could make 2-isobutyl-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-Isobutyl-4,5-dimethyloxazole.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-iso-Butyl-4,5-dimethyloxazole	HMDB
2-Isobutyl-4,5-dimethyl-1,3-oxazole	HMDB
2-Isobutyl-4,5-dimethyloxazole, 8ci	HMDB
4,5-Dimethyl-2-(2-methylpropyl)-oxazole	HMDB
4,5-Dimethyl-2-isobutyloxazole	HMDB
Oxazole, 4,5-dimethyl-2-isobutyl	HMDB

Chemical Formula

C₉H₁₅NO

Average Molecular Weight

153.2215

Monoisotopic Molecular Weight

153.115364107

IUPAC Name

4,5-dimethyl-2-(2-methylpropyl)-1,3-oxazole

Traditional Name

4,5-dimethyl-2-(2-methylpropyl)-1,3-oxazole

CAS Registry Number

26131-91-9

SMILES

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

InChI Identifier

InChI=1S/C9H15NO/c1-6(2)5-9-10-7(3)8(4)11-9/h6H,5H2,1-4H3

InChI Key

SNRVAFQIIFPYDR-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

Membrane (HMDB: HMDB0037880)
Cell membrane (HMDB: HMDB0037880)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037880)

Source

Exogenous

Exogenous (HMDB: HMDB0037880)

Food

Food (HMDB: HMDB0037880)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Endogenous

Plant

Plant (HMDB: HMDB0037880)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037880)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	227.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	121.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.501 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	3.1	ALOGPS
logP	1.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	1.79	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	2	ChemAxon
Refractivity	44.73 m³·mol⁻¹	ChemAxon
Polarizability	18.5 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]+	134.725	31661259
DarkChem	[M-H]-	133.839	31661259
DeepCCS	[M+H]+	145.519	30932474
DeepCCS	[M-H]-	142.604	30932474
DeepCCS	[M-2H]-	179.328	30932474
DeepCCS	[M+Na]+	154.682	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	136.9	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	135.5	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	139.0	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.	4.41 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6133 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1490.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	572.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	340.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	559.6 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	694.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1184.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	461.7 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	1433.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	560.2 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	17.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Isobutyl-4,5-dimethyloxazole	CC(C)CC1=NC(C)=C(C)O1	1295.0	Standard polar	33892256
2-Isobutyl-4,5-dimethyloxazole	CC(C)CC1=NC(C)=C(C)O1	1044.3	Standard non polar	33892256
2-Isobutyl-4,5-dimethyloxazole	CC(C)CC1=NC(C)=C(C)O1	1051.6	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-Isobutyl-4,5-dimethyloxazole EI-B (Non-derivatized)	splash10-03di-6900000000-44a7ebda9027de4ddda2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole EI-B (Non-derivatized)	splash10-03di-6900000000-44a7ebda9027de4ddda2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9700000000-9b24b926761de7867e68	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 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-Isobutyl-4,5-dimethyloxazole 10V, Positive-QTOF	splash10-0udi-0900000000-ea704c6500356bbbe099	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 20V, Positive-QTOF	splash10-0udi-8900000000-0bf0f601062d24a0e9e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 40V, Positive-QTOF	splash10-0pb9-9000000000-782becae163f71203011	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 10V, Negative-QTOF	splash10-0udi-2900000000-4cc02aaa8f88fac6c044	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 20V, Negative-QTOF	splash10-0nmi-2900000000-84390fa12e028b3247a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 40V, Negative-QTOF	splash10-0006-9000000000-95e173a1a8dc611194aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 10V, Positive-QTOF	splash10-0udi-3900000000-0c8eeeb6347e6473d2a1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 20V, Positive-QTOF	splash10-08fr-9600000000-59bca40f2e1e2142a589	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 40V, Positive-QTOF	splash10-066r-9000000000-7d701fbd675190a9c868	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 10V, Negative-QTOF	splash10-0udi-0900000000-b2ed86f1c5b38edbfb88	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 20V, Negative-QTOF	splash10-0udi-6900000000-261d1505c7bb25ab16da	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isobutyl-4,5-dimethyloxazole 40V, Negative-QTOF	splash10-02tc-9000000000-d733a67f1f985359d31d	2021-09-25	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

Membrane

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

FDB017033

KNApSAcK ID

Not Available

Chemspider ID

499137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

574068

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1584111

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-Isobutyl-4,5-dimethyloxazole (HMDB0037880)

MOL for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

3D MOL for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

3D SDF for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

3D-SDF for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

PDB for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

3D PDB for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

SMILES for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

INCHI for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

Structure for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

3D Structure for HMDB0037880 (2-Isobutyl-4,5-dimethyloxazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra