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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:24:00 UTC

Update Date

2023-02-21 17:25:39 UTC

HMDB ID

HMDB0037156

Secondary Accession Numbers

HMDB37156

Metabolite Identification

Common Name

4-Methyl-2-(1-methylethyl)thiazole

Description

4-Methyl-2-(1-methylethyl)thiazole, also known as fema 3555 or 2-isopropyl-4-methyl-thiazole, belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. 2,4-disubstituted thiazoles are compounds containing a thiazole ring substituted at the positions 2 and 3. A 1,3-thiazole that is substituted at positions 2 and 4 by isopropyl and methyl groups, respectively. 4-Methyl-2-(1-methylethyl)thiazole is an earthy, fruit, and green tasting compound. 4-Methyl-2-(1-methylethyl)thiazole has been detected, but not quantified, in several different foods, such as cocoa and cocoa products, fruits, garden tomato, herbs and spices, and mushrooms. This could make 4-methyl-2-(1-methylethyl)thiazole a potential biomarker for the consumption of these foods. A fruit flavour intensifier, it has a peach flavour with distinct vegetable and tropical notes. Present in Indonesian durian fruit (Durio zibethinus), red tomatoes, yeast extract, coriander seed oil, and roast meats. Also used in apricot, nectarine, durian, mango, pear and blackcurrant flavours.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
FEMA 3555	ChEBI
Isopropyl methyl thiazole	ChEBI
Peach thiazole	ChEBI
Tropical thiazole	ChEBI
2-Isopropyl-4-methyl-1,3-thiazole	HMDB
2-Isopropyl-4-methyl-thiazole	HMDB
2-Isopropyl-4-methylthiazole	HMDB
4-Methyl-2-(1-methylethyl)-thiazole	HMDB
4-Methyl-2-(1-methylethyl)thiazole, 9ci	HMDB
Thiazole, 4-methyl-2-isopropyl	HMDB
4-Methyl-2-(1-methylethyl)thiazole	ChEBI

Chemical Formula

C₇H₁₁NS

Average Molecular Weight

141.234

Monoisotopic Molecular Weight

141.061220047

IUPAC Name

4-methyl-2-(propan-2-yl)-1,3-thiazole

Traditional Name

2-isopropyl-4-methyl-1,3-thiazole

CAS Registry Number

15679-13-7

SMILES

CC(C)C1=NC(C)=CS1

InChI Identifier

InChI=1S/C7H11NS/c1-5(2)7-8-6(3)4-9-7/h4-5H,1-3H3

InChI Key

OFLXNHNYPQPQKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. 2,4-Disubstituted thiazoles are compounds containing a thiazole ring substituted at the positions 2 and 3.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

2,4-disubstituted thiazoles

Alternative Parents

Substituents

2,4-disubstituted 1,3-thiazole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0037156)
Cell membrane (HMDB: HMDB0037156)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037156)

Source

Exogenous

Exogenous (HMDB: HMDB0037156)

Food

Food (HMDB: HMDB0037156)

Vegetable

Mushroom

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037156)
Theobroma cacao (HMDB: HMDB0037156)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037156)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.68 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.13	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	3.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.5 m³·mol⁻¹	ChemAxon
Polarizability	16.14 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]+	129.478	31661259
DarkChem	[M-H]-	126.599	31661259
DeepCCS	[M+H]+	134.54	30932474
DeepCCS	[M-H]-	132.231	30932474
DeepCCS	[M-2H]-	168.583	30932474
DeepCCS	[M+Na]+	143.453	30932474
AllCCS	[M+H]+	127.7	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	129.0	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-2-(1-methylethyl)thiazole	CC(C)C1=NC(C)=CS1	1349.0	Standard polar	33892256
4-Methyl-2-(1-methylethyl)thiazole	CC(C)C1=NC(C)=CS1	997.4	Standard non polar	33892256
4-Methyl-2-(1-methylethyl)thiazole	CC(C)C1=NC(C)=CS1	1022.2	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 - 4-Methyl-2-(1-methylethyl)thiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9700000000-d21f27003c2a3231ea61	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00bc-8900000000-9506455d99f99f7e5f8b	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 - 4-Methyl-2-(1-methylethyl)thiazole 10V, Positive-QTOF	splash10-0006-0900000000-5171a337d8817fbdcc08	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 20V, Positive-QTOF	splash10-0006-0900000000-35523c2c81e2f2c4a6d8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 40V, Positive-QTOF	splash10-0096-9200000000-1695cf7d99cbe630e9af	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 10V, Negative-QTOF	splash10-0006-0900000000-cb26c5613cd6f1526bda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 20V, Negative-QTOF	splash10-0006-3900000000-2a1faaf47eee0e1fe145	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 40V, Negative-QTOF	splash10-00di-9000000000-a5c4a1bc863ac8f78f02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 10V, Positive-QTOF	splash10-0006-2900000000-699cba3383fa03f781b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 20V, Positive-QTOF	splash10-0006-4900000000-9ba564de77ccef70eb04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 40V, Positive-QTOF	splash10-0k96-9000000000-6d1ed0482ac3355db3db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 10V, Negative-QTOF	splash10-0006-1900000000-8a484c543c849c327ef9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 20V, Negative-QTOF	splash10-0fkc-9700000000-feee894e1de91db40454	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2-(1-methylethyl)thiazole 40V, Negative-QTOF	splash10-052f-9400000000-33f50df2e66763841652	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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

FDB016151

KNApSAcK ID

Not Available

Chemspider ID

55688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61808

PDB ID

Not Available

ChEBI ID

133679

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 4-Methyl-2-(1-methylethyl)thiazole (HMDB0037156)

MOL for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

3D MOL for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

3D SDF for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

3D-SDF for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

PDB for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

3D PDB for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

SMILES for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

INCHI for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

Structure for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

3D Structure for HMDB0037156 (4-Methyl-2-(1-methylethyl)thiazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra