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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:59 UTC

Update Date

2023-02-21 17:21:24 UTC

HMDB ID

HMDB0031858

Secondary Accession Numbers

HMDB31858

Metabolite Identification

Common Name

4-Methyl-5-vinylthiazole

Description

4-Methyl-5-vinylthiazole belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only. 4-Methyl-5-vinylthiazole is a cocoa, musty, and nutty tasting compound. 4-Methyl-5-vinylthiazole is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). 4-Methyl-5-vinylthiazole has also been detected, but not quantified in, several different foods, such as garden onions (Allium cepa), welsh onions (Allium fistulosum), fruits, green onion, and red onion. This could make 4-methyl-5-vinylthiazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methyl-5-vinylthiazole.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Methyl-5-vinyl thiazole	HMDB
4-Methyl-5-vinyl-1,3-thiazole	HMDB
4-Methyl-5-vinyl-thiazole	HMDB
5-Ethenyl-4-methyl-thiazole	HMDB
5-Ethenyl-4-methylthiazole	HMDB
5-Vinyl-4-methylthiazole	HMDB
FEMA 3313	HMDB
4-Methyl-5-vinylthiazole	MeSH

Chemical Formula

C₆H₇NS

Average Molecular Weight

125.191

Monoisotopic Molecular Weight

125.029919919

IUPAC Name

5-ethenyl-4-methyl-1,3-thiazole

Traditional Name

thiazole, 5-ethenyl-4-methyl-

CAS Registry Number

1759-28-0

SMILES

CC1=C(SC=N1)C=C

InChI Identifier

InChI=1S/C6H7NS/c1-3-6-5(2)7-4-8-6/h3-4H,1H2,2H3

InChI Key

QUAMMXIRDIIGDJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

4,5-disubstituted thiazoles

Alternative Parents

Substituents

4,5-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

Extracellular (HMDB: HMDB0031858)
Cytoplasm (HMDB: HMDB0031858)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031858)

Source

Endogenous

Endogenous (HMDB: HMDB0031858)

Plant

Plant (HMDB: HMDB0031858)
Theobroma cacao (HMDB: HMDB0031858)

Exogenous

Food

Food (HMDB: HMDB0031858)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)
Soft-necked garlic (FooDB: FOOD00850)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031858)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-15 °C	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	1.39 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.63	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	2.84	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	35.33 m³·mol⁻¹	ChemAxon
Polarizability	13.25 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]+	122.522	31661259
DarkChem	[M-H]-	117.292	31661259
DeepCCS	[M+H]+	123.148	30932474
DeepCCS	[M-H]-	120.001	30932474
DeepCCS	[M-2H]-	156.968	30932474
DeepCCS	[M+Na]+	131.803	30932474
AllCCS	[M+H]+	122.4	32859911
AllCCS	[M+H-H2O]+	117.5	32859911
AllCCS	[M+NH4]+	126.9	32859911
AllCCS	[M+Na]+	128.2	32859911
AllCCS	[M-H]-	123.3	32859911
AllCCS	[M+Na-2H]-	125.8	32859911
AllCCS	[M+HCOO]-	128.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-5-vinylthiazole	CC1=C(SC=N1)C=C	1479.9	Standard polar	33892256
4-Methyl-5-vinylthiazole	CC1=C(SC=N1)C=C	1029.8	Standard non polar	33892256
4-Methyl-5-vinylthiazole	CC1=C(SC=N1)C=C	1025.3	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-5-vinylthiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9400000000-2d64c94989a9adba5d3a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-5-vinylthiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-5-vinylthiazole 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 - 4-Methyl-5-vinylthiazole 10V, Positive-QTOF	splash10-004i-0900000000-6a3080d223373681b515	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 20V, Positive-QTOF	splash10-004i-1900000000-2341758419d14108e5ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 40V, Positive-QTOF	splash10-0wor-9300000000-c23f29f0dfb3d67ba06d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 10V, Negative-QTOF	splash10-00di-2900000000-1fdba7bfc799d4f11065	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 20V, Negative-QTOF	splash10-00dj-9500000000-5dffcbd8aa3db3888230	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 40V, Negative-QTOF	splash10-0904-9000000000-7042cf638bcbcc421b4c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 10V, Positive-QTOF	splash10-004i-1900000000-5e472ae576bb63ba3c8c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 20V, Positive-QTOF	splash10-004i-9600000000-2783a52336210003331d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 40V, Positive-QTOF	splash10-014l-9000000000-6dade7426dfad6c5d956	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 10V, Negative-QTOF	splash10-00di-7900000000-6bfd96b08703b2df7656	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 20V, Negative-QTOF	splash10-00xr-9000000000-20f3b8ffd49cda4f20d5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-5-vinylthiazole 40V, Negative-QTOF	splash10-0a4i-9000000000-74f5dd14b522f1edd338	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB008542

KNApSAcK ID

Not Available

Chemspider ID

14889

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15654

PDB ID

Not Available

ChEBI ID

Not Available

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-5-vinylthiazole (HMDB0031858)

MOL for HMDB0031858 (4-Methyl-5-vinylthiazole)

3D MOL for HMDB0031858 (4-Methyl-5-vinylthiazole)

3D SDF for HMDB0031858 (4-Methyl-5-vinylthiazole)

3D-SDF for HMDB0031858 (4-Methyl-5-vinylthiazole)

PDB for HMDB0031858 (4-Methyl-5-vinylthiazole)

3D PDB for HMDB0031858 (4-Methyl-5-vinylthiazole)

SMILES for HMDB0031858 (4-Methyl-5-vinylthiazole)

INCHI for HMDB0031858 (4-Methyl-5-vinylthiazole)

Structure for HMDB0031858 (4-Methyl-5-vinylthiazole)

3D Structure for HMDB0031858 (4-Methyl-5-vinylthiazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra