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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:53:05 UTC

Update Date

2023-02-21 17:22:56 UTC

HMDB ID

HMDB0032985

Secondary Accession Numbers

HMDB32985

Metabolite Identification

Common Name

5-(2-Hydroxyethyl)-4-methylthiazole

Description

5-(2-Hydroxyethyl)-4-methylthiazole, also known as 4-methyl-5-(2'-hydroxyethyl)-thiazole or 4-methyl-5-thiazolethanol, 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. 5-(2-Hydroxyethyl)-4-methylthiazole exists in all living species, ranging from bacteria to humans. 5-(2-Hydroxyethyl)-4-methylthiazole is a sulfur tasting compound. 5-(2-Hydroxyethyl)-4-methylthiazole has been detected, but not quantified, in several different foods, such as kohlrabis, red bell peppers, citrus, avocado, and black-eyed pea. This could make 5-(2-hydroxyethyl)-4-methylthiazole a potential biomarker for the consumption of these foods. A 1,3-thiazole that is thiazole substituted by a methyl group at position 4 and a 2-hydroxyethyl group at position 5.

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-(2'-hydroxyethyl)-thiazole	ChEBI
4-Methyl-5-(2-hydroxyethyl)-thiazole	ChEBI
4-Methyl-5-thiazolethanol	ChEBI
Hemineurine	ChEBI
4-Methyl-5-(2-hydroxyethyl)thiazole	Kegg
HET	Kegg
2-(4-Methyl-1,3-thiazol-5-yl)ethanol	HMDB
2-(4-Methyl-5-thiazolyl)ethanol	HMDB
2-(4-METHYL-thiazol-5-yl)-ethanol	HMDB
2-(4-Methylthiazol-5-yl)ethanol	HMDB
2-(4-Methylthiazole-5-yl)ethanol	HMDB
4-METHYL-5-(beta-hydroxyethyl)-thiazole	HMDB
4-Methyl-5-(beta-hydroxyethyl)thiazole	HMDB
4-Methyl-5-hydroxethylthiazole	HMDB
4-Methyl-5-hydroxyethylthiazole	HMDB
4-Methyl-5-thiazoleethanol	HMDB
4-Methyl-5-thiazoleethanol, 9ci	HMDB
4-Methyl-5-thiazolylethanol	HMDB
4-Metyl-5-(beta-hydroxyethyl)thiazole	HMDB
5-(2-Hydroxyethyl)-4-methylthiazole (sulfurol)	HMDB
5-(beta-Hydroxyethyl)-4-methylthiazole	HMDB
5-(Hydroxyethyl)-4-methylthiazole	HMDB
FEMA 3204	HMDB
MHT	HMDB
Sulfurol	HMDB
Thiamine breakdown product 4-methyl-5-thiazoleethanol- from	HMDB
Thiamine thiazole	HMDB
Thiazole, 5-(2-hydroxyethyl)-4-methyl	HMDB
TZE	HMDB
Thiamine thiazole hydrochloride	HMDB
Thiamine thiazole phosphate	HMDB
4-Methyl-5-(2-thiazoleethanol)	HMDB
4-Methyl-5-(β-hydroxyethyl)thiazole	HMDB
5-(Β-hydroxyethyl)-4-methylthiazole	HMDB
THZ	HMDB
5-(2-Hydroxyethyl)-4-methylthiazole	MeSH

Chemical Formula

C₆H₉NOS

Average Molecular Weight

143.207

Monoisotopic Molecular Weight

143.040484605

IUPAC Name

2-(4-methyl-1,3-thiazol-5-yl)ethan-1-ol

Traditional Name

4-methyl-5-thiazoleethanol

CAS Registry Number

137-00-8

SMILES

CC1=C(CCO)SC=N1

InChI Identifier

InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3

InChI Key

BKAWJIRCKVUVED-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
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazole (CHEBI:17957 )
primary alcohol (CHEBI:17957 )
Thiazole alkaloids (C04294 )
a thiazole (THZ )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032985)
Cytoplasm (HMDB: HMDB0032985)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Beer (FooDB: FOOD00268)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Vegetable

Mushroom

Root vegetable

Swede (FooDB: FOOD00028)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	135.00 °C. @ 7.00 mm Hg	The Good Scents Company Information System
Water Solubility	9081 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.275 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.26 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.32 m³·mol⁻¹	ChemAxon
Polarizability	14.92 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]+	126.755	31661259
DarkChem	[M-H]-	123.171	31661259
DeepCCS	[M+H]+	133.26	30932474
DeepCCS	[M-H]-	130.043	30932474
DeepCCS	[M-2H]-	167.03	30932474
DeepCCS	[M+Na]+	142.003	30932474
AllCCS	[M+H]+	128.7	32859911
AllCCS	[M+H-H2O]+	124.1	32859911
AllCCS	[M+NH4]+	132.9	32859911
AllCCS	[M+Na]+	134.1	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(2-Hydroxyethyl)-4-methylthiazole	CC1=C(CCO)SC=N1	2264.0	Standard polar	33892256
5-(2-Hydroxyethyl)-4-methylthiazole	CC1=C(CCO)SC=N1	1207.9	Standard non polar	33892256
5-(2-Hydroxyethyl)-4-methylthiazole	CC1=C(CCO)SC=N1	1260.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(2-Hydroxyethyl)-4-methylthiazole,1TMS,isomer #1	CC1=C(CCO[Si](C)(C)C)SC=N1	1377.5	Semi standard non polar	33892256
5-(2-Hydroxyethyl)-4-methylthiazole,1TBDMS,isomer #1	CC1=C(CCO[Si](C)(C)C(C)(C)C)SC=N1	1620.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-MS (1 TMS)	splash10-0udi-3910000000-2c7da803c60f23e92cb8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole EI-B (Non-derivatized)	splash10-03di-3900000000-373fe84bca11e1b9a8e8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-MS (Non-derivatized)	splash10-0udi-3910000000-2c7da803c60f23e92cb8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-EI-TOF (Non-derivatized)	splash10-0udi-2910000000-917762a1db7938b1744a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-5900000000-a533361156b4169f3662	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9320000000-2699a9d0d4585266a9fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QQ , positive-QTOF	splash10-0006-0900000000-752807b0316740b2f094	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QQ , positive-QTOF	splash10-0006-0900000000-78f29564099d057faa39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QQ , positive-QTOF	splash10-03di-1900000000-eed8b0468f9906ba231c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QQ , positive-QTOF	splash10-03di-3900000000-f44ad5d4a3225d9b0bcc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QQ , positive-QTOF	splash10-03di-9700000000-33a95f67a6613491886d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QTOF , positive-QTOF	splash10-01ox-0900000000-06db10539c8be16d6109	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole LC-ESI-QTOF , positive-QTOF	splash10-03di-1900000000-0c0977714e57292d99f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 35V, Positive-QTOF	splash10-03dl-0900000000-88e26c627663843f9708	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 30V, Positive-QTOF	splash10-03di-1900000000-0c0977714e57292d99f9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 10V, Positive-QTOF	splash10-004l-0900000000-77f0167f1adcb7bd13de	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 20V, Positive-QTOF	splash10-004i-1900000000-7716ea7b3c8440649464	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 40V, Positive-QTOF	splash10-01ta-9500000000-67d0defea9e8825ae1aa	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 10V, Negative-QTOF	splash10-01ox-1900000000-11ac5d4965cdb773ab47	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 20V, Negative-QTOF	splash10-006w-9600000000-fbed1a518b95bea3510c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 40V, Negative-QTOF	splash10-0006-9000000000-7872cc957fe09907a8b7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 10V, Positive-QTOF	splash10-004l-0900000000-2e5c326d07e929018d95	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 20V, Positive-QTOF	splash10-01u3-8900000000-c889afd6f3bb43d37fdb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 40V, Positive-QTOF	splash10-001i-9100000000-b0bb72c5777ad7b7b1a1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 10V, Negative-QTOF	splash10-0002-9100000000-b34c758ceec8653ad03f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 20V, Negative-QTOF	splash10-00dl-9300000000-70a6aa386fb75b9d9b36	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Hydroxyethyl)-4-methylthiazole 40V, Negative-QTOF	splash10-0a4i-9000000000-bb4dcf1719345df44077	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)	2021-09-25	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

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+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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs