CAS 137-00-8 4-Methyl-5-(2-hydroxyethyl)thiazole (HCID 1136)

Overview

5-(2-hydroxyethyl)-4-methylthiazole is a 1,3-thiazole that is thiazole substituted by a methyl group at position 4 and a 2-hydroxyethyl group at position 5. It has a role as a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a primary alcohol and a member of 1,3-thiazoles. It is functionally related to a 5-(2-hydroxyethyl)-1,3-thiazole. It derives from a hydride of a thiazole.

Names & identifiers

Preferred name: 4-Methyl-5-(2-hydroxyethyl)thiazole
IUPAC: 2-(4-methyl-1,3-thiazol-5-yl)ethanol
English name: 5-(2-Hydroxyethyl)-4-methylthiazole
Molecular formula: C6H9NOS
Molecular weight: 143.21

Names & synonyms

4-METHYL-5-THIAZOLEETHANOL137-00-85-(2-Hydroxyethyl)-4-methylthiazoleHemineurine5-Thiazoleethanol, 4-methyl-2-(4-Methyl-1,3-thiazol-5-yl)ethanol4-Methyl-5-thiazolethanol4-Methyl-5-(2-hydroxyethyl)thiazole4-Methyl-5-thiazolylethanol2-(4-Methylthiazole-5-yl)ethanol4-Methyl-5-hydroxyethylthiazole4-Methyl-5-hydroxethylthiazole

Show more names

SULFUROL2-(4-METHYLTHIAZOL-5-YL)ETHANOLFEMA 3204MHTSulfurol(Meat)METHYLHYDROXYETHYLTHIAZOLE5-THIAZOLEETHANOL,4-METHYL

2-(4-Methyl-1,3-Thiazol-5-Yl)Ethan-1-OlFEMA No. 32045-(beta-Hydroxyethyl)-4-methylthiazoleNSC-23262NSC-418314-methyl-5-(2-hydroxyethyl)-thiazole3XYV4I47I84-Methyl-5-(2'-hydroxyethyl)-thiazole

Database identifiers

CAS: 137-00-8
PubChem CID: 1136
DTXSID: DTXSID3044382
ChEMBL: CHEMBL1236482
ChEBI: CHEBI:17957
UNII: 3XYV4I47I8
EC Number: 205-272-6
Nikkaji: J5.626J

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 61.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 9
Formal charge: 0
Complexity: 89.1

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

FragrancesFragrance Ingredient (4-Methyl-5-thiazoleethanol) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.196-1.210

Flavoring AgentsEU Flavoring substances

Solubility · 2 items

Soluble in water, ether, benzene, chloroform

Miscible at room temperature (in ethanol)

Physicochemical properties

Melting point: 25 °C · <25 °C
Boiling point: 135 °C7 · 135 °C7 mm Hg(lit.)
Density: 1.196 g/mL · 1.196 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.550(lit.)
FEMA: 3204 · 3204 | 4-METHYL-5-THIAZOLEETHANOL
FLAVIS Number: 15.014 · 15.014 | 5-(2-Hydroxyethyl)-4-methylthiazole
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: alcohol: soluble(lit.)
form: liquid (clear, viscous)
pka: 14.58 · 14.58±0.10(Predicted)
color: deep yellow
Specific Gravity: 1.196 · 1.196
Odor: meaty, roasted odor
Odor Type: meaty
biological source: synthetic
Sensitive: Stench
Merck: 14 · 14,6126
JECFA Number: 1031 · 1031
BRN: 114249 · 114249
Major Application: flavors and fragrances
Cosmetics Ingredients Functions: PERFUMING
InChI: 1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3
InChIKey: BKAWJIRCKVUVED-UHFFFAOYSA-N
SMILES: Cc1ncsc1CCO
LogP: 0.04 · 0.04
Substances Added to Food (formerly EAFUS): 4 · 4-METHYL-5-THIAZOLEETHANOL
CAS DataBase Reference: 137 · 137-00-8(CAS DataBase Reference)
NCI Dictionary of Cancer Terms: MHT
FDA UNII: 3 XYV4I47I8 · 3XYV4I47I8
NIST Chemistry Reference: 5 · 5-Thiazoleethanol, 4-methyl-(137-00-8)
EPA Substance Registry System: 5 · 5-Thiazoleethanol, 4-methyl- (137-00-8)
UNSPSC Code: 85151701 · 85151701
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
F: 13 · 13
Hazard Note: Irritant/Stench
TSCA: TSCA listed
HS Code: 29341000 · 29341000
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 82.5% (350 of 424) of all reports.

Warning

H315 (17.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 424 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: 5-Thiazoleethanol, 4-methyl-

Regulation (EC) No 1831/2003 (amended)

5-Thiazoleethanol, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 5-Thiazoleethanol, 4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 19-07-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20105

5-Thiazoleethanol, 4-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazard Classes and CategoriesSkin Irrit. 2 (17.2%)

Safety data

F: 13
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
hs_code: 29341000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant/Stench
safety_code: 24/25
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

U.S. Production2023: 9 lb

Consumer UsesFragrance

Household ProductsInformation on 3 consumer products that contain 2-(4-Methyl-1,3-thiazol-5-yl)ethanolÃ¢â¬Â¨ in the following categories is provided:

Use Classification · 6 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information5-Thiazoleethanol, 4-methyl-: ACTIVE

Applications · 4 items

Description4-Methy 1-5-thiazoleethanol has the characteristic disagreeable odor of thiazole compounds. It is somewhat pleasant and nut-like on extreme dilution. It may be prepared by reduction of ethyl- 4-methylthiazole-5-acetate using LiAlH4; by condensation of thioformamide with bromoacetopropanol or with y,y-dichloro-y,ydiacetodipropyl ether.

OccurrenceReported found in grilled and roasted beef, cognac, brandy, Finnish whiskey, cocoa, peanuts, beans and malt.

Uses5-(2-Hydroxyethyl)-4-methylthiazole has been used in the synthesis of novel thiazolium halogenide ionic liquids.

General Description4-Methyl-5-thiazoleethanol is a sulfur-containing heterocyclic flavor compound that is reported to occur in Comté cheese and Panax ginseng.

Preparation methods

PreparationIt is obtained from the reduction of 4-methyl thiazole 5-ethyl acetate reduction with lithium aluminum hydride.

Preparation5-(2-Hydroxyethyl)-4-methylthiazole is prepared by reduction of ethyl-4-methylthiazole-5-acetate using LiAlH4; by condensation of thioformamide with bromoacetopropanol or with γ, y-dichloro-γ,γ-diacetodipropyl ether

Upstream & downstream products

Upstream raw materials

Downstream products

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide Thiamine hydrochloride 3,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodide 4-Methylthiazole-5-carboxylic acid 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride 3-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide Furfural Thiamine hydrochloride

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

枣庄九星生物科技有限公司0632-3759569 13589608009

济南远泽生物科技有限公司15063396929; 15063396929

Additional notes

DefinitionChEBI: A 1,3-thiazole that is thiazole substituted by a methyl group at position 4 and a 2-hydroxyethyl group at position 5.

Related reactions

59 records

New reaction record

HRID 2832As reactantuspto-grants-1998_03

HRID 194460As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)

HRID 227381As reactantuspto-grants-2009_07

HRID 259665As reactantuspto-grants-1996_06

HRID 272697As reactantuspto-grants-2008_11

HRID 272732As reactantuspto-grants-2008_11

HRID 272739As reactantuspto-grants-2008_11

HRID 294791As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)

Compound notes

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Basic information