Tetrahydrothiophen-3-one

Tetrahydrothiophen-3-one Basic information
Product Name:Tetrahydrothiophen-3-one
Synonyms:3-Oxotetrahydrothiophene;3-Thiacyclopentanone;dihydro-3(2h)-thiophenon;Dihydro-3-Thiophenone;Thiolan-3-one;4,5-DIHYDRO-3(2H)-THIOPHENONE;3-THIOPHANONE;dihydrothiophen-3(2h)-one
CAS:1003-04-9
MF:C4H6OS
MW:102.15
EINECS:213-698-9
Product Categories:Thiophene&Benzothiophene;thiophene Flavor;Thiophen flavors
Mol File:1003-04-9.mol
Tetrahydrothiophen-3-one Structure
Tetrahydrothiophen-3-one Chemical Properties
Boiling point 175 °C(lit.)
density 1.194 g/mL at 25 °C(lit.)
vapor density >1 (vs air)
FEMA 3266 | 4,5-DIHYDRO-3(2H)THIOPHENONE
refractive index n20/D 1.528(lit.)
Fp 171 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in DMSO
form Liquid
Specific Gravity1.194
color Colorless to pale yellow
Odorat 0.10 % in dipropylene glycol. garlic meaty green vegetables clams buttery
Odor Typealliaceous
JECFA Number498
BRN 105201
LogP-0.29
CAS DataBase Reference1003-04-9(CAS DataBase Reference)
NIST Chemistry ReferenceDihydro-3-(2H)-thiophenone(1003-04-9)
EPA Substance Registry System3(2H)-Thiophenone, dihydro- (1003-04-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-36/37/39
RIDADR UN 3334
WGK Germany 3
8-13
Hazard Note Irritant
TSCA Yes
HS Code 29349990
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Tetrahydrothiophen-3-one Usage And Synthesis
DescriptionTetrahydro-thiophene-3-one is a heterocyclic nonaromatic ketone. It has a garlic meaty, green vegetable, buttery odor. It is present in cooked beef, coffee, roast filbert, and roasted peanut.
Tetrahydro-thiophene-3-one is used as a food flavoring agent. It is also a valuable organic substance key that opens the synthetic access to numerous derivatives of thiophene.
Chemical Properties4,5-Dihydro-3-(2H)thiophenone has a garlic meaty, green vegetable, buttery odor. It is a heterocyclic nonaromatic ketone.
Chemical PropertiesClear light yellow liquid
OccurrenceReported found in cooked beef, coffee, roasted filberts and roasted peanuts.
Uses4,5-Dihydro-3(2H)-thiophenone is a volatile organic sulfur compound (VOSC) produced by basidiomycetous yeasts.
UsesUsed for blending soft drinks, beverage, meat products, confectionery, and milk product flavors.
PreparationFrom 4-methoxycarboxyl-3-oxothiophane treated with 10% sulfuric acid.
Taste threshold valuesTaste characteristics at 15 ppm: onion, garlic, cooked meaty with vegetables nuances
Synthesis Reference(s)Journal of the American Chemical Society, 68, p. 2229, 1946 DOI: 10.1021/ja01215a034
References[1] George A. Burdock (2010) Fenaroli's Handbook of Flavor Ingredients, Sixth Edition
[2] https://pubchem.ncbi.nlm.nih.gov
[3] Patent 0127121 A1: Process for the preparation of tetrahydro-thiophen-3-one

Tetrahydrothiophen-3-one Preparation Products And Raw materials
Raw materialsBENZHYDRYL ACETATE-->TETRAHYDRO-THIOPHEN-3-OL-->danosteine-->Methyl 4-oxotetrahydrothiophene-3-carboxylate
Preparation Products3-methylthiolan-3-ol
Tetrahydrothiophene 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine 4-METHYLTETRAHYDROTHIOPHEN-3-ONE 4-Bromo-1,1-dioxo-tetrahydrothiophen-3-one 5-(Thien-2-yl)tetrahydrothiophen-3-one,5-(2-THIENYL)TETRAHYDROTHIOPHEN-3-ONE 4-OXOTETRAHYDROTHIOPHENE-2,3-DICARBOXYLIC ACID DIMETHYL ESTER 2-methyl-3-oxothiophane-1-dioxide 2-Bromothiophene Methyl 4-oxotetrahydrothiophene-3-carboxylate Sulfolane Thiophene POLYTHIOPHENE 3-Oxo-tetrahydro-thiophene-2-carboxylic acid ethyl ester AKOS BBS-00004814 1-BENZOYL-2-HYDROXY-7-THIA-1-AZASPIRO[4.4]NONAN-9-ONE 1,1-DIOXO-TETRAHYDRO-1LAMBDA*6*-THIOPHEN-3-ONE N-(TETRAHYDRO-4-OXO-3-THIENYL)BENZAMIDE Tetrahydrothiophen-3-one

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