1003-04-9

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 NO: 1003-04-9
• Molecular Formula: C₄H₆OS
• Molecular Weight: 102.15
• EINECS: 213-698-9
• Product Categories: Thiophene&Benzothiophene;thiophene Flavor;Thiophen flavors
• Mol File: 1003-04-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 175 °C(lit.)
• Flash Point: 171 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.194 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 1.16mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: 2-8°C
• BRN: 105201
• CAS DataBase Reference: Tetrahydrothiophen-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydrothiophen-3-one(1003-04-9)
• EPA Substance Registry System: Tetrahydrothiophen-3-one(1003-04-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39
• RIDADR: UN 3334
• WGK Germany: 3
• F: 8-13
• TSCA: Yes
• Hazardous Substances Data: 1003-04-9(Hazardous Substances Data)

Usage

Description

Tetrahydrothiophen-3-one, also known as 4,5-Dihydro-3(2H)-thiophenone, is a heterocyclic nonaromatic ketone with a distinct garlic meaty, green vegetable, and buttery odor. It is a volatile organic sulfur compound (VOSC) produced by basidiomycetous yeasts and is found in various cooked foods such as beef, coffee, roasted filberts, and roasted peanuts.

Uses

1. Used in Flavor Industry:
Tetrahydrothiophen-3-one is used as a flavoring agent for blending soft drinks, beverages, meat products, confectionery, and milk product flavors. Its unique taste characteristics, such as onion, garlic, and cooked meaty notes with vegetable nuances at 15 ppm, make it a valuable addition to the flavor industry.
2. Used in Food Industry:
Tetrahydrothiophen-3-one is used as a food flavoring agent, enhancing the taste and aroma of various cooked foods. Its natural occurrence in cooked beef, coffee, roasted filberts, and roasted peanuts makes it a suitable choice for replicating and enhancing these flavors in the food industry.
3. Used in Organic Synthesis:
Tetrahydrothiophen-3-one is a valuable organic substance that serves as a key compound for the synthesis of numerous thiophene derivatives. Its chemical properties, such as being a clear light yellow liquid with a garlic meaty, green vegetable, and buttery odor, make it an important building block in the development of new compounds and materials.

Preparation

From 4-methoxycarboxyl-3-oxothiophane treated with 10% sulfuric acid.

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

InChI:InChI=1/C4H6OS/c5-4-1-2-6-3-4/h1-3H2

Upstream product

• 2689-69-2 methyl tetrahydrothiophen-3-one-2-carboxylate 
• 2689-68-1 methyl 4-oxotetrahydrothiophene-3-carboxylate 
• 408326-28-3 1-chloro-4-iodo-butan-2-one 
• 127-08-2 potassium acetate 
• 64-17-5 ethanol 
• 57-48-7 D-Fructose 
• 70-18-8 GLUTATHIONE 
• 50-99-7 D-glucose 
• 3334-05-2 tetrahydrothiophene-3-ol 
• 4938-00-5 3-((carboxymethyl)thio)propanoic acid 
• 68-11-1 mercaptoacetic acid 
• 79-10-7 acrylic acid 
• 2365-48-2 Methyl thioglycolate 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 34722-01-5 3-butylthiophene 
• 58451-54-0 2,4-di-((Ξ)-benzylidene)-dihydro-thiophen-3-one 
• 99059-46-8 2,3-dihydro-4-phenylthiophene 
• 91060-88-7 3-phenyl-tetrahydro-thiophen-3-ol 
• 176-41-0 1,4,7-trithia-spiro[4.4]nonane 
• 7311-85-5 dihydro-thiophen-3-one-(2,4-dinitro-phenylhydrazone) 
• 128862-26-0 tetrahydrothiophen-3-one oxime 
• 1006-74-2 3-Morpholino-tetrahydro-thiophen 
• 1006-76-4 4-(thiophen-3-yl)morpholine 
• 212710-51-5 7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione 

Relevant articles and documents

Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars

Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.

Preparation method of substituted thiophene-3-one compound

The invention provides a preparation method of a substituted thiophene-3-one compound, comprising: subjecting material A and material B to Michael addition reaction to obtain an addition product; subjecting the addition product to Dieckmann condensation reaction to obtain a substituted thiophene-3-one compound having a structure shown as formula (IV) that is shown in the description. The preparation method provided by the application has the advantages that using solvents and strong bases is not required, reaction materials are low in price and easy to obtain, no wastewater is produce, and therefore, the preparation method has good environmental friendliness; compared with existing preparation methods, the preparation method has a short synthetic route, can be performed under mild conditions and features good yield stability and good repeatability, which is helpful for greatly increasing total yield of the substituted thiophene-3-one compound and helpful for industrial popularization.

FACILE REDUCTION OF SULFOXIDES AND SULFILIMINES TO SULFIDES BY USING METAL/CHLOROMETHYLSILANES

-