55764-23-3

Basic information

• Product Name: 2,5-Dimethylfuran-3-thiol
• Synonyms: FEMA 3451;2,5-DIMETHYLFURAN-3-THIOL;2,5-DIMETHYL-3-FURYLMERCAPTAN;2,5-DIMETHYL-3-FURANTHIOL;2,5-DIMETHYL-3-MERCAPTOFURAN;2,5-dimethyl-3-furanthio;dimethylfuranthiol,2,5-dimethyl-3-furanthiol;3-Furanthiol, 2,5-dimethyl-
• CAS NO: 55764-23-3
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• EINECS: 259-800-5
• Product Categories: THIOL;thiol Flavor
• Mol File: 55764-23-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 175-177 °C
• Flash Point: 54 °C
• Appearance: clear amber to orange liquid
• Density: 1.05
• Vapor Pressure: 1.91mmHg at 25°C
• Refractive Index: 1.505-1.515
• Storage Temp.: Flammables area
• PKA: 6.43±0.50(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: 2,5-Dimethylfuran-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethylfuran-3-thiol(55764-23-3)
• EPA Substance Registry System: 2,5-Dimethylfuran-3-thiol(55764-23-3)

Safety Data

• Hazard Codes: T,Xn
• Statements: 36/37/38-23/24/25-10-22-2017/10/22
• Safety Statements: 45-36/37/39-16-15
• RIDADR: 3336
• RTECS: LU6230000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 55764-23-3(Hazardous Substances Data)

Usage

Description

2,5-Dimethylfuran-3-thiol is an organic compound with a distinct meaty aroma. It is a clear amber to orange liquid with a taste threshold value of 2 ppm, exhibiting characteristics such as meaty, metallic, beefy, savory drippings, sulfurous, rubbery, and roasted. Its aroma threshold value is 0.10%, with characteristics like sulfurous, meaty, green onion, brown and roasted, brothy, rubbery, HVP-like, fatty, and slightly tomato-like.

Uses

Used in Flavor and Fragrance Industry:
2,5-Dimethylfuran-3-thiol is used as a flavoring agent for its meaty aroma, adding depth and complexity to various food products. It is particularly useful in enhancing the flavor of meat and meat-based dishes, as well as in the development of savory and umami flavors in other food items.
Used in Perfumery:
2,5-Dimethylfuran-3-thiol is used as a fragrance ingredient, providing a unique and complex scent profile. Its meaty, sulfurous, and slightly tomato-like aroma characteristics make it suitable for creating distinctive and long-lasting fragrances in perfumes and other scented products.

InChI:InChI=1/C6H8OS/c1-4-3-6(8)5(2)7-4/h3,8H,1-2H3

Upstream product

• 149428-23-9 2,5-dimethylfur-3-yl thiocyanate 
• 28588-73-0 bis (2,5-dimethyl-furan-3-yl)-disulfide 
• 60-24-2 2-hydroxyethanethiol 
• 55764-22-2 S-(2,5-dimethylfur-3-yl) thioacetate 
• 15441-67-5 5-hydroxyhex-3-yn-2-one 

Downstream Products

• 1029521-09-2 2-benzyl-5-(2,5-dimethyl-furan-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 

Relevant articles and documents

An analysis of substituent effects on 1H and 13C NMR parameters of substituted furans. Linear free energy relationships and PM3 semiempirical calculations

Forty five furans have been obtained in a synthetic project designed to evaluate monothiosubstituted furans as potential food flavourings. A full NMR (1H and 13C) study and PM3 molecular orbital semiempirical calculations have been carried out. Substituent-induced chemical shifts (SCS) for six and nine substituents at the 2- and 3-positions have been calculated and a separation of inductive and resonance effects of these substituents has been proposed. Finally, a linear correlation between the net atomic charges localized at ring carbons and their 13C NMR chemical shifts has been established.

182. Novel Access to Furan-3-thiols and Derivatives, Impact Meat-Flavor Compounds

A versatile process for the preparation of a number of 3-thio-substituted furans 1-4 is described.These products have very low odor thresholds and are thus potent flavor compounds.Fur-3-yl thiocyanates 10a,b as well as other S-containing analogues (2b, 7a, b, and 8) were prepared by a Michael-type addition of thiocyanic acid, thioacetic acid, alkanethiols, and sodium thiosulfate to alkynones 6 and 15, followed by cyclization (Schemes 3 and 4).The thiocyanates 10a, b were converted to mixed disulfides 3, symmetric disulfides 4, thioethers 2, and thiols 1, using 'hard' or 'soft' nucleophiles or reducing agents, respectively (Scheme 6).