28588-75-2

Basic information

• Product Name: Bis(2-methyl-3-furyl)disulfide
• Synonyms: 3,3'-dithiobis(2-methylfuran);3,3'-DITHIO-2,2'-DIMETHYLDIFURAN;2-METHYL-3-FURYL DISULPHIDE;FEMA 3259;BIS(2-METHYL-3-FURYL)DISULFIDE;BIS(2-METHYL-3-FURYL)DISULPHIDE;3,3’-dithiobis[2-methyl-fura;Bis(2-methyl-3-furyI)-disulfide
• CAS NO: 28588-75-2
• Molecular Formula: C₁₀H₁₀O₂S₂
• Molecular Weight: 226.32
• EINECS: 249-095-2
• Product Categories: Pharmaceutical Intermediates;sulfide Flavor
• Mol File: 28588-75-2.mol

Chemical Properties

• Boiling Point: 280 °C
• Flash Point: 110 °C
• Appearance: Clear yellow to amber or orange/Liquid
• Density: 1.211 g/mL at 25 °C
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.572-1.583
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Bis(2-methyl-3-furyl)disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-methyl-3-furyl)disulfide(28588-75-2)
• EPA Substance Registry System: Bis(2-methyl-3-furyl)disulfide(28588-75-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-41-38
• Safety Statements: 37/39-26-39
• WGK Germany: 3
• Hazardous Substances Data: 28588-75-2(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Bis(2-methyl-3-furyl)disulfide is used as a flavoring agent for its distinct roasty, meat-like, and sulfur-like odor. It is particularly useful in the creation of artificial meat flavors, enhancing the taste and aroma of various food products.
Used in Tea Production:
Bis(2-methyl-3-furyl)disulfide is used as a natural flavor enhancer in the production of black and green tea. Its unique odor and taste profile contribute to the overall flavor profile of these teas, providing a more robust and authentic taste experience for consumers.
Used in Aromatherapy:
Due to its distinct and pleasant odor, Bis(2-methyl-3-furyl)disulfide can be used in the aromatherapy industry as a component in various scent blends. Its roasty and meat-like aroma can provide a comforting and grounding effect, making it a valuable addition to aromatherapy products.

InChI:InChI=1/C10H10O2S2/c1-7-9(3-5-11-7)13-14-10-4-6-12-8(10)2/h3-6H,1-2H3

Upstream product

• 149428-24-0 2-methylfur-3-yl thiocyanate 
• 5188-07-8 sodium thiomethoxide 
• 67633-97-0 3-mercaptopentan-2-one 
• 28588-74-1 2-methylfuran-3-thiol 
• 98-02-2 2-thiolomethyl-furan 
• 431-03-8 dimethylglyoxal 
• 18350-46-4 4-hydroxy-2-pentylacetaldehyde diethyl acetal 

Downstream Products

• 55764-25-5 S-2-methylfuran-3-yl ethanethioate 

Relevant articles and documents

Sulfur-Containing Furans in Commercial Meat Flavorings

The volatiles of eight commercially available meat flavorings were enriched by dynamic headspace extraction.The resulting aroma extracts were analyzed by high-resolution gas chromatography and gas chromatography/mass spectrometry (GC/MS).Among the compounds identified were 16 sulfur-containing furans. 2-Methyl-3-(ethyldithio)furan, 1--2-propanone, and the spectroscopic data of 3--2-butanone, 2--3-pentanone and 3--2-pentanone are reported here for the first time.Possible formation pathways are discussed.Keywords: Processed meat flavorings; dynamic headspace analysis; aroma chemicals; sulfur-containing furans

Method for synthesizing bis(2-methyl-3-furyl) disulfide

The invention relates to a method for synthesizing bis(2-methyl-3-furyl) disulfide. The method comprises the following steps: (1) enabling acrolein to react with bromine to obtain a product 1; (2) adding the product 1 into an absolute ethyl alcohol solution of sodium hydroxide to prepare propiolaldehyde diethyl acetal; (3) enabling ethyl ether and bromoethane to react with chloroethane in presence of magnesium, then adding mixed liquid of the propiolaldehyde diethyl acetal and the ethyl ether and subsequently adding mixed liquid of acetaldehyde and ethyl ether for carrying out a reaction, and hydrolyzing to prepare 4-hydroxy-2-pentyne propanal diethyl acetal; (4) adding the 4-hydroxy-2-pentyne propanal diethyl acetal into a water solution containing sulfuric acid, pentane and potassium thiocyanate to prepare a product 4; (5) adding the product 4 into a sodium hydroxide water solution to prepare the bis(2-methyl-3-furyl) disulfide. Compared with the existing synthesis method, the method provided by the invention is easy in control of reaction conditions, fewer in side reactions, easy in control of intermediate products and higher in yield of a target product, thus having wide application prospect.

An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert-butyl nitrite

An efficient and convenient tert-butyl nitrite-catalyzed selective aerobic oxidation of thiols has been developed. Under the optimal reaction conditions, a number of thiol derivatives including aromatic thiols, heteroaromatic thiols and aliphatic thiols can be converted into their corresponding disulfides in good to excellent yields.

Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base

An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.

Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane

An efficient oxidative coupling of thiols to give disulfides via thionitrite (S-nitrosothiol) intermediate is described using trichloronitromethane as efficient reagent in organic solvents and water. Cysteine and glutathione are converted into the corresponding disulfides in water in high yields.

Some Novel Meatlike Aroma Compounds from the Reactions of Alkanediones with Hydrogen Sulfide and Furanthiols

The products of reactions of hydrogen sulfide with 2,3-butanedione and with 2,3-pentanedione in dilute ethanolic solution were analyzed by GC-MS and GC-odor port analysis.Components were also collected from the GC column and analyzed by 1H NMR.Mercaptoketones were formed which readily oxidized to the corresponding disulfides with traces of mono- and trisulfides.When 2-methyl-3-furanthiol or 2-furylmethanethiol was added to the reaction mixtures, a series of disulfides containing alkanone, 2-methyl-3-furyl and 2-furanmethyl moieties were formed.Some of these compounds have been found recently in the volatiles of cooked meat and in meatlike model systems.GC-odor port evaluation of the components of the reaction systems showed that disulfides containing the 2-methyl-3-furyl group had meaty aromas, whereas those without this group were sulfurous or onion-like in character.Keywords: Aroma; meat; mercaptoketones; disulfides

Process for the manufacture of furan derivatives

The invention is concerned with a process for the manufacture of substituted furans which are, in particular, flavorants; thereby 4-hydroxy-2-yn-1-ones or acetals or ketals thereof are cyclized with nucleophilic S-compounds to 3-S-furans, whereby this 3-S atom can be optionally substituted, and the acetylene derivatives, the 4-hydroxy-2-yn-1-ones, can be optionally 1- and/or 4-alkyl or alkenyl substituted.

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).

Certain 3-furyl sulfides

Novel 3-sulfur derivatives of furan including alkyl furan-3-thiols and bis(alkyl-3-furyl) sulfides and di- and tetrahydro derivatives thereof having meaty and/or roasted aromas and flavors; processes for producing such 3-sulfur derivatives; novel flavoring compositions containing such derivatives; and novel food compositions containing such derivatives.