2-Furfuryl disulfide

Furfuryl chloride, 35, 68 2-Furfuryl disulfide, 35, 68 S-2-Furfurylisothiourea, 35, 67 2-Furfuryl mercaptan, 35, 66 2-Furoic acid, 36, 36 Furylacrylic acid, 33, 25 Fusion, caustic, of vanillin, 30, 103... 

Furfuryl mercaptan cannot be prepared according to the classical method using furfuryl chloride and potassium sulfide.2 It has been prepared by reduction of 2-furfuryl disulfide, obtained from furfural and ammonium hydrosulfide.3 The mercaptan has also been obtained in 33% yield 2 by the reaction of furfuryl chloride with thiourea and subsequent decomposition of the intermediate S-2-furfurylisothiourea according to the general method described in Organic Syntheses.4 In the present method, which has been published previously, the use of the very unstable and difficultly available furfuryl halides is avoided.6... 

Bis (ethylphenylcarbamodithioato-S,S )-(T-4)-zinc. See Zinc ethylphenyidithiocarbamate Bis(N-ethyl-N-phenyl) urea. See N,N -Diethyl-N,N -diphenylurea Bis (ethyixanthic) disulfide Bis (ethyixanthogen) disulfide. See Diethyl xanthogen disulfide Bis (4-fluorophenyl) sulfone. See 4,4 -Difluorodiphenyl sulfone 1,4-Bis (1-formamido-2,2,2-trichloroethyl) piperazine N,N -Bis (1-formamido-2,2,2-trichloroethyl) piperazine. SeeTriforine Bis (2-furfuryl) disulfide. See Difurfuryl disulfide... 

Furfuryl disulfide 2-Furfuryl disulfide. See Difurfuryl disulfide Furfuryl mercaptan... 

Synthetic allithiamin derivatives, such as thiamin propyl and tetrahydro-furfuryl disulfides, have been used for the prevention and treatment of thiamin deficiency. Because they are lipid soluble, and are not subject to the normal control of thiamin absorption by saturation of the intestinal transport system, they have potential benefits in the treatment of thiamin-deficient alcoholics, whose absorption of thiamin is impaired. 

We believe the mechanisms of the reaction are as shown in equation 9. The final step is an unusual one. The thiofurfural intermediate undergoes a redox reaction with Hydrogen Sulfide to produce Difurfuryl Disulfide and Sulfur (equation 9). The reaction is carried out in a Nitrogen atmosphere, which would preclude the facile oxidation of Furfuryl Mercaptan to Furfuryl Disulfide. 

The oxidation of mercaptans can be useful to prepare other flavor molecules. Furfuryl Mercaptan and Methyl Mercaptan can be oxidized together to give Methyl Furfuryl Disulfide, a potent material useful for bread, pork and other meat products. It is also the third most active flavor material in fresh brewed coffee, being present at 0.38 ppm or 9,623 times its flavor threshold (0.04 ppb) (equation 11). 

The synthesis of furan-2-methanethiol was described by Reichstein and Staudinger (1928). Furfural (1.63) is converted into furfuryl disulfide (difurfuryl disulfide, 1.136) by treatment with the sulfide or hydrosulfide of an alkaline-earth metal or of ammonia. The disulfide in an alcoholic solution can be reduced, for example, by addition of zinc dust and a small quantity of acetic acid. A method has been described by Kofod (1955). 

Difurfuryl disulfide Furfuryl disulfide CigHggOgSg 4437-20-1 226.315 10 167 vs EtOH... 

Field and his associates prepared a variety of novel disulfides and observed "good" protection in mice with 2-acetamidoethyl acetyl disul-fide (< 50 mg/kg), with p-cyanobenzyl 2-(n-decylamino)ethyl disulfide (p-CHo, p-CHO and p-Cl analogs were Inactive) and with. 3-acetamidopropyl 2-(n-decylamino)ethyl disulfide l (30-50 mg/kg). The 2-acetamido isomer of the last-named compound was much less protective. Thiamine tetrahydro-furfuryl disulfide (40 mg/kg, i.p., post-irradiation) protected mice against 600-700r with a dose reduction factor of 1.34. ... 

Furfural comes from pentose sugars in cereal straws and brans. Furfural is the precursor of furfuryl mercaptan and its disulfide, difurfuryl disulfide, which are both important chemicals for coffee, meat and roasted flavours. They are prepared by the reaction of furfural and hydrogen sulfide (Scheme 13.15). 

Methyldithio)methyDfuran (Furfuryl methyl disulfide) CH2SSCH3... 

Some of these reaction flavors occur in nature. The oxidation of mercaptans to form disulfides and other products is in part responsible for the loss of flavor from fresh roasted coffee only a short time after brewing. Furfiiryl Mercaptan is one of the most potent flavor components in coffee and is responsible for a fresh brewed coffee flavor. While it is present at only 1.55 ppm versus Furfuryl Alcohol (515 ppm) and Furfural (157 ppm), its flavor contribution is 310,014 times its flavor threshold (0.005 ppb). If there were a 100% conversion of Furfuryl Mercaptan to Diflirfuryl Disulfide, the coffee would appear to be 10 times weaker due to Difurfliryl Disulfide s flavor threshold being 0.05 ppb, or ten times weaker than Furfuryl Mercaptan (equation 10). The overall effect of this oxidation is that the coffee has lost its flavor. 

Furan, 2- (methyldithio)methyl]-, 2-[ ( methyldisulfanyl) methyl]furan, furfuryl] methyl) disulfane, furfuryl methyl disulfide, (furfuryldithio)methane [57500-00-2] FEMA 3362... 

Class II. Butyl glycol, chlorobenzene, cyclohexanone, dimethylformamide, diisobutyl ketone, ethyl glycol, ethylbenzene, furfuryl alcohol, isopropylbenzene, carbon disulfide, methyl glycol, methyl acetate, methyl cyclohexanones, methyl formate, styrene, tetrachloroethylene, tetrahydro-furan, toluene, 1,1.1-trichloroethane, trimethylbenzenes, xylenes. 

Triforine cure accelerator Dipentaerythrityl acrylate cure activator, oxidation butyl rubber Benzothiazyl disulfide cure inhibitor, RTV systems Dimethicone, vinyidimethyl-terminated cure moderator, RTV systems Dimethicone, vinyidimethyl-terminated cure promoter, polyesters Benzene phosphinic acid cure promoter amine-cured epoxies Furfuryl alcohol curing agent... 

Particularly important substances for the basic flavour of baked and cooked meat are aliphatic thiols (such as methanethiol), sulfides (such as dimethyldisulfide, dimethytrisulfide and dimethyltetra-sulfide), aldehydes (such as acetaldehyde, 2-methylpropanal and 3-methylbutanal), furans, pyridines and thiophenes with a mer-capto group in position C-3 and their corresponding disulfides and some other aliphatic and heterocyclic sulfur compounds. Examples of important aliphatic thiols are 3-mercaptobutan-2-one (8-179) and 3-mercaptopentan-2-one found in cooked beef. A mixture of 3-mercapto-2-methylpentane-l-ol diastereoisomers (Figure 8.86) has a broth-like, sweaty and leek-hke flavour. Very low odour threshold concentrations and an odour reminiscent of roasted meat are found in 2-methylfuran-3-thiol (8-180), which also occurs in beef broth, roasted coffee and other foods, 2,5-dimethylfuran-3-thiol, their corresponding disulfides and 2-furanmethanethiol (furfuryl mercaptan). The typical aroma of roast beef is found in... 

Furfurylthiol is the primary character impact compound for the aroma of roasted Arabica coffee (45). It has a threshold of 5 ppt and smells like freshly brewed coffee at concentrations between 0.01 and 0.5 ppb (46). At higher concentrations it exhibits a stale coffee, sulfury note. Other potent odorants in roasted coffee include 5-methylfurfurylthiol (0.05 ppb threshold), which smells meaty at 0.5-1 ppb, and changes character to a sulfury mercaptan note at higher levels (46). Furfuryl methyl disulfide has a sweet mocha coffee aroma (15). A key aromatic that markedly contributes to coffee aroma is 3-mercapto-3-methylbutyl formate. The pure compound has a blackcurrant-like, catty note, however, in the context of brewed coffee, it contributes roast coffee likeness (47,48). 

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