23654-92-4

Basic information

• Product Name: 3,5-Dimethyl-1,2,4-trithiolane
• Synonyms: 3,5-dimethyl-1,2,4-trithiolane;1,2,4-Trithiolane, 3,5-dimethyl-;3,5-DIMETHYL-1,2,4-TRITHIOLAN;2,5-Dimethyl-1,3,4-trithiolane;3，5-Dimethyl-1,2,4-trithidane
• CAS NO: 23654-92-4
• Molecular Formula: C₄H₈S₃
• Molecular Weight: 152.3
• EINECS: 245-808-6
• Product Categories: Flavor
• Mol File: 23654-92-4.mol

Chemical Properties

• Boiling Point: 228.3 ºC at 760 mmHg
• Flash Point: 97.3 ºC
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 0.111mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 3,5-Dimethyl-1,2,4-trithiolane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethyl-1,2,4-trithiolane(23654-92-4)
• EPA Substance Registry System: 3,5-Dimethyl-1,2,4-trithiolane(23654-92-4)

Safety Data

• Hazardous Substances Data: 23654-92-4(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
3,5-Dimethyl-1,2,4-trithiolane is used as a flavoring agent for its characteristic meaty aroma. It is particularly useful in the food and beverage industry to enhance the taste of meat-based products or to provide a meaty flavor to vegetarian and vegan alternatives.
Used in Fragrance Industry:
In the fragrance industry, 3,5-Dimethyl-1,2,4-trithiolane is used as a component in the creation of various scent profiles. Its meaty aroma can be utilized to add depth and complexity to perfumes, colognes, and other fragrance products.
Used in Chemical Research:
3,5-Dimethyl-1,2,4-trithiolane is also used in chemical research as a starting material or intermediate for the synthesis of more complex organic compounds. Its unique structure and properties make it a valuable tool for scientists and researchers working on the development of new chemicals and materials.
Occurrence:
3,5-Dimethyl-1,2,4-trithiolane has been reported to be found in various cooked and processed food items, such as boiled beef, cooked chicken, pork, mutton, roasted filberts, dried kidney beans, shrimps, clams, and mushrooms. This natural occurrence further highlights its potential use as a flavoring agent in the food industry.

InChI:InChI=1/C4H8S3/c1-3-5-4(2)7-6-3/h3-4H,1-2H3

Upstream product

• 75-07-0 acetaldehyde 
• 67411-27-2 3,6-dimethyl-1,2,4,5-tetrathiane 
• 7783-06-4 hydrogen sulfide 
• 52-90-4 L-Cysteine 
• 50-81-7 ascorbic acid 
• 23769-40-6 2,4,6-trimethyl-1,3,5-trithiane 
• 1226972-19-5 trithioacetaldehyde 
• 40709-87-3 bis(1-chloroethyl) sulfide 

Relevant articles and documents

1,3,5-Trithianes and sulfur monochloride/sodium sulfide: an alternative route to 3,5-disubstituted 1,2,4-trithiolanes

Treatment of substituted 1,3,5-trithianes with S2Cl2 and Na2S under mild conditions provides 3,5-disubstituted 1,2,4-trithiolanes, as mixture of diastereoisomers.

Aroma compounds generated from thermal reaction of l-ascorbic acid with l-cysteine

The reaction of l-ascorbic acid with l-cysteine in heated aqueous solution (141 ± 1 °C) at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.00) for 2 h, resulted in the formation of a complex mixture of aroma volatiles. The volatile compounds generated were analysed by SPME-GC-MS. The results gave 43 aroma compounds. The reaction between l-ascorbic acid and l-cysteine led mainly to the formation of alicyclic sulphur compounds, thiophenes, thienothiophenes, thiophenones, thiazoles and pyrazines, most of which contain sulphur. Many of these volatiles had meaty flavour. The origin of many of the compounds was explained. The studies showed that thienothiophenes and thienones were formed mainly at acidic pH. In contrast, higher pH values could promote the production of thiophenes, thiazoles and pyrazines.

Evidence for heterolytic cleavage of C-S bonds in the photolysis of 1,3,5-trithianes

The homolytic/heterolytic nature of photolytic C-S bond cleavage was studied in 1,3,5-trithianes. The mechanism of photolysis was refined from previous studies. First, evidence was presented for the existence of a precursor of the biradical-like transient (I) which itself was identified in previous studies. Second, the nature of I was further clarified through methanol-scavenging experiments where the results could be interpreted as lending credibility to the notion that I has significant bipolar character. Kinetic and spectral analyses of transient absorptions, following laser excitation of the trithianes, showed that I was reacting with methanol. Complementary steady-state photolytic quantum yields supported this finding, and additional, but unidentified, stable products from irradiations in methanol were seen in the HPLC. The formation of these products was interpreted as likely arising from a nucleophilic attack of methanol at the carbocationic end of the bipolar structure of I.

A Novel Method for the Generation of Thial S-Sulfides from 2,4,6-Trisubstituted 5,6-Dihydro-1,3,5-dithiazines

Treatment of 2,4,6-trisubstituted 5,6-dihydro-1,3,5-dithiazines with NCS or NBS afforded highly reactive thial S-sulfides, which underwent dimerization to give the corresponding 1,2,4,5-tetrathianes.The products were also selectively converted into naturally-occurring cyclic polysulfides, 1,2,4-trithiolanes and 1,2,3,5,6-pentathiepanes, by treatment with Ph3P, KCN, or Na2S4.

Gas Phase Reactions, 24. The Thermal Generation of Thiocarbonyl Compounds

Thiocarbonyl derivatives R1R2C=S with R1, R2 = H, CH3, C6H5 can be generated thermally in the gas phase from a variety of precursors.Especially advantageous are the cleavage of propene from allyl sulfides or, for their preparation in pure form, the pyrolysis of dithietane or trithiolane derivatives.Photoelectron spectroscopy proves to be well-suited for gas analysis in the flow tube used, for the optimization of the decomposition conditions, and via assignment of the observed ionization patterns for the characterization of the thioaldehydes and thioketones prepared.