4740-00-5

Usage

Uses

Used in Food Industry:
3-Methylthiolane is used as a flavoring agent for its strong roasted aroma, enhancing the taste of various food products.
Used in Tobacco Industry:
3-Methylthiolane is used as an additive in the tobacco industry, contributing to the overall flavor profile of tobacco products.
Used in Flavor Compounds:
3-Methylthiolane is used as a key component in creating flavor compounds, particularly those that mimic the 'meaty' flavor of cooked foods, due to its sulfur content. This application is crucial in the development of meat substitutes and vegetarian food products, as well as in the enhancement of the flavor of meat-based dishes.

InChI:InChI=1/C5H10S/c1-5-2-3-6-4-5/h5H,2-4H2,1H3

Upstream product

• 314056-82-1 1-phenylselenyl-2-thia-5-hexene 

Downstream Products

• 111082-40-7 1-(2,5-Dihydroxy-phenyl)-3-methyl-tetrahydro-thiophenium; chloride 
• 28335-08-2 1-(2,5-dihydroxyphenyl)thiolanium chloride monohydrate 
• 872-93-5 3-methylsulfolane 

Relevant academic research and scientific papers

The regiochemistry of cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl radicals: Procedures leading to regioselective syntheses of cyclic sulfones and sulfoxides

A study of the cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl and 5-methyl-5-hexenyl radicals reveals a unique contrast in the mode of ring closure of the radicals. In the case of the 5-hexenyl radicals, the sulfinyl-substituted species displays unexpected regioselectivity relative to its analogues. Thus, while the α-S- and α-SO2-5-hexenyl radicals give measurable and increasing quantities of 6-endo product, the α-sulfinyl species cyclizes with high selectivity (95.5:4.5) via a 5-exo mode. By contrast, ring closure of the 5-methyl-5-hexenyl radicals is found to give substantially the 6-endo product in all cases. It is the α-sulfonyl-5-methyl-5-hexenyl radical that now exhibits high regioselectivity (97.5:2.5) for 6-endo closure: an illustration of the synthetic value of this observation is the independent synthesis of the model cyclohexyl sulfone 61 in high yield. It is found that ring closure under the conditions employed occurs irreversibly in all cases.

Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals

Reductive cyclisation of the 2-sulfonyl-5-hexenyl radical with tributyltin hydride in benzene at 80°C affords a 73:23 mixture of the sulfones derived from 5-exo- and 6-endo- ring closure with a small quantity (4%) of reduced material; under identical conditions, the 2-thia-5-hexenyl radical gives a 70:13:17 mixture of the corresponding sulfides. (C) 2000 Elsevier Science Ltd.