2,3-Dihydrothiophene

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2,3-Dihydrothiophene
2,3-Dihydrothiophene.svg
Names
Preferred IUPAC name
2,3-Dihydrothiophene
Other names
2-Thiolene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2 Yes check.svgY
    Key: OXBLVCZKDOZZOJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H6S/c1-2-4-5-3-1/h1,3H,2,4H2
    Key: OXBLVCZKDOZZOJ-UHFFFAOYAG
  • C1CSC=C1
  • S1\C=C/CC1
Properties [1]
C4H6S
Molar mass 86.16 g/mol
Appearancecolorless liquid
Density 1.04 g·cm−3 (20 °C)
Melting point −110 °C (−166 °F; 163 K)
Boiling point 112 °C (234 °F; 385 K)
1.53 (20 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,3-Dihydrothiophene is a heterocyclic compound and an organosulfur compound with the formula SC4H6. It is isomeric with the more symmetrical 2,5-dihydrothiophene. Both isomers of dihydrothiophene are colorless liquids with a thioether-like odor. In terms of their reactivity, both isomers exhibit characteristics of alkenes and thioethers, undergoing addition reactions at carbon and oxidation at sulfur. In contrast, thiophene engages in neither reaction. [1]

Dihydrothiophenes in nature

2,3-dihydrothiophene is present in dry fermented sausages, a product of the fermentation process. It has a nutty aroma. [2]

Dihydrothiophenes contribute to the aroma of the white truffle. The major component is 3-methyl-4,5-dihydrothiophene (alternative name:4-methyl-2,3-dihydrothiophene), produced by bacterial colonies in the truffle's fruiting bodies. [3]

References

  1. 1 2 Shvekhgeimer, M.-G. A. (October 1998). "Dihydrothiophenes. Synthesis and Properties (review)". Chemistry of Heterocyclic Compounds. 34 (10): 1101–1122. doi:10.1007/BF02319487. S2CID   95679838.
  2. ↑ Corral, Sara; Leitner, Erich; Siegmund, Barbara; Flores, Mónica (January 2016). "Determination of sulfur and nitrogen compounds during the processing of dry fermented sausages and their relation to amino acid generation". Food Chemistry. 190: 657–664. doi:10.1016/j.foodchem.2015.06.009.
  3. ↑ Splivallo, R.; Ebeler, S. E. (2015). "Sulfur Volatiles of microbial origin are key contributors to human-sensed truffle aroma". Appl. Microbiol. Biotechnol. 99 (6): 2583–92. doi:10.1007/s00253-014-6360-9. PMID   25573471. S2CID   16749990.
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