Pentathiepane

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Pentathiepane
Pentathiepanes.svg
Isomers of pentathiepane: 1,2,3,4,5- (left), 1,2,3,4,6- (center), and 1,2,3,5,6-pentathiapane (right)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 1,2,3,4,5:InChI=1S/C2H4S5/c1-2-4-6-7-5-3-1/h1-2H2
    Key: RBTUCNGNEMKWGJ-UHFFFAOYSA-N
  • 1,2,3,4,6:InChI=1S/C2H4S5/c1-3-2-5-7-6-4-1/h1-2H2
    Key: VUWWZQBBXCOVBJ-UHFFFAOYSA-N
  • 1,2,3,5,6:InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2
    Key: DZKOKXZNCDGVRY-UHFFFAOYSA-N
  • 1,2,3,4,5:C1CSSSSS1
  • 1,2,3,4,6:C1SCSSSS1
  • 1,2,3,5,6:C1SSCSSS1
Properties
C2H4S5
Molar mass 188.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentathiepanes are organosulfur compounds and sulfur heterocycles with the formula (CH2)2S5. [1] Three isomers exist depending on the location of the C atoms in the ring. These compounds are uncommon except for the 1,4-derivative, which is called lenthionine. It contributes to the aroma of shiitake mushroooms. [2]

More common than the pentathiepanes are pentathiepines, which have a C=C bond in the ring. Only one isomer exists for this class of rings.

References

  1. ↑ Konstantinova, Lidia S.; Amelichev, Stanislav A.; Rakitin, Oleg A. (2007). "1,2,3,4,5-Pentathiepines and 1,2,3,4,5-pentathiepanes". Russian Chemical Reviews. 76 (3): 195–211. Bibcode:2007RuCRv..76..195K. doi:10.1070/RC2007v076n03ABEH003676.
  2. ↑ Dermiki, Maria; Phanphensophon, Natalie; Mottram, Donald S.; Methven, Lisa (2013). "Contributions of non-volatile and volatile compounds to the umami taste and overall flavour of shiitake mushroom extracts and their application as flavour enhancers in cooked minced meat". Food Chemistry. 141 (1): 77–83. doi:10.1016/j.foodchem.2013.03.018. PMID   23768330.
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