Lenthionine

Not to be confused with Lanthionine or Lanthanide.

Lenthionine

Names

IUPAC name

1,2,3,5,6-Pentathiepane

Other names

1,2,3,5,6-Pentathiacycloheptane

Identifiers

CAS Number

292-46-6^Y

3D model (Jmol)

CHEBI:6408^N

60844^N

C08382^N

InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2^N
Key: DZKOKXZNCDGVRY-UHFFFAOYSA-N^N
InChI=1/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2
Key: DZKOKXZNCDGVRY-UHFFFAOYAF

SMILES

C1SSCSSS1

Properties

Chemical formula

C₂H₄S₅

Molar mass

188.38 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

Lenthionine is a cyclic organosulfur compound found in shiitake mushrooms and partly responsible for their flavor.^[1] The mechanism of its formation is unclear, but it probably involves the enzyme C–S lyase.

Besides giving flavor to shiitake mushrooms, lenthionine inhibits platelet aggregation, so it is a promising treatment for thrombosis.^[2] Other organosulfur compounds found in garlic have a similar effect.

References

↑ Block, Eric; Deorazio, Russell (1994). "Chemistry in a salad bowl: Comparative organosulfur chemistry of garlic, onion and shiitake mushrooms" (PDF). Pure & Appl. Chem. 66 (10–11): 2205–2206. doi:10.1351/pac199466102205.
↑ Shibuya, T.; Shimada, S.; Sakurai, H.; Kumagai, H. (2005). "Mechanism of inhibition of platelet aggregation by lenthionine, a flavor component from shiitake mushroom". IFT Annual Meeting: Presentation 54G–9.

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