Lenthionine

Lenthionine

Names
IUPAC name 1,2,3,5,6-Pentathiepane
Other names 1,2,3,5,6-Pentathiacycloheptane
Identifiers
CAS Number	292-46-6
3D model (Jmol)	Interactive image
ChEBI	CHEBI:6408
ChemSpider	60844
KEGG	C08382
PubChem	67521
InChI InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2 Key: DZKOKXZNCDGVRY-UHFFFAOYSA-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

1. 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.
2. 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.