Lenthionine

Lenthionine

Names
Preferred IUPAC name 1,2,3,5,6-Pentathiepane
Other names 1,2,3,5,6-Pentathiacycloheptane 1,4-Dicarbacycloheptasulfane
Identifiers
CAS Number	292-46-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6408 N
ChemSpider	60844 N
KEGG	C08382 N
PubChem CID	67521
UNII	71G9U1CIRD Y
CompTox Dashboard (EPA)	DTXSID20183460
InChI 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	188.35 g·mol−1
Density	1.549 g/cm3
Melting point	60.5 °C (140.9 °F; 333.6 K)
Boiling point	287 °C (549 °F; 560 K)[1]
Solubility in water	532.7 mg/L[1]
log P	4.238[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Lenthionine is a cyclic organosulfur compound found in shiitake mushrooms, onions, and garlic, and it is partly responsible for their flavor.^[2] The mechanism of its formation is unclear, but it likely involves the enzyme C–S lyase.^{[citation needed]}

Preparation

Lenthionine has been isolated from mushrooms by submerging them in water and allowing them to set overnight. The mushrooms were then centrifuged, and dissolved in chloroform, which was later evaporated to form a yellow oil layer. Chromatography was then used to isolate the lenthionine.^[3]

Lenthionine has been prepared in situ bubbling hydrogen sulfide gas through a solution of sulfur and sodium sulfide until the pH reached 8. Then, the solution had a large amount of dichloromethane added, and it was stirred at room temperature until an organic layer formed, which contained the lenthionine.^[3]

References