Lenthionine

Lenthionine
Skeletal structure of lenthionine	3D structure of 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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6408 ;
ChemSpider	60844 ;
KEGG	C08382 ;
PubChem CID	67521;
UNII	71G9U1CIRD ;
CompTox Dashboard (EPA)	DTXSID20183460 ;
	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	188.35 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). verify (what is ?) 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.

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

"Showing metabocard for Lenthionine (HMDB0031258)". Human Metabolome Database. March 23, 2022. Retrieved November 12, 2022.
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. S2CID 97296030.
Morita, Katsura; Kobayashi, Shigeru (1967). "Isolation, Structure, and Synthesis of Lenthionine and Its Analogs". Chemical and Pharmaceutical Bulletin. 15 (7): 988–993. doi:10.1248/cpb.15.988. ISSN 0009-2363. PMID 5625860.

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[HMDB-1] "Showing metabocard for Lenthionine (HMDB0031258)". Human Metabolome Database. March 23, 2022. Retrieved November 12, 2022.

[Block-2] 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. S2CID 97296030.

[:0-3] Morita, Katsura; Kobayashi, Shigeru (1967). "Isolation, Structure, and Synthesis of Lenthionine and Its Analogs". Chemical and Pharmaceutical Bulletin. 15 (7): 988–993. doi:10.1248/cpb.15.988. ISSN 0009-2363. PMID 5625860.