Lenthionine

Not to be confused with Lanthionine or Lanthanide.

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  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 an organosulfur compound with the formula (CH₂)₂S₅. The compound consists of a 1,4-C2S5 ring (pentathiepane). Lenthionine is a major component of the organosulfur compounds found in shiitake mushrooms (Lentinula edodes). ^[2] onions, and garlic, and it is partly responsible for their flavor. ^[3] The mechanism of its formation is unclear, but it likely involves the enzyme C–S lyase. ^[4]

Preparation

Lenthionine has been prepared by treating dichloromethane with polysulfide solutions. ^[5]

Further reading

• Liu, Qin; Cui, Xiao; Song, Zhibo; Kong, Weiwei; Kang, Yuanchun; Kong, Weili; Ng, Tzi Bun (2021). "Coating shiitake mushrooms (Lentinus edodes) with a polysaccharide from Oudemansiella radicata improves product quality and flavor during postharvest storage". Food Chemistry. 352 129357. doi:10.1016/j.foodchem.2021.129357. PMID   33714165.
• Wratten, Stephen J.; Faulkner, D. John (1976). "Cyclic polysulfides from the red alga Chondria californica". The Journal of Organic Chemistry. 41 (14): 2465–2467. doi:10.1021/jo00876a025. PMID   932864.

References

1. "Showing metabocard for Lenthionine (HMDB0031258)". Human Metabolome Database. March 23, 2022. Retrieved November 12, 2022.
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.
3. 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.
4. Xi, Jiapei; Chen, Xiao; Du, Jiaxin; Zhong, Lei; Hu, Qiuhui; Zhao, Liyan (2023). "Biosynthesis, behavior and fate of volatile organic sulfide in Lentinus edodes (Berk.) upon hot-air drying treatment". Food Chemistry. 412 135528. doi:10.1016/j.foodchem.2023.135528. PMID   36716624.
5. 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.