Lenthionine
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |||
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| Preferred IUPAC name
1,2,3,5,6-Pentathiepane | |||
| Other names
1,2,3,5,6-Pentathiacycloheptane 1,4-Dicarbacycloheptasulfane | |||
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| Properties | |||
| (CH2)2S5 | |||
| 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] | ||
| 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).
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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.