Lenthionine
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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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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
[edit]Lenthionine has been prepared by treating dichloromethane with polysulfide solutions.[5]
Further reading
[edit]- 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
[edit]- 1 2 3 "Showing metabocard for Lenthionine (HMDB0031258)". Human Metabolome Database. March 23, 2022. Retrieved November 12, 2022.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.