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 | |||
| Identifiers | |||
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PubChem CID |
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CompTox Dashboard (EPA) |
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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) | ||
| 532.7 mg/L | |||
| log P | 4.238 | ||
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), onions, and garlic, and it is partly responsible for their flavor. The mechanism of its formation is unclear, but it likely involves the enzyme C–S lyase.
Preparation
Lenthionine has been prepared by treating dichloromethane with polysulfide solutions.
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.
- Shimada, Shoichiro; Kumagai, Kazuki; Mochizuki, Soichiro; Hirata, Ryuji; Tanabe, Yuki; Yamada, Kyohei; Yamaguchi, Yusuke; Kumagai, Hitomi (2024). "Lenthionine, a key flavour compound of shiitake mushrooms, prevents platelet aggregation by inhibiting αIIbβ3 activation". Journal of Food Bioactives: 50–58. doi:10.26599/JFB.2024.95028395. ISSN 2637-8752.
References
- 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.