Lenthionine

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Lenthionine
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Names
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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3D model (JSmol)
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  • 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
  • C1SSCSSS1
Properties
Page Module:Chem2/styles.css has no content.(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).

Template:Chembox Footer/trackingTemplate:Short description

Lenthionine is an organosulfur compound with the formula Page Module:Chem2/styles.css has no content.(CH2)2S5. The compound consists of a 1,4-Page Module:Chem2/styles.css has no content.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

References

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  1. ^ a b c Page Module:Citation/CS1/styles.css has no content."Showing metabocard for Lenthionine (HMDB0031258)". Human Metabolome Database. March 23, 2022. Retrieved November 12, 2022.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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.