Sotolon

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Sotolon
160px
Ball-and-stick model of the sotolon molecule
Names
IUPAC name
3-Hydroxy-4,5-dimethylfuran-2(5H)-one
Other names
Sotolone
Caramel furanone
Sugar lactone
Fenugreek lactone
Identifiers
28664-35-9 YesY
Jmol 3D model Interactive image
PubChem 5325921
  • O=C1OC(C)C(C)=C1O
Properties
C6H8O3
Molar mass 128.13 g·mol−1
Density 1.049 g/cm3
Melting point 26 to 29 °C (79 to 84 °F; 299 to 302 K)
Boiling point 184 °C (363 °F; 457 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. Sotolon is the major aroma and flavor component of fenugreek seed and lovage,[1] and is one of several aromatic and flavor components of artificial maple syrup.[2] It is also present in molasses, aged rum, aged sake and white wine, flor sherry, roast tobacco,[3] and dried fruiting bodies of the mushroom Lactarius helvus.[4] Sotolon can pass through the body relatively unchanged, and consumption of foods high in sotolon, such as fenugreek, can impart a maple syrup aroma to one's sweat and urine. In some individuals with the genetic disorder maple syrup urine disease, it is spontaneously produced in their bodies and excreted in their urine, leading to the disease's characteristic smell.[5]

This molecule is thought to be responsible for the mysterious maple syrup smell that has occasionally wafted over Manhattan since 2005.[6]

Sotolon was first isolated in 1975 from the herb fenugreek.[7] The compound was named in 1980 when it was found to be responsible for the flavor of raw cane sugar: soto- means "raw sugar" in Japanese and -olon signifies that the molecule is an enol lactone.[8]

French vin jaune

Vin jaune is marked by the formation of sotolon from α-ketobutyric acid.[9][10]

See also

  • Candy cap (Lactarius mushroom species whose maple syrup aroma derives from quabalactone III, which hydrolyzes into sotolon)

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Sigma-Aldrich
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ F. Rijkens and H. Boelens (1975) "The future of aroma research," Proceedings of the International Symposium on Aroma Research, H. Maarse and P.J. Groenen, eds. (Wageningen, Netherlands: Pudoc, 1975), pp. 203-220.
  8. ↑ Tokitomo, Yukiko; Kobayashi, Akio; Yamanishi, Tei; Muraki, Shigeru (1980) "Studies on the "sugary flavor" of raw cane sugar. III. Key compound of the sugary flavor," Proceedings of the Japan Academy, series B, 56 (7) : 457-462 ; see footnote on p. 457.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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