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Sotolon



Sotolon
IUPAC name 3-Hydroxy-4,5-dimethylfuran-2(5H)-one
Other names Sotolone
Caramel furanone
Sugar lactone
Fenugreek lactone
Identifiers
CAS number 28664-35-9
PubChem 5325921
SMILES O=C1OC(C)C(C)=C1O
Properties
Molecular formula C6H8O3
Molar mass 128.13 g/mol
Density 1.049 g/cm3
Boiling point

184 °C, 457 K, 363 °F

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Sotolon (also known as sotolone, caramel furanone, sugar lactone and fenugreek lactone) 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 maple syrup.[2] It is also present in molasses, 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. Some individuals with the genetic disorder maple syrup urine disease produce it in their bodies and excrete it in their urine.[5]

References

  1. ^ Imre Blank, Peter Schieberle (1993). "Analysis of the seasoning-like flavour substances of a commercial lovage extract". Flavour and Fragrance Journal 8: 191-195. doi:10.1002/ffj.2730080405.
  2. ^ Caracteristiques chemiques et nutritives du sirop d'erable
  3. ^ Sigma-Aldrich
  4. ^ Sylvie Rapior,a Françoise Fons,a and Jean-Marie Bessièreb. "The fenugreek odor of Lactarius helvus". Mycologia 92 (2): 305-308.
  5. ^ F. Podebrad, M. Heil, S. Reichert1, A. Mosandl, A. C. Sewell and H. Böhles (1999). "4,5-Dimethyl-3-hydroxy-2[5H-furanone (sotolone) — The odour of maple syrup urine disease]". Journal of Inherited Metabolic Disease 22 (2): 107-114. doi:10.1023/A:1005433516026.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sotolon". A list of authors is available in Wikipedia.
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