Sotolon
| Sotolon | |
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3-Hydroxy-4,5-dimethylfuran-2(5H)-one |
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Other names
Sotolone |
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| Identifiers | |
| CAS number | 28664-35-9  |
| PubChem | 5325921 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H8O3 |
| Molar mass | 128.13 g/mol |
| Density | 1.049 g/cm3 |
| Melting point |
26-29C |
| Boiling point |
184 °C, 457 K, 363 °F |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 it 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]
[edit] Sotolon in French vin jaune
Vin jaune is marked by the formation of sotolon from alpha-ketobutyric acid.[7][8]
[edit] References
- ^ Imre Blank, Peter Schieberle (1993). "Analysis of the seasoning-like flavour substances of a commercial lovage extract" (abstract). Flavour and Fragrance Journal 8 (4): 191–195. doi:10.1002/ffj.2730080405. http://www3.interscience.wiley.com/cgi-bin/abstract/112664676/ABSTRACT.
- ^ Caractéristiques chimiques et nutritives du sirop d'érable
- ^ Sigma-Aldrich
- ^ Sylvie Rapior, Françoise Fons and Jean-Marie Bessièreb (2000). "The fenugreek odor of Lactarius helvus" (abstract). Mycologia (Mycological Society of America) 92 (2): 305–308. doi:10.2307/3761565. JSTOR 3761565. http://apt.allenpress.com/aptonline/?request=get-abstract&issn=0027-5514&volume=092&issue=02&page=0305.
- ^ 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. PMID 10234605. http://www.springerlink.com/content/j833777550q24723/.
- ^ http://www.scientificamerican.com/blog/post.cfm?id=mystery-of-nyc-maple-syrup-smell-so-2009-02-05
- ^ Optimal Conditions for the Formation of Sotolon from .alpha.-Ketobutyric Acid in the French "Vin Jaune". Pham Thu Thuy, Guichard Elisabeth, Schlich Pascal and Charpentier Claudine, J. Agric. Food Chem., 1995, 43 (10), pages 2616–2619, doi:10.1021/jf00058a012
- ^ Quantitative determination of sotolon in wines by high-performance liquid chromatography. E. Guichard, T. T. Pham and P. Etievant, Chromatographia, Volume 37, Numbers 9-10, pages 539-542, doi:10.1007/BF02275793
