Sotolon
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| Sotolon | |
|---|---|
| Image:Sotolon chemical structure.png | |
| IUPAC name | 3-Hydroxy-4,5-dimethylfuran-2(5H)-one |
| Other names | Sotolone Caramel furanone Sugar lactone Fenugreek lactone |
| Identifiers | |
| CAS number | |
| PubChem | |
| 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
- ↑ 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.
- ↑ Caracteristiques chemiques et nutritives du sirop d'erable
- ↑ Sigma-Aldrich
- ↑ Sylvie Rapior,a Françoise Fons,a and Jean-Marie Bessièreb. "The fenugreek odor of Lactarius helvus". Mycologia 92 (2): 305-308.
- ↑ 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.
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
