Sotolon

Chembox new
ImageFile = Sotolon_chemical_structure.png ImageSize =
IUPACName = 3-Hydroxy-4,5-dimethylfuran-2("5H")-one
OtherNames = Sotolone
Caramel furanone
Sugar lactone
Fenugreek lactone
Section1 = Chembox Identifiers
CASNo = 28664-35-9
PubChem = 5325921
SMILES = O=C1OC(C)C(C)=C1O
Section2 = Chembox Properties
Formula = C₆H₈O₃
MolarMass = 128.13 g/mol
Appearance =
Density = 1.049 g/cm³
MeltingPt =
BoilingPtC = 184
Solubility =
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

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, [cite journal | author =Imre Blank, Peter Schieberle | title =Analysis of the seasoning-like flavour substances of a commercial lovage extract | journal =Flavour and Fragrance Journal | year =1993 | volume =8 | issue = | pages =191–195 | doi =10.1002/ffj.2730080405 | url =http://www3.interscience.wiley.com/cgi-bin/abstract/112664676/ABSTRACT | format =abstract] and is one of several aromatic and flavor components of maple syrup. [ [http://www.centreacer.qc.ca/publications/chimie/PDF/321-fin-0394.pdf Caracteristiques chemiques et nutritives du sirop d'erable] ] It is also present in molasses, aged rum, aged sake and white wine, flor sherry, roast tobacco, [ [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W363405 Sigma-Aldrich] ] and dried fruiting bodies of the mushroom "Lactarius helvus". [cite journal | author =Sylvie Rapior,a Françoise Fons,a and Jean-Marie Bessièreb | title =The fenugreek odor of Lactarius helvus | journal = Mycologia | year = | volume =92 | issue =2 | pages =305–308 | doi = 10.1043/0027-5514(2000)092 [0305:TFOOH] 2.3.CO;2| url =http://apt.allenpress.com/aptonline/?request=get-abstract&issn=0027-5514&volume=092&issue=02&page=0305 | format =abstract | doi_brokendate =2008-06-23] 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. [cite journal | author =F. Podebrad, M. Heil, S. Reichert1, A. Mosandl, A. C. Sewell and H. Böhles | title =4,5-Dimethyl-3-hydroxy-2 [5H] -furanone (sotolone) — The odour of maple syrup urine disease | journal =Journal of Inherited Metabolic Disease | year =1999 | volume =22 | issue =2 | pages =107–114 | doi =10.1023/A:1005433516026 | url =http://www.springerlink.com/content/j833777550q24723/ ]

References