Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of

fenugreek Fenugreek (; ''Trigonella foenum-graecum'') is an annual plant in the family Fabaceae, with leaves consisting of three small obovate to oblong leaflets. It is cultivated worldwide as a semiarid crop. Its seeds and leaves are common ingredients ...

curry A curry is a dish with a sauce seasoned with spices, mainly associated with South Asian cuisine. In southern India, leaves from the curry tree may be included. There are many varieties of curry. The choice of spices for each dish in tradit ...

at high concentrations and

maple syrup Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple tree ...

caramel Caramel ( or ) is an orange-brown confectionery product made by heating a range of sugars. It can be used as a flavoring in puddings and desserts, as a filling in bonbons, or as a topping for ice cream and custard. The process of caramelizatio ...

, or burnt sugar at lower concentrations. Sotolon is the major aroma and flavor component of fenugreek seed and

lovage Lovage (), ''Levisticum officinale'', is a tall perennial plant, the sole species in the genus ''Levisticum'' in the family Apiaceae, subfamily Apioideae. It has been long cultivated in Europe, the leaves being used as a herb, the roots as a veg ...

, and is one of several aromatic and flavor components of artificial maple syrup. It is also present in

molasses Molasses () is a viscous substance resulting from refining sugarcane or sugar beets into sugar. Molasses varies in the amount of sugar, method of extraction and age of the plant. Sugarcane molasses is primarily used to sweeten and flavour foods ...

, aged rum, aged sake and white wine,

flor Flor (Spanish and Portuguese for ''flower'') in winemaking, is a film of yeast on the surface of wine, important in the manufacture of some styles of sherry. The flor is formed naturally under certain winemaking conditions, from indigenous yeast ...

sherry, roast tobacco, and dried fruiting bodies of the mushroom ''

Lactarius helvus ''Lactarius helvus'', commonly known as fenugreek milkcap, is a member of the large milkcap genus ''Lactarius'' in the order Russulales. Fruiting bodies can be found in ''Sphagnum'' moss in coniferous and deciduous woodland in Europe, and possib ...

''. 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 Maple syrup urine disease (MSUD) is an autosomal recessive metabolic disorder affecting branched-chain amino acids. It is one type of organic acidemia. The condition gets its name from the distinctive sweet odor of affected infants' urine and ear ...

, it is spontaneously produced in their bodies and excreted in their urine, leading to the disease's characteristic smell. This molecule is thought to be responsible for the mysterious maple syrup smell that has occasionally wafted over Manhattan since 2005. Sotolon was first isolated in 1975 from the herb

. 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 In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The te ...

lactone. Several aging-derived compounds have been pointed out as playing an important role on the aroma of fortified wines; however, sotolon (3-hydroxy-4,5-dimethyl-2(5H)-furanone) is recognized as being the key odorant and has also been classified as a potential aging marker of these type of wines. This chiral lactone is a powerful odorant, which can impart a nutty, caramel, curry, or rancid odor, depending on its concentration and enantiomeric distribution. Despite being pointed out as a key odorant of other fortified wines, the researchers’ attention has also been directed to its off-flavor character, associated to the premature oxidative aging of young dry white wines, overlapping the expected fruity, flowery, and fresh character. This compound can be detected by miniaturized emulsification extraction followed by GC–MS/SIM and single-step miniaturized liquid-liquid extraction followed by LC-MS/MS analysis

French ''vin jaune''

Vin jaune ''Vin jaune'' (French language, French for "yellow wine") is a special and characteristic type of white wine made in the Jura (wine), Jura region in eastern France. It is similar to dry fino Sherry and gets its character from being matured in a ...

'' is marked by the formation of sotolon from α-ketobutyric acid.

References

{{Reflist Flavors Furanones Enols

French ''vin jaune''

See also

References