Sotolon (also known as sotolone) is a

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the c ...

and an extremely powerful

aroma compound An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently vol ...

, 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 trad ...

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 ...

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 caramelizati ...

, 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 v ...

, 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 fo ...

, aged rum, aged sake and white wine, flor

sherry Sherry ( es, jerez ) is a fortified wine made from white grapes that are grown near the city of Jerez de la Frontera in Andalusia, Spain. Sherry is produced in a variety of styles made primarily from the Palomino grape, ranging from light ve ...

, roast tobacco, and dried fruiting bodies of the mushroom '' Lactarius helvus''. 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 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 ...

. 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 Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...

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

References

{{Reflist Flavors Furanones Enols

French ''vin jaune''

See also

References