Chemical Properties
3-Hydroxy-4,5-dimethyl-2(5H)-furanone was found in, for example, fenugreek, coffee, sake, and florsherry.
Its aroma characteristic changes from caramel-like at low concentrations
to curry-like at high concentrations. A method described for its preparation comprises
condensation of ethyl propionate with diethyl oxalate and reaction of the intermediately formed diethyl oxalylpropionate with acetaldehyde. Acidic decarboxylation
of the ethyl 4,5-dimethyl-2,3-dioxodihydrofuran-4-carboxylate gives
the title compound.
Chemical Properties
clear yellow liquid
Occurrence
Reported found in roasted Virginia tobacco, beef broth, beer, sherry, botryized wine, coffee, tea, fenugreek,
sake and rice wine.
Uses
4,5-Dimethyl-3-hydroxy-2(5H)-furanone-13C3 is a labelled analogue of 4,5-Dimethyl-3-hydroxy-2(5H)-furanone (D473600). 4,5-Dimethyl-3-hydroxy-2(5H)-furanone is a fragrant compound that is a key indicator of maple syrup urine disease, a disorder affecting newborn children that is the result of its inability to properly metabolize Valine (V094205), Leucine (L330110) and Isoleucine (I820175). 4,5-Dimethyl-3-hydroxy-2(5H)-furanone is naturally found in fenugreek seeds, and is an odourant present in sherry wines.
Definition
ChEBI: Sotolone is a butenolide. It has a role as a metabolite.
Aroma threshold values
Aroma characteristics at 1.0%; sweet, strong brown, cyclotene and maple like, caramel, toffee, maltol-like
and burnt, brown sugar fenugreek-like, cooked and syrupy.
Taste threshold values
Taste characteristics at 5–25 ppm; sweet, caramel, maple, walnut, brown sugar, nutty, cotton candy, fenugreek and celery-like, rum, roasted meaty with a honey nuance
