4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one

Chemical properties

clear yellow liquid

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.

Occurrence

Reported found in roasted Virginia tobacco, beef broth, beer, sherry, botryized wine, coffee, tea, fenugreek, sake and rice wine.

The Uses of 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one

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