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

Melting point:

26-29 °C(lit.)

Boiling point:

184 °C(lit.)

Density 

1.049 g/mL at 25 °C

refractive index 

n20/D 1.491(lit.)

FEMA 

3634 | 4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE

Flash point:

>230 °F

storage temp. 

Sealed in dry,2-8°C

pka

9.28±0.40(Predicted)

Odor

at 0.01 % in propylene glycol. extremely sweet strong caramel maple burnt sugar coffee

Odor Type

caramellic

JECFA Number

243

InChIKey

UNYNVICDCJHOPO-UHFFFAOYSA-N

LogP

-0.44

CAS DataBase Reference

28664-35-9(CAS DataBase Reference)

NIST Chemistry Reference

2(5H)-furanone, 3-hydroxy-4,5-dimethyl-(28664-35-9)

EPA Substance Registry System

2(5H)-Furanone, 3-hydroxy-4,5-dimethyl- (28664-35-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22

Safety Statements 

36

WGK Germany 

3

HS Code 

29329990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one Usage And Synthesis

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.

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

4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one(28664-35-9)Related Product Information

• CHLOROPHOSPHONAZO III
• Acetone oxime
• Dimethyl phthalate
• ETHANE
• Dimethyl sulfide
• Furazolidone
• Spironolactone
• Common Fenugreek Seed P.E.
• 2-Methylfuran
• Dimethyl sulfoxide
• Dimethyl fumarate
• Dimethyl ether
• N,N-Dimethylformamide
• DIMETHYLGLYOXIME DISODIUM SALT
• (-)-Corey lactone diol
• TRIOXSALEN
• 4'-Hydroxyacetophenone
• D-(+)-Glucono-1,5-lactone