4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one CAS 28664-35-9

Introduction：Basic information about 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one CAS 28664-35-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

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

• Product Name: 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
• Synonyms: 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one AKA sugar lactone;CARAMEL FURANONE (3% IN TRIACETIN);3-HYDROXY-4,5-DIMETHYL-2(5H)-FURANONE;4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE;4,5-DIMETHYL-3-HYDROXY-2(5H)-FURANONE;FEMA 3634;Fenugreck Lactone;FENUGREEK LACTONE
• CAS: 28664-35-9
• MF: C6H8O3
• MW: 128.13
• EINECS: 249-136-4
• Product Categories: food additives;food additive
• Mol File: 28664-35-9.mol

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
• FEMA: 3634 | 4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE
• refractive index: n20/D 1.491(lit.)
• Fp: >230 °F
• storage temp.: Sealed in dry,2-8°C
• pka: 9.28±0.40(Predicted)
• Appearance: White to off-white Solid
• Odor: at 0.01 % in propylene glycol. extremely sweet strong caramel maple burnt sugar coffee
• Odor Type: caramellic
• biological source: synthetic
• JECFA Number: 243
• Major Application: flavors and fragrances
• InChI: 1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
• InChIKey: UNYNVICDCJHOPO-UHFFFAOYSA-N
• SMILES: CC1OC(=O)C(O)=C1C
• 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
• TSCA: TSCA listed
• HS Code: 29329990
• Storage Class: 10 - Combustible liquids
• Hazard Classifications: Acute Tox. 4 Oral

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 concentrationsto curry-like at high concentrations. A method described for its preparation comprisescondensation of ethyl propionate with diethyl oxalate and reaction of the intermediately formed diethyl oxalylpropionate with acetaldehyde. Acidic decarboxylationof the ethyl 4,5-dimethyl-2,3-dioxodihydrofuran-4-carboxylate givesthe 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-likeand 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

Biological Activity

Odor at 1.0%', 'Taste at 5-25 ppm