| Identification | More | [Name]
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one | [CAS]
28664-35-9 | [Synonyms]
2,3-DIMETHYL-4-HYDROXY-2,5-DIHYDROFURAN-5-ONE
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
CARAMEL FURANONE
FEMA 3634
Fenugreck Lactone
FENUGREEK LACTONE
SOTOLON
SOTOLONE
SUGAR LACTONE
2(5H)-Furanone, 3-hydroxy-4,5-dimethyl-
3-Hydoxy-4,5-dimethyl-2(5H)-furanone
3-hydroxy-4,5-dimethyl-2(5h)-furanon
3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon)
3-hydroxy-4,5-dimethyl-5H-furan-2-one
4,5-dimethyl-3-hydroxy-2(5H)-furanone (sotolon)
dimethylhydroxyfuranone
Furan-2(5H)-one, 3-hydroxy-4,5-dimethyl-
4,5-Dimethyl-3-hydroxy-2(5H)-furanone (ca. 14% in propylene glycol) | [EINECS(EC#)]
249-136-4 | [Molecular Formula]
C6H8O3 | [MDL Number]
MFCD00059957 | [Molecular Weight]
128.13 | [MOL File]
28664-35-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [Melting point ]
26-29 °C(lit.)
| [Boiling point ]
184 °C(lit.)
| [density ]
1.049 g/mL at 25 °C
| [FEMA ]
3634 | [refractive index ]
n20/D 1.491(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Refrigerator (+4°C) | [form ]
neat | [pka]
9.28±0.40(Predicted) | [Odor]
at 0.01 % in propylene glycol. extremely sweet strong caramel maple burnt sugar coffee | [biological source]
synthetic | [Odor Type]
caramellic | [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]
28664-35-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [HS Code ]
29329990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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 | [Biological Activity]
Odor at 1.0%''Taste at 5-25 ppm |
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