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4077-47-8

4077-47-8 Structure

4077-47-8 Structure
IdentificationMore
[Name]

4-Methoxy-2,5-dimethyl-3(2H)-furanone
[CAS]

4077-47-8
[Synonyms]

2,5-dimethyl-4-methoxy-2,3-dihydro-3-furanone
2,5-DIMETHYL-4-METHOXY-3(2H)-FURANONE
4-METHOXY-2,5-DIMETHYL-3(2H)-FURANONE
FEMA 3664
FRAISION METHYL ETHER
FURANEOL METHYL ETHER
Mesifurane
2,5-dimethyl 4-methoxy furan-3-one
3(2H)-Furanone, 2,5-dimethyl-4-methoxy
3(2H)-Furanone, 4-methoxy-2,5-dimethyl-
4-methoxy-2,5-dimethyl-3(2h)-furanon
mesifuran
4-methoxy-2,5-dimethylfuran-3(2H)-one
dimethylmethoxyfuranone,2,5-dimethyl-4-methoxy-2,3-dihydro-3-furanone
2,5-Dimethyl-4-Methoxy-2,3-Dih
2,5-Dimethyl-4-methoxy-2,3-dihydro-furan-3-one
4-METHOXY-2,5-DIMETHYL-3(2H)-FURANONE FEMA NO.3664 97+%
4-Methoxy-2,5-dimethyl-3(2H)-furfuran ketone
Furfuran ketone methyl ether
Methoxyfuraneol
[EINECS(EC#)]

223-797-9
[Molecular Formula]

C7H10O3
[MDL Number]

MFCD00209504
[Molecular Weight]

142.15
[MOL File]

4077-47-8.mol
Questions And AnswerBack Directory
[Synthesis]

Synthesis of 4077-47-8

In a 1000 mL three-necked flask, 300 g of tetrahydrofuran and 26 g of sodium hydride were added. While stirring and cooling to 0–5 °C, 120 g of natural ethyl lactate was added dropwise. After reacting for 30 minutes, the reaction solution was heated to 60 °C, and 74 g of natural crotonitrile was added dropwise. After the addition was completed over two hours, the mixture was refluxed to obtain nitrile furanone with a yield of 96%. The nitrile furanone was then oxidized with potassium persulfate, and refluxed with water as the solvent. The mixture was then subjected to pyrolysis of the nitrile using a strong-base anion exchange resin, Dowex 2, to obtain furanone with a yield of 28%.

Take 60 g of the natural equivalent furanone obtained by the above method, 480 g of natural methanol, and 3 g of p-toluenesulfonic acid, add them to a 1000 mL three-necked flask, and reflux for 8 hours. Cool the reaction solution to room temperature, add 90 g of sodium bicarbonate, stir for 30 minutes, and then filter off the sodium bicarbonate. Distill methanol under normal pressure until no more distillate is obtained, then distill 4-Methoxy-2,5-dimethyl-3(2H)-furanone under reduced pressure, yielding a purity of 97% and a molar yield of 65%.
Chemical PropertiesBack Directory
[Boiling point ]

63°C/0.3mmHg(lit.)
[density ]

1.097 g/mL at 25 °C(lit.)
[FEMA ]

3664
[refractive index ]

n20/D 1.478(lit.)
[Fp ]

167 °F
[storage temp. ]

2-8°C
[form ]

clear liquid
[color ]

Colorless to Yellow
[Specific Gravity]

1.097
[Odor]

at 1.00 % in dipropylene glycol. sweet moldy mushroom vegetable potato burnt sugar nut skin wasabi caramellic fruity brandy
[biological source]

synthetic
[Odor Type]

moldy
[JECFA Number]

1451
[Major Application]

flavors and fragrances
[InChI]

1S/C7H10O3/c1-4-6(8)7(9-3)5(2)10-4/h4H,1-3H3
[InChIKey]

SIMKGHMLPVDSJE-UHFFFAOYSA-N
[SMILES]

COC1=C(C)OC(C)C1=O
[LogP]

0.54
[CAS DataBase Reference]

4077-47-8(CAS DataBase Reference)
[NIST Chemistry Reference]

3(2H)-furanone, 4-methoxy-2,5-dimethyl-(4077-47-8)
[EPA Substance Registry System]

4077-47-8(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P301+P312+P330
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

24/25
[WGK Germany ]

3
[TSCA ]

TSCA listed
[HS Code ]

29329990
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Acute Tox. 4 Oral
Hazard InformationBack Directory
[Chemical Properties]

2,5-Dimethyl-4-methoxy-3(2H)-furanone has a sweet, cooked caramellic, burnt sugar odor
[Occurrence]

Taste characteristics at 1.0–5.0 ppm:musty, vegetative,savorymeaty with a brown jamy fullnessin the aftertaste. Natural occurrence: Reported found in grape, mango, pineapple, wild raspberry, wild strawberry, (Fragaria vesca), cultivated strawberry, strawberry wine, strawberry jam, blackberries, kiwifruit and Cape gooseberry.
[Uses]

flavors and fragrances
[Definition]

ChEBI: Mesifurane is a member of oxolanes.
[General Description]

2,5-Dimethyl-4-methoxy-3(2H)-furanone is one of the key volatile aroma compounds that contribute to the characteristic aroma of strawberries.
[Biochem/physiol Actions]

Odor at 1.0% PG
Spectrum DetailBack Directory
[Spectrum Detail]

4-Methoxy-2,5-dimethyl-3(2H)-furanone(4077-47-8)1HNMR
4-Methoxy-2,5-dimethyl-3(2H)-furanone(4077-47-8)FT-IR
4-Methoxy-2,5-dimethyl-3(2H)-furanone(4077-47-8)IR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

4077-47-8(sigmaaldrich)
[TCI AMERICA]

2,5-Dimethyl-4-methoxy-3(2H)-furanone,>97.0%(GC)(4077-47-8)
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