5-Methyl-2-acetylfuran

Identification

Description

A light yellow liquid with strong, nutty aroma.

Usage

Reported uses (ppm): (FEMA, 1994)

Natural occurrence

Reported found in coffee, roasted filberts, tomato juice, raisin, roasted onion, French fried potato, crispbread, smoked fatty fish, boiled/cooked beef, fried cured pork, beer, cognac, rum, malt whiskey, cocoa, black tea, wild rice (Zizania aquatuca), and squid.

Chemical Properties

Colorless to light yellow liqui

Chemical Properties

A light yellow liquid with strong, nutty aroma.

Occurrence

Reported found in coffee, roasted filberts, tomato juice, raisin, roasted onion, French fried potato, crispbread, smoked fatty fish, boiled/cooked beef, fried cured pork, beer, cognac, rum, malt whiskey, cocoa, black tea, wild rice (Zizania aquatuca), and squid.

Uses

Glucose was transformed to various furan compounds and carboxylic acids derivatives by heat treatment of autoclave such as levulinic acid, 2-acetylfuran and 2-acetyl-5-methylfuran. using 2-acetyl-5-methylfuran or 1,5-dimethyl-2-pyrrolecarbonitrile as reactants, that the formation of the 4-arylation products. Reaction of 2-acetyl-5-methylfuran 6a with 2-aminoethanol pioduced in 79% yield the aminal.

Definition

ChEBI: A furan carrying acetyl and methyl substituents at the 2- and 5-positions respectively.

Taste threshold values

Taste characteristics at 50 ppm: nutty, cocoa-like with toasted, bready nuance

General Description

s-cis-trans isomerism of 2-acetyl-5-methylfuran was investigated by IR and NMR spectroscopy.

Synthesis

534-22-5

108-24-7

1193-79-9

General procedure for the synthesis of 5-methyl-2-acetylfuran from 2-methylfuran and ethanoic anhydride: continuous acylation of 2-methylfuran (2-MF) by acetic anhydride (AA) on parent Hb, AC-Hb, TA-Hb, Si-Hb zeolites in a fixed-bed reactor (Fig. 1) at atmospheric pressure. The reactor consisted of a glass tube (inner diameter 10 mm) and an electric heater. Before carrying out the acylation reaction, an equal amount of zeolite was activated for 2 h in a drying oven at 200 °C. The activated zeolites need to be transferred to the reactor immediately to avoid exposure to the atmosphere. In standard experiments, the acylation temperature was first controlled at 60 °C by a water bath. Subsequently, 5.9 g of zeolite catalyst was immobilized in the center of the fixed-bed reactor. A mixture of 2-MF and AA (molar ratio of 1:2.5 or 1:4) was delivered to the catalytic column via a metering pump at a set flow rate (0.07 mL/min). Liquid acylation products were periodically collected from the reactor outlet and quantitatively analyzed using a gas chromatograph (GC, Agilent 7890A) equipped with a flame ionization detector (FID) and a DB-FFAP capillary column (30 m length, 0.25 μm film thickness, and 0.25 mm diameter). The target product 2-acetyl-5-methylfuran (2-AC-5-MF) was obtained by acylation reaction and identified using a mass spectrometer (MS, Agilent 5975C) equipped with a mass selective detector.

References

[1] Research on Chemical Intermediates, 2017, vol. 43, # 3, p. 1557 - 1574
[2] ChemSusChem, 2017, vol. 10, # 1, p. 91 - 98
[3] Molecules, 2007, vol. 12, # 3, p. 634 - 640
[4] Liebigs Annalen der Chemie, 1985, # 10, p. 1935 - 1950
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1981 - 1986