| Identification | More | [Name]
5-Methyl-2-acetylfuran | [CAS]
1193-79-9 | [Synonyms]
1-(5-METHYL-2-FURYL)ETHAN-1-ONE
2-ACETYL-5-METHYLFURAN
2-METHYL-5-ACETYLFURAN
5-METHYL-2-ACETYL FURAN
FEMA 3609
METHYL 5-METHYL-2-FURYL KETONE
1-(5-methyl-2-furanyl)-ethanon
1-(5-Methyl-2-furyl)ethanone
1-(5-Methyl-furan-2-yl)-ethanone
2-Acetyl, 5-mefuran
2-acetyl-5-methyl-fura
5-Acetyl-2-methylfuran
5-Methyl-2-furylethanone
5-methyl-2-furylmethylketone
5-Methyl-Z-acetylfuran
Ethanone, 1-(5-methyl-2-furanyl)-
Ethanone,1-(5-methyl-2-furanyl)-
Furan, 2-acetyl-5-methyl-
Ketone, methyl 5-methyl-2-furyl
Ketone,methyl5-methyl-2-furyl | [EINECS(EC#)]
214-779-1 | [Molecular Formula]
C7H8O2 | [MDL Number]
MFCD00003243 | [Molecular Weight]
124.14 | [MOL File]
1193-79-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Melting point ]
2 °C | [Boiling point ]
100-101 °C/25 mmHg (lit.) | [density ]
1.066 g/mL at 25 °C(lit.)
| [vapor density ]
>1 (vs air)
| [FEMA ]
3609 | [refractive index ]
n20/D 1.512(lit.)
| [Fp ]
176 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Soluble), Methanol (Slightly) | [form ]
clear liquid | [color ]
Light yellow to Brown | [Specific Gravity]
1.066 | [Odor]
at 0.10 % in dipropylene glycol. strong musty nutty hay coconut coumarin milky | [biological source]
synthetic | [Odor Type]
nutty | [Water Solubility ]
Slightly soluble in water. Soluble in alcohol. | [JECFA Number]
1504 | [BRN ]
110853 | [Major Application]
cleaning products
cosmetics
food and beverages
personal care | [InChI]
1S/C7H8O2/c1-5-3-4-7(9-5)6(2)8/h3-4H,1-2H3 | [InChIKey]
KEFJLCGVTHRGAH-UHFFFAOYSA-N | [SMILES]
CC(=O)c1ccc(C)o1 | [LogP]
0.98 | [CAS DataBase Reference]
1193-79-9(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Acetyl-5-methylfuran(1193-79-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
2810 | [WGK Germany ]
3
| [RTECS ]
LT8528000
| [Hazard Note ]
Harmful | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29321900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
mouse,LD50,oral,438mg/kg (438mg/kg),Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980. |
| Questions And Answer | Back Directory | [Identification]
CAS.No.:
1193-79-9
FL.No.:
13.083
FEMA.No.:
3609
NAS.No.:
3609
CoE.No.:
11038
EINECS.No.:
214-779-1
JECFA.No.:
1504
| [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.
|
| Hazard Information | Back Directory | [Chemical Properties]
A light yellow liquid with strong, nutty aroma. | [Chemical Properties]
Colorless to light yellow liqui | [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]
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 |
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