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W316318

Sigma-Aldrich

2-Furyl methyl ketone

≥99%, FG

Synonym(s):

2-Acetylfuran

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About This Item

Empirical Formula (Hill Notation):
C6H6O2
CAS Number:
1192-62-7
Molecular Weight:
110.11
FEMA Number:
3163
Beilstein:
107909
EC Number:
214-757-1
Council of Europe no.:
4113
MDL number:
MFCD00003242
UNSPSC Code:
12164502
PubChem Substance ID:
24901503
Flavis number:
13.054
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002

Assay

≥99%

color

light yellow to orange, darkens over time

refractive index

n20/D 1.5070 (lit.)

bp

67 °C/10 mmHg (lit.)

mp

26-28 °C (lit.)

density

1.098 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

almond; caramel; cocoa; nutty; brown

storage temp.

2-8°C

SMILES string

CC(=O)c1ccco1

InChI

1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3

InChI key

IEMMBWWQXVXBEU-UHFFFAOYSA-N

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General description

2-Furyl methyl ketone is a heterocyclic flavor compound that is reported to be formed by Maillard reaction between glucose and amino acids in foods.

Biochem/physiol Actions

Taste at 10 ppm

Other Notes

Natural occurrence: Burley tobacco, chestnuts, cocoa, coffee, cooked beef and pork, raisins, roasted almonds and peanuts. tamarind, tea, yogurt and wheat bread.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H330 - H311 - H319

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Irrit. 2

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

159.8 °F - closed cup

Flash Point(C)

71 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Amino acid-dependent formation pathways of 2-acetylfuran and 2, 5-dimethyl-4-hydroxy-3 [2H]-furanone in the Maillard reaction
Wang Y, et al.
Food Chemistry, 115(1), 233-237 (2009)
T R Bailey et al.
Journal of medicinal chemistry, 37(24), 4177-4184 (1994-11-25)
As a probe of the 3-methylisoxazole portion of our broad-spectrum antipicornaviral series, a panel of 2-acetylfuran analogues was prepared as replacements for the 3-methylisoxazole ring. Comparison of the two series showed remarkable similarity in potency, spectrum of activity, logP, and
Yu Wang et al.
Journal of agricultural and food chemistry, 56(24), 11997-12001 (2008-12-19)
Sugar type is a major factor regulating the reaction rates and pathways in Maillard reaction. Ribose and glucose were used to compare their reactivities and pathways of 2-acetylfuran formation. A stable isotope labeling method was used to study their reactivity.
T Kawai et al.
International archives of occupational and environmental health, 63(4), 285-291 (1991-01-01)
The concentrations of 2,5-hexanedione (2,5-HD), an n-hexane metabolite, and 2-acetylfuran (2-AF) were measured in urine samples from 123 workers who had predominantly been exposed to n-hexane vapor and 53 workers who had experienced no exposure to solvents. The time-weighted average
Thomas Magauer et al.
Organic letters, 13(20), 5584-5587 (2011-10-01)
A 9-step synthetic route to the complex carbohydrate methyl α-trioxacarcinoside B from 2-acetylfuran is described. Anomerically activated forms, including 1-phenylthio, 1-O-(4'-pentenyl), 1-fluoro, and 1-O-acetyl derivatives are also prepared.
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Protocols

HPLC Analysis of Furans on Ascentis® Express Phenyl-Hexyl as listed in ASTM method D5837-99

Separation of 5-Hydroxymethyl-2-furaldehyde; Furfuryl alcohol; Furfural; 2-Furyl methyl ketone; 5-Methyl-2-furaldehyde

HPLC Analysis of Furans on Ascentis® Express C18

HPLC Analysis of Furans on Ascentis® Express C18

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