2,3-Pentanedione

Chemical properties

2,3-Pentanedione is a colourless or deep green-yellow colour liquid that has a somewhat sweet odor similar to quinone. This compound has a penetrating, buttery taste on dilution. It is used as flavoring agent or adjuvant.

Occurrence

2,3-Pentanedione occurs in butter, bread, milk, yogurt, chicken, meat, cocoa, coffee, potato chips, roasted almonds, pecans, beer, red and white wine, rum and whiskey. The organoleptic profile can be described as creamy, penetrating, cheesy, oily, sweet, buttery, almondlike, brown roasted, and somewhat caramellic, with a fruity nuance.

The Uses of 2,3-Pentanedione

2,3-Pentanedione may be used as a reference standard in the determination of 2,3-pentanedione in beer samples using headspace-gas chromatographic technique (HS-GC).

What are the applications of Application

2,3-Pentanedione can be used as a reactant to synthesize:
Bisphenol derivatives by acid-catalyzed condensation reaction with phenols.
2-Ethyl-3-methyl-1H-indole by Pd-catalyzed reaction with aniline under reductive conditions.
2-Ethyl-3-methylquinoxaline by condensation reaction with o-phenylenediamine using citric acid as a catalyst.

Definition

ChEBI: 2,3-Pentanedione is an alpha-diketone that is pentane substituted at the 2- and 3-positions by oxo groups. It has a role as a flavouring agent. It is an alpha-diketone and a methyl ketone. It derives from a hydride of a pentane.

Preparation

By oxidation of methyl propyl ketone with excess NaNO2 and diluted HCl in the presence of hydroxylamine hydrochloride under a nitrogen blanket.

Aroma threshold values

Detection: 20 ppb. Aroma characteristics at 1.0%: buttery diacetyl-like, fermented dairy and creamy, popcorn buttery.

Taste threshold values

Taste characteristics at 1 to 5 ppm: sweet buttery, creamy, cheesy, slightly toasted dairy, with a rich baked goods nuance and a good mouthfeel.

General Description

2,3-Pentanedione (acetylpropionyl) is one of the aroma active compounds of cereal coffee brew.

Biochem/physiol Actions

Taste at 1-5.0 ppm

Safety Profile

Confirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes. See also NICKEL COMPOUNDS