2,3-Pentanedione

Synonym(s):2,3-Pentanedione;Acetylpropionyl

CAS NO.：600-14-6
Empirical Formula: C5H8O2
Molecular Weight: 100.12
MDL number: MFCD00009313
EINECS: 209-984-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-05 08:26:49

What is 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

Properties of 2,3-Pentanedione

Melting point:	-52 °C (lit.)
Boiling point:	110-112 °C (lit.)
Density	0.957 g/mL at 25 °C (lit.)
vapor pressure	28.5 hPa (20 °C)
FEMA	2841 \| 2,3-PENTANEDIONE
refractive index	n20/D 1.404(lit.)
Flash point:	66 °F
storage temp.	2-8°C
solubility	60g/l
form	Liquid
color	very deep green-yellow
PH	4 (H2O)
Odor	at 1.00 % in dipropylene glycol. pungent sweet butter creamy caramel nutty cheese
explosive limit	1.8-10.9%(V)
Water Solubility	60 g/L (15 ºC)
JECFA Number	410
BRN	1699638
Exposure limits	NIOSH: TWA 9.3 ppb; STEL 31 ppb
Stability:	Stable. Highly flammable - store cool. Incompatible with strong oxidizing agents, reducing agents, strong bases.
CAS DataBase Reference	600-14-6(CAS DataBase Reference)
NIST Chemistry Reference	2,3-Pentanedione(600-14-6)
EPA Substance Registry System	2,3-Pentanedione (600-14-6)

Safety information for 2,3-Pentanedione

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H225:Flammable liquids H317:Sensitisation, Skin H373:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P314:Get medical advice/attention if you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.