2,3-hexanedione

Structural formula
General
Surname	2,3-hexanedione
other names	Hexane-2,3-dione; Propyl diketone; Methylpropylglyoxal; Acetyl butyryl;
Molecular formula	C 6 H 10 O 2
Brief description	yellow liquid with a characteristic odor
External identifiers / databases
EC number	223-350-8
ECHA InfoCard	100.021.229
PubChem	19707
ChemSpider	18563
Wikidata	Q11186388
properties
Molar mass	114.14 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−30 ° C
boiling point	130 ° C
Vapor pressure	13 hPa (20 ° C)
solubility	soluble in water (31 g l −1 at 20 ° C); soluble in propylene glycol , ethanol and oils;
Refractive index	1.412 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: 210-370 + 378
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2,3-Hexanedione is a chemical compound from the group of alkanediones .

Occurrence

The compound has been detected in fermented soybeans , peaches , fried chicken, beer , coffee , shoyu, and clams.

Extraction and presentation

2,3-Hexanedione can be prepared from propionyl aldehyde , which is condensed over ethyl acetylacetate. The resulting product is then oxidized (with hydrogen peroxide and sodium tungstate ), hydrolyzed, and finally decarboxylated to 2,3-hexanedione. The compound can also be prepared from methyl butyl ketone and ethyl propyl ketone via the monoxime and also from acetoxymesityl oxide .

properties

As a technical product, 2,3-hexanedione is a yellow liquid with a characteristic odor, which is soluble in water. It has a strong, creamy, sweet and buttery odor (less than diacetyl) and a buttery cheese taste.

Safety-related parameters

The compound forms highly flammable vapor-air mixtures. It has a flash point of 28 ° C. The explosion range is between 1.2 vol.% As the lower explosion limit (LEL) and 5.9 vol.% As the upper explosion limit (UEL). The ignition temperature is 245 ° C. The substance therefore falls into temperature class T3.

use

2,3-Hexanedione is used to evaluate the influence of the xanthan gum concentration on the release of flavoring substances in xanthan gum thickened food model systems. It is also used as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 2,3-hexanedione in the GESTIS substance database of the IFA , accessed on June 11, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 782 ( limited preview in Google Book search).
↑ Data sheet 2,3-Hexanedione, ≥95%, FG from Sigma-Aldrich , accessed on June 11, 2019 ( PDF ).
^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
↑ Data sheet 2,3-Hexanedione, 94% from AlfaAesar, accessed on June 11, 2019 ( PDF )(JavaScript required) .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 2,3-hexanedione in the GESTIS substance database of the IFA , accessed on June 11, 2019(JavaScript required) .

[George_A._Burdock-2] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 782 ( limited preview in Google Book search).

[Sigma-3] Data sheet 2,3-Hexanedione, ≥95%, FG from Sigma-Aldrich , accessed on June 11, 2019 ( PDF ).

[Brandes-4] E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[Alfa-5] Data sheet 2,3-Hexanedione, 94% from AlfaAesar, accessed on June 11, 2019 ( PDF )(JavaScript required) .