Octane-2,3-dione Chemical Properties

Boiling point:

173 °C

Density 

0.9311 g/cm3

FEMA 

4060 | 2,3-OCTANEDIONE

solubility 

Slightly soluble in water, soluble in alcohol and oils, in propylene glycol and Glycerin.

Odor

Powerful and sweet, oily-buttery odor with herbaceous-cheesy undenone, yet not rancid or unpleasant in dilution. Creamy-cheesy, mildly buttery taste in dilutions near 10 ppm.

Odor Type

dill

JECFA Number

2036

InChI

InChI=1S/C8H14O2/c1-3-4-5-6-8(10)7(2)9/h3-6H2,1-2H3

InChIKey

XCBBNTFYSLADTO-UHFFFAOYSA-N

SMILES

CC(=O)C(=O)CCCCC

LogP

0.79

Octane-2,3-dione Usage And Synthesis

Chemical Properties

2,3-Octanedione has a “warmed-over” flavor (off-flavor).

Occurrence

Reportedly present in fish, turkey, chicken, beef, lamb, mutton, coffee, tea, peanut, mushroom, prickly pear and lavage leaf.

Uses

The title Octane-2,3-dione is used on a very limited scale in perfume compositions, mainly as a trace component in topnote compositions, }vhere it gives interesting effects in the presence of Civet and Phenylacetic acid, or certain Labdanum products, etc. It is also of good use in Ylang Ylang compositions and in many other flower bases.

Definition

ChEBI: 2,3-Octanedione is an alpha-diketone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 6338, 1994 DOI: 10.1021/jo00100a040

Synthesis

Octane-2,3-dione is prepared in three steps. 1) Preparation of composite catalyst: 5-Methoxytriazole is refluxed with chlorobenzene and acetonitrile to give component 1 (5-methoxy-triphenyl-1,2,4-triazolium salt). 5-Methoxythiazole is refluxed with benzyl chloride and acetonitrile to give component 2 (5-methoxy-2-benzylthiazolium salt). The two are mixed 1:1 to form the composite catalyst. 2) Preparation of Fe3+-Fe2+ redox system: Ferrous sulfate and sulfuric acid react with hydrogen peroxide. 3) Preparation of octane-2,3-dione: Acetaldehyde and hexanal are coupled using the composite catalyst. The crude product is distilled. The distillate is oxidized in the presence of the Fe3+-Fe2+ redox system in a reaction-distillation apparatus. The distillate is collected as the product.

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