Levulinic acid

Description

Levulinic acid has a tart, whiskey taste. It may be synthesized by the action of more or less concentrated HCL on sucrose, glucose, or fructose; hence, its reported presence in caramels.

Description

Levulinic acid, or 4-oxopentanoic acid, is prepared from natural sugar (saccharide) sources (e.g., starch, cellulose, or cane sugar) by boiling the saccharide in a strong acid such as HCl. It gets its name from the sugar levulose, another name for fructose. It is used in the manufacture of nylon, synthetic rubber, plastics, and pharmaceuticals.

Chemical properties

Levulinic acid has a tart, whiskey taste.

Physical properties

Levulinic acid forms colorless crystals that are readily soluble in water, ethanol, and diethyl ether. 

Occurrence

Reported found in papaya, wheat bread, rice, sake and Chinese quince.

The Uses of Levulinic acid

Levulinic acid may be used as an analytical reference standard for the quantification of the analyte in the following:
Soy sauce using liquid chromatography coupled to mass spectrometry (LC–MS).
Liquid food samples using gas chromatography with flame ionization detection (GC-FID).

The Uses of Levulinic acid

Replenisher (calcium).

The Uses of Levulinic acid

Levulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels.
It can also be used in:
The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural.
The synthesis of a commercial fragrance, fraistone.
The synthesis of pyrrolidone derivatives via reductive amination.
The total synthesis of mycobacterial arabinogalactan.

Preparation

By action of more or less concentrated HCl on sucrose, glucose or fructose; hence, its reported presence in caramels.

Definition

ChEBI: 4-oxopentanoic acid is an oxopentanoic acid with the oxo group in the 4-position. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and an oxopentanoic acid. It is a conjugate acid of a 4-oxopentanoate.

Taste threshold values

Taste characteristics at 70 ppm: acidic, sweet, creamy and slight dairy.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 5329, 1989 DOI: 10.1016/S0040-4039(01)93778-5

General Description

Levulinic acid, an organic acid, is mainly used as a cigarette additive.