Levulinic acid

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Levulinic acid
IUPAC name 4-Oxopentanoic acid
Other names Levulinic acid
Laevulinic acid
β-Acetylpropionic acid
3-Acetopropionic acid
Identifiers
CAS number [123-76-2]
SMILES OC(CCCC(C)=O)=O
Properties
Molecular formula C5H8O3
Molar mass 116.11 g/mol
Density 1.1447 g/cm3
Melting point

33-35 °C

Boiling point

245-246 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Levulinic acid, or 4-oxopentanoic acid, is a white crystalline keto acid prepared from levulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulfuric acids. It is soluble in water, ethanol, and diethyl ether, but essentially insoluble in aliphatic hydrocarbons.

Levulinic acid is used in the manufacture of nylons, synthetic rubbers, plastics, and pharmaceuticals. It is a precursor in the industrial production of other chemical commodities such as methyltetrahydrofuran, valerolactone, and ethyl levulinate. As well, Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.[1]

[edit] References

  1. ^ Doris Cullen et al., A Guide to Deciphering the Internal Codes Used by the Tobacco Industry, Harvard School of Public Health Division of Public Health Practice Tobacco Research Program, August 2005