Levulinic acid

Levulinic acid^[1]


IUPAC name 4-Oxopentanoic acid
Other names Levulinic acid, Laevulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid, 4-oxopentanoic acid
Identifiers
CAS number	123-76-2^Y
PubChem	11579
ChemSpider	11091^Y
UNII	RYX5QG61EI^Y
DrugBank	DB02239
ChEBI	CHEBI:45630^Y
ChEMBL	CHEMBL1235931^N
Jmol-3D images	Image 1
SMILES CC(=O)CCC(=O)O
InChI InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)^Y Key: JOOXCMJARBKPKM-UHFFFAOYSA-N^Y InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) Key: JOOXCMJARBKPKM-UHFFFAOYAR
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
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH₃C(O)CH₂CH₂CO₂H. It is a keto acid. This white crystalline is soluble in water, ethanol, and diethyl ether.

Synthesis and uses

Related to its original synthesis,^[2] levulinic acid is prepared in the laboratory by heating sucrose with concentrated hydrochloric acid.^[3] The process proceeds via the intermediacy of glucose, which is isomerized to fructose and then hydroxymethylfurfural. Other sugar-derivatives - e.g., levulose(=D-fructose), inulin, starch - and other acids - e.g., sulfuric acids - can be used.

Levulinic acid is a potential precursor to nylon-like polymers, synthetic rubbers, and plastics. It is a versatile synthetic intermediate, e.g., in the synthesis of pharmaceuticals. It is a precursor in the industrial production of other chemical commodities such as methyltetrahydrofuran, valerolactone, and ethyl levulinate.

Levulinic acid is also a photosensitizer for photodynamic therapy.

Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.^[4]

Safety

Levulinic acid is relatively nontoxic, with an LD₅₀ of 1850 mg/kg.

References

^ Merck Index, 11th Edition, 5352
^ A. Freiherrn, V. Grote, B. Tollens, "Untersuchungen über Kohlenhydrate. I. Ueber die bei Einwirkung von Schwefelsäure auf Zucker entstehende Säure (Levulinsäure)" Justus Liebigs Annalen der Chemie volume 175, pp. 181-204 (1875). doi: 10.1002/jlac.18751750113
^ B. F. McKenzie (1941), "Levulinic acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0335 ; Coll. Vol. 1: 335
^ 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.

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.