Levulinic acid

Levulinic acid

Names
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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:45630 Y
ChEMBL	ChEMBL1235931 N
ChemSpider	11091 Y
DrugBank	DB02239 Y
ECHA InfoCard	100.004.228
PubChem CID	11579
UNII	RYX5QG61EI Y
CompTox Dashboard (EPA)	DTXSID8021648
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
SMILES CC(=O)CCC(=O)O
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH₃C(O)CH₂CH₂CO₂H. It is classified as a keto acid. This white crystalline is soluble in water, ethanol, and diethyl ether. It is derived from degradation of cellulose and is a potential precursor to biofuels.

Synthesis and uses

Related to its original synthesis, levulinic acid is prepared in the laboratory by heating sucrose with concentrated hydrochloric acid. The process proceeds via the intermediacy of glucose, which is isomerized to fructose and then hydroxymethylfurfural. Other sugar-derivatives can be used in this process including levulose (D-fructose), inulin and starch as well as other acids such as sulfuric.

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 production of other chemical commodities such as methyltetrahydrofuran, valerolactone, and ethyl levulinate. Dehydration of levulinic acid gives α-Angelica lactone (CAS#591-12-8). The first manufacturing facility able to produce levulinic acid at an industrial scale is Green Future based in Caserta, Italy.

Niche uses

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.

For the biogen production of fuel, bacteria are genetically modified, to be able to feed on levulinic acid rather than sugar.

Safety

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

References

• This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. {{cite encyclopedia}}: Missing or empty |title= (help)