Levulinic acid
2927184
224640266
2008-07-09T19:46:26Z
79.218.234.155
{{Chembox new
| Name = Levulinic acid
| ImageFile = Levulinic acid.svg
<!-- | ImageSize = 200px -->
| ImageName =
| IUPACName = 4-Oxopentanoic acid
| OtherNames = Levulinic acid<br />Laevulinic acid<br />β-Acetylpropionic acid<br />3-Acetopropionic acid
| Section1 = {{Chembox Identifiers
| CASNo = 123-76-2
| SMILES = OC(CCCC(C)=O)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>3</sub>
| MolarMass = 116.11 g/mol
| Density = 1.1447 g/cm<sup>3</sup>
| MeltingPt = 33-35 °C
| BoilingPt = 245-246 °C
}}
}}
'''Levulinic acid''', or 4-oxopentanoic acid, is a white crystalline [[keto acid]] prepared from [[levulose]], [[inulin]], [[starch]], etc., by boiling them with dilute [[hydrochloric acid|hydrochloric]] or [[sulfuric acid]]s. It is soluble in water, [[ethanol]], and [[diethyl ether]], but essentially insoluble in [[aliphatic compound|aliphatic]] [[hydrocarbon]]s.
Levulinic acid is used in the manufacture of [[nylon]]s, synthetic [[rubber]]s, [[plastic]]s, and pharmaceuticals. It is a precursor in the industrial production of other chemical commodities such as [[methyltetrahydrofuran]], [[gamma-Valerolactone|valerolactone]], and [[ethyl levulinate]]. As well, Levulinic acid is used in [[cigarette]]s to increase [[nicotine]] delivery in smoke and binding of nicotine to neural receptors.<ref>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</ref>
==References==
{{reflist}}
* ''Merck Index'', 11th Edition, '''5352'''.
* {{1911}}
[[Category:Carboxylic acids]]
[[Category:Ketones]]
{{organic-compound-stub}}
[[de:Lävulinsäure]]
[[it:Acido levulinico]]
[[lv:Levulīnskābe]]
[[nl:Levulinezuur]]
[[pl:Kwas lewulinowy]]