Levulinic acid

Levulinic acid

Chembox new
Name = Levulinic acid
ImageFile = Levulinic acid.svg
ImageName =
IUPACName = 4-Oxopentanoic acid
OtherNames = Levulinic acid
Laevulinic acid
β-Acetylpropionic acid
3-Acetopropionic acid
Section1 = Chembox Identifiers
CASNo = 123-76-2
SMILES = OC(CCCC(C)=O)=O
Section2 = Chembox Properties
Formula = C5H8O3
MolarMass = 116.11 g/mol
Density = 1.1447 g/cm3
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 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. [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]

References

* "Merck Index", 11th Edition, 5352.
*


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  • levulinic acid — levulino rūgštis statusas T sritis chemija formulė CH₃COCH₂CH₂COOH atitikmenys: angl. levulinic acid rus. левулиновая кислота ryšiai: sinonimas – 4 oksopentano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • levulinic acid — | ̷ ̷ ̷ ̷|linik noun Etymology: levulinic International Scientific Vocabulary levulin substance yielding levulose on hydrolysis (International Scientific Vocabulary levul from levulose + in) + ic : a crystalline keto acid CH3CO(CH2)2COOH obtained …   Useful english dictionary

  • levulinic acid — 4 Oxopentanoic acid; formed by the action of hot, strong acids on hexoses. SEE ALSO: δ aminolevulinic acid. SYN: levulic acid. * * * lev·u·lin·ic acid .lev yə .lin ik or Brit lae·vu·lin·ic acid .lēv n a crystalline keto acid C5H8O3 obtained by… …   Medical dictionary

  • levulinic acid — noun 4 oxopentanoic acid, a keto acid used as a synthetic intermediate …   Wiktionary

  • levulinic acid — /ˌlɛvjəlɪnɪk ˈæsəd/ (say .levyuhlinik asuhd) noun US → laevulic acid. Also, levulic acid …  

  • levulinic acid — /lev yeuh lin ik, lev /, Chem. a white or colorless, water soluble solid, C5H8O3, produced by the hydrolysis of cane sugar, starch, or cellulose; used chiefly in the organic synthesis of nylon, plastics, and pharmaceuticals. [LEVUL(OSE) + IN2 +… …   Universalium

  • Levulinic — Lev u*lin ic ( l[i^]n [i^]k), a. (Chem.) Pertaining to, or denoting, an acid (called also {acetyl propionic} acid), {C5H8O3}, obtained by the action of dilute acids on various sugars (as levulose). [Written also {l[ae]vulinic}.] [1913 Webster] …   The Collaborative International Dictionary of English

  • Diphenolic acid — IUPAC name 4,4 Bis(p hydroxyphenyl)pentanoic acid …   Wikipedia

  • Keto acid — Keto acids are organic acids containing a ketone functional group and a carboxylic acid group.Common types of keto acids include: *Alpha keto acids, or 2 oxo acids, such as pyruvic acid have the keto group adjacent to the carboxylic acid *Beta… …   Wikipedia

  • laevulic acid — /liˌvjulɪk ˈæsəd/ (say lee.vyoohlik asuhd) noun a hygroscopic acid, CH3COCH2CH2COOH, obtained industrially from sugar by reaction with hydrochloric acid, and used to clean metals, such as milk cans, to guard against bacterial infection. Also,… …  

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