Ibuprofen

• Formula: C₁₃H₁₈O₂
• Molecular weight: 206.2808
• IUPAC Standard InChI: InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) Copy

  
• IUPAC Standard InChIKey: HEFNNWSXXWATRW-UHFFFAOYSA-N Copy
• CAS Registry Number: 15687-27-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Stereoisomers:
  • S-ibuprofen
• Other names: Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-; 4-Isobutyl-α-methylphenylacetic acid; α-(p-isobutylphenyl)propionic acid; α-(4-Isobutylphenyl)propionic acid; (.+/-.)-p-Isobutylhydratropic acid; (.+/-.)-2-(p-Isobutylphenyl)propionic acid; p-Isobutylhydratropic acid; Acide (isobutyl-4 phenyl)-2 propionique; Andran; Brufen; Buburone; Dolgit; Ebufac; Hydratropic acid, p-isobutyl-; Ibu-slo; Ibuprocin; IP-82; Liptan; Motrin; Nobfelon; Pantrop; R.D. 13621; Rebugen; U-18,573; 2-(p-Isobutylphenyl)propionic acid; 2-(4-Isobutylphenyl)propanoic acid; 4-Isobutylhydratropic acid; Adran; Anflagen; Artril 300; Bluton; Brufanic; Butylenin; Dolgin; Emodin; Epobron; Ibufen; Lamidon; Mynosedin; Napacetin; Nobfen; Nobgen; Nurofen; Roidenin; Benzeneacetic acid, α-methyl-4-(2-methylpropyl), (.+/-.)-; Advil; Haltran; Medipren; Midol 200; Nuprin; PediaProfen; Trendar; α-2-(p-Isobutylphenyl)propionic acid; Propanoic acid, 2-(4-isobutylphenyl); RD 13621; 4-Isobutylphenyl)-α-methylacetic acid; (RS)-Ibuprofen; p-Isobutyl-2-phenylpropionic acid; Burana; Butacortelone; Carol; Cobo; Optifen; Ostofen; Panafen; Proartinal; Proflex; Quadrax; Uprofen; Dibufen; Ibupril; Apsifen; α-Methyl-4-(2-methylpropyl)benzeneacetic acid; Advil Cold & Sinus (Salt/Mix); Children's Elixsure IB (Salt/Mix); Combunox (Salt/Mix); Motrin IB Gelcaps (Salt/Mix); Sine-Aid IB Caplets (Salt/Mix); (±) α-methyl-4-(isobutyl)phenylacetic acid (ibuprofen)
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• Information on this page:
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of fusion

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Cilurzo, Alberti, et al., 2010
Cilurzo, F.; Alberti, E.; Minghetti, P.; Gennari, C.G.M.; Casiraghi, A.; Montanari, L., Effect of drug chirality on the skin permeability of ibuprofen, International Journal of Pharmaceutics, 2010, 386, 1-2, 71-76, https://doi.org/10.1016/j.ijpharm.2009.10.053 . [all data]

Hong, Hua, et al., 2010
Hong, Jindui; Hua, Dan; Wang, Xia; Wang, Hongtao; Li, Jun, Solid-Liquid-Gas Equilibrium of the Ternaries Ibuprofen + Myristic Acid + CO ₂ and Ibuprofen + Tripalmitin + CO ₂, J. Chem. Eng. Data, 2010, 55, 1, 297-302, https://doi.org/10.1021/je900342a . [all data]

Wassvik, Holmén, et al., 2006
Wassvik, Carola M.; Holmén, Anders G.; Bergström, Christel A.S.; Zamora, Ismael; Artursson, Per, Contribution of solid-state properties to the aqueous solubility of drugs, European Journal of Pharmaceutical Sciences, 2006, 29, 3-4, 294-305, https://doi.org/10.1016/j.ejps.2006.05.013 . [all data]

Gracin and Rasmuson, 2002
Gracin, Sandra; Rasmuson, Åke C., Solubility of Phenylacetic Acid, p -Hydroxyphenylacetic Acid, p -Aminophenylacetic Acid, p -Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents, J. Chem. Eng. Data, 2002, 47, 6, 1379-1383, https://doi.org/10.1021/je0255170 . [all data]

Xu, Sun, et al., 2004
Xu, Fen; Sun, Li-Xian; Tan, Zhi-Cheng; Liang, Jian-Guo; Li, Rui-Lian, Thermodynamic study of ibuprofen by adiabatic calorimetry and thermal analysis, Thermochimica Acta, 2004, 412, 1-2, 33-57, https://doi.org/10.1016/j.tca.2003.08.021 . [all data]

Li, Zell, et al., 1999
Li, Z. Jane; Zell, Mark T.; Munson, Eric J.; Grant, David J.W., Characterization of racemic species of chiral drugs using thermal analysis, thermodynamic calculation, and structural studies, J. Pharm. Sci., 1999, 88, 3, 337-346, https://doi.org/10.1021/js980205u . [all data]

Phillips, Logan, et al., 1990
Phillips, A.M.; Logan, B.K.; Stafford, D.T., Further applications for capillary gas chromatography in routine quantitative toxicological analyses, J. Hi. Res. Chromatogr., 1990, 13, 11, 754-758, https://doi.org/10.1002/jhrc.1240131106 . [all data]

Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M., Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography, J. Chromatogr., 1989, 472, 1-92, https://doi.org/10.1016/S0021-9673(00)94099-8 . [all data]

Macek and Smolková-Keulemansová, 1985
Macek, J.; Smolková-Keulemansová, E., Correlation of the chromatographic retention of some phenylacetic and phenylpropionic acid derivatives with molecular structure, J. Chromatogr., 1985, 333, 309-317, https://doi.org/10.1016/S0021-9673(01)87361-1 . [all data]

Perrigo, Peel, et al., 1985
Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 1985, 341, 81-88, https://doi.org/10.1016/S0378-4347(00)84011-6 . [all data]

Perrigo, Ballantyne, et al., 1984
Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 1984, 17, 2, 41-49, https://doi.org/10.1080/00085030.1984.10757360 . [all data]

Tret'yakov, 2008
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2008. [all data]

Anderson and Fuller, 1987
Anderson, W.H.; Fuller, D.C., A simplified procedure for the isolation, characterization, and identification of weak acid and neutral drugs from whole blood, J. Anal. Toxicol., 1987, 11, 5, 198-204, https://doi.org/10.1093/jat/11.5.198 . [all data]

Sharp, 1987
Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 1987, 11, 1, 8-11, https://doi.org/10.1093/jat/11.1.8 . [all data]

Notes

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• Symbols used in this document:
  

  ΔfusH

  Enthalpy of fusion

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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