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
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• 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
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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

Go To: Top, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

Go To: Top, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  ΔfusH

  Enthalpy of fusion

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