Tyrosine

• Formula: C₉H₁₁NO₃
• Molecular weight: 181.1885
• IUPAC Standard InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1 Copy

  
• IUPAC Standard InChIKey: OUYCCCASQSFEME-MRVPVSSYSA-N Copy
• CAS Registry Number: 60-18-4
• 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:
  • Tyrosine
  • 2-Amino-3-(4-hydroxyphenyl)-propanoic acid
• Other names: L-Tyrosine; Tyrosine, L-; α-Amino-β-(4-hydroxyphenyl)propionic acid; (-)-α-Amino-p-hydroxyhydrocinnamic acid; p-Tyrosine; Benzenepropanoic acid, α-amino-4-hydroxy-, (S)-; L-p-Tyrosine; L-Phenylalanine, 4-hydroxy-; Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-; L-2-Amino-3-p-hydroxyphenylpropanoic acid; (S)-α-Amino-4-hydroxybenzenepropanoic acid; (S)-Tyrosine; NSC 82624
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase ion energetics data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess

De-protonation reactions

 +  =

By formula: C₉H₁₀NO₃^- + H⁺ = C₉H₁₁NO₃

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

References

Go To: Top, Gas phase ion energetics data, IR Spectrum, Notes

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

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Tian, Wang, et al., 2009
Tian, Z.X.; Wang, X.B.; Wang, L.S.; Kass, S.R., Are Carboxyl Groups the Most Acidic Sites in Amino Acids? Gas-Phase Acidities, Photoelectron Spectra, and Computations on Tyrosine, p-Hydroxybenzoic Acid, and Their Conjugate Bases, J. Am. Chem. Soc., 2009, 131, 3, 1174-1181, https://doi.org/10.1021/ja807982k . [all data]

Jones, Bernier, et al., 2007
Jones, C.M.; Bernier, M.; Carson, E.; Colyer, K.E.; Metz, R.; Pawlow, A.; Wischow, E.D.; Webb, I.; Andriole, E.J.; Poutsma, J.C., Gas-phase Acities of the 20 Protein Amino Acids, Int. J. Mass Spectrom., 2007, 267, 1-3, 54-62, https://doi.org/10.1016/j.ijms.2007.02.018 . [all data]

O'Hair, Bowie, et al., 1992
O'Hair, R.J.; Bowie, J.H.; Gronert, S., Gas Phase Acidity of the alpha-Amino Acids, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 23, https://doi.org/10.1016/0168-1176(92)80083-D . [all data]

Notes

Go To: Top, Gas phase ion energetics data, IR Spectrum, References

• Symbols used in this document:
  

  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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