CHCA.gifJMOL view

Name: alpha-cyano-4-hydroxycinnamic acid
Common Names: CHCA, HCCA
IUPAC Name: (2E)-2-cyano-3-(4-hydroxyphenyl)acrylic acid

CAS RN: 28166-41-8
SMILES: Oc1ccc(/C=C(\C#N)C(O)=O)cc1
InChI=1/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
InChIKey: AFVLVVWMAFSXCK-VMPITWQZBB

ChemSpider Permalink:
http://www.chemspider.com/Chemical-Structure.4485953.html

Molecular Formula: C10H7NO3
Molecular Weight (average): 189.1675
Molecular Weight (monisotopic): 189.04259
Melting point:
LogP (ACD v5.0 logD calculated): 1.53 +/-0.75
pKa (ACD v5.0 pKa calculated): 1.17 +/-0.31
Proton affinity [1]: 201.0 +/- 0.27 kcal/mol (841.0 +/- 1.1 kJ/mol)
Sodium affinity [2]: 165 +/- 3 kJ/mol
Vapor pressure (ACD calculated): 4.73E-07 mmHg at 25°C

Spectral Information:
IR spectrum ATR 1 cm-1 resolution
UV spectrum 1 nm resolution in methanol
UV spectrum 1 nm resolution in acetonitrile
SS-UV spectrum 1 nm resolution solid state diffuse reflectance measurement
337nm MALDI spectrum 337nm Positive ion spectrum acquired on a Bruker Reflex III
355nm MALDI spectrum 355nm Positive ion spectrum acquired on a Bruker Ultraflex TOF-TOF
355nm MALDI Spectrum 355nm Negative ion spectrum acquired on a Bruker Autoflex III
355nm MALDI Spectrum 355nm Positive ion spectrum acquired on a Bruker Autoflex III

Sample Info:
Aldrich PN: 47687-0 lot #: 12828JU

Notes:

References:
[1] Mirza, S.P.; Raju, N.P.; Vairamani, M., Estimation of the Proton Affinity Values of Fifteen MALDI Matrices under Electrospray Ionization Conditions using the Kinetic Method, J. Amer. Soc. Mass Spectrom., 2004, 15, 431-5, http://dx.doi.org/10.1016/j.jasms.2003.12.001
[2] Zhang, J., Knochenmuss, R., Stevenson, E., Zenobi, R., The gas-phase sodium basicities of common matrix-assisted laser desorption/ionization matrices, International Journal of Mass Spectrometry, 2002, 213, 237–250, http://dx.doi.org/S1387-3806(01)00542-5
[3] Hendrik Neubert, John M. Halket, Mireia Fernandez Ocana, Raj K.P. Patel, MALDI Post-Source Decay and LIFT-TOF/TOF Investigation of alpha-Cyano-4-Hydroxycinnamic Acid Cluster Interferences, J. Am. Soc. Mass Spectrom., 2004, 15, 336–343.
http://dx.doi.org/10.1016/j.jasms.2003.11.002