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CHEBI:64340 - α-cyano-4-hydroxycinnamic acid

ChEBI IDCHEBI:64340
ChEBI Nameα-cyano-4-hydroxycinnamic acid
Stars
ASCII Namealpha-cyano-4-hydroxycinnamic acid
DefinitionA monohydroxycinnamic acid that is 4-hydroxycinnamic acid in which the hydrogen α- to the carboxy group is replaced by a cyano group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of peptides and oligonucleotides.
Last Modified3 April 2012
Submittergerma2
DownloadsMolfile
FormulaC10H7NO3
Net Charge0
Average Mass189.170
Monoisotopic Mass189.04259
SMILESN#C/C(=C\c1ccc(O)cc1)C(=O)O
InChIInChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
InChIKeyAFVLVVWMAFSXCK-VMPITWQZSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Application:
MALDI matrix material  A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
ChEBI Ontology
Outgoing Relation(s)
α-cyano-4-hydroxycinnamic acid (CHEBI:64340) has role MALDI matrix material (CHEBI:64345)
α-cyano-4-hydroxycinnamic acid (CHEBI:64340) is a monohydroxycinnamic acid (CHEBI:24688)
α-cyano-4-hydroxycinnamic acid (CHEBI:64340) is a nitrile (CHEBI:18379)
α-cyano-4-hydroxycinnamic acid (CHEBI:64340) is a phenols (CHEBI:33853)
IUPAC Name 
(2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
Synonyms  Source
CHCASUBMITTER
alpha-CyanoSUBMITTER
2-cyano-3-(4-hydroxyphenyl)acrylic acidChemIDplus
Manual XrefsDatabases
Alpha-cyano-4-hydroxycinnamic_acidWikipedia
Registry NumbersSources
Reaxys:2645333Reaxys
CAS:28166-41-8ChemIDplus
Citations