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

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ChEBI Name α-cyano-4-hydroxycinnamic acid
ChEBI ID CHEBI:64340
ChEBI ASCII Name alpha-cyano-4-hydroxycinnamic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Gerhard Mayer
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Formula C10H7NO3
Net Charge 0
Average Mass 189.16750
InChI InChI=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+
InChIKey AFVLVVWMAFSXCK-VMPITWQZSA-N
SMILES OC(=O)C(\C#N)=C\c1ccc(O)cc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): 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).
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ChEBI Ontology
Outgoing 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 Sources
2-cyano-3-(4-hydroxyphenyl)acrylic acid ChemIDplus
alpha-Cyano SUBMITTER
CHCA SUBMITTER
Database Link Database
Alpha-cyano-4-hydroxycinnamic_acid Wikipedia
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Registry Numbers Types Sources
2645333 Reaxys Registry Number Reaxys
28166-41-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11217742 PubMed citation CiteXplore
14715888 PubMed citation CiteXplore
15144210 PubMed citation CiteXplore
15150841 PubMed citation CiteXplore
15694775 PubMed citation CiteXplore
16401911 PubMed citation CiteXplore
19435303 PubMed citation CiteXplore
19927305 PubMed citation CiteXplore
8750232 PubMed citation CiteXplore
Last Modified
03 April 2012
General Comment
2012-04-03 MALDI matrix solution [PubChem_Compound:5328791]