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C2020

Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

≥98% (TLC), powder

Synonym(s):

α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA

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About This Item

Linear Formula:
HOC6H4CH=C(CN)CO2H
CAS Number:
28166-41-8
Molecular Weight:
189.17
Beilstein:
3271427
EC Number:
248-879-1
MDL number:
MFCD00004204
UNSPSC Code:
12352106
PubChem Substance ID:
24892459
NACRES:
NA.77

Quality Level

300

Assay

≥98% (TLC)

form

powder

color

yellow

mp

245-250 °C (lit.)

solubility

H2O: slightly soluble
methanol: water: soluble
polar organic solvents: soluble

storage temp.

2-8°C

SMILES string

OC(=O)\C(=C\c1ccc(O)cc1)C#N

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+

InChI key

AFVLVVWMAFSXCK-VMPITWQZSA-N

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Application

α-Cyano-4-hydroxycinnamic acid has been used to block monocarboxylate transporters.
α-Cyano-4-hydroxycinnamic acid is a useful hydrophobic matrix solution for matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Antibiotics, peptide nucleic acids (a new class of DNA mimics), and proteins with masses as high as 66,000 Da have been successfully analyzed by using this as a matrix solution.

Biochem/physiol Actions

α-Cyano-4-hydroxycinnamic acid acts as a specific inhibitor of monocarboxylic acid transport, including lactate and pyruvate transport. It is also reported to block β-cell apical anion exchange (IC50 of 2.4 mM).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J P Barnard et al.
The Journal of biological chemistry, 268(5), 3654-3661 (1993-02-15)
The protozoan parasite Trypanosoma brucei derives its metabolic energy exclusively from a unique type of glycolysis in which pyruvate derived from glucose catabolism is released into the host bloodstream. In this study, this terminal metabolic step has been examined in
L-Lactate Promotes Adult Hippocampal Neurogenesis
Lev-Vachnish Y, et al.
Frontiers in Neuroscience, 13 (2019)
E T Sze et al.
Journal of the American Society for Mass Spectrometry, 9(2), 166-174 (1998-07-29)
We report a simple method for converting solid matrices into useful matrix solutions for matrix-assisted laser desorption/ionization (MALDI). This method is based on the dissolution of the solid matrix in a liquid support of low volatility such as glycerol. An
C Emmons
The American journal of physiology, 276(4 Pt 2), F635-F643 (1999-04-13)
To functionally characterize transport properties of the apical anion exchanger of rabbit beta-intercalated cells, the mean change in anion exchange activity, dpHi/dt (where pHi is intracellular pH), was measured in response to lumen Cl- replacement with gluconate in perfused cortical
Y C Ling et al.
Rapid communications in mass spectrometry : RCM, 12(6), 317-327 (1998-04-16)
Comparative studies of the matrix-assisted laser desorption/ionization (MALDI) of 30 antibiotics were made using alpha-cyano-4-hydroxycinnamic acid (HCCA), 2,5-dihydroxybenzoic acid (DHB), 5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphyrin and meso-tetra(N-methyl-4-pyridyl)porphyrin matrices. Most antibiotics generated intense protonated molecules in HCCA and DHB matrices, and sodium or potassium adduct
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