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Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

≥98% (TLC), powder, monocarboxylic acid transport inhibitor

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Synonym(s):
α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA
Linear Formula:
HOC6H4CH=C(CN)CO2H
CAS Number:
Molecular Weight:
189.17
Beilstein/REAXYS Number:
3271427
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1B

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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U Schneider et al.
Neuroscience, 53(4), 1153-1162 (1993-04-01)
Exposure of nervous tissue to hypoxia results in interstitial acidification. There is evidence for concomitant decrease in extracellular pH to the increase in tissue lactate. In the present study, we used double-barrelled pH-sensitive microelectrodes to investigate the link between lactate
Adaptive cellular mechanisms in response to Glutamine-starvation
Eliasen MM, et al.
Frontiers in Bioscience, 11, 3199-3211 (2006)
R J Williams et al.
Neuroscience, 74(2), 461-468 (1996-09-01)
Glucose deprivation potentiates the glutamate receptor-evoked release of arachidonic acid from cultured mouse striatal neurons. In this study we investigated whether this potentiation would be modified by the end-products of glycolysis. These enhanced responses were completely reversed by the addition
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

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