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C2020

α-Cyano-4-hydroxycinnamic acid

Name: &#945;-Cyano-4-hydroxycinnamic acid
Brand: SIGMA

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

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

NACRES:

NA.77

PubChem Substance ID:

24892459

UNSPSC Code:

12352106

EC Number:

248-879-1

MDL number:

MFCD00004204

Beilstein/REAXYS Number:

3271427

Assay:

≥98% (TLC)

Form:

powder

Quality level:

300

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Product Name

α-Cyano-4-hydroxycinnamic acid, ≥98% (TLC), powder

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

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.

α-Cyano-4-hydroxycinnamic acid has been used to block monocarboxylate transporters.

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

GHS07

signalword

Warning

hcodes

H317

pcodes

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

Hazard Classifications

Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Lactate-proton co-transport and its contribution to interstitial acidification during hypoxia in isolated rat spinal roots.

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

An automated system for delivery of an unstable transcription factor to hematopoietic stem cell cultures.

Elizabeth Csaszar et al.

Biotechnology and bioengineering, 103(2), 402-412 (2009-03-07)

An automated delivery system for cell culture applications would permit studying more complex culture strategies and simplify measures taken to expose cells to unstable molecules. We are interested in understanding how intracellular TAT-HOXB4 protein concentration affects hematopoietic stem cell (HSC)

Adaptive cellular mechanisms in response to Glutamine-starvation

Eliasen MM, et al.

Frontiers in Bioscience, 11, 3199-3211 (2006)

L-Lactate Promotes Adult Hippocampal Neurogenesis

Lev-Vachnish Y, et al.

Frontiers in Neuroscience, 13 (2019)

Glucose catabolism in African trypanosomes. Evidence that the terminal step is catalyzed by a pyruvate transporter capable of facilitating uptake of toxic analogs.

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

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Global Trade Item Number

SKU	GTIN
C2020-10G	04061833475003
C2020-25G	04061833475010

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