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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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Properties

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

Description

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).