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Merck

C2020

α-Cyano-4-hydroxycinnamic acid

≥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:
Molecular Weight:
189.17
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352106
EC Number:
248-879-1
MDL number:
Beilstein/REAXYS Number:
3271427
Assay:
≥98% (TLC)
Form:
powder
Quality level:

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Product Name

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

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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1 of 4

This Item
C898214550539468
form

powder

form

powder

form

powder

form

solid

assay

≥98% (TLC)

assay

-

assay

97%

assay

-

Quality Level

300

Quality Level

500

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

solubility

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

solubility

-

solubility

methanol: soluble 50 mg/mL, clear to slightly hazy, light yellow to yellow

solubility

methanol: 10 mg/mL, clear

color

yellow

color

-

color

-

color

-

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.[1][2][3] It is also reported to block β-cell apical anion exchange (IC50 of 2.4 mM).[4]

pictograms

Exclamation mark

signalword

Warning

hcodes

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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Adaptive cellular mechanisms in response to Glutamine-starvation
Eliasen MM, et al.
Frontiers in Bioscience, 11, 3199-3211 (2006)
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
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)
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
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

Global Trade Item Number

SKUGTIN
C2020-10G04061833475003
C2020-25G04061833475010

Questions

1–2 of 2 Questions  
  1. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  2. What can be used for solublization of α-Cyano-4-hydroxycinnamic acid?

    1 answer
    1. α-Cyano-4-hydroxycinnamic acid (α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA) is soluble in methanol (up to 50 mg/ml). It is also soluble at 10 mg/ml using 50% acetonitrile in 0.05% TFA for MALDI-MS. The acetonitrile concentration can be adjusted for individual preferences.For biological applications, it has been solubilized at 100 mM in DMSO or 50 mM in ethanol.

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