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Merck

C2020

α-Cyano-4-hydroxycinnamic acid

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

Sinónimos:

α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA

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Fórmula lineal:
HOC6H4CH=C(CN)CO2H
Número CAS:
28166-41-8
Peso molecular:
189.17
NACRES:
NA.77
PubChem Substance ID:
24892459
UNSPSC Code:
12352106
EC Number:
248-879-1
MDL number:
MFCD00004204
Beilstein/REAXYS Number:
3271427

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Nombre del producto

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

InChI key

AFVLVVWMAFSXCK-VMPITWQZSA-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+

SMILES string

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

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

Quality Level

300

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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).

hcodes

H317

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Skin Sens. 1B

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
MKCN9036
MKCK1270
MKCJ2237
MKCH2027
MKCG5046

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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. 

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

    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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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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