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Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

99%

Synonym(s):

alpha-Cyano-4-hydroxycinnamic acid, 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
Beilstein/REAXYS Number:
3271427
EC Number:
248-879-1
MDL number:
MFCD00004204
UNSPSC Code:
12352100
PubChem Substance ID:
24871310
NACRES:
NA.22

assay

99%

form

solid

mp

245-250 °C (lit.)

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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General description

α-Cyano-4-hydroxycinnamic acid is the commonly used matrix for analyzing peptides by matrix-assisted laser desorption/ionization mass spectrometry. It inhibits the monophenolase activity and diphenolase activity of mushroom tyrosinase.

Application

α-Cyano-4-hydroxycinnamic acid (CHC) was used in encapsulation of CHC into NaY zeolite. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1B

Storage Class

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Claudia Ryppa et al.
International journal of pharmaceutics, 368(1-2), 89-97 (2008-11-11)
The alpha(v)beta(3) integrin is overexpressed on proliferating endothelial cells such as those present in growing tumors as well as on tumor cells of various origins. Tumor-induced angiogenesis can be inhibited in vivo by antagonizing the alpha(v)beta(3) integrin with small peptides
Encapsulation of α-cyano-4-hydroxycinnamic acid into a NaY zeolite.
Vilaca N, et al.
J. Mater. Sci., 46(23), 7511-7516 (2011)
Yusaku Hioki et al.
Journal of mass spectrometry : JMS, 48(11), 1217-1223 (2013-11-22)
We describe here an optimization study of the sample preparation conditions for sensitive detection of peptides by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS). Among many factors in the conditions, we varied the percent acetonitrile in the peptide solution, the percent
Inhibitory effects of α-cyano-4-hydroxycinnamic acid on the activity of mushroom tyrosinase.
Qiu L, et al.
Food Chemistry, 112(3), 609-613 (2009)
Mohammadreza Shariatgorji et al.
Analytical chemistry, 84(16), 7152-7157 (2012-08-07)
D(4)-α-Cyano-4-hydroxycinnamic acid (D(4)-CHCA) has been synthesized for use as a matrix for matrix-assisted laser desorption ionization-mass spectrometry (MALDI-MS) and MALDI-MS imaging (MSI) of small molecule drugs and endogenous compounds. MALDI-MS analysis of small molecules has historically been hindered by interference
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