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Merck

476870

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24871310
EC Number:
248-879-1
Beilstein/REAXYS Number:
3271427
MDL number:
MFCD00004204
Assay:
99%
Form:
solid

Key Documents

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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

99%

form

solid

Quality Level

100

mp

245-250 °C (lit.)

functional group

carboxylic acid, nitrile

storage temp.

2-8°C

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN6411
BCCC6873
SHBH7541
SHBH4780V
SHBH4006V

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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)
Encapsulation of α-cyano-4-hydroxycinnamic acid into a NaY zeolite.
Vilaca N, et al.
J. Mater. Sci., 46(23), 7511-7516 (2011)
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
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
Robert Erne et al.
Analytical chemistry, 91(6), 4132-4139 (2019-03-01)
Contamination is a highly controversial issue in hair analysis. Therefore, hair testing protocols typically include wash steps to remove contamination. However, recent studies claim that washing could also lead to permanent incorporation of contaminants into hair, thus questioning the validity
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