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Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

99%

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Synonym(s):
alpha-Cyano-4-hydroxycinnamic acid, α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA
Linear Formula:
HOC6H4CH=C(CN)CO2H
CAS Number:
Molecular Weight:
189.17
Beilstein/REAXYS Number:
3271427
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1B

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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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
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
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)
Svend Dam et al.
Plant physiology, 149(3), 1325-1340 (2009-01-09)
We have characterized the development of seeds in the model legume Lotus japonicus. Like soybean (Glycine max) and pea (Pisum sativum), Lotus develops straight seed pods and each pod contains approximately 20 seeds that reach maturity within 40 days. Histological

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