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145505

Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

97%

Synonym(s):

alpha-Cyano-4-hydroxycinnamic acid, α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA

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$76.20
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$158.65

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5 G
$76.20
25 G
$158.65

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:
24848731
NACRES:
NA.22

$76.20

Available to ship onMay 02, 2025Details

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Quality Level

100

assay

97%

form

powder

mp

245-250 °C (lit.)

solubility

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

functional group

carboxylic acid
nitrile

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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This Item
4768707099039468
α-Cyano-4-hydroxycinnamic acid 97%

145505

α-Cyano-4-hydroxycinnamic acid

α-Cyano-4-hydroxycinnamic acid 99%

476870

α-Cyano-4-hydroxycinnamic acid

α-Cyano-4-hydroxycinnamic acid suitable for matrix substance for MALDI-MS, ≥99.0% (HPLC)

70990

α-Cyano-4-hydroxycinnamic acid

α-Cyano-4-hydroxycinnamic acid suitable for matrix substance for MALDI-MS, Ultra pure

39468

α-Cyano-4-hydroxycinnamic acid

assay

97%

assay

99%

assay

≥99.0% (HPLC)

assay

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

solubility

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

solubility

-

solubility

methanol: 10 mg/mL, clear

solubility

methanol: 10 mg/mL, clear

form

powder

form

solid

form

solid

form

solid

mp

245-250 °C (lit.)

mp

245-250 °C (lit.)

mp

245-250 °C (lit.)

mp

245-250 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

General description

α-Cyano-4-hydroxycinnamic acid is the commonly used matrix for analyzing peptides by matrix-assisted laser desorption/ionization mass spectrometry[1]. It inhibits the monophenolase activity and diphenolase activity of mushroom tyrosinase[2].

Application

α-Cyano-4-hydroxycinnamic acid(CHC) was used as a matrix for peptides[3] and nucleotides[4] in mass spectroscopic analysis. It was used in encapsulation of CHC into NaY zeolite[5]. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays[6].

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

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCS4672
    MKCP1551
    MKCJ1026
    MKCD5516
    SHBJ0165

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    S D Patterson et al.
    Analytical chemistry, 66(21), 3727-3732 (1994-11-01)
    During the analysis of an Asp-N digest of a recombinant hematopoietic growth factor by matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS), we observed pseudomolecular ions corresponding to reduced forms of peptides known to be present only in single disulfide linkages.
    G M Hathaway
    BioTechniques, 17(1), 150-155 (1994-07-01)
    A commercially available, matrix-assisted, laser desorption/ionization (MALDI), time-of-flight mass spectrometer has been used for the successful characterization of picomole quantities of modified deoxyoligonucleotides. The procedure was found to be applicable to the analysis of a variety of modified synthetic structures
    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)
    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)
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