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α-Cyano-4-hydroxycinnamic acid

matrix substance for MALDI-MS, ≥99.0% (HPLC)

Synonym(s):
α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA
Linear Formula:
HOC6H4CH=C(CN)CO2H
CAS Number:
Molecular Weight:
189.17
Beilstein:
3271427
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

grade

matrix substance for MALDI-MS

Quality Level

Assay

≥99.0% (HPLC)

form

solid

analyte chemical class(es)

glycans, peptides, proteins

technique(s)

MALDI-MS: suitable

mp

245-250 °C (lit.)
245-250 °C

solubility

methanol: 10 mg/mL, clear

cation traces

Ba: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
K: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤10 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

absorption

≥2000 at 337 nm (mol. absorption)

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
C898239468145505
form

solid

form

powder

form

solid

form

powder

technique(s)

MALDI-MS: suitable

technique(s)

-

technique(s)

MALDI-MS: suitable

technique(s)

-

solubility

methanol: 10 mg/mL, clear

solubility

-

solubility

methanol: 10 mg/mL, clear

solubility

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

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

-

grade

matrix substance for MALDI-MS

grade

-

grade

matrix substance for MALDI-MS

grade

-

General description

α-Cyano-4-hydroxycinnamic acid (α-CHCA) is widely used as a matrix in order to facilitate ionization of peptides and proteins in a matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometer.

Application

α-CHCA was used as matrix in improving the detection of low concentration protein digests on MALDI-TOF.

Other Notes

Matrix substance used in MALDI-MS (matrix-assisted laser desorption ionization MS) peptide analysis in proteomics.

related product

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Description
Pricing

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Sigma-Aldrich

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S.D. Patterson, V. Katta
Analytical Chemistry, 66, 3729-3729 (1994)
J Gobom et al.
Analytical chemistry, 73(3), 434-438 (2001-02-24)
We present a new MALD1 sample preparation technique for peptide analysis using the matrix alpha-cyano-4-hydroxy-cinnamic acid (CHCA) and prestructured sample supports. The preparation integrates sample purification, based on the affinity of microcrystalline CHCA for peptides, thereby simplifying the analysis of
Bin Li et al.
Toxicological sciences : an official journal of the Society of Toxicology, 116(1), 23-31 (2010-04-17)
Studies in mice and guinea pigs have shown that albumin is a new biomarker of organophosphorus toxicant (OP) and nerve agent exposure. Our goal was to determine whether OP-labeled albumin could be detected in the blood of humans exposed to
Xiangping Zhu et al.
Journal of biomolecular techniques : JBT, 14(4), 298-307 (2004-01-13)
Alpha-cyano-4-hydroxycinnamic acid (alpha-CHCA) as a matrix facilitates the ionization of proteins and peptides in a matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometer. The matrix itself also ionizes and so do its sodium and potassium adducts. Matrix clusters and metal
Yifei Zhong et al.
Journal of neurochemistry, 150(1), 74-87 (2019-05-12)
Soluble oligomers of the 42-amino acid amyloid beta (Aβ42) peptide are highly toxic and suspected as the causative agent of synaptic dysfunction and neuronal loss in Alzheimer's disease (AD). Previously, we have shown that a small, D-amino acid Aβ42-oligomer interacting

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