• USA Home
  • C2020 - α-Cyano-4-hydroxycinnamic acid

C2020 Sigma-Aldrich

α-Cyano-4-hydroxycinnamic acid

≥98% (TLC), powder

Synonym: α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA

  • CAS Number 28166-41-8

  • Linear Formula HOC6H4CH=C(CN)CO2H

  • Molecular Weight 189.17

  •  Beilstein/REAXYS Number 3271427

  •  EC Number 248-879-1

  •  MDL number MFCD00004204

  •  PubChem Substance ID 24892459

  •  NACRES NA.77



Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, CI-CZ, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥98% (TLC)
form   powder
color   yellow
mp   245-250 °C (lit.)
solubility   H2O: slightly soluble
  methanol: water: soluble
  polar organic solvents: soluble
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+



α-Cyano-4-hydroxycinnamic acid has been used to block monocarboxylate transporters.

α-Cyano-4-hydroxycinnamic acid is a useful hydrophobic matrix solution for matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Antibiotics, peptide nucleic acids (a new class of DNA mimics), and proteins with masses as high as 66,000 Da have been successfully analyzed by using this as a matrix solution.


10, 25 g in poly bottle

Biochem/physiol Actions

α-Cyano-4-hydroxycinnamic acid acts as a specific inhibitor of monocarboxylic acid transport, including lactate and pyruvate transport. It is also reported to block β-cell apical anion exchange (IC50 of 2.4 mM).

Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
What can be used for solublization ofα-Cyano-4-hydroxycinnamic acid?
α-Cyano-4-hydroxycinnamic acid (α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA) is soluble in methanol (up to 50 mg/ml). It is also soluble at 10 mg/ml using 50% acetonitrile in 0.05% TFA for MALDI-MS. The acetonitrile concentration can be adjusted for individual preferences.For biological applications, it has been solubilized at 100 mM in DMSO or 50 mM in ethanol.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
Show more questions
Protocols & Articles


Aerobic Glycolysis and the Warburg Effect

The Warburg effect is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer ce...
BioFiles v7 n4
Keywords: Aerobic, Cancer, Cell proliferation, Clinical, Glycolysis, Phosphorylations, Transcription

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

Peer-Reviewed Papers


Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?