C2020

α-Cyano-4-hydroxycinnamic acid

≥98% (TLC), powder, monocarboxylic acid transport inhibitor

• Synonym(s): α-CCA, α-CHCA, α-Cyano, 4-HCCA, ACCA
• 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: 12352106
• PubChem Substance ID: 24892459
• NACRES: NA.77

Properties

• Quality Level: 300
• 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+
• InChI key: AFVLVVWMAFSXCK-VMPITWQZSA-N

Description

Application

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.

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 Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• 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