(2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid

• ChemBase ID: 134194
• Molecular Formular: C10H7NO3
• Molecular Mass: 189.16748
• Monoisotopic Mass: 189.04259309
• SMILES: c1cc(ccc1/C=C(\C#N)/C(=O)O)O
• Canonical SMILES: N#C/C(=C\c1ccc(cc1)O)/C(=O)O
• InChI: 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+
• InChIKey: AFVLVVWMAFSXCK-VMPITWQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: α-cyano-4-hydroxycinnamic acid
• Synonyms: α-CCA; α-CHCA; 4-HCCA; ACCA; α-Cyano-4-hydroxycinnamic acid; α-氰基; α-氰基-4-羟基肉桂酸

Database IDs

• CAS Number: 28166-41-8
• EC Number: 248-879-1
• MDL Number: MFCD00004204
• Beilstein Number: 3271427
• PubChem SID: 24892459; 162228471
• PubChem CID: 5328791

CALCULATED PROPERTIES

• Acid pKa: 2.1885846
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.4621235
• LogD (pH = 7.4): -1.9085766
• Log P: 1.6443796
• Molar Refractivity: 50.0944 cm^3
• Polarizability: 18.514715 Å^3
• Polar Surface Area: 81.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: slightly soluble; methanol: water: soluble; polar organic solvents: soluble
• Apperance: yellow powder
• Melting Point: 245-250 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - C2020

Biochem/physiol Actions
Specific inhibitor of monocarboxylic acid transport, including lactate and pyruvate transport.1,2,3 Also reported to block β-cell apical anion exchange (IC50 of 2.4 mM).4
包装
10, 25 g in poly bottle
Application
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.