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

• ChemBase ID: 125711
• 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)
• InChIKey: AFVLVVWMAFSXCK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: α-cyano-4-hydroxycinnamic acid
• Synonyms: alpha-cyano-4-hydroxycinnamic acid; alpha-cyano-4-hydroxycinnamate; 2-cyano-4-hydroxycinnamate; Alpha-Cyano-4-hydroxycinnamic acid; α-CCA; α-CHCA; 4-HCCA; ACCA; alpha-Cyano-4-hydroxycinnamic acid; α-Cyano; α-Cyano-4-hydroxycinnamic acid; 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic 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: 24886140; 24848731; 162220061; 24893121; 24871310
• PubChem CID: 6931228; 9794103
• CHEBI ID: 64340
• Wikipedia Title: Alpha-Cyano-4-hydroxycinnamic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.3885844
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3273188
• LogD (pH = 7.4): -1.9034323
• 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: methanol: soluble10 mg/mL, clear
• Apperance: Yellow powder
• Melting Point: 235-250 °C; 237 - 239°C; 245-250 °C; 245-250 °C(lit.); 245–250 °C
• Hydrophobicity(logP): 0.895

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; room temp

Product Information

• Purity: ≥99.0% (HPLC); 95%; 97%; 99%
• Grade: matrix substance for MALDI-MS; purum
• Suitability: suitable for MALDI-TOF MS
• Cation Traces: Al: ≤1 mg/kg; Ba: ≤1 mg/kg; Ba: ≤5 mg/kg; Ca: ≤1 mg/kg; Ca: ≤10 mg/kg; Cd: ≤1 mg/kg; Cd: ≤5 mg/kg; Co: ≤1 mg/kg; Co: ≤5 mg/kg; Cr: ≤1 mg/kg; Cr: ≤5 mg/kg; Cu: ≤1 mg/kg; Cu: ≤5 mg/kg; Fe: ≤1 mg/kg; K: ≤1 mg/kg; K: ≤5 mg/kg; Li: ≤1 mg/kg; Mg: ≤1 mg/kg; Mg: ≤5 mg/kg; Mn: ≤1 mg/kg; Mn: ≤5 mg/kg; Na: ≤1 mg/kg; Na: ≤10 mg/kg; Ni: ≤1 mg/kg; Ni: ≤5 mg/kg; Pb: ≤1 mg/kg; Pb: ≤5 mg/kg; Sr: ≤1 mg/kg; Zn: ≤1 mg/kg; Zn: ≤5 mg/kg
• Analyte suitability: glycans; peptides; proteins
• abs.: absorption/337 nm ≥2000 (mol. absorption)
• Linear Formula: HOC6H4CH=C(CN)CO2H

DETAILS

Sigma Aldrich - C8982

Application
Specially purified and qualified as a matrix for peptide MALDI-MS calibration standards. Also available as part of our ProteoMass™ MALDI calibration kits (MS-CAL1 and MS-CAL3).
Legal Information
ProteoMass is a trademark of Sigma-Aldrich Co. LLC
Protocols & Applications
Methods of glycosylated protein analysis by Mass Spectrometry

Sigma Aldrich - 145505

Application
Used as a matrix for peptides1 and nucleotides2 in mass spectroscopy analyses.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 476870

Packaging
2, 10 g in glass bottle

Sigma Aldrich - 70990

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Other Notes
Matrix substance used in MALDI-MS (matrix-assisted laser desorption ionization MS) peptide analysis in proteomics1,2.