Alpha-Cyano-4-Hydroxycinnamic Acid
Basic information
- CAS
28166-41-8- Standard SMILES
N#CC(=Cc1ccc(O)cc1)C(=O)O- InChIKey
AFVLVVWMAFSXCK-UHFFFAOYSA-N- Molecular formula
- C10H7NO3
- Average molar mass
- 189.17 g/mol
- Monoisotopic mass
- 189.04259308
Overview
specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure
Names & identifiers
- Preferred name
- Alpha-Cyano-4-Hydroxycinnamic Acid
- IUPAC
- 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
- English name
- alpha-Cyano-4-hydroxycinnamic acid
- Molecular formula
- C10H7NO3
- Molecular weight
- 189.17
Names & synonyms
alpha-cyano-4-hydroxycinnamic acid28166-41-8alpha-Cyano-4-hydroxycinnamate2-cyano-4-hydroxycinnamateNL5EEM9E2G4-hydroxy-alpha-cyanocinnamateACCADTXSID5010182952-Cyano-3-(4-hydroxyphenyl)acrylic acid2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acidNSC-173138CHEBI:64340
Show more names
α-Cyano-4-hydroxycinnamic Acidα-CHCAα-CCA4-HCCAα-CyanoALPHA-CYANO
RefChem:111141DTXCID701040402248-879-1a-Cyano-4-hydroxycinnamic acidalpha-CCANSC 173138alpha-CHCA2-Propenoic acid, 2-cyano-3-(4-hydroxyphenyl)-
Database identifiers
- CAS
28166-41-8- PubChem CID
- 2102
- DTXSID
DTXSID501018295- ChEMBL
CHEMBL76602- UNII
- NL5EEM9E2G
- EC Number
- 248-879-1
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 81.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 292
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Biochemical Research
Physical DescriptionPowder; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 245 · 245-250 °C(lit.)
- Boiling point
- 324.41 °C · 324.41°C (rough estimate)
- Density
- 1.3175 · 1.3175 (rough estimate)
- refractive index
- 1.54 · 1.5400 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL, · methanol: 10 mg/mL, clear
- form
- powder
- pka
- 0.85 · 0.85±0.10(Predicted)
- color
- yellow
- Water Solubility
- 2 O: · H2O: slightly solublemethanol: water: solublepolar organic solvents: soluble
- BRN
- 3271427 · 3271427
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (98.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 165 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (98.8%)
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29269090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H317-H319-H335
- Hazard Classifications
- Skin Sens. 1B
- Precautionary statements
- P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Uses
Specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes. [ChemIDplus]
Synthetic Polymer MALDI Matrix Compounds
Applications
Usesinhibitor of mitochondrial pyruvate transport
Usesα-Cyano-4-hydroxycinnamic acid (CHC) was used in encapsulation of CHC into NaY zeolite. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays.
Usesα-Cyano-4-hydroxycinnamic acid(CHC) was used as a matrix for peptides and nucleotides in mass spectroscopic analysis. It was used in encapsulation of CHC into NaY zeolite. It was used as matrix to investigate the activity of the paclitaxel derivatives using several well-established in vitro angiogenesis assays.
General Descriptionα-Cyano-4-hydroxycinnamic acid is the commonly used matrix for analyzing peptides by matrix-assisted laser desorption/ionization mass spectrometry. It inhibits the monophenolase activity and diphenolase activity of mushroom tyrosinase.
Additional notes
DefinitionChEBI: Alpha-cyano-4-hydroxycinnamic acid is a monohydroxycinnamic acid that is 4-hydroxycinnamic acid in which the hydrogen alpha- to the carboxy group is replaced by a cyano group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of peptides and oligonucleotides. It has a role as a MALDI matrix material. It is a nitrile, a member of phenols and a monohydroxycinnamic acid.
Related reactions
39 records
Compound notes
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