CAS 28166-41-8|α-Cyano-4-hydroxycinnamic acid
| Common Name | α-Cyano-4-hydroxycinnamic acid | ||
|---|---|---|---|
| CAS Number | 28166-41-8 | Molecular Weight | 189.167 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 398.1±32.0 °C at 760 mmHg |
| Molecular Formula | C10H7NO3 | Melting Point | 245-250 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 194.5±25.1 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | α-cyano-4-hydroxycinnamic acid |
|---|---|
| Synonym | More Synonyms |
α-Cyano-4-hydroxycinnamic acid BiologicalActivity
| Description | α-Cyano-4-hydroxycinnamic acid (α-Cyano-4-hydroxycinnamate) is a potent and non-competitive inhibitor of monocarboxylate transporters (MCTs). α-Cyano-4-hydroxycinnamic acid inhibits mitochondrial pyruvate transporter with a Ki of 6.3 μM. α-Cyano-4-hydroxycinnamic acid is used as a matrix to facilitate peptide ionization in matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry applications[1][2]. |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>Monocarboxylate TransporterResearch Areas >>Metabolic Disease |
| In Vitro | α-Cyano-4-hydroxycinnamic acid (α-Cyano-4-hydroxycinnamate) inhibits monocarboxylates transport such as lactate and pyruvate[2]. α-Cyano-4-hydroxycinnamic acid (CHC; 0.5 mM and 1 mM) of 1 mM has a significant inhibitory effect on branching morphogenesis and decreases the epithelial perimeter and area of lung explants in a dose dependent way[2]. At 100 μM concentration, α-Cyano-4-hydroxycinnamic acid rapidly and almost totally inhibits O2 uptake by rat heart mitochondria oxidizing pyruvate. Inhibition can be detected at concentrations of inhibitor as low as 1 μM although inhibition took time to develop at this concentration. Inhibition can be reversed by diluting out the inhibitor[1]. |
| References | [1]. A P Halestrap, et al. The mitochondrial pyruvate carrier. Kinetics and specificity for substrates and inhibitors. Biochem J. 1975 Apr; 148(1): 85-96. [2]. Sara Granja, et al. The Monocarboxylate Transporter Inhibitor α-cyano-4-hydroxycinnamic Acid Disrupts Rat Lung Branching. Cell Physiol Biochem. 2013;32(6):1845-56. [3]. Makoto Watanabe, et al. Improvement of Mass Spectrometry Analysis of Glycoproteins by MALDI-MS Using 3-aminoquinoline/α-cyano-4-hydroxycinnamic Acid. Anal Bioanal Chem. 2013 May;405(12):4289-93. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 398.1±32.0 °C at 760 mmHg |
| Melting Point | 245-250 °C(lit.) |
| Molecular Formula | C10H7NO3 |
| Molecular Weight | 189.167 |
| Flash Point | 194.5±25.1 °C |
| Exact Mass | 189.042587 |
| PSA | 81.32000 |
| LogP | 1.53 |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
| Index of Refraction | 1.674 |
| InChIKey | AFVLVVWMAFSXCK-UHFFFAOYSA-N |
| SMILES | N#CC(=Cc1ccc(O)cc1)C(=O)O |
| Storage condition | 2-8°C |
| Water Solubility | methanol: 10 mg/mL, clear |
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi: Irritant; |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| HS Code | 2926909090 |
Customs
| HS Code | 2926909090 |
|---|---|
| Summary | HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0% |
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Synonyms
| (2E)-2-Cyano-3-(4-hydroxyphenyl)acrylic acid |
| Ganaxolone |
| 2-Propenoic acid, 2-cyano-3-(4-hydroxyphenyl)-, (2E)- |
| 4-HCCA |
| α-cyano-4-hydroxycinnamic acid |
| 2-Cyano-3-(4-hydroxyphenyl)acrylic Acid |
| alpha-Cyano-4-hydroxycinnamic acid |
| MFCD00004204 |
| (2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid |
| EINECS 248-879-1 |
| A-CYANO-4-HYDROXYCINNAMIC ACID |
| ACCA |
