α-Cyano-4-hydroxycinnamic acid

Names

[ Name ]:
α-Cyano-4-hydroxycinnamic acid

[Synonym ]:
(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

Biological Activity

[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 Transporter

Research 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

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: 10 mg/mL, clear

MSDS

Click to get detail MSDS

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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