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28166-41-8

28166-41-8 structure
28166-41-8 structure
  • Name: α-Cyano-4-hydroxycinnamic acid
  • Chemical Name: α-cyano-4-hydroxycinnamic acid
  • CAS Number: 28166-41-8
  • Molecular Formula: C10H7NO3
  • Molecular Weight: 189.167
  • Catalog: Chemical reagent Organic reagent fatty acid
  • Create Date: 2019-02-18 00:33:42
  • Modify Date: 2025-08-20 18:09:02
  • 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].
Name α-cyano-4-hydroxycinnamic acid
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
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
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.
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
Symbol GHS07
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
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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