GLPBio

α-Cyano-4-hydroxycinnamic acid (CHC)

Catalog No.: GC10877Purity:>98.00%Synonyms: CHC, α-CHCA, NSC 173138
COASDSData Sheet
CHC (α-Cyano-4-hydroxycinnamate) is a potent and non-competitive inhibitor of monocarboxylate transporters (MCTs).

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α-Cyano-4-hydroxycinnamic acid (CHC)
Cas No.: 28166-41-8
10mM (in 1mL DMSO)In Stock
$30.00
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50mgIn Stock
$27.00
1
100mgIn Stock
$38.00
1
250mgIn Stock
$65.00
1
500mgIn Stock
$91.00
1
1gIn Stock
$126.00
1
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Description

α-Cyano-4-hydroxycinnamic acid (CHC) is a non-competitive inhibitor of the mitochondrial pyruvate transporter with a Ki of 6.3μM[1]. α-Cyano-4-hydroxycinnamic acid inhibits both the monophenolase activity and diphenolase activity of mushroom tyrosinase, with IC50 values of 48µM and 2.17mM, respectively[2]. α-Cyano-4-hydroxycinnamic acid regulates isolated mouse muscle fatigue and recovery by blocking the transport of lactate and hydrogen ions[3]. α-Cyano-4-hydroxycinnamic acid has been extensively used for protein and peptide analysis as a matrix for ultraviolet matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)[4].

In vitro, α-Cyano-4-hydroxycinnamic acid treatment for 72 hours significantly inhibited the viability of HeLa and HCT116 cells, with IC50 values of 2.41mM and 1.65mM, respectively[5]. Treatment with 400µM α-Cyano-4-hydroxycinnamic acid for 24 hours altered the activities of protein kinase C (PKC)-δ and PKC-ζ, and reduced the occurrence of malformations in rat embryos cultured in high-glucose conditions[6].

In vivo, a single intraperitoneal injection of α-Cyano-4-hydroxycinnamic acid (200mg/kg) stimulated food intake in rats within 4 hours, without affecting blood glucose levels[7].

References:

[1] Halestrap A P. The mitochondrial pyruvate carrier. Kinetics and specificity for substrates and inhibitors[J]. Biochemical Journal, 1975, 148(1): 85-96.

[2] Qiu L, Chen Q H, Zhuang J X, et al. Inhibitory effects of α-cyano-4-hydroxycinnamic acid on the activity of mushroom tyrosinase[J]. Food Chemistry, 2009, 112(3): 609-613.

[3] Clarke P D, Clift D L, Dooldeniya M, et al. Effects of α-cyano-4-hydroxycinnamic acid on fatigue and recovery of isolated mouse muscle[J]. Journal of Muscle Research & Cell Motility, 1995, 16(6): 611-617.

[4] Mojica E R E, Vedad J, Desamero R Z B. Vibrational analysis of α-cyanohydroxycinnamic acid[J]. Journal of molecular structure, 2015, 1094: 203-209.

[5] Ji H, Tan Y, Gan N, et al. Synthesis and anticancer activity of new coumarin-3-carboxylic acid derivatives as potential lactate transport inhibitors[J]. Bioorganic & Medicinal Chemistry, 2021, 29: 115870.

[6] Gäreskog M, Wentzel P. N-Acetylcysteine and α-cyano-4-hydroxycinnamic acid alter protein kinase C (PKC)-δ and PKC-ζ and diminish dysmorphogenesis in rat embryos cultured with high glucose in vitro[J]. Journal of endocrinology, 2007, 192(1): 207-214.

[7] Del Prete E, Lutz T A, Scharrer E. Inhibition of glucose oxidation by α-cyano-4-hydroxycinnamic acid stimulates feeding in rats[J]. Physiology & behavior, 2004, 80(4): 489-498.

Protocol

Cell experiment [1]:

Cell lines

 HCT116 cells

Preparation Method

 HCT116 cells were cultured in DMEM medium supplemented with 100U/ml penicillin, 100ug/ml streptomycin, and 10% fetal bovine serum, at 37°C in an incubator with 5% CO2. HCT116 (3000 cells/well) cells were seeded in 96-well microtiter plates overnight. α-Cyano-4-hydroxycinnamic acid was then diluted in DMEM and added 10µl into per well with varying final concentrations (0, 0.001, 0.001, 0.1, 1, and 10mM) for 72h exposure, and cell viability was measured.

Reaction Conditions

 0, 0.001, 0.001, 0.1, 1, and 10mM; 72h

Applications

 α-Cyano-4-hydroxycinnamic acid reduced cell viability of HCT116 cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

 Male Sprague-Dawley rat

Preparation Method

Male Sprague-Dawley rats (6-week-old) were housed individually in a temperature-controlled (21±1°C) colony room and kept on a 12-h light/dark cycle. Rats were adapted to the diet (16.5kJ/g) for at least 2 weeks. Rats were injected with 200mg/kg α-Cyano-4-hydroxycinnamic acid or saline in the middle of the light phase. Cumulative food intake was measured by weighing the food cups (±0.1g) just before injection and 1, 2, and 4h afterward.

Dosage form

200mg/kg; once; i.p.

Applications

α-Cyano-4-hydroxycinnamic acid treatment enhanced cumulative food intake in rats in 4h.

References:

[1] Ji H, Tan Y, Gan N, et al. Synthesis and anticancer activity of new coumarin-3-carboxylic acid derivatives as potential lactate transport inhibitors[J]. Bioorganic & Medicinal Chemistry, 2021, 29: 115870.

[2] Del Prete E, Lutz T A, Scharrer E. Inhibition of glucose oxidation by α-cyano-4-hydroxycinnamic acid stimulates feeding in rats[J]. Physiology & behavior, 2004, 80(4): 489-498.

Product Documents

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
28166-41-8
Synonyms
CHC, α-CHCA, NSC 173138
Chemical Name
(Z)-2-cyano-3-(4-hydroxyphenyl)acrylic acid
SMILES
OC1=CC=C(/C=C(C#N)\C(O)=O)C=C1
Molecular Formula
C10H7NO3
Molecular Weight
189.17
Solubility
≥ 37.8 mg/mL in DMSO, ≥ 20.9 mg/mL in EtOH with ultrasonic, ≥ 1.03 mg/mL in Water with ultrasonic and warming
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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