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19309-14-9

19309-14-9 structure
19309-14-9 structure
  • Name: Cardamonin
  • Chemical Name: (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one
  • CAS Number: 19309-14-9
  • Molecular Formula: C16H14O4
  • Molecular Weight: 270.280
  • Catalog: Natural product Chalcone
  • Create Date: 2018-04-02 08:00:00
  • Modify Date: 2024-01-02 08:11:35
  • Cardamonin is a novel antagonist of hTRPA1 cation channel with an IC50 of 454 nM.
Name (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one
Synonyms 2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenyl-, (2E)-
(E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one
(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one
(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
Cardamomin
alpinetin chalcone
Cardamonin
Description Cardamonin is a novel antagonist of hTRPA1 cation channel with an IC50 of 454 nM.
Related Catalog
Target

IC50: 454 nM (hTRPA1 cation channel)[1]

In Vitro Cardamonin selectively blocksTRPA1 activation (IC50=454 nM) while does not interact with TRPV1 nor TRPV4 channel. Docking analysis of cardamonin demonstrates a compatible interaction with A-967079-binding site of TRPA1. Cardamonin does not significantly reduce HEK293 cell viability, nor does it impair cardiomyocyte constriction[1]. Cardamonin suppresses the expression of Tgase-2, cyclooxygenase-2 (COX-2), and p65 (nuclear factor-κB) in a concentration-dependent manner, and restores the expression of IκB in MG63 and Raw264.7 cells[2].
In Vivo Cardamonin (3-30 mg/kg, orally administered) significantly inhibits PBQ-induced writhing. CDN also produces a significant, dose-dependent increase in the withdrawal response latencies in carrageenan-induced hyperalgesia[2].
Cell Assay HEK293 cells are treated with cardamonin (0-90 μM). The cells treated in the absence of the test compound are the negative control. After incubated for 24 h, Cell Titer-Glo reagent is added to the cells and Luminescence is acquired on the plate reader[1].
Animal Admin Rats: The rats are divided into groups of six according to their nociceptive pressure thresholds, after which carrageenan (0.1 mL, 1%) is injected into the plantar surface of the left hind paw. The rats received vehicle or cardamonin (3-30 mg/kg) or indomethacin (3 mg/kg) orally 2 h after carrageenan injection and are evaluated for paw hyperalgesia 0, 1 and 2 h after administration of compounds. Indomethacin is used as a positive control[2]. Mice: Acute pain is induced by an intraperitoneal injection of 0.2 mL of 0.02% PBQ 54 min after oral administration of cardamonin. Six minutes after the PBQ injection, the total number of writhes is counted for 6 min. The control animals received an appropriate volume of dosing vehicle (80% saline, 10% ethanol and 10% Tween 80). Indomethacin is used as a positive control[2].
References

[1]. Wang S, et al. Cardamonin, a Novel Antagonist of hTRPA1 Cation Channel, Reveals Therapeutic Mechanism of Pathological Pain. Molecules. 2016 Aug 29;21(9). pii: E1145.

[2]. Park MK, et al. Novel anti-nociceptive effects of cardamonin via blocking expression of cyclooxygenase-2 andtransglutaminase-2. Pharmacol Biochem Behav. 2014 Mar;118:10-5.
Density 1.3±0.1 g/cm3
Boiling Point 484.5±45.0 °C at 760 mmHg
Molecular Formula C16H14O4
Molecular Weight 270.280
Flash Point 182.7±22.2 °C
Exact Mass 270.089203
PSA 66.76000
LogP 3.62
Appearance yellow
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.658
Storage condition Store at +4°C
Water Solubility DMSO: ≥20mg/mL
Symbol GHS09
GHS09
Signal Word Warning
Hazard Statements H400
Precautionary Statements P273
Hazard Codes N
Risk Phrases 50/53
Safety Phrases 61-24/25
RIDADR UN 3077 9 / PGIII
HS Code 2914509090
1070781-88-2 structure

1070781-88-2

~10%

19309-14-9 structure

19309-14-9

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 1 p. 100 - 103
100-52-7 structure

100-52-7

~%

19309-14-9 structure

19309-14-9

Literature: Chemische Berichte, , vol. 77/79, p. 99,105 Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500
480-39-7 structure

480-39-7

~%

19309-14-9 structure

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500
111441-88-4 structure

111441-88-4

~%

19309-14-9 structure

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500
77-78-1 structure

77-78-1

140632-64-0 structure

140632-64-0

~%

19309-14-9 structure

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500
HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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