19309-14-9

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	Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel Natural Products >> Flavonoids Research Areas >> Neurological Disease
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
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

~10%

19309-14-9

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

100-52-7

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

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500

111441-88-4

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500

77-78-1

140632-64-0

19309-14-9

Literature: Journal of Scientific and Industrial Research, , vol. 15B, p. 287,290 Chem.Abstr., , p. 3500

Precursor 5
1070781-88-2 100-52-7 480-39-7 111441-88-4
77-78-1
DownStream 1
1090-65-9

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%

19309-14-9	18956-16-6
1775-97-9	54849-74-0