Cardamonin

Modify Date: 2024-01-02 08:11:35

Cardamonin Structure
Cardamonin structure
 Common Name Cardamonin
CAS Number 19309-14-9 Molecular Weight 270.280
Density 1.3±0.1 g/cm3 Boiling Point 484.5±45.0 °C at 760 mmHg
Molecular Formula C16H14O4 Melting Point N/A
MSDS Chinese USA Flash Point 182.7±22.2 °C
Symbol GHS09
GHS09		 Signal Word Warning

 Use of Cardamonin


Cardamonin is a novel antagonist of hTRPA1 cation channel with an IC50 of 454 nM.

 Names

Name (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one
Synonym More Synonyms

 Cardamonin Biological Activity

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.

 Chemical & Physical Properties

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 of Characters 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

 Safety Information

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

 Synthetic Route

(2E)-1-[2-methoxy-4,6-bis(2-propenyloxy)phenyl]-3-(phenyl)-2-propen-1-one structure

(2E)-1-[2-metho...

CAS#:1070781-88-2

~10%

Cardamonin Structure

Cardamonin

CAS#:19309-14-9

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

Benzaldehyde

CAS#:100-52-7

~%

Cardamonin Structure

Cardamonin

CAS#: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
Pinocembrin structure

Pinocembrin

CAS#:480-39-7

~%

Cardamonin Structure

Cardamonin

CAS#:19309-14-9

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

Pinocembrin dia...

CAS#:111441-88-4

~%

Cardamonin Structure

Cardamonin

CAS#:19309-14-9

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

Dimethyl sulfate

CAS#:77-78-1

N/A structure

N/A

CAS#:140632-64-0

~%

Cardamonin Structure

Cardamonin

CAS#:19309-14-9

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

 Customs

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%

 Articles7

More Articles
Palmitate-induced inflammatory pathways in human adipose microvascular endothelial cells promote monocyte adhesion and impair insulin transcytosis.

Am. J. Physiol. Endocrinol. Metab. 309 , E35-44, (2015)

Obesity is associated with inflammation and immune cell recruitment to adipose tissue, muscle and intima of atherosclerotic blood vessels. Obesity and hyperlipidemia are also associated with tissue in...

Cardamonin inhibits agonist-induced vascular contractility via Rho-kinase and MEK inhibition.

Korean J. Physiol. Pharmacol. 20 , 69-74, (2016)

The present study was undertaken to investigate the influence of cardamonin on vascular smooth muscle contractility and to determine the mechanism(s) involved. Denuded aortic rings from male rats were...

Cardamonin induces apoptosis by suppressing STAT3 signaling pathway in glioblastoma stem cells.

Tumour Biol. 36 , 9667-76, (2015)

Glioblastoma stem cells (GSCs) are the initiating cells in glioblastoma multiforme (GBM) and contribute to the resistance of GBM to chemotherapy and radiation. In the present study, we investigated th...

 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
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