19309-14-9

Basic information

• Product Name: CARDAMONIN
• Synonyms: Alpinetin chalcone;Chalcone, 2', 4'-dihydroxy-6'-methoxy-;(E)-2',4'-Dihydroxy-6'-methoxychalcone;(E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one;Cardamonin;(E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one;2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenyl-, (2E)-;CARDAMONIN(RG)
• CAS NO: 19309-14-9
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.27996
• Product Categories: Chalcones;Inhibitors
• Mol File: 19309-14-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 199～200℃
• Boiling Point: 484.468 °C at 760 mmHg
• Flash Point: 182.744 °C
• Appearance: yellow/
• Density: 1.283 g/cm³
• Vapor Pressure: 5.2E-10mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥20mg/mL
• PKA: 7.00±0.40(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 weeks.
• CAS DataBase Reference: CARDAMONIN(CAS DataBase Reference)
• NIST Chemistry Reference: CARDAMONIN(19309-14-9)
• EPA Substance Registry System: CARDAMONIN(19309-14-9)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 61-24/25
• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 19309-14-9(Hazardous Substances Data)

Usage

Description

Cardamonin, with the chemical formula 19309-14-9, is a naturally occurring compound that has been identified as a primary reference substance. It is characterized by its assigned absolute purity, which takes into account chromatographic purity, water, residual solvents, and inorganic impurities. The exact purity value can be found on the certificate provided by PhytoLab GmbH & Co. KG. Cardamonin is known for its ability to inhibit NF-κB activation through various mechanisms, including the inhibition of IκBα degradation and phosphorylation, IκB kinase activation, and NF-κB nuclear translocation. It also exhibits anti-inflammatory activity in various models and is cell permeable.

Uses

Used in Pharmaceutical Applications:
CARDAMONIN is used as a glycogen synthase kinase 3 (GSK3) inhibitor for studying its effects on β-catenin loss and gain-of-function in human preimplantation embryos. This application is significant in understanding the role of CARDAMONIN in early human development and its potential therapeutic applications.
Used in Anti-inflammatory Applications:
CARDAMONIN is used as an anti-inflammatory agent due to its ability to inhibit NF-κB activation, a key regulator of the inflammatory response. By blocking this activation, CARDAMONIN can help reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Research and Development:
CARDAMONIN is used as a primary reference substance in research and development, particularly in the fields of pharmacology and biochemistry. Its assigned absolute purity makes it an ideal candidate for studying the mechanisms of action and potential applications of this compound in various biological systems.

Biological Activity

Chalone analog that display anti-inflammatory activity. Inhibits NO and PGE 2 production from LPS- and IFN- γ -induced RAW cells and inhibits TXB 2 production via the COX-1 and COX-2 pathways. Inhibits NF- κ B activation via inhibition of I κ B α degradation and phosphorylation, I κ B kinase activation and NF- κ B nuclear translocation.

Biochem/physiol Actions

Cardamonin is a calchone from Aplinia species (zingiberaceous plant species). Cardamonin inhibits pigmentation in melanocytes through suppression of Wnt/b-catenin signaling pathway. Cardamonin suppressed Wnt/b-catenin signaling by a mechanism involving proteasome-mediated degradation of b-catenin (GSK-3b-independent pathway). Research has shown that Cardamonin possesses anti-inflammatory activity via suppression of NF-kB nuclear translocation and Ik-Ba phosphorylation.

References

1) Lee?et al. (2006),?Blockade of nuclear factor-kappaB signaling pathway and anti-inflammatory activity of cardamonin, a chalcone analog from Alpinia conchigera; J. Pharmacol. Exp. Ther.,?316?271 2) Israf?et al. (2007),?Cardamonin inhibits COX and iNOS expression via inhibition of p65NF-kappaB nuclear translocation and Ikappa-B phosphorylation in RAW 264.7 macrophage cells; Mol. Immunol.,?44?673 3) Ahmad?et al. (2006),?Cardamonin, inhibits pro-inflammatory mediators in activated RAW 264.7 cells and whole blood; Eur. Pharmacol. Exp. Ther., 538?188

InChI:InChI=1/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+

Upstream product

• 77-78-1 dimethyl sulfate 
• 140632-64-0 (+/-)-7-acetoxy-5-hydroxy-2-phenyl-chroman-4-one 
• 100-52-7 benzaldehyde 
• 111441-88-4 Pinocembrin diacetate 
• 1070781-88-2 (2E)-1-[2-methoxy-4,6-bis(2-propenyloxy)phenyl]-3-(phenyl)-2-propen-1-one 
• 108-73-6 3,5-dihydroxyphenol 
• 119136-14-0 2,4-bis(benzyloxy)-6-methoxyacetophenone 
• 84457-60-3 2'-hydroxy-4'-benzyloxy-6'methoxychalkone 
• 39548-89-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 1013662-04-8 (E)-1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)-3-phenylprop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 93208-46-9 boesenbergin B 
• 1090-65-9 alpinetin 
• 76444-56-9 Uvangoletin 
• 1620631-18-6 (2E,2'E)-1,1'-[methylenebis(2,4-dihydroxy-6-methoxy-3,1-phenylene)]bis(3-phenylprop-2-en-1-one) 
• 1036-72-2 5,7-dimethoxyflavone 
• 145629-35-2 (E)-3-phenyl-1-(2, 4, 6-trimethoxyphenyl)prop-2-en-1-one 
• 93175-91-8 (+/-)-(E)-(5'-isopropylidene-7',9'-dimethoxy-2'-methyl-3',4',5',6'-tetrahydro-2',6'-methano-2'H-1-benzoxocin-8'-yl)-3-phenylprop-2-en-1-one 
• 93175-88-3 (+/-)-(E)-1-<5',7'-dimethoxy-2'-methyl-2'-(4methylpent-3-enyl)-2'H-1-benzopyran-6'-yl>-3-phenylprop-2-en-1-one 
• 93175-90-7 (+/-)-5-isopropylidene-11-methoxy-2-methyl-8-phenyl-3,4,5,6,8,9-hexahydro-2,6-methano-2H,10H-pyrano<2,3-h>-1-benzoxocin-10-one 
• 93175-89-4 (+/-)-(E)-1-(7'-hydroxy-5'-isopropylidene-9'-methoxy-2'-methyl-3',4',5',6'-tetrahydro-2',6'-methano-2'H-1-benzoxocin-8'-yl)-3-phenylprop-2-en-1-one 
• 84457-61-4 Acetic acid 5-acetoxy-3-methoxy-2-(3-phenyl-propionyl)-phenyl ester 

Relevant articles and documents

Studies on the constituents of Alpinia. XII. On the constituents of the seeds of Alpinia katsumadai hayata. I. The structure of cardamomin

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Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

In vitro and in vivo anti-Leishmania activity of polysubstituted synthetic chalcones

The in vitro screening of 43 polysubstituted chalcones against Leishmania amazonensis axenic amastigotes, led to the evaluation of 9 of them in a macrophage-infected model with the two other most infectious Leishmania species prevalent in Peru (L. braziliensis and L. peruviana). The five most active and selective chalcones were studied in vivo, resulting on the identification of two chalcones with high reduction parasite burden percentages.