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C8249

Sigma-Aldrich

Cardamonin

≥98% (HPLC)

Synonyme(s) :

(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one, (8CI); Alpinetin chalcone, (E)-2′,4′-Dihydroxy-6′-methoxy-chalcone

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About This Item

Formule empirique (notation de Hill):
C16H14O4
Numéro CAS:
19309-14-9
Poids moléculaire :
270.28
Numéro MDL:
MFCD00238554
Code UNSPSC :
12352200
ID de substance PubChem :
329775163
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

light yellow to dark brown

Solubilité

DMSO: ≥20 mg/mL

Température de stockage

room temp

Chaîne SMILES 

O=C(/C=C/C1=CC=CC=C1)C2=C(O)C=C(O)C=C2OC

InChI

1S/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+

Clé InChI

NYSZJNUIVUBQMM-BQYQJAHWSA-N

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Application

Cardamonin has been used as a glycogen synthase kinase 3 (GSK3) inhibitor to study its effects on β-catenin loss and gain-of-function in human preimplantation embryos.
Cardamonin has been used as a standard in high performance liquid chromatography (HPLC) to analyze phenolic compounds in acacia honey samples.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Peiguang Niu et al.
Oncology letters, 15(3), 3991-3997 (2018-02-20)
The mammalian target of rapamycin (mTOR) is well-known as a promising therapeutic target in various cancer cells. mTOR activation decreases the sensitivity of ovarian cancer to cisplatin. Cardamonin inhibits the proliferation of various cancer cells by mTOR suppression. The present
Ning Wu et al.
Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine, 36(12), 9667-9676 (2015-07-08)
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 the effects of cardamonin (3,4,2,4-tetrahydroxychalcone) on the self-renewal and apoptosis of
Sen Lu et al.
Oncology letters, 15(6), 9641-9646 (2018-06-22)
It has previously been reported that cardamonin is able to regulate glycometabolism and vasodilation whilst also exhibiting anti-inflammatory and antitumor properties. The antitumor effect of cardamonin is multifaceted, and so it is necessary to investigate the antitumor mechanisms of cardamonin
Sudesh Pawaria et al.
PloS one, 7(11), e50365-e50365 (2012-12-12)
The cell surface receptor CD91/LRP-1 binds to immunogenic heat shock proteins (HSP) and α(2)M ligands to elicit T cell immune responses. In order to generate specific immune responses, the peptides chaperoned by HSPs or α(2)M are cross-presented on MHC molecules
Hyun Dong Je et al.
The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology, 20(1), 69-74 (2016-01-26)
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 used and isometric contractions were recorded and combined with molecular experiments.
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