C8249

Sigma-Aldrich

Cardamonin

≥98% (HPLC)

Synonym(s):
(8CI); Alpinetin chalcone, (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one, (E)-2′,4′-Dihydroxy-6′-methoxy-chalcone
Empirical Formula (Hill Notation):
C16H14O4
CAS Number:
Molecular Weight:
270.28
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

light yellow to dark brown

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

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+

InChI key

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.

Packaging

5, 25 mg in glass bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8249.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Environment

Signal Word

Warning

Hazard Statements

Precautionary Statements

RIDADR

UN 3077 9 / PGIII

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Phenolics and abscisic acid identified in acacia honey comparing different SPE cartridges coupled with HPLC-PDA
Sun C, et al.
Journal of food composition and analysis, 53 (2016)
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....
Deyong Jia et al.
Oncotarget, 7(1), 771-785 (2015-10-28)
The failure of cytotoxic chemotherapy in breast cancers has been closely associated with the presence of drug resistant cancer stem cells (CSCs). Thus, screening for small molecules that selectively inhibit growth of CSCs may offer great promise for cancer control...
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...
Xuekun Nie et al.
Cell biology international, 44(11), 2192-2201 (2020-07-25)
Autophagy is closely related to the formation and development of multiple human tumors including ovarian cancer. As a major regulator of this process, the role of mTOR (mammalian target of rapamycin) has been well proven. Cardamonin, a kind of flavonoid...

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