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C8249

Sigma-Aldrich

Cardamonin

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C16H14O4
CAS Number:
19309-14-9
Molecular Weight:
270.28
MDL number:
MFCD00238554
UNSPSC Code:
12352200
PubChem Substance ID:
329775163
NACRES:
NA.77

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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Chih-Chien Wang et al.
Medicina (Kaunas, Lithuania), 57(9) (2021-09-29)
Background and Objectives: Gouty arthritis is an acute inflammatory response caused by the precipitation of monosodium urate (MSU) crystals in joints. The triggering of MSU leads to increased production of inflammatory cytokines, such as interleukin-1β, which in turn lead to
Jianqing Jiang et al.
Journal of microbiology and biotechnology, 31(6), 794-802 (2021-05-25)
In this study we investigated the role and mechanism of cardamonin on IL-1β induced injury in OA. CHON-001 cells were treated with cardamonin and IL-1β and transfected with silencing nuclear factor erythroid 2-related factor 2 (siNrf2). Cell viability was detected
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
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