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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

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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Bokyung Sung et al.
PloS one, 8(5), e64118-e64118 (2013-05-22)
Bone loss/resorption or osteoporosis is a disease that is accelerated with aging and age-associated chronic diseases such as cancer. Bone loss has been linked with human multiple myeloma, breast cancer, and prostate cancer and is usually treated with bisphosphonates, and
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
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
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
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
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