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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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

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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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
Ying Liu et al.
BMC complementary medicine and therapies, 23(1), 336-336 (2023-09-26)
mTORC1 (mechanistic target of rapamycin complex 1) is associated with lymphoma progression. Oncogenic RRAGC (Rag guanosine triphosphatase C) mutations identified in patients with follicular lymphoma facilitate the interaction between Raptor (regulatory protein associated with mTOR) and Rag GTPase. It promotes
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
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)
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