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SMB00702

Sigma-Aldrich

Apigenin

≥97% (TLC), from citrus

Synonym(s):

4′,5,7-Trihydroxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
Molecular Weight:
270.24
Beilstein:
262620
EC Number:
MDL number:
UNSPSC Code:
12352212
NACRES:
NA.79

Quality Level

Assay

≥97% (TLC)

form

powder

mp

>300 °C (lit.)

solubility

DMSO: 27 mg/mL
1 M KOH: 50 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

Oc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2

InChI

1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

InChI key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

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General description

Apigenin (ApI) is also called as 5,7,4′-trihydroxyflavone. It is a natural compound, found in several fruits and herbs, like, oranges, onions and parsley.

Application

Apigenin has been used:
  • to test its anti-cancer effects as a reference agent to treat various digestive track and liver cancer cells in in vitro studies
  • as stimuli and inhibitor to test its anti-inflammatory effects on in vitro inflammatory responses due to dietary and metabolic changes of rural- and urban-living Tanzanians
  • as a reference standard to identify the phenolic compounds in olive mill wastewater and pomace

Biochem/physiol Actions

A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53. Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication.
Apigenin (ApI) blocks the development of thyroid cancer cells by attenuating epidermal growth factor receptor (EGF-R) tyrosine phosphorylation and phosphorylation of ERK mitogen-activated protein (MAP) kinase. Apigenin participates in the modulation of different signaling cascades. It possesses several functions such as, antiapoptosis, anti-inflammation, anticancer, antibacterial and antioxidant effects.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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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Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects
Viola H, et al.
Planta Medica, 61(03), 213-216 (1995)
Godfrey S Temba et al.
Nature immunology, 22(3), 287-300 (2021-02-13)
Sub-Saharan Africa currently experiences an unprecedented wave of urbanization, which has important consequences for health and disease patterns. This study aimed to investigate and integrate the immune and metabolic consequences of rural or urban lifestyles and the role of nutritional
Apigenin inhibits growth and induces G2/M arrest by modulating cyclin-CDK regulators and ERK MAP kinase activation in breast carcinoma cells.
Yin F, et al.
Anticancer Research, 21(1A), 413-420 (2001)
Lukasz Szoka et al.
Journal of cellular and molecular medicine, 25(24), 11085-11096 (2021-11-11)
Flavonoids are bioactive secondary metabolites of plants, which exert anti-cancer effects. However, metabolism in enterocytes and the liver can influence the biological activity of flavonoids contained in the diet. Therefore, results from in vitro studies on cancer cells from the
Effect of apigenin on apoptosis induced by renal ischemia reperfusion injury in vivo and in vitro
Wang Xiao, et al.
Renal Failure, 40(1), 498-505 (2018)

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