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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/REAXYS Number:
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.

wgk_germany

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 7-glucoside primary reference standard

00720585

Apigenin 7-glucoside

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)
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)
Apigenin as an effective anticancer natural product: Spotlight on TRAIL, WNT beta-catenin, JAK-STAT pathways, and microRNAs
Ozbey U, et al.
Journal of Cellular Biochemistry (2018)
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)
Ana Miklavčič Višnjevec et al.
Molecules (Basel, Switzerland), 26(1) (2020-12-31)
The valorization of olive pomace through the extraction of phenolic compounds at an industrial scale is influenced by several factors that can have a significant impact on the feasibility of this approach. These include the types and levels of phenolic

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