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Merck
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SMB00702

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
EC Number:
208-292-3
UNSPSC Code:
12352212
NACRES:
NA.79
Beilstein/REAXYS Number:
262620
MDL number:
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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

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

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.
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.
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. Inhibitory effects on tumor promotion may also be due to inhibition of kinase activity and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I catalyzed DNA religation and enhance gap junctional intercellular communication.


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Storage Class

11 - Combustible Solids

wgk

WGK 3



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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)



Global Trade Item Number

SKUGTIN
SMB00702-100MG04061831595222
SMB00702-25MG04061831595239
SMB00702-5MG04061838356895