SMB00702

Apigenin

≥97% (TLC), from citrus

• Synonym(s): 4′,5,7-Trihydroxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
• Empirical Formula (Hill Notation): C₁₅H₁₀O₅
• CAS Number: 520-36-5
• Molecular Weight: 270.24
• Beilstein/REAXYS Number: 262620
• EC Number: 208-292-3
• MDL number: MFCD00006831
• UNSPSC Code: 12352212
• NACRES: NA.79

Properties

• Quality Level: 200
• 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
• Gene Information: human ... ADORA3(140) , CDC2(983) , CDK5(1020) , CDK6(1021) , CYP1A2(1544) , ESR1(2099) , ESR2(2100) , GSK3A(2931) ; mouse ... Hexa(15211) ; rat ... Adora1(29290) , Adora2a(25369) , IL4(287287) , Tnf(24835)

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3