SMB00702

Apigenin

≥97% (TLC), from citrus

• Synonym(e): 4′,5,7-Trihydroxy-flavon, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyron
• Empirische Formel (Hill-System): C₁₅H₁₀O₅
• CAS-Nummer: 520-36-5
• Molekulargewicht: 270.24
• Beilstein: 262620
• EG-Nummer: 208-292-3
• MDL-Nummer: MFCD00006831
• UNSPSC-Code: 12352212
• NACRES: NA.79

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥97% (TLC)
• Form: powder
• mp (Schmelzpunkt): >300 °C (lit.)
• Löslichkeit: DMSO: 27 mg/mL; 1 M KOH: 50 mg/mL
• Anwendung(en): metabolomics; vitamins, nutraceuticals, and natural products
• Lagertemp.: −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
• InChIKey: KZNIFHPLKGYRTM-UHFFFAOYSA-N
• Angaben zum Gen: 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)

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3