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
• EC Number: 208-292-3
• UNSPSC Code: 12352212
• NACRES: NA.79
• Beilstein/REAXYS Number: 262620
• MDL number: MFCD00006831

Eigenschaften

• Quality Segment: 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)

Beschreibung

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. 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.

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

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3