10798

Apigenin

≥95.0% (HPLC)

• 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: 12352202
• PubChem Substance ID: 57646817
• NACRES: NA.77

Properties

• assay: ≥95.0% (HPLC)
• impurities: ~2% water
• mp: >300 °C (lit.)
• 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 is a 270 Da flavonoid, which belongs to the flavone group of glycosides. It is synthesized by a wide variety of plants including cereals, grains, tea and oranges.

Application

Apigenin has been used as a calibration standard for the quantification of Hieracium pannosum Boiss, Juniperus sp, using high-performance liquid chromatography (HPLC) with Diode-Array Detection (DAD). It has been used to study effect on hormone secretion in the human adrenocortical H295R cells.

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 is a class II pharmaceutical drug and highly intestine permeable. It has antioxidant, anti-inflammatory and antitumorigenic functionality. It is a potent inhibitor of the cluster of differentiation 38 (CD30) nucleotide adenine dinucleotide (NAD⁺) nucleosidase and could be used to suppress CD30 mediated metabolic syndrome.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Inhibitor of human estrogen synthetase

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves