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: 262620
• EC Number: 208-292-3
• MDL number: MFCD00006831
• UNSPSC Code: 12352202
• PubChem Substance ID: 57646817
• NACRES: NA.77

Properties

• Quality Level: 100
• 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.[1]

Application

Apigenin has been used as a calibration standard for the quantification of Hieracium pannosum Boiss,[2] Juniperus sp,[3] 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.[4]

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.

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.

Apigenin is a class II pharmaceutical drug and highly intestine permeable. It has antioxidant, anti-inflammatory and antitumorigenic functionality.[5] 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.[6]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Inhibitor of human estrogen synthetase[7]

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves