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Key Documents

10798

Sigma-Aldrich

Apigenin

≥95.0% (HPLC)

Synonym(s):

4′,5,7-Trihydroxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
Molecular Weight:
270.24
Beilstein:
262620
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mixture effects of dietary flavonoids on steroid hormone synthesis in the human adrenocortical H295R cell line
Ohlsson A, et al.
Food And Chemical Toxicology, 48(11), 3194-3200 (2010)
Health functionality of apigenin: A review
Ali F, et al.
International journal of food properties, 20(6), 1197-1238 (2017)
Apigenin in cancer therapy: anti-cancer effects and mechanisms of action
Yan X, et al.
Cell & Bioscience, 7(1), 50-50 (2017)
Phenolic compounds characterization, carbohydrate digestive enzyme inhibitory and antioxidant activities of Hieracium pannosum Boiss
Gokbulut A, et al.
South African Journal of botony, 108, 387-392 (2017)
Amy A Mrazek et al.
Pancreas, 48(5), 711-718 (2019-05-16)
Chronic pancreatitis is the consequence of multiple episodes of recurrent acute pancreatitis (RAP). We hypothesized that apigenin can minimize the sequelae of RAP by limiting acinar cells' proinflammatory signaling pathways. AR42J acinar cells were treated in vitro with transforming growth

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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