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MilliporeSigma

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:
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

Key Documents

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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)

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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.
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. 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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
445301/1
444548/1
307580/1

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Apigenin in cancer therapy: anti-cancer effects and mechanisms of action
Yan X, et al.
Cell & Bioscience, 7(1), 50-50 (2017)
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)
Comparative Analysis of Chemical Profile, Antioxidant, In-vitro and In-vivo Antidiabetic Activities of Juniperus foetidissima Willd. and Juniperus sabina L.
Orhan N, et al.
The Iranian Journal of Pharmaceutical Research, 16(Suppl), 64-64 (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)
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Articles

Dietary Antioxidants

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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