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Merck

10798

Apigenin

≥95.0% (HPLC)

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C15H10O5
Numéro CAS:
520-36-5
Poids moléculaire :
270.24
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
57646817
EC Number:
208-292-3
Beilstein/REAXYS Number:
262620
MDL number:
MFCD00006831
Assay:
≥95.0% (HPLC)
Quality level:
100

Principaux documents

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InChI key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

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

SMILES string

Oc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2

assay

≥95.0% (HPLC)

impurities

~2% water

mp

>300 °C (lit.)

storage temp.

−20°C

Quality Level

100

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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

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

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Consulter la Bibliothèque de documents

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)
Apigenin in cancer therapy: anti-cancer effects and mechanisms of action
Yan X, et al.
Cell & Bioscience, 7(1), 50-50 (2017)
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)
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
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