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Merck

01760595

Apigenin

primary reference standard

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C15H10O5
Número de CAS:
Peso molecular:
270.24
Beilstein/REAXYS Number:
262620
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

mp

>300 °C (lit.)

application(s)

food and beverages

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

Flavonoids belong to polyphenolic class of compounds. They play crucial role in biological activities which include tumor growth inhibition and chemoprevention. Apigenin is a plant flavonoid mostly used to inhibit ornithine decarboxylase activity and skin tumor.
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

It may be used as internal standard for determining peurarin and its metabolites, using LC-ESI-MS/MS, in blood and urine of rats.

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.

Other Notes

This compound is commonly found in plants of the genus: achillea mentha pimpinella primula salvia silybum thymus

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3


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Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry.
Prasain JK
Journal of Agricultural and Food Chemistry, 52(12), 3708-3712 (2004)
Flavonoids apigenin and quercetin inhibit melanoma growth and metastatic potential.
Caltagirone S
International Journal of Cancer. Journal International Du Cancer, 87(4), 595-600 (2000)
Inhibition of ultraviolet light induced skin carcinogenesis in SKH-1 mice by apigenin, a plant flavonoid.
Birt DF
Anticancer Research, 17(1A), 85-91 (1997)
Ding-Guo Wu et al.
Toxicology letters, 224(1), 157-164 (2013-10-24)
Apigenin is a potential chemopreventive agent for cancer prevention. Because of the central role of transcription factor nuclear factor-κB (NF-κB) in pancreatic cancer, we investigated the roles of NF-κB in apigenin-induced growth inhibition in pancreatic cancer cells. It showed that
Griangsak Eumkeb et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(3-4), 262-269 (2012-12-12)
The purpose of this investigation was to examine the antibacterial and synergistic effect of naturally occurring flavonoids, apigenin, quercetin, naringenin and ceftazidime when use singly and in combination against ceftazidime-resistant Enterobacter cloacae strains by minimum inhibitory concentration (MIC), checkerboard and

Protocolos

HPTLC fingerprinting enables rapid identification of passion flower with related reference materials.

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