01760595

Apigenin

primary reference standard

Synonym(s):
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone, 4′,5,7-Trihydroxyflavone
Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
Molecular Weight:
270.24
Beilstein/REAXYS Number:
262620
EC Number:
MDL number:
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.)

Featured Industry

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.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

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...
Émilie C Lefort et al.
Molecular nutrition & food research, 57(1), 126-144 (2012-12-01)
Apigenin (4',5,7-trihydroxyflavone, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many fruits, vegetables, and herbs, the most abundant sources being the leafy herb parsley and dried flowers of chamomile. Present in dietary sources as a glycoside, it is cleaved in the gastrointestinal...
Mano Horinaka et al.
Molecular cancer therapeutics, 5(4), 945-951 (2006-05-02)
Dietary flavonoid apigenin is expected to have preventive and therapeutic potential against malignant tumors. In this report, we show for the first time that apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble...
Protocols
Effective analysis of passion flower by HPTLC fingerprinting, in conjunction with a comprehensive range of related reference materials, enables fast and efficient identification of this plant material.
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