1040683
USP
Apigenin
United States Pharmacopeia (USP) Reference Standard
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/REAXYS Number:
262620
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
grade
pharmaceutical primary standard
API family
apigenin
manufacturer/tradename
USP
mp
>300 °C (lit.)
application(s)
pharmaceutical (small molecule)
format
neat
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
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.
Application
Apigenin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
- Powdered Soy Isoflavones Extract
- Soy Isoflavones Capsules
- Soy Isoflavones Tablets
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.
Analysis Note
These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.
Other Notes
Sales restrictions may apply.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
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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)
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)
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)
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