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Apigenin

Name: Apigenin
Brand: SIGMA

≥97% (TLC), from citrus

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

EC Number:

208-292-3

UNSPSC Code:

12352212

NACRES:

NA.79

Beilstein/REAXYS Number:

262620

MDL number:

MFCD00006831

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Properties

Quality Segment

200

assay

≥97% (TLC)

form

powder

mp

>300 °C (lit.)

solubility

DMSO: 27 mg/mL, 1 M KOH: 50 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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)

Description

General description

Apigenin (ApI) is also called as 5,7,4′-trihydroxyflavone. It is a natural compound, found in several fruits and herbs, like, oranges, onions and parsley.

Application

Apigenin has been used:

to test its anti-cancer effects as a reference agent to treat various digestive track and liver cancer cells in in vitro studies
as stimuli and inhibitor to test its anti-inflammatory effects on in vitro inflammatory responses due to dietary and metabolic changes of rural- and urban-living Tanzanians
as a reference standard to identify the phenolic compounds in olive mill wastewater and pomace

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 (ApI) blocks the development of thyroid cancer cells by attenuating epidermal growth factor receptor (EGF-R) tyrosine phosphorylation and phosphorylation of ERK mitogen-activated protein (MAP) kinase. Apigenin participates in the modulation of different signaling cascades. It possesses several functions such as, antiapoptosis, anti-inflammation, anticancer, antibacterial and antioxidant effects.

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This Item	42251	PHL89159	178278
Sigma-Aldrich SMB00702 Apigenin	Supelco 42251 Apigenin	PHL89159 Apigenin	Sigma-Aldrich 178278 Apigenin
description ≥97% (TLC), from citrus	description analytical standard	description phyproof^® Reference Substance	description Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 µM).
assay ≥97% (TLC)	assay ≥99% (HPLC)	assay ≥95.0% (HPLC)	assay ≥98% (HPLC)
form powder	form -	form powder	form crystalline solid
application(s) metabolomics vitamins, nutraceuticals, and natural products	application(s) food and beverages	application(s) -	application(s) -
Quality Level 200	Quality Level 100	Quality Level -	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. -	storage temp. 2-8°C
solubility DMSO: 27 mg/mL, 1 M KOH: 50 mg/mL	solubility -	solubility -	solubility hot ethanol: 1 mg/mL, DMSO: 10 mg/mL

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Storage Class

11 - Combustible Solids

WGK

WGK 3

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