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10798

Sigma-Aldrich

Apigenin

≥95.0% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C15H10O5
Numéro CAS:
520-36-5
Poids moléculaire :
270.24
Numéro Beilstein :
262620
Numéro CE :
208-292-3
Numéro MDL:
MFCD00006831
Code UNSPSC :
12352202
ID de substance PubChem :
57646817
Nomenclature NACRES :
NA.77

Pureté

≥95.0% (HPLC)

Impuretés

~2% water

Pf

>300 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

KZNIFHPLKGYRTM-UHFFFAOYSA-N

Informations sur le gène

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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Description générale

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.

Actions biochimiques/physiologiques

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.
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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

Inhibitor of human estrogen synthetase

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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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)
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)
Health functionality of apigenin: A review
Ali F, et al.
International journal of food properties, 20(6), 1197-1238 (2017)
Apigenin in cancer therapy: anti-cancer effects and mechanisms of action
Yan X, et al.
Cell & Bioscience, 7(1), 50-50 (2017)
J T Kellis et al.
Science (New York, N.Y.), 225(4666), 1032-1034 (1984-09-07)
Several naturally occurring and synthetic flavones were found to inhibit the aromatization of androstenedione and testosterone to estrogens catalyzed by human placental and ovarian microsomes. These flavones include (in order of decreasing potency) 7,8-benzoflavone, chrysin, apigenin, flavone, flavanone, and quercetin;
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