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A3145

Sigma-Aldrich

Apigenin

≥97% (TLC), from parsley, powder

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
Beilstein:
262620
Numéro CE :
208-292-3
Numéro MDL:
MFCD00006831
Code UNSPSC :
12352200
ID de substance PubChem :
24278212

Source biologique

parsley

Essai

≥97% (TLC)

Forme

powder

Couleur

yellow

Pf

>300 °C (lit.)

Solubilité

DMSO: 27 mg/mL
1 M KOH: 50 mg/mL

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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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.
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.

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

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Certificats d'analyse (COA)

Lot/Batch Number
SLBN2876V
SLBL4733V
SLBJ3647V
SLBG8924V
SLBD7060V

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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
Benjamin Dilberger et al.
Nutrients, 11(8) (2019-08-16)
(1) Background: Polyphenols (PP) play an important role in the prevention of non-communicable diseases and may contribute to healthy aging. To investigate the molecular and cellular aspects of PP metabolites on longevity with a focus on mitochondrial function, we applied
Naiara Silva Dourado et al.
Frontiers in aging neuroscience, 12, 119-119 (2020-06-06)
Neurodegenerative disorders (ND) are characterized by the progressive and irreversible loss of neurons. Alzheimer's Disease (AD) is the most incident age-related ND, in which the presence of a chronic inflammatory compound seems to be related to its pathogenesis. Different stimuli
Yusuke Sekiguchi et al.
Bioorganic & medicinal chemistry letters, 19(11), 2920-2923 (2009-05-06)
We determined the 2.35-A crystal structure of a human CK2 catalytic subunit (referred to as CK2alpha complexed with the ATP-competitive, potent CK2 inhibitor ellagic acid. The inhibitor binds to CK2alpha with a novel binding mode, including water-mediated hydrogen bonds. This
Sivaprakasam Balasubramanian et al.
The Journal of biological chemistry, 281(47), 36162-36172 (2006-09-20)
Apigenin is a plant-derived flavanoid that has significant promise as a skin cancer chemopreventive agent. In the present study, we examine the mechanism whereby apigenin regulates normal human keratinocyte differentiation. Expression of involucrin (hINV), a marker of keratinocyte differentiation, is
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