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A3145

Sigma-Aldrich

Apigenin

≥97% (TLC), from parsley, powder

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Synonym(s):
4′,5,7-Trihydroxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
520-36-5
Molecular Weight:
270.24
Beilstein:
262620
EC Number:
208-292-3
MDL number:
MFCD00006831
UNSPSC Code:
12352200
PubChem Substance ID:
24278212

biological source

parsley

Assay

≥97% (TLC)

form

powder

color

yellow

mp

>300 °C (lit.)

solubility

DMSO: 27 mg/mL
1 M KOH: 50 mg/mL

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)

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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.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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
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
Kaihui Lu et al.
Journal of natural products, 76(4), 672-678 (2013-03-26)
Adipocyte dysfunction is a major cause of obesity, which is associated strongly with many disorders including psychological and medical morbidities, metabolic abnormalities, and cardiovascular diseases as well as a series of cancers. This study investigated the antiadipogenic activity of scutellarin
John Sanseverino et al.
Toxicological sciences : an official journal of the Society of Toxicology, 107(1), 122-134 (2008-11-11)
Saccharomyces cerevisiae bioluminescent bioreporter assays were developed previously to assess a chemical's estrogenic or androgenic disrupting potential. S. cerevisiae BLYES, S. cerevisiae BLYAS, S. cerevisiae BLYR, were used to assess their reproducibility and utility in screening 68, 69, and 71
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