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Merck
CN

A3145

Apigenin

≥97% (TLC), from parsley, powder

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:
12352200
PubChem Substance ID:
24278212
Beilstein/REAXYS Number:
262620
MDL number:
MFCD00006831

Key Documents

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InChI key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

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

SMILES string

Oc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)cc3O2

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

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.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (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
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
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
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
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
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