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C80105

Sigma-Aldrich

Chrysin

97%

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Synonym(s):
5,7-Dihydroxyflavone
Empirical Formula (Hill Notation):
C15H10O4
CAS Number:
480-40-0
Molecular Weight:
254.24
Beilstein:
233276
EC Number:
207-549-7
MDL number:
MFCD00006834
PubChem Substance ID:
24893009
NACRES:
NA.47

Quality Level

100

Assay

97%

form

powder

mp

284-286 °C (lit.)

solubility

0.1 M NaOH: 0.008 g/L

λmax

348 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Oc1cc(O)c2C(=O)C=C(Oc2c1)c3ccccc3

InChI

1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

InChI key

RTIXKCRFFJGDFG-UHFFFAOYSA-N

Gene Information

human ... CDC2(983) , CDK5(1020) , CDK6(1021) , CYP19A1(1588) , CYP1A2(1544) , GSK3A(2931)
mouse ... Hexa(15211) , Ptgs2(19225)
rat ... Gabra2(29706)

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Application

  • Chrysin has been used to study the effect of bioflavonoids on the inhibition of ATP synthase in Escherichia coli.
  • It has been used to study the effect of Chrysin on eIF4E (eukaryotic translation initiation factor 4E) expression in AGS cell (human gastric carcinoma cell) line.
  • It has been used to study the effect of chrysin on human ovarian cancer cells.

Biochem/physiol Actions

Chrysin is a flavonoid and an analog of apigenin. It inhibits aromatase and also suppresses human immunodeficiency virus (HIV) activation in models with latent infection. Chrysin exhibits anti-inflammatory and anti-oxidant effects. This molecule induces apoptosis in various cells, thereby exhibiting cancer chemopreventive activity. Chrysin can modulate the activity of GABAA (Type-A γ-aminobutyric acid) and GABAC receptors, it downregulates expression of PCNA (proliferating cell nuclear antigen), reduces activity of CDK2 (cyclin-dependent kinase 2) and CDK4 and induces p38-MAPK (mitogen-activated protein kinase) activation.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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H J Jeong et al.
Archives of pharmacal research, 22(3), 309-312 (1999-07-14)
In searching for potent cancer chemopreventive agents from synthetic or natural products, 28 randomly selected flavonoids were screened for inhibitory effects against partially purified aromatase prepared from human placenta. Over 50% of the flavonoids significantly inhibited aromatase activity, with greatest
Chrysin induces G1 phase cell cycle arrest in C6 glioma cells through inducing p21Waf1/Cip1 expression: involvement of p38 mitogen-activated protein kinase.
Weng MS, et al.
Biochemical Pharmacology, 69, 1815-1815 (2005)
Dietary bioflavonoids inhibit Escherichia coli ATP synthase in a differential manner.
Chinnam N, et al.
International Journal of Biological Macromolecules, 46, 478-478 (2010)
Apoptotic effects of chrysin in human cancer cell lines.
Khoo BY, et al.
International Journal of Molecular Sciences, 11, 2188-2188 (2010)
Mahaboob S Khan et al.
Toxicology and applied pharmacology, 251(1), 85-94 (2010-12-21)
Flavonoids possess strong anti-oxidant and cancer chemopreventive activities. Chrysin (5,7-dihydroxyflavone) occurs naturally in many plants, honey, and propolis. In vitro, chrysin acts as a general anti-oxidant, causes cell cycle arrest and promotes cell death. However, the mechanism by which chrysin
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