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C80105

Sigma-Aldrich

Chrysin

≥96.5%

Synonym(s):

5,7-Dihydroxyflavone

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About This Item

Empirical Formula (Hill Notation):
C15H10O4
CAS Number:
480-40-0
Molecular Weight:
254.24
Beilstein:
233276
EC Number:
207-549-7
MDL number:
MFCD00006834
UNSPSC Code:
12171500
PubChem Substance ID:
24893009
NACRES:
NA.47

Quality Level

100

Assay

≥96.5%

form

powder

color

beige

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Apoptotic effects of chrysin in human cancer cell lines.
Khoo BY, et al.
International Journal of Molecular Sciences, 11, 2188-2188 (2010)
Evaluation of the effect of Chrysin and Caffeic acid phenethyl ester on eIF4E expression in AGS cell line.
Abolhasani M, et al.
Journal of HerbMed Pharmacology, 3 (2014)
Dietary bioflavonoids inhibit Escherichia coli ATP synthase in a differential manner.
Chinnam N, et al.
International Journal of Biological Macromolecules, 46, 478-478 (2010)
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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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