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C80105

Sigma-Aldrich

Chrysin

≥96.5% purity, powder

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

product name

Chrysin, ≥96.5%

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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Cytotoxic and Pro-Apoptotic Effects of Honey Bee Venom and Chrysin on Human Ovarian Cancer Cells.
Amini E, et al.
Asia Pacific Journal of Medical Toxicology, 4 (2015)
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)
Chin-Shiu Huang et al.
Archives of toxicology, 87(1), 167-178 (2012-08-07)
Chrysin, apigenin, and luteolin are flavones that differ in their number of hydroxyl groups in the B ring. In this study, we investigated the protection by chrysin, apigenin, and luteolin against tert-butyl hydroperoxide (tBHP)-induced oxidative stress and the possible mechanisms
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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