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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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)
F Khaligh et al.
Journal of animal physiology and animal nutrition, 102(1), e413-e420 (2017-06-22)
An experiment was conducted to evaluate the effects of in ovo injection of chrysin, quercetin and ascorbic acid on hatchability, somatic attributes, hepatic antioxidant status and early post-hatch growth performance of broiler chicks. Four hundred and eighty embryonated broiler breeder
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
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