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229075

Sigma-Aldrich

1,8-Dihydroxy-3-methylanthraquinone

98%

Sinónimos:

3-Methylchrysazin, Chrysophanic acid

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About This Item

Fórmula empírica (notación de Hill):
C15H10O4
Número de CAS:
481-74-3
Peso molecular:
254.24
Beilstein/REAXYS Number:
1252300
EC Number:
207-572-2
MDL number:
MFCD00001208
UNSPSC Code:
51102829
PubChem Substance ID:
57648009
NACRES:
NA.85

assay

98%

form

crystalline

color

yellow-orange

solubility

chloroform: 1%

antibiotic activity spectrum

neoplastics
viruses

mode of action

enzyme | inhibits

SMILES string

Cc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1

InChI

1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

InChI key

LQGUBLBATBMXHT-UHFFFAOYSA-N

Gene Information

human ... ELA2(1991)

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Application

Chrysophanic acid, a natural anthraquinone, is used to study anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells . It is also used to study the inhibition of replication of poliovirus types 2 and 3 (Picornaviridae) in vitro .

Biochem/physiol Actions

Anticancer activity for chrysophanic acid is via the EGFR/mTOR mediated signaling transduction pathway . Chrysophanic acid has two hydrophobic positions on the molecule (C-6 and the methyl group attached to C-3) which are responsible for the compound′s activity against poliovirus .

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Anthraquinones, a class of naturally occurring polyphenolic compounds, exhibit a wide range of bioactivities. However, most free anthraquinones are lipophilic bioactive compounds. Bovine β-lactoglobulin (βLG), a major whey protein, has a high affinity for small hydrophobic compounds. In this study
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Traumatic brain injury triggers a massive glutamate efflux, activation of NMDA receptor channels, and cell death. Recently, we reported that NMDA receptors in mice are down-regulated from hours to days following closed head injury (CHI), and treatment with NMDA improved
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Phytotherapy research : PTR, 25(6), 833-837 (2010-11-23)
Inactivation of epidermal growth factor receptor (EGFR) is a prime method used in colon cancer therapy. Here it is shown that chrysophanic acid, a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid preferentially blocked
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