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Safety Information

229075

Sigma-Aldrich

1,8-Dihydroxy-3-methylanthraquinone

98%

Synonym(s):

3-Methylchrysazin, Chrysophanic acid

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About This Item

Empirical Formula (Hill Notation):
C15H10O4
CAS Number:
481-74-3
Molecular Weight:
254.24
Beilstein:
1252300
EC Number:
207-572-2
MDL number:
MFCD00001208
UNSPSC Code:
51101500
PubChem Substance ID:
57648009
NACRES:
NA.85

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Haoxie Xu et al.
Food chemistry, 281, 28-35 (2019-01-20)
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
Anne C Jones et al.
Die Naturwissenschaften, 99(7), 583-586 (2012-06-23)
The nonnative hemlock woolly adelgid (Adelges tsugae Annand, Hemiptera: Sternorrhyncha: Adelgidae) has been a significant mortality agent of eastern hemlock (Tsuga canadensis Carriere) throughout a large portion of its geographic range. During a study investigating adelgid vigor in relation to
Hee-Yun Kim et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 68(5), 387-395 (2019-03-16)
AST2017-01 is developed to be used for treatment and prevention of allergic diseases and composed of processed-Cordyceps militaris and processed-Rumex crispus. But, effect of AST2017-01 remains unclear in an allergic rhinitis (AR). So, this study aimed to explore the effects
Su-Jin Kim et al.
Molecules (Basel, Switzerland), 15(9), 6436-6451 (2010-09-30)
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of chrysophanol
Rami Yaka et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 21(9), 2033-2041 (2007-03-14)
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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