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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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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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
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
Myung Sun Lee et al.
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
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
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
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