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D108103

Sigma-Aldrich

1,8-Dihydroxyanthraquinone

96%

Synonym(s):

Chrysazine, Danthron

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About This Item

Empirical Formula (Hill Notation):
C14H8O4
CAS Number:
117-10-2
Molecular Weight:
240.21
Beilstein/REAXYS Number:
2054727
EC Number:
204-173-5
MDL number:
MFCD00001211
UNSPSC Code:
12352100
PubChem Substance ID:
24893346
NACRES:
NA.22

assay

96%

form

powder

mp

191-193 °C (lit.)

SMILES string

Oc1cccc2C(=O)c3cccc(O)c3C(=O)c12

InChI

1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H

InChI key

QBPFLULOKWLNNW-UHFFFAOYSA-N

Gene Information

human ... RXRA(6256)

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Application

1,8-Dihydroxyanthraquinone can be used:
  • To prepare an inclusion complex with β-cyclodextrin, applicable as a sensor in the estimation of Cu2+ ions in an aqueous solution.[1]
  • As a starting material in the synthesis of 1,4,5,8-tetramethoxyanthracene.[2]
  • As an aromatic scavenger in the modification of lignin, which acts as a corrosion inhibitor for steel.[3]

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

No data available

flash_point_c

No data available

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6527V
WXBC6772V
WXBC4791V
WXBC2887V
WXBB7902V

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Improved corrosion inhibition of mild steel by chemically modified lignin polymers from Elaeis guineensis agricultural waste
Hussin MH, et al.
Materials Chemistry and Physics, 163(05), 201-212 (2015)
A Practical Synthesis of 1, 4, 5, 8-Tetramethoxyanthracene from Inexpensive and Readily Available 1, 8-Dihydroxyanthraquinone
Navale TS and Rathore R
Synthesis, 44(05), 805-809 (2012)
Jo-Hua Chiang et al.
Chemical research in toxicology, 24(1), 20-29 (2010-12-04)
Anthraquinones have been shown to induce apoptosis in different types of tumor cells, but the mechanisms of danthron-induced cytotoxicity and apoptosis in human gastric cancer cells have not been adequately explored. This study investigated the roles of caspase cascades, ROS
Haitao Zhang et al.
The Journal of biological chemistry, 286(3), 1868-1875 (2010-11-19)
Retinoic X receptor (RXR) is a promising target for drug discovery against cancer and metabolic syndromes. Here, we identified a specific RXRα antagonist, danthron, from the traditional Chinese medicine rhubarb. Danthron repressed all tested RXRα-involved response element transcription, including the
Yong-Soo Kwon et al.
Biological & pharmaceutical bulletin, 27(5), 723-726 (2004-05-11)
Oxidative stress caused by an elevation in reactive oxygen species (ROS) plays an important role in Alzheimer's disease and other neurodegenerative diseases. In this study, we examined the neuroprotective effect of danthron (1,8-dihydroxyanthraquinone) against neurotoxicities induced by beta-amyloid (25-35), excitotoxins
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