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Merck
CN

37480

Sigma-Aldrich

1,4-Dihydroxyanthraquinone

purum, ≥98.0% (HPLC), powder, red-brown

Synonym(s):

Quinizarin

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About This Item

Empirical Formula (Hill Notation):
C14H8O4
CAS Number:
81-64-1
Molecular Weight:
240.21
Beilstein:
1914036
EC Number:
201-368-7
MDL number:
MFCD00001209
UNSPSC Code:
12352103
PubChem Substance ID:
329755654
NACRES:
NA.23

Key Documents

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grade

purum

Quality Level

200

Assay

≥98.0% (HPLC)

form

powder

ign. residue

≤1.0%

color

red-brown

mp

195-200 °C

SMILES string

Oc1ccc(O)c2C(=O)c3ccccc3C(=O)c12

InChI

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

InChI key

GUEIZVNYDFNHJU-UHFFFAOYSA-N

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General description

1,4-Dihydroxyanthraquinone is an organic dye molecule with an aromatic structure. It is a derivative of anthraquinone bearing hydroxyl moieties. They may find uses in pharmacological, biochemical and dye industries. Anthraquinone dye are resistant to degradation.

Application

1,4-Dihydroxyanthraquinone may be used in the synthesis of cyclopentanoids by cyclization of α,β-unsaturated aldehyde with 1, 4 1,4-Dihydroxyanthraquinone. It has been studied as a long range emissive ratiometric fluorescent probe for live cell imaging.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

431.6 °F

Flash Point(C)

222 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000142002
0000101487
0000131135
0000131136
0000124136

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Exploring 1,4-dihydroxyanthraquinone as long-range emissive ratiometric fluorescent probe for signaling Zn2+/PO43-: ensemble utilization for live cell imaging
Sinha S, et al.
Journal of Photochemistry and Photobiology. B, Biology (2015)
Petronela Pascariu Dorneanu et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 134, 218-224 (2014-07-12)
Absorption and fluorescence spectra of a polyquinoneimine, PQI, built on 1,4-dihydroxyanthraquinone and a siloxane diamine, 1,3-bis(amino-phenylene-ester-methylene)tetramethyldisiloxane, have been investigated in solvents of different polarities. The effect of solvents on the spectral properties was investigated using Lippert-Mataga and Bakhshiev polarity functions
Cyclization of 1,4-Dihydroxyanthraquinone with a,?-Unsaturated Aldehyde: A New Strategy for the Synthesis of Cyclopentanoids
Cao FX, et al.
Tetrahedron Letters (2015)
X Ma et al.
Biochimica et biophysica acta, 781(1-2), 173-182 (1984-02-24)
The effect of dihydroxyanthraquinone (DHAQ), a new antitumor drug, on mammalian chromosome replication was investigated using simian virus 40 (SV40) as a model system. The maximum effect of inhibition on viral DNA synthesis was observed within 30-40 min after the
N J Hao et al.
Mutation research, 328(2), 183-191 (1995-05-01)
The antimutagenicity of 17 natural and synthetic anthraquinones was determined using Salmonella typhimurium TA98 against 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in the presence of Aroclor 1254-induced rat hepatic S9. In general, the relationship between the chemical structures of anthraquinones and their antimutagenicity was
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