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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/REAXYS Number:
1914036
EC Number:
201-368-7
MDL number:
MFCD00001209
UNSPSC Code:
12352103
PubChem Substance ID:
329755654
NACRES:
NA.23

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.[1] 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.[2]

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.[3] It has been studied as a long range emissive ratiometric fluorescent probe for live cell imaging.[4]

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Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

431.6 °F

flash_point_c

222 °C

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB4673
BCCB4672
BCCB1275
BCBW8138
BCBW2401

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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)
Photochemical hole-burning study of 1,4-dihydroxyanthraquinone doped in amorphous silica prepared by alcoholate method
Tani T, et al.
Journal of Applied Physics, 58, 3559-3559 (1985)
Cyclization of 1,4-Dihydroxyanthraquinone with a,?-Unsaturated Aldehyde: A New Strategy for the Synthesis of Cyclopentanoids
Cao FX, et al.
Tetrahedron Letters (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
Christopher Batchelor-McAuley et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(50), 19891-19895 (2011-11-24)
After 35 years the hunt for improved anthracycline antibiotics is unabated but has yet to achieve the levels of clinical success desired. Electrochemical techniques provide a large amount of kinetic and thermodynamic information, but the use of such procedures is
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