37480

Sigma-Aldrich

1,4-Dihydroxyanthraquinone

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

Synonym(s):
Quinizarin
Empirical Formula (Hill Notation):
C14H8O4
CAS Number:
Molecular Weight:
240.21
Beilstein/REAXYS Number:
1914036
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

grade

purum

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3077 9 / PGIII

WGK Germany

WGK 2

Flash Point(F)

431.6 °F

Flash Point(C)

222 °C

Certificate of Analysis

Certificate of Origin

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)
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)
E Tramontano et al.
Journal of chemotherapy (Florence, Italy), 23(5), 273-276 (2011-10-19)
Human immunodeficiency virus 1 (HIV-1) and Hepatitis C virus (HCV) affect 60 and 170 million infected individuals worldwide, respectively, and co-infection by both pathogens is often observed. This represents a serious public health problem that requires the identification of new...
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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