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A89502

Sigma-Aldrich

Anthraflavic acid

technical grade, 90%

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Synonym(s):
2,6-Dihydroxyanthraquinone, Anthraflavine
Empirical Formula (Hill Notation):
C14H8O4
CAS Number:
Molecular Weight:
240.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

Assay

90%

form

powder

mp

>320 °C (lit.)

SMILES string

Oc1ccc2C(=O)c3cc(O)ccc3C(=O)c2c1

InChI

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

InChI key

APAJFZPFBHMFQR-UHFFFAOYSA-N

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Application

Anthraflavic acid can be used as a starting material to synthesize tetrahydroxy tetrathiafulvalene (TTF) derivatives, which are used as redox-active building blocks in supramolecular and materials science. It is also utilized to prepare phosphanylidene anthra[2,1-b]furans by reacting with dialkyl acetylenedicarboxylates and triphenylphosphine.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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A D Ayrton et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 26(11-12), 909-915 (1988-11-01)
Administration of the antimutagen anthraflavic acid to rats gave rise to significant increases in the hepatic microsomal O-deethylations of ethoxyresorufin and ethoxycoumarin, but not in the O-dealkylation of pentoxyresorufin nor in cytosolic glutathione S-transferase activity. Immunoblot studies of solubilized microsomes
Regioselective synthesis of novel functionalized phosphanylidene anthra [2, 1-b] furan derivatives under solvent-free conditions
Nourmohammadian F and Gholami MD
Phosphorus, Sulfur, and Silicon and the Related Elements, 185(2), 340-346 (2010)
A D Ayrton et al.
Biochimica et biophysica acta, 916(3), 328-331 (1987-12-18)
Consideration of the computer-optimised dimensions of anthraflavic acid indicates that it is essentially a planar molecule with a large area/depth ratio, that would preferentially interact with the polycyclic aromatic hydrocarbon-induced family of cytochrome P-450 proteins (cytochromes P-448). Anthraflavic acid was
Synthesis of tetrahydroxy-?-extended tetrathiafulvalenes as new supramolecular redox building blocks
Diaz Marta C, et al.
Tetrahedron Letters, 44(5), 945-948 (2003)
María Elena Sánchez-Vergara et al.
Molecules (Basel, Switzerland), 17(9), 10000-10013 (2012-08-28)
Semiconducting thin films were grown on quartz substrates and crystalline silicon wafers, using dilithium phthalocyanine and the organic ligands 2,6-dihydroxyanthraquinone and 2,6-diaminoanthraquinone as the starting compounds. The films, thus obtained, were characterized by Fourier Transform infrared (FTIR), fast atomic bombardment

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