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A89502

Sigma-Aldrich

Anthraflavic acid

technical grade, 90%

Synonym(s):

2,6-Dihydroxyanthraquinone, Anthraflavine

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About This Item

Empirical Formula (Hill Notation):
C14H8O4
CAS Number:
84-60-6
Molecular Weight:
240.21
EC Number:
201-544-3
MDL number:
MFCD00001228
UNSPSC Code:
12352100
PubChem Substance ID:
24891386
NACRES:
NA.22

grade

technical grade

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extrapolation of in vitro antimutagenicity to the in vivo situation: the case for anthraflavic acid.
C Ioannides et al.
Basic life sciences, 61, 103-110 (1993-01-01)
H Mukhtar et al.
Cancer research, 48(9), 2361-2365 (1988-05-01)
Our recent studies have shown that naturally occurring dietary plant phenols such as tannic acid, quercetin, myricetin, and anthraflavic acid are capable of inhibiting polycyclic aromatic hydrocarbon (PAH) metabolism and subsequent PAH-DNA adduct formation in epidermis of SENCAR mice (M.
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
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
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