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Product Code B1401-10g
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A widely used anthraquinone building block

Used for the synthesis of semiconducting molecules and polymers in the application of OFETs, OLEDs OPVs, and batteries

2,6-Dihydroxyanthraquinone, also known as anthraflavic acid, a plant metabolite, is a 9,10-anthraquinone derivative with the central ring bearing two carbonyl groups being fused to two fully aromatic six-membered rings. It is an isomer of the alizarin dye with a crystal packing as superimposed molecular sheets. Carbonyl dyes has been well  known to provide a wide range of colors almost covering the entire visible spectrum, in particular, 9,10-anthraquinone derivatives can give rise to a complete range of shades.

2,6-Dihydroxyanthraquinone is a potent inhibitor of the O-deethylations of ethoxycoumarin and ethoxyresorufin, both catalysed primarily by cytochromes P-448. Anthraflavic acid is a potent inhibitor of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) mutagenicity by virtue of its ability to inhibit both its microsomal and cytosolic activation pathways.

It has also been demonstrated that protons can be reversibly intercalated and deintercalated in crystalline 2,6-dihydroxyanthraquinone (DHAQ) at a potential of −0.21 V in acidic solution with a specific capacity of 110 mAh g-1. The quinone proton battery delivers an equilibrium voltage of 1.1 V, and the capacity retention rate could be as high as 100% after 2600 cycles.

General Information

CAS Number 84-60-6
Chemical Formula C14H8O4
Full Name 2,6-Dihydroxyanthraquinone
Molecular Weight 240.21 g/mol
Synonyms 2,6-DHAQ, 2,6-Dihydroxyanthracene-9,10-dione, Anthraflavic acid, Anthraflavin
Classification / Family Anthraquinone derivatives, Dyes, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

2,6-dihydroxyanthraquinone chemical strucutre, 84-60-6
2,6-Dihydroxyanthraquinone (2,6-DHAQ) chemical structure, CAS 84-60-6

Product Details

Purity >98% (1H NMR)
Melting Point Tm >320 °C (lit.)
Appearance Yellow/golden powder/crystals

MSDS Documentation

2,6-dihydroxyanthraquinone2,6-Dihydroxyanthraquinone MSDS Sheet

Literature and Reviews

  1. Anthraflavic acid inhibits the mutagenicity of the food mutagen IQ: Mechanism of action, A. Ayrton et al., Mutat. Res. Lett., 207 (3-4); 121-125 (1988); DOI: 10.1016/0165-7992(88)90075-9.
  2. Induction of rat hepatic cytochrome P-450 I proteins by the antimutagen anthraflavic acid, A. Ayrton et al., Food Chem. Toxicol., 26 (11-12), 909-915 (1988); DOI: 10.1016/0278-6915(88)90088-9.
  3. The Redox-Mediated Nickel–Metal Hydride Flow Battery, T. Páez et al., Adv. Energy Mater., 12 (1), 2102866 (2022); DOI: 10.1002/aenm.202102866.
  4. A crystalline dihydroxyanthraquinone anodic material for proton batteries, J. Yu et al., Mater. Today Energy, 22, 100872 (2021); 10.1016/j.mtener.2021.100872.
  5. Integrating Reverse-Electrodialysis Stacks with Flow Batteries for Improved Energy Recovery from Salinity Gradients and Energy Storage, X Zhu et al, ChemSusChem, 10, 1 – 8 (2017); DOI: 10.1002/cssc.201601220.
  6. Enhancing the Cycling Stability of Anthraquinone-Based Redox Flow Batteries by Using Thermally Oxidized Carbon Felt, L. Xia et al., ACS Appl. Energy Mater., 5 (2), 1984–1991 (2022); DOI: 10.1021/acsaem.1c03507.
  7. Fabricating a high-energy-density supercapacitor with asymmetric aqueous redox additive electrolytes and free-standing activated-carbon-felt electrodes, M. Tian et al., Chem. Eng. J., 363, 183-191 (2019); DOI: 10.1016/j.cej.2019.01.070.
  8. A highly reversible anthraquinone-based anolyte for alkaline aqueous redox flow batteries, J. Cao et al., J. Power Sources, 386, 40-46 (2018); DOI: 10.1016/j.jpowsour.2018.03.041.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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