Anthragallol
Basic information
- CAS
602-64-2- Standard SMILES
O=C1c2ccccc2C(=O)c2c1cc(O)c(O)c2O- InChIKey
AHKDJQYHVWSRLT-UHFFFAOYSA-N- Molecular formula
- C14H8O5
- Average molar mass
- 256.21 g/mol
- Monoisotopic mass
- 256.03717335
Overview
Anthragallol is a trihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1, 2 and 3. It has a role as a plant metabolite.
Names & identifiers
- Preferred name
- Anthragallol
- IUPAC
- 1,2,3-trihydroxyanthracene-9,10-dione
- English name
- Anthracene brown
- Molecular formula
- C14H8O5
- Molecular weight
- 256.21
Names & synonyms
Anthragallol602-64-2Anthracene brown1,2,3-TrihydroxyanthraquinoneAnthragallic acid1,2,3-trihydroxyanthracene-9,10-dioneAntragallolAlizarine Brown RAnthracene Brown GAnthracene Brown NAnthracene Brown SAlizarine Brown HD
Show more names
c.i.58200alizarinebrownralizarinebrownhdanthracenebrownganthracenebrownnanthragallicacidantracromobrowndMordant Brown 42
Antracromo Brown DAnthracene Brown FDAnthracene Brown FFAnthracene Brown WHAnthracene Brown WL1,2,3-Trihydroxy-9,10-anthracenedioneC.I. Mordant Brown 42Chrome Fast Brown FC
Database identifiers
- CAS
602-64-2- PubChem CID
- 11768
- DTXSID
DTXSID80208946- ChEMBL
CHEMBL192032- ChEBI
CHEBI:2755- UNII
- 845J3299E1
- EC Number
- 210-022-4
- Nikkaji
- J1.653E
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 407
Experimental & physicochemical properties
Chemical ClassesDyes -> Anthraquinone Dyes
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionBrown solid; [Merck Index] Crystalline solid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 312 · 312-313°
- Boiling point
- 359.45 °C · 359.45°C (rough estimate)
- Density
- 1.3683 · 1.3683 (rough estimate)
- refractive index
- 1.4825 · 1.4825 (estimate)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 6.7 · 6.70±0.20(Predicted)
- color
- Orange Red to Very Dark Orange
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See Anthrarufin, Sodium alizarinesulfonate, 1,2,4-Trihydroxy-9,10-anthracenedione, 1-Hydroxyanthraquinone, 1,4-Dihydroxy-9,10-anthracenedione, and Alizarin.
Safety data
- rtecs
- CB8198000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319
- Precautionary statements
- P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501
Chemistry & industry
Applications
UsesAnthragallol is the most active inhibitor against xanthine oxidase.
Preparation methods
PreparationCommonly known as Anthragallol. (A)3,4,5-Trihydroxybenzoic acid and Benzoic acid and sulfuric acid heated; (b) in the presence of zinc chloride, heating gallic acid and Phthalic anhydride; (c) 2-Hydroxy-1,3-dinitroanthraquinonereduction in strong alkaline solution; (d)1,3-Diamino-2-hydroxyanthracene-9,10-dione and hydrochloric acid heated under pressure. Note: The product is a free acid state paste; powdery product is sodium
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A trihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1, 2 and 3.
Related reactions
2 records
Compound notes
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