2,6-Dihydroxyanthraquinone (HCID 6776)

Overview

Anthraflavic acid is a dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10. It has a role as an antimutagen and a plant metabolite. It derives from a hydride of an anthracene.

Names & identifiers

Preferred name: 2,6-Dihydroxyanthraquinone
IUPAC: 2,6-dihydroxyanthracene-9,10-dione
English name: 2,6-DIHYDROXYANTHRAQUINONE
Molecular formula: C14H8O4
Molecular weight: 240.21

Names & synonyms

2,6-DihydroxyanthraquinoneAnthraflavic acid84-60-62,6-dihydroxyanthracene-9,10-dioneAnthraflavin9,10-Anthracenedione, 2,6-dihydroxy-NSC-335312,6-dihydroxy-9,10-anthraquinoneAnthraquinone, 2,6-dihydroxy-2,6-dihydroxy-9,10-anthracenedioneCHEBI:34250W83883330W

Show more names

2,6-dihydroxy-anthraquinon2,6-DHAQanthraflavicaciAnthraflaric acidAnthraflavic Acid >

RefChem:445580201-544-32,6-Dihydroxyanthra-9,10-quinoneAz-FAnthrafravic acid2,6-DIHYDROXY-ANTHRAQUINONEMFCD000012282,6-dihydroxy-9,10-dihydroanthracene-9,10-dione

Database identifiers

CAS: 84-60-6
PubChem CID: 6776
DTXSID: DTXSID6036546
ChEMBL: CHEMBL298398
ChEBI: CHEBI:34250
UNII: W83883330W
EC Number: 201-544-3
Nikkaji: J55.275E

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 74.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 18
Formal charge: 0
Complexity: 342

Experimental & physicochemical properties

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 320 °C · >320 °C(lit.)
Boiling point: 342.92 °C · 342.92°C (rough estimate)
Density: 1.3032 · 1.3032 (rough estimate)
refractive index: 1.543 · 1.5430 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: Soluble in DMSO
form: powder to crystal
pka: 6.72 · 6.72±0.20(Predicted)
color: Light yellow to Brown to Dark green
Stability: Stable. Incompatible with strong oxidizing agents.
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
InChIKey: APAJFZPFBHMFQR-UHFFFAOYSA-N
SMILES: Oc1ccc2C(=O)c3cc(O)ccc3C(=O)c2c1
LogP: 3.36 · 3.360 (est)
CAS DataBase Reference: 84 · 84-60-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 83883330 W · W83883330W
EPA Substance Registry System: 9 · 9,10-Anthracenedione, 2,6-dihydroxy- (84-60-6)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-37/39-36/37
WGK Germany: 3 · 3
RTECS: 6675000 · CB6675000
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29146990 · 29146990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationChemical: 9,10-Anthracenedione, 2,6-dihydroxy-

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: CB6675000
hs_code: 29146990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-37/39-36/37
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information9,10-Anthracenedione, 2,6-dihydroxy-: ACTIVE

Applications · 1 item

UsesAnthraflavic 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.