1,5-dihydroxy-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 119209
• Molecular Formular: C14H8O4
• Molecular Mass: 240.21092
• Monoisotopic Mass: 240.04225874
• SMILES: C1(=O)c2c(C(=O)c3c1cccc3O)cccc2O
• Canonical SMILES: Oc1cccc2c1C(=O)c1cccc(c1C2=O)O
• InChI: InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H
• InChIKey: JPICKYUTICNNNJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dihydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: anthrarufin
• Synonyms: 1,5-dihydroxyanthracene-9,10-dione; Anthrarufin; 1,5-Dihydroxyanthraquinone; 9,10-Dihydro-9,10-dioxo-2,3-anthracenedicarboxylic Acid; Anthraquinone-2,3-dicarboxylic Acid; 2,3-Anthraquinonedicarboxylic Acid; 1,5-Dihydroxyanthraquinone; Anthrarufin; 蒽绛酚; 1,5-二羟基蒽醌; 1,5-二羟基蒽醌; 蒽绛酚

Database IDs

• CAS Number: 117-12-4; 27485-15-0
• EC Number: 204-175-6
• MDL Number: MFCD00001210
• Beilstein Number: 1881718
• Merck Index: 14689
• PubChem SID: 24860758; 162107419
• PubChem CID: 8328

CALCULATED PROPERTIES

• Acid pKa: 7.914277
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6099172
• LogD (pH = 7.4): 3.4892383
• Log P: 3.6115754
• Molar Refractivity: 65.1128 cm^3
• Polarizability: 24.5238 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 268-273 °C; 279 °C (dec.)(lit.); ca 280°C dec.
• Vapor Density: 8.3 (vs air)

Safety Information

• RTECS: CB6630000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥85% (HPLC); 85%; 95+%; tech. 90%
• Grade: technical; technical grade
• Description: Tautomers
• Sublimation Residue: ~5%
• Empirical Formula (Hill Notation): C14H8O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

InterBioScreen - BB_NC-0492

Tautomers

Sigma Aldrich - 340014

Packaging
100 g in glass bottle

Toronto Research Chemicals - A679250

2,3-Anthraquinonedicarboxylic Acid is an ozonolysis degradation product of polycyclic aromatic hydrocarbons (PCA). 2,3-Anthraquinonedicarboxylic Acid is used in the preparation of anthraquinonedicarboximide dyes.

REFERENCES

• Moriconi, E.J. et al.: Arch. Biochem. Biophys., 83, 283 (1959)
• Meineke, I. et al.: FRes. Zeitsch. Anal. Chem., 293, 201 (1959)