4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

• ChemBase ID: 122735
• Molecular Formular: C19H12O8
• Molecular Mass: 368.29378
• Monoisotopic Mass: 368.05321734
• SMILES: c12C(=O)c3c(C(=O)c1cc(C(=O)O)cc2OC(=O)C)cccc3OC(=O)C
• Canonical SMILES: CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
• InChI: InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)
• InChIKey: TYNLGDBUJLVSMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: diacerein; 4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• Synonyms: 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid; 1,8-Diacetoxy-3-carboxyanthraquinone; Diacerein; 4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid; 4,5-Diacetoxyanthraquinone-2-carboxylic Acid; 4,5-Diacetylrhein; Artrodar; DAR; Diacerhein; Diacetylrhein; Fisiodar; SF 277; Diacerein

Database IDs

• CAS Number: 13739-02-1
• EC Number: 237-310-2
• MDL Number: MFCD00468030
• PubChem SID: 162217088; 24894281
• PubChem CID: 26248

CALCULATED PROPERTIES

• Acid pKa: 3.373035
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.32252544
• LogD (pH = 7.4): -1.6187639
• Log P: 1.790811
• Molar Refractivity: 90.672 cm^3
• Polarizability: 34.626415 Å^3
• Polar Surface Area: 124.04 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 234-236°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: CB8781000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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

Pharmacology Properties

• Target: Others
• Mechanism of Action: Interleukin-1 inhibitor

Product Information

• Salt Data: Free Base
• Application(s): Nonsteroidal antiinflammatory agent

DETAILS

Sigma Aldrich - D9302

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Diacerin is an inhibitor of Interleukin-1B (IL-1B) production.

Toronto Research Chemicals - D303000

A diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic.

REFERENCES

• Kay, A.G., et al.: Curr. Med. Res. Opin., 6, 548 (1980)
• Raimondi, L., et al.: Pharmacol. Res. Commun., 14, 103 (1980)
• Adami, S., et al.: Clin. Ter., 112, 439 (1980)
• Hauptmann, H. et al., J.A.C.S., 1950, 72, 1492, (occur)
• Nawa, H. et al., J.O.C., 1961, 26, 979, (struct)
• Romanova, A.S. et al., Khim. Prir. Soedin., 1966, 2, 143; Chem. Nat. Compd. (Engl. Transl.), 1966, 2, 113, (isol, glucosides)
• Murty, V.K. et al., Tetrahedron, 1967, 23, 515, (synth, deriv)
• Romonova, A.S. et al., CA, 1969, 70, 9366, (isol)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1297, (occur)
• Ger. Pat., 1977, 2 711 493; CA, 88, 37504k, (synth)
• Hauser, F.M. et al., J.O.C., 1982, 47, 383, (synth)
• Gallagher, P.T. et al., Tet. Lett., 1994, 35, 289, (synth)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 34
• Dahms, M. et al., Drug Metab. Dispos., 1997, 25, 442, (metab, bibl)
• Spencer, C.M. et al., Drugs, 1997, 53, 98-106, (Diacerein, rev)