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13739-02-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:122735 http://www.chembase.cn/molecule-122735.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
13739-02-1
EC Number
237-310-2
MDL Number
MFCD00468030
PubChem SID
162217088
24894281
PubChem CID
26248

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.373035  H Acceptors
H Donor LogD (pH = 5.5) -0.32252544 
LogD (pH = 7.4) -1.6187639  Log P 1.790811 
Molar Refractivity 90.672 cm3 Polarizability 34.626415 Å3
Polar Surface Area 124.04 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
234-236°C expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
CB8781000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Target
Others expand Show data source
Mechanism of Action
Interleukin-1 inhibitor expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Nonsteroidal antiinflammatory agent expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - D9302 external link
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 external link
A diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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