4,5-dihydroxy-9,10-dioxo-9,10-dihydro(5,6,7,8,8a,10a-13C6)anthracene-2-carboxylic acid

• ChemBase ID: 177499
• Molecular Formular: C15H8O6
• Molecular Mass: 290.17634903
• Monoisotopic Mass: 290.052217
• SMILES: [13cH]1[13cH][13cH][13c]2[13c]([13c]1O)C(=O)c1c(C2=O)cc(cc1O)C(=O)O
• Canonical SMILES: Oc1cc(cc2c1C(=O)[13c]1[13c](C2=O)[13cH][13cH][13cH][13c]1O)C(=O)O
• InChI: InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)/i1+1,2+1,3+1,7+1,9+1,11+1
• InChIKey: FCDLCPWAQCPTKC-UVUZSWIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-dihydroxy-9,10-dioxo-9,10-dihydro(5,6,7,8,8a,10a-^1^3C₆)anthracene-2-carboxylic acid
• IUPAC Traditional name: 4,5-dihydroxy-9,10-dioxo(5,6,7,8,8a,10a-^1^3C₆)anthracene-2-carboxylic acid
• Synonyms: 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic Acid-13C6; 4,5-Dihydroxy-2-anthraquinonecarboxylic Acid-13C6; Chrysazin-3-carboxylic Acid-13C6; Monorhein-13C6; NSC 38629-13C6; Rheic Acid-13C6; Rhubarb Yellow-13C6; Rhein-13C6

Database IDs

• CAS Number: 1330166-42-1
• PubChem SID: 164233409
• PubChem CID: 71752058

CALCULATED PROPERTIES

• Acid pKa: 3.3988245
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.1803527
• LogD (pH = 7.4): -0.14276648
• Log P: 3.2691584
• Molar Refractivity: 72.369 cm^3
• Polarizability: 26.928041 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; Ether; Pyridine
• Apperance: Yellow Crystalline Solid
• Melting Point: 321-322°C

DETAILS

Toronto Research Chemicals - R318502

Found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb) and in Senna leaves.A potential antioxidant resource: endophytic fungi from medicinal plants.

REFERENCES

• Wanitschke, Pharmacology, 20, Suppl. 1, 21 (1980)
• Raimondi, L., et al.: Pharmacol. Res. Commun., 14, 103 (1980)
• Franchi-Micheli, S., et al.: J. Pharm. Pharmacol., 35, 262 (1980)