1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 167982
• Molecular Formular: C14H8O6
• Molecular Mass: 272.20972
• Monoisotopic Mass: 272.03208798
• SMILES: c1(cc(cc2c1C(=O)c1c(C2=O)cc(cc1O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O
• InChI: InChI=1S/C14H8O6/c15-5-1-7-11(9(17)3-5)14(20)12-8(13(7)19)2-6(16)4-10(12)18/h1-4,15-18H
• InChIKey: NTGIIKCGBNGQAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,6,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1,3,6,8-tetrahydroxyanthracene-9,10-dione
• Synonyms: 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione; 1,6,8-Trihydroxy-3-methylanthraquinone; 4,5,7-Trihydroxy-2-methylanthraquinone; Archin; Emodin; Emodol; Frangula Emodin; Frangulic Acid; NSC 408120; NSC 622947; Rheum Emodin; Schuttgelb; Emodin

Database IDs

• CAS Number: 518-82-1
• PubChem SID: 162262114
• PubChem CID: 3016789

CALCULATED PROPERTIES

• Acid pKa: 7.0920224
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.993488
• LogD (pH = 7.4): 2.4034452
• Log P: 3.0044448
• Molar Refractivity: 69.0746 cm^3
• Polarizability: 25.80946 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: Orange Powder
• Melting Point: 258-260°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E523000

Occurs mostly as the rhamnoside (see Frangulin) in rhubarb root. Cathartic.

REFERENCES

• Pan, X., et al.: Biochem. Eng. J., 5, 173 (2000)
• Srinivas, G., et al.: Eur. J. Pharmacol., 473, 117 (2000)
• Xiang, H., et al.: Chin. Pharm. J., 40, 96 (2000)
• Mokhtarani, B., et al.: Biochem. Eng. J., 38, 241 (2000)