4-(2,4-dimethoxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid

• ChemBase ID: 179750
• Molecular Formular: C20H22O7
• Molecular Mass: 374.38448
• Monoisotopic Mass: 374.13655304
• SMILES: c1(C(=O)Oc2c(c(c(c(c2)C)C(=O)O)O)C)c(c(c(cc1C)OC)C)OC
• Canonical SMILES: COc1cc(C)c(c(c1C)OC)C(=O)Oc1cc(C)c(c(c1C)O)C(=O)O
• InChI: InChI=1S/C20H22O7/c1-9-8-14(11(3)17(21)15(9)19(22)23)27-20(24)16-10(2)7-13(25-5)12(4)18(16)26-6/h7-8,21H,1-6H3,(H,22,23)
• InChIKey: MIJKZXWOOXIEEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,4-dimethoxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid
• IUPAC Traditional name: 4-(2,4-dimethoxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid
• Synonyms: Barbatic acid; Diffractic acid; Dirhizonic acid; Diffractaic acid

Database IDs

• CAS Number: 436-32-8
• PubChem SID: 164235660
• PubChem CID: 94870

CALCULATED PROPERTIES

• Acid pKa: 2.8433888
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.7740917
• LogD (pH = 7.4): 1.8865563
• Log P: 5.377042
• Molar Refractivity: 100.1892 cm^3
• Polarizability: 37.57781 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth

Product Information

• Biological Source: Isol. from Usnea diffracta, Usnea longisima and Alectoria ochroleuca
• Application(s): Analgesic

REFERENCES

• St. Pfau, A., Helv. Chim. Acta, 1928, 11, 864, (struct)
• Asahina, Y. et al., Ber., 1932, 65, 175; 583; 1668; 1933, 66, 641, (isol, struct, synth)
• Robertson, A. et al., J.C.S., 1932, 1675, (isol)
• Elix, J.A. et al., Aust. J. Chem., 1975, 28, 1113, (synth)
• Elix, A. et al., Aust. J. Chem., 1987, 40, 1581; 1989, 42, 1191; 1990, 43, 191, (derivs)