6,6'-Dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-dicarboxaldehyde

Chemical Properties

White solid; fruity vanilla aroma.

Uses

Dehydrodivanillin is used as a reactant in the preparation of antioxidant phenolic diaryl hydrazones as antiangiogenic agents for atherosclerosis therapy. Also used as a taste enhancer.

Synthesis

General procedure for the synthesis of 6,6'-dihydroxy-5,5'-dimethoxy-(1,1'-biphenyl)-3,3'-dicarboxaldehyde from vanillin: 5 g of vanillin (33 mmol, purchased from Wako Pure Chemical Industries, Ltd.) was dissolved in 200 ml of ion-exchanger water preheated to 80 °C. To this solution, 200 mg (0.72 mmol) of iron sulfate (purchased from Wako Pure Chemical Industries, Ltd.) and 5 g (19 mmol) of potassium peroxydisulfate (purchased from Wako Pure Chemical Industries, Ltd.) were sequentially added, followed by heating and refluxing for 1 hr at 120 °C. Upon completion of the reaction, unreacted vanillin was removed by thermal filtration to afford intermediate (a1) in 97% yield.

References

[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2537 - 2546
[2] European Journal of Organic Chemistry, 2013, # 1, p. 173 - 179
[3] Patent: JP2017/14122, 2017, A. Location in patent: Paragraph 0051
[4] Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 125, p. 34 - 41
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 11, p. 3171 - 3181