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| | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE Basic information |
| Product Name: | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE | | Synonyms: | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE;6,6'-dihydroxy-5,5'-dimethoxy-(1,1'-biphen -yl)-3;6 6'-DIHYDROXY-5 5'-DIMETHOXY-(1 1'-BIP&;dehydrodivanillin;DIVANILLIN;6,6'-dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarbaldehyde;2,2'-Dihydroxy-3,3'-dimethoxy-1,1'-biphenyl-5,5'-dicarbaldehyde;5,5'-Bivanillin | | CAS: | 2092-49-1 | | MF: | C16H14O6 | | MW: | 302.28 | | EINECS: | | | Product Categories: | | | Mol File: | 2092-49-1.mol | ![6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE Structure](CAS/GIF/2092-49-1.gif) |
| | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE Chemical Properties |
| Melting point | 315 °C(lit.) | | Boiling point | 486.3±45.0 °C(Predicted) | | density | 1.356±0.06 g/cm3(Predicted) | | FEMA | 4107 | DIVANILLIN | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly), Ethanol (Slightly, Heated), Methanol (Slightly) | | form | Solid | | pka | 6.62±0.48(Predicted) | | color | Dark Brown to Very Dark Gray | | Odor | at 100.00 %. fruity vanilla | | Odor Type | vanilla | | JECFA Number | 1881 | | LogP | 1.57 |
| | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE Usage And Synthesis |
| 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 |
| | 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE Preparation Products And Raw materials |
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