| Identification | Back Directory | [Name]
6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE | [CAS]
2092-49-1 | [Synonyms]
DIVANILLIN
Dehydrovanillin
5,5'-Bivanillin
dehydrodivanillin
6 6'-DIHYDROXY-5 5'-DIMETHOXY-(1 1'-BIP&
6,6'-dihydroxy-5,5'-dimethoxy-(1,1'-biphen -yl)-3
5,5'-Dimethoxy-6,6'-dihydroxybiphenyl-3,3'-dicarbaldehyde
6,6'-dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarbaldehyde
3,3'-Biphenyldicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
2,2'-Dihydroxy-3,3'-dimethoxy-1,1'-biphenyl-5,5'-dicarbaldehyde
6,6'-Dihydroxy-5,5'-dimethoxy-1,1'-biphenyl-3,3'-dicarbaldehyde
3,3'-Biphenyldicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy- (8
3,3-Biphenyldicarboxaldehyde, 6,6-dihydroxy-5,5-diMethoxy- (8CI)
6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBOXALDEHYDE
[1,1'-Biphenyl]-3,3'-dicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde
3-(5-formyl-2-hydroxy-3-methoxy-phenyl)-4-hydroxy-5-methoxy-benzaldehyde
4-hydroxy-3-(2-hydroxy-5-methanoyl-3-methoxy-phenyl)-5-methoxy-benzaldehyde
(1,1'-Biphenyl)-3,3'-dicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy- (9CI) | [Molecular Formula]
C16H14O6 | [MDL Number]
MFCD00156888 | [MOL File]
2092-49-1.mol | [Molecular Weight]
302.28 |
| Chemical Properties | Back Directory | [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. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
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