2,4,6-Trihydroxybenzaldehyde

Chemical Properties

pale pink crystalline powder

Uses

Reactant involved in the synthesis of biologically active molecules including:• ;2,4,6-trichlorophenyl hydrazones with potential inhibition of protein glycation1• ;Esculentoside A derivatives with haemolytic activity and LPS-induced nitric oxide production inhibition2• ;α-Nucleophiles for hydrolysis of organophosphorus nerve agents3• ;Xanthine oxidase inhibitors4• ;Non-complexes Schiff base hydrazones5• ;Methylated (±)-epigallocatechin gallate library for anticancer activity studies6

Uses

2,4,6-Trihydroxybenzaldehyde is a reactant involved in the synthesis of 2,4,6-trichlorophenyl hydrazones with potential inhibition of protein glycation and Xanthine oxidase inhibitors.

Definition

ChEBI: 2,4,6-trihydroxybenzaldehyde is a carboxylic ester. It is functionally related to a phloroglucinol.

Synthesis

108-73-6

68-12-2

487-70-7

To a solution of ethyl acetate (20 ml) containing resorcinol (1.9 g, 15 mmol), N,N-dimethylformamide (1.26 ml, 16.5 mmol) and trichlorophosphorus (1.5 ml, 16.5 mmol) were sequentially added at 0°C under ice bath conditions. After removing the ice bath, the reaction mixture was stirred at room temperature for 2 hours. Subsequently, water was added and the mixture was refluxed for 30 minutes. After the reaction solution was cooled to room temperature, it was extracted with ethyl acetate. The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel fast column chromatography (petroleum ether-ethyl acetate, 4:1) to give resorcinol formaldehyde (2.12 g, 92% yield) as a white solid. The product was characterized by 1H NMR (500 MHz, DMSO-d6) and 13C NMR (126 MHz, DMSO-d6) with the following data: 1H NMR δ 9.92 (s, 1H), 5.78 (s, 2H); 13C NMR δ 191.4, 167.6, 164.5, 105.0, 94.6.

in vivo

References

[1] Organic Letters, 2015, vol. 17, # 16, p. 4110 - 4113
[2] Tetrahedron Letters, 2016, vol. 57, # 17, p. 1856 - 1859
[3] Synthetic Communications, 1998, vol. 28, # 15, p. 2861 - 2869
[4] Organic Letters, 2010, vol. 12, # 8, p. 1676 - 1679
[5] Synlett, 2007, # 1, p. 129 - 130