2,3-DIHYDROXY-4-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

69.5 °C

Boiling point:

172-178 °C

Density 

1.378±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Solid

pka

7.63±0.15(Predicted)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43

Safety Statements 

26-36/37

2,3-DIHYDROXY-4-METHOXYBENZALDEHYDE Usage And Synthesis

Uses

DHMB (2,3-Dihydroxy-4-methoxybenzaldehyde) is a small organic molecule with anti-fungal and anti-inflammatory activity. DHMB has protective effect on intestinal epithelial cells[1].

Synthesis Reference(s)

Synthetic Communications, 16, p. 645, 1986 DOI: 10.1080/00397918608057734

Synthesis

General procedure for the synthesis of 2-hydroxy-3,4-dimethoxybenzaldehyde (29) and 2,3-dihydroxy-4-methoxybenzaldehyde (29') from 2,3,4-trimethoxybenzaldehyde: 2,3,4-trimethoxybenzaldehyde (5.00 g, 25.5 mmol) was dissolved in anhydrous dichloromethane (15 mL) at 0 °C and under nitrogen protection. Anhydrous boron trichloride (28.0 mL, 1.0 M solution in dichloromethane) was added slowly through a dropping funnel and the reaction mixture was stirred at this temperature for 5 hours. Upon completion of the reaction, the reaction was quenched with distilled water (10 mL), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (2 x 25 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure. 2-Hydroxy-3,4-dimethoxybenzaldehyde (29) (3.75 g, 20.6 mmol, 81% yield) was obtained as a white powder, as well as 2,3-dihydroxy-4-methoxybenzaldehyde (29') (0.20 g, 1.2 mmol, 5% yield) as an off-white powder.1H NMR (500 MHz, CDCl3) δ 11.2 (1H, s 2-OH), 9.75 (1H, s, 1-CHO), 7.29 (1H, d, J=9.0Hz, 6-H), 6.61 (1H, d, J=9.0Hz, 5-H), 3.95 (3H, s, 4-OCH3), 3.91 (3H, s, 3-OCH3).13C NMR (126MHz, CDCl3) δ 194.9 (1-CHO), 159.4 (C-4), 155.7 (C-2), 136.2 (C-3), 130.2 (6-CH), 116.6 (C-1), 104.0 (5-CH), 60.8 (3-OCH3), 56.3 (4-OCH3).

References

[1] Bortolus C, et al. A Small Aromatic Compound Has Antifungal Properties and Potential Anti-Inflammatory Effects against Intestinal Inflammation. Int J Mol Sci. 2019 Jan 14;20(2):321. DOI:10.3390/ijms20020321

2,3-DIHYDROXY-4-METHOXYBENZALDEHYDE(4055-69-0)Related Product Information

• 2',3',4'-TRIMETHOXYACETOPHENONE
• EUPATORIN-5-METHYL ETHER
• 2,3,4-Trimethoxybenzaldehyde
• 2,3,4-Trimethoxy-6-methylbenzaldehyde
• 3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE
• MARITIMEIN
• 2,3-DIHYDROXY-4-METHOXYBENZOIC ACID
• 2-HYDROXY-3,4-DIMETHOXYBENZOIC ACID
• 2,3,4-Trimethoxybenzoic acid
• 3,7,3',4'-TETRAMETHYLGOSSYPETIN
• 4,5-Dihydroxy-3-methoxybenzaldehyde,3,4-DIHYDROXY-5-METHOXYBENZALDEHYDE
• 2,3-DIHYDROXY-4-METHOXYACETOPHENONE
• MELICOPIDINE
• 2'-HYDROXY-3',4'-DIMETHOXYACETOPHENONE
• 2,4-DIMETHOXY-3-HYDROXYACETOPHENONE
• 2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE
• 2,3-DIHYDROXY-4-METHOXYBENZALDEHYDE
• 3'-ACETOXY-2',4'-DIMETHOXYACETOPHENONE