3,4,5-Trihydroxybenzaldehyde Chemical Properties

Melting point:

211-213°C

Boiling point:

237.46°C (rough estimate)

Density 

1.3725 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in DMSO and Methanol.

pka

7.46±0.23(Predicted)

form 

Solid

color 

White to Pale Yellow

Sensitive 

Air Sensitive

BRN 

2091654

InChI

InChI=1S/C7H6O4/c8-3-4-1-5(9)7(11)6(10)2-4/h1-3,9-11H

InChIKey

RGZHEOWNTDJLAQ-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(O)=C(O)C(O)=C1

CAS DataBase Reference

13677-79-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-37

HS Code 

29130000

MSDS

• Language:English Provider:ALFA

3,4,5-Trihydroxybenzaldehyde Usage And Synthesis

Chemical Properties

Tan Solid

Uses

3,4,5-trihydroxybenzaldehyde from Geum japonicum has dual inhibitory effect on matrix metalloproteinase 9; inhibition of gelatinoytic activity as well as MMP-9 expression in TNF-α induced HASMC.

Uses

THBA

Synthesis

The general procedure for the synthesis of 3,4,5-trihydroxybenzaldehyde from butyraldehyde was as follows: 2.0 g of butyraldehyde was accurately weighed into a 250 ml two-necked flask, and about 100 ml of 1,2-dichloroethane was added as a solvent, and stirred thoroughly until dissolved. After cooling the reaction system to 0°C, 7.3 g of anhydrous aluminum trichloride was slowly added and the reaction was stirred for 30 minutes at this temperature. Subsequently, 8.7 g of pyridine was added dropwise through a constant pressure dropping funnel over a period of 20 min, and the reaction mixture was heated to 90 °C and refluxed for 4 h after completion of the dropwise addition. Upon completion of the reaction, the system was cooled to 0 °C and neutralized to pH neutral with a 3 mol/L hydrochloric acid solution. Extraction was carried out with about 250 mL of ethyl acetate and the extract was washed 5 times with ice water to remove impurities. The organic layers were combined, dried by adding anhydrous sodium sulfate, filtered and distilled under reduced pressure to remove the solvent to give a brown solid crude product. The crude product was purified by 200-300 mesh silica gel column chromatography to give 0.83 g of 3,4,5-trihydroxybenzaldehyde in 49% yield. For further purification, the resulting product was recrystallized from water to give an acicular light white solid.

References

[1] Biochemical Pharmacology, 2010, vol. 79, # 11, p. 1658 - 1666
[2] Biochemical Pharmacology, 2010, vol. 79, # 11, p. 1658 - 1666
[3] Patent: CN106188113, 2016, A. Location in patent: Paragraph 0015
[4] Natural Product Research, 2011, vol. 25, # 3, p. 203 - 221

3,4,5-Trihydroxybenzaldehyde(13677-79-7)Related Product Information

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