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260843

Sigma-Aldrich

2,3,4-Trihydroxybenzaldehyde

98%

Synonym(s):

Pyrogallol-4-carboxaldehyde

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About This Item

Linear Formula:
(HO)3C6H2CHO
CAS Number:
2144-08-3
Molecular Weight:
154.12
Beilstein:
2328658
EC Number:
218-404-2
MDL number:
MFCD00003325
UNSPSC Code:
12352100
PubChem Substance ID:
24855773
NACRES:
NA.22

Quality Level

200

Assay

98%

form

powder

mp

159-161 °C (lit.)

SMILES string

[H]C(=O)c1ccc(O)c(O)c1O

InChI

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

InChI key

CRPNQSVBEWWHIJ-UHFFFAOYSA-N

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General description

Antimicrobial activity of carbohydrazone derived from 2,3,4-trihydroxybenzaldehyde against bacteria and fungi has been investigated. 2,3,4-trihydroxybenzaldehyde forms Schiff bases via [1+1] condensation with anthranilic acid.

Application

2,3,4-Trihydroxybenzaldehyde has been used in the preparation of 1,5-dimethyl-2-phenyl-4-[(1E)-(2,3,4-trihydroxybenzylidene)amino]-1H-pyrazol-3(2H)-one.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1, 5-Dimethyl-2-phenyl-4-[(1E)-(2, 3, 4-trihydroxybenzylidene) amino]-1H-pyrazol-3 (2H)-one.
Sun Y-F, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(5), o2522-o2523 (2007)
Sari Honda et al.
Free radical biology & medicine, 106, 228-235 (2017-02-23)
In this study, the mechanism of the xanthine oxidase (XO) inhibitory activity of pyrogallol, the main inhibitor found in roasted coffee, was investigated. Pyrogallol was unstable and readily converted to purpurogallin in a pH 7.4 solution, a physiological model of
Eila Pelttari et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 62(7-8), 483-486 (2007-10-05)
Certain substituted salicylaldehydes are known to have highly potent antimicrobial activity against bacteria and fungi, but the mechanism underlying this remarkable activity is not known, and almost nothing has been reported on the effects of further modification of the structures
Yuan Chen et al.
International journal of biological macromolecules, 143, 714-723 (2019-11-15)
In this study, the structure of inulin was chemically modified by Schiff bases in order to improve its biological activity. A total of 6 kinds of inulin derivatives were synthesized according to aza-Wittig reaction. Their structures were confirmed by FTIR
Ning Han et al.
Biomaterials science, 8(11), 3164-3172 (2020-05-05)
In this work, a tunicate-inspired gelatin-based hydrogel is prepared by simply mixing 2,3,4-trihydroxybenzaldehyde (THB)-tethered gelatin solution with a small amount of Fe3+ ions via the Schiff-base reaction and simultaneous formation of hexavalent Fe-complexes. The resulting hydrogel (termed GelTHB-Fe) exhibits not
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