ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic aldehydes 2,4,6-TRIHYDROXYBENZALDEHYDE

2,4,6-TRIHYDROXYBENZALDEHYDE

Product Name2,4,6-TRIHYDROXYBENZALDEHYDE
CAS487-70-7
MFC7H6O4
MW154.12
EINECS207-663-7
MOL File487-70-7.mol

Chemical Properties

Melting point	195 °C (dec.)(lit.)
Boiling point	237.46°C (rough estimate)
Density	1.3725 (rough estimate)
refractive index	1.6400 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMSO (Slightly), Methanol (Slightlly, Heated)
form	Solid
pka	7.37±0.23(Predicted)
color	Orange to Dark Orange
Water Solubility	Soluble in water.
Sensitive	Air Sensitive
BRN	2254429
InChI	1S/C7H6O4/c8-3-5-6(10)1-4(9)2-7(5)11/h1-3,9-11H
InChIKey	BTQAJGSMXCDDAJ-UHFFFAOYSA-N
SMILES	[H]C(=O)c1c(O)cc(O)cc1O
LogP	1.370 (est)
CAS DataBase Reference	487-70-7(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	2
RTECS	CU8440000
HS Code	29124990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

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

2,4,6-Trihydroxybenzaldehyde (oral administration; 5 and 25 mg/kg for 13 weeks) reduces the HFD-induced increase in weight gain, reduces serum levels of glucose, triglycerides, and total cholesterol^[1].

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

2,4,6-TRIHYDROXYBENZALDEHYDE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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