Ethyl gallate
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Ethyl gallate
structure -
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CAS No:
831-61-8
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Formula:
C9H10O5
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Chemical Name:
Ethyl gallate
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Synonyms:
Benzoic acid,3,4,5-trihydroxy-,ethyl ester;Gallic acid,ethyl ester;Phyllemblin;Ethyl gallate;Nipagallin A;Nipa No. 48;Progallin A;3,4,5-Trihydroxybenzoic acid ethyl ester;Ethyl 3,4,5-trihydroxybenzoate;NSC 402626;52441-13-1
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CAS No:
Description
Ethyl gallate is a nonflavonoid phenolic compound and also a scavenger of hydrogen peroxide.
Solid
Ethyl gallate is a gallate ester obtained by the formal condensation of gallic acid with ethanol. It has a role as a plant metabolite.
Ethyl gallate Basic Attributes
198.17
198.17
2116014
212-608-5
235I6UDD3L
402626
DTXSID2061195
2918290000
Characteristics
87
1.3
White to slightly beige Fine Powder
1.4±0.1 g/cm3
154-155 °C
255.48°C (rough estimate)
185.0±20.8 °C
1.611
H2O: soluble
Store below +30°C.
Ethyl gallate Use and Manufacturing
100 g of gallic acid and 150 g of ethanol were weighed into a reactor, 35 g of the brominated modified sulfonic acid resin obtained in Referential was weighed, heated to 80 ° C for 5 h, filtered to obtain a filtrate, and bromine Modified sulfonic acid resin;the filtrate obtained in step (1) is distilled off excess alcohol to obtain crude product, and then recrystallization, dewatering and drying are carried out by deionized water to obtain ethyl gallate in 98percent yield and purity of 99.9percent .To a 50 mL round bottom flask, the gallic acid (2.0 g, 11.8 mmol), ethanol (30 mL, 1.94 mol) and 10percent of concentrated sulfuric acid (0.2 mL) were vigorously stirred at 70°C in reflux apparatus. The reaction was monitored by TLC until end of reaction (24 h). The product was extracted using 20 mL of saturated solution of sodium bicarbonate (NaHCOGeneral procedure: A microwave vial was loaded with gallic acid 1 (0.3mmol, 50mg), the corresponding alcohol (0.9mmol), and concentrated HGeneral procedure: To the solution containing gallic acid (250 mg, 1.47 mmol) in THF solvent at 0° C is added alcohol (2.94 mmol) and the DIC (0.34 mL, 2.205 mmol) as an activator. The reaction mixture was stirred for 1 h at 0° C, then added DMAP catalyst(18 mg, 0.147 mmol), and stirred again for the next 6 h at 0° C, then allowed to reach room temperature.The reaction was terminated when the TLC analysis showed no spot of the remaining gallic acid. After the reaction is complete, the reaction mixture is diluted with ether, filtered, evaporated, and purified by column silica gel chromatography. Pure compounds were analyzed by Thin Layer Chromatography (TLC), Nuclear Magnetic Resonance Spectrometer (NMR), and High Resolution Mass Spectrometer (HRMS)General procedure: In 50 ml_ of the alcohol of interest, 3, 4, 5-trihydroxybenzoic acid (1 ) (1 .5 g, 8.85 mmol) was dissolved, followed by addition of 10 drops of sulfuric acid. The solution was refluxed overnight. Afterwards, the solution was allowed to cool to room temperature. The residual alcohol was evaporated, yielding the gallic acid ester derivatives 22, 23, 24 as a solid compound.In a flask was charged 15.1 g of 3, 4, 5-trihydroxybenzoic acid (1), and 160 ml of ethanol and 5 ml of sulfuric acid were added thereto in the order cited and heating with stirring was performed for 40 hours under reflux. Thereafter, the solvent was distilled off, the residue was extracted with ether and the organic layer was dried over magnesium sulfate. After the magnesium sulfate was filtered off, and the organic solvent was evaporated to afford a white solid (2) (yield of the reaction: 17.6 g, percent yield:47.2percent).
Antioxidants for oils, food additives and intermediates for certain pharmaceuticals
Benzoic acid, 3,4,5-trihydroxy-, ethyl ester: ACTIVE
Computed Properties
Molecular Weight:198.17
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:198.05282342
Monoisotopic Mass:198.05282342
Topological Polar Surface Area:87
Heavy Atom Count:14
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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