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Chemical Structure| 149-91-7 Chemical Structure| 149-91-7
Chemical Structure| 149-91-7

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Gallic acid is an organic acid that found in a variety of foods and herbs with effective antioxidant activity.

Synonyms: 3,4,5-Trihydroxybenzoic acid; NSC 20103; HSDB 2117

4.5 *For Research Use Only !

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Product Details of Gallic Acid

CAS No. :149-91-7
Formula : C7H6O5
M.W : 170.12
SMILES Code : OC1=CC(C(O)=O)=CC(O)=C1O
Synonyms :
3,4,5-Trihydroxybenzoic acid; NSC 20103; HSDB 2117
MDL No. :MFCD00002510

Safety of Gallic Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Gallic Acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 149-91-7 ]

[ 149-91-7 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 149-91-7 ]
  • [ 99-14-9 ]
  • 3
  • [ 92631-82-8 ]
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  • [ 4773-96-0 ]
  • 4
  • [ 79786-01-9 ]
  • [ 863-03-6 ]
  • [ 149-91-7 ]
  • malabathrin A [ No CAS ]
  • 5
  • [ 2922-42-1 ]
  • [ 99-50-3 ]
  • [ 99-14-9 ]
  • [ 149-91-7 ]
  • [ 184105-29-1 ]
  • [ 87-66-1 ]
  • 7
  • [ 3337-62-0 ]
  • [ 7732-18-5 ]
  • barium hydroxide [ No CAS ]
  • [ 149-91-7 ]
  • 8
  • [ 3337-62-0 ]
  • [ 7758-99-8 ]
  • KOH-solution [ No CAS ]
  • [ 149-91-7 ]
  • 9
  • [ 3337-62-0 ]
  • KOH [ No CAS ]
  • [ 149-91-7 ]
  • 12
  • [ 149-91-7 ]
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
  • [ 34218-97-8 ]
  • [ 5146-12-3 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (0.5 g) and gallic acid (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1 :10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 20 mg epitheaflavic acid 3-gallate, 40 theaflavate A and 10 mg purpurogallin carboxylic acid were obtained. [0112] 1H NMR (CD3OD, 600 MHz): deltaH 8.64 1H s, 7.84 1H s, 7.83 1H s, 6.83 2H s, 6.02 1H d, J=2.4 Hz, 5.98 1H d, J=2.4, 5.61 1H s, 4.37 1H, m, 3.03 1H dd, J=4.8, 16.8 Hz, 2.87 d, J=16.8 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.5, 170.1, 167.1, 158.0, 156.9, 155.1, 151.7, 148.9, 146.2, 139.8, 132.8, 131.6, 126.8, 122.6, 122.5, 120.8, 116.3, 110.0, 99.3, 96.9, 96.0, 75.7, 68.6, 27.2 ppm.
  • 13
  • [ 32566-01-1 ]
  • [ 149-91-7 ]
  • [ 677297-27-7 ]
YieldReaction ConditionsOperation in experiment
68% With 1,2-dichloro-ethane; In dichloromethane; 3,4,5-trihydroxy-N-[2-(1H-indol-2-yl)-phenyl]-benzamide A 25-mL one-necked recovery flask equipped with a stirring bar and a septum was charged with gallic acid (176 mg; 1.03 mmol; 1.00 equiv). A clear, colorless solution was formed on addition of 5 mL of dichloromethane. Solid EDC (197 mg; 1.03 mmol; 1.00 equiv) and <strong>[32566-01-1]2-(2-aminophenyl)indole</strong> (194 mg; 0.932 mmol; 0.904 equiv) were added sequentially as solids. The reaction was worked up after 24 h by extraction with 10 mL of NaHCO3 (satd aq). The organic layer was dried (anhydrous sodium sulfate), filtered and concentrated by rotary evaporation to yield a yellow oily paste. The crude was purified using DCM-MeOH (19:1) to yield a light yellow solid (230 mg; 68%).
  • 14
  • [ 149-91-7 ]
  • [ 7768-28-7 ]
  • C15H14O6 [ No CAS ]
  • 16
  • [ 6638-05-7 ]
  • [ 149-91-7 ]
  • 17
  • [ 149-91-7 ]
  • [ 863-03-6 ]
  • [ 34218-97-8 ]
YieldReaction ConditionsOperation in experiment
polyphenol oxidase; at 20℃; for 5.0h;pH 5.0;Phosphate-citrate buffer; Enzymatic reaction; EC (1.160 g, 4.0 mmole) and gallic acid (0.520 g, 4.0 mmole) were dissolved in the 100 mL of phosphate-citrate buffer (50 mM, pH 5.0), and 1.2 g of crude PPO enzyme was added into the reaction solution with stirring. The enzymatic oxidation was carried out at room temperature for 3.5 hour. After the reaction, the solution extracted with the same volume of ethyl acetate with three times. Then, the ethyl acetate extracts was concentrated in vacuo. The resulting residues were then subjected to Sephadex LH-20, eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 168 (each c.a. 15 mL) fractions, 4752 fractions were combined, and it was concentrated under reduced pressure. The resulting residue was applied on a RP-18 silica gel column eluting with gradient of 20%50% of aqueous methanol, and it was afforded compound 5. Then, 7285 fractions, isolated from Sephadex LH-20, were combined, and it was subjected to RP-18 column chromatography eluting with gradient of 10%50% of aqueous methanol, and compound 6 was isolated. [0137] ECG (0.66 g) and gallic acid (0.26 g) were dissolved in the 50 mL of phosphate-citrate buffer (50 mM, pH 5.0), and 1.2 g of crude PPO enzyme was dissolved in the reaction solution. The enzymatic oxidation was performed at room temperature for 5 hour. The reaction solution was then extracted with ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 128 fractions (each c.a. 15 mL), 1820 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected for further purification on a RP-18 silica gel column eluting with gradient of 20%50% of aqueous methanol, and afforded compound 7. The 3748 fractions were combined and subjected to RP-18 column chromatography for further purification eluting with gradient of 10%30% of aqueous methanol, and afforded compound 8. The 90108 fractions were combined and subjected to RP-18 column chromatography eluting with gradient of 40%50% of aqueous methanol, and it was then afforded compound 9.
  • 20
  • [ 149-91-7 ]
  • [ 363-52-0 ]
  • [ 1416324-76-9 ]
YieldReaction ConditionsOperation in experiment
9% With dihydrogen peroxide; horseradish peroxidase; In acetone;pH 5.0; General procedure: A: Catechol (110 mg, 1.00 mmol ) and pyrogallol (126 mg, 1.00 mmol) were dissolved in a mixture of acetone-pH 5.0 phosphate-citrate (1 : 1=0.2 M Na2HP04: 0.1 M citrate) buffer (1 :5 v/v, 5 lnL), which contained 0.1 mg horseradish peroxidase (cas 9003-99-0, 5KU, Fisher). Four aliquots of 3percent H2O2 (2 mL each) were added eveiy 10 min over 40 min while stirring. After 2-3 h, the resulting orange precipitate was filtered off, washed with water (3 x 6 mL) and dried under high vacuum condition to give a mixture of 2 and NCI35676 (purpurogallin). The mixture was purified by flash chromatography on silica gel, using ethyl acetate/hexane ( 1 :4) as eluent, to give 2 as an orange solid (23 mg, 1 1 percent). 3,4,6-trihydroxy-5H-benzo[7]annulen-5-one (2). Following the general method IA, gave 2 as an orange solid (23 mg, 11 percent). Following the general method IA, using <strong>[363-52-0]3-fluorocatechol</strong> (128 mg, 1.00 mmol) instead of catechol, gave an orange solid. The mixture was purified by flash chromatography on silica gel, using ethyl acetate/hexane (1 :4) as eluent, to give 3 as an orange solid (20 mg, 9 percent): NMR (300 MHz, DMSO) delta 15.45 (s, 1H), 9.81 (s, 2H), 7.53-7.37 (m, 2H), 7.19 (dd, J= 9.6, 0.7 Hz, 1H), 6.86 (dd, J= 11.4, 9.6 Hz, 1H); 13C NMR (75 MHz, DMSO) delta 184.20, 155.77, 154.17, 152.58, 134.70, 132.41, 124.98, 118.61, 118.17, 110.76, 110.50; HRMS (ESI): calcd for: C?H7F04 [M-H]' = 221.0255, obsd [M-H]"= 221.0255.
  • 21
  • [ 94-26-8 ]
  • [ 99-50-3 ]
  • [ 2474-72-8 ]
  • [ 89-86-1 ]
  • [ 149-91-7 ]
  • C7H6O5 [ No CAS ]
  • [ 123-31-9 ]
  • [ 106-51-4 ]
  • [ 108-95-2 ]
  • [ 99-96-7 ]
  • 22
  • bismuth(III) nitrate [ No CAS ]
  • [ 149-91-7 ]
  • [ 7732-18-5 ]
  • [ 99-26-3 ]
YieldReaction ConditionsOperation in experiment
at 60 - 80℃; for 0.333333h; 57.8 g of bismuth oxide was dissolved in 80 ml of concentrated nitric acid having a mass fraction of 68%After bismuth trioxide was dissolved, the mixture was cooled to room temperature and 50 ml of deionized water was added,To obtain bismuth nitrate solution; At 80 ,50 g of gallic acid was dissolved in 200 ml of deionized water,To obtain a gallic acid aqueous solution;To be dissolved in gallic acid,The gallic acid aqueous solution was cooled to 60 C,After which the gallic acid aqueous solution was slowly added to the bismuth nitrate solution,Insulation reaction 20min,That is yellow precipitate;And then filtered yellow to obtain a filter cake,The filter cake was washed with 50 C deionized water until the pH of the deionized water was close to 7,Followed by vacuum drying at 80 C for 3 hoursBasic bivalence of gallic acidOf the powder 100 g, the yield was 98%.
  • 23
  • [ 149-91-7 ]
  • [ 363-52-0 ]
  • (2-fluoro-3,4-dihydroxyphenyl)(3,4,5-trihydroxyphenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride; trichlorophosphate; at 80℃; for 2h; 3,4,5-trihydroxybenzoic acid, 3-fluorobenzene-l,2-diol, anhydrous zinc chloride and phosphorous oxychloride were combined in a round bottom flask, stirred and heated to 80°C for 2 hours. After cooling, the product was precipitated from the reaction mixture by addition of a mixture of water and ice. The product was washed with water, treated with a solution of sodium bicarbonate, washed again with water and finally recrystallized from aqueous solution to yield the desired product.
  • 24
  • [ 149-91-7 ]
  • [ 19387-91-8 ]
  • C8H13N3O4S*C7H6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; for 1.66667h; General procedure: The TN salts/molecular salts was preparedby grinding an equimolar mixture containing 200mg (1 mmol) of TN and 1mmol of correspondingcarboxylic acids/PTSA wetted with few drops of waterwas manually grounded in an agate mortar for 100minutes until a dried powder was obtained.
 

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