3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With water at 80℃; for 6h; Reagent/catalyst; | 96.99% |
Conditions | Yield |
---|---|
With water at 60℃; for 6h; Reagent/catalyst; | A n/a B 91.5% |
Conditions | Yield |
---|---|
With pyridinium hydrobromide perbromide In xylene for 1.5h; Heating; | 75% |
With hydrogen iodide |
(-)-3-dehydroshikimic acid
A
3,4-Dihydroxybenzoic acid
B
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With copper diacetate In water; acetic acid at 40℃; for 36h; Oxidation; aromatization; | A 0.7% B 62% |
With copper diacetate; oxygen; zinc(II) oxide In acetic acid at 50℃; under 760.051 Torr; for 14h; Kinetics; Product distribution; Further Variations:; Reagents; Oxidation; aromatization; |
propan-1-ol
methyl galloate
A
Propyl gallate
B
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose at 25℃; pH=5; aq. acetate buffer; Enzymatic reaction; | A 55% B n/a |
gallaldehyde
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium bromate; hydrogenchloride; potassium bromide In water for 12h; Time; | 53% |
Conditions | Yield |
---|---|
With recombinant lipase B from Candida antarctica, expressed in Aspergillus niger, and immobilized on a macroporous hydrophobic resin In neat (no solvent) at 70℃; for 120h; Catalytic behavior; Time; Enzymatic reaction; | A n/a B 33.02% |
A
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With water at 60℃; for 4h; | A 24.7% B 3.3% C 5.6% D 5.6% |
Conditions | Yield |
---|---|
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Glovebox; | 15% |
Multi-step reaction with 2 steps 1: bromine 2: bei der Kalischmelze View Scheme |
(-)-3-dehydroshikimic acid
A
3,4-Dihydroxybenzoic acid
B
tricarallylic acid
C
3,4,5-trihydroxybenzoic acid
D
dihydrogallic acid
E
2-hydroxyresorcinol
Conditions | Yield |
---|---|
With air; Na1.5H1.5PO4 at 40℃; for 50h; Rate constant; Mechanism; other oxidant, var. time; | A 12 % Spectr. B 14 % Spectr. C 13% D n/a E 3 % Spectr. |
tetrachloromethane
3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
at 20℃; |
Conditions | Yield |
---|---|
With potassium hydroxide beim Schmelzen; |
Conditions | Yield |
---|---|
With potassium hydroxide beim Schmelzen; |
3,5-dihydroxy-4-bromobenzoic acid
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide beim Schmelzen; |
3-bromo-4,5-dihydroxybenzoic acid
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide beim Schmelzen; | |
bei der Kalischmelze; |
Conditions | Yield |
---|---|
With barium dihydroxide; water at 175℃; im Kupferkessel; | |
With potassium hydroxide; copper(I) sulfate; water; copper(II) sulfate at 150℃; |
Conditions | Yield |
---|---|
With potassium hydroxide at 130℃; for 1.5h; | |
durch Kalischmelze; |
4-galloyloxy-benzoic acid
A
3,4,5-trihydroxybenzoic acid
B
4-hydroxy-benzoic acid
chebulic acid
3,4,5-trihydroxybenzoic acid
diazomethane
A
alpha-D-glucopyranose
B
3,4,5-trihydroxybenzoic acid
C
tetramethylellagic acid
D
sanguisorbic acid dilactone heptamethyl ether
Conditions | Yield |
---|---|
With sulfuric acid 1.) reflux, 7.5 h, 2.) ether, overnight; Yield given. Multistep reaction. Yields of byproduct given; |
2,3-di-O-galloyl-D-4C1-glucopyranose
A
D-glucose
B
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 3h; | |
With hydrogenchloride at 100℃; for 3h; |
quercetin-3-O-(2”-galloyl)-β-D-galactopyranoside
A
Hyperoside
B
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With tannase In water at 37℃; for 2h; |
3,4,5-Trihydroxy-benzoic acid (2R,3S,4S,5R,6S)-6-(2,6-dihydroxy-4-hydroxymethyl-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester
A
3,4,5-trihydroxybenzoic acid
B
3,4,5-trihydroxybenzyl alcohol 4-O-β-D-glucopyranoside
Conditions | Yield |
---|---|
With tannase for 0.5h; Ambient temperature; incubation; | A 29 mg B 61 mg |
2',5-di-O-galloyl-D-hamamelofuranose
A
3,4,5-trihydroxybenzoic acid
B
2-hydroxymethyl-D-ribose
Conditions | Yield |
---|---|
With tannase In water at 37℃; for 1.5h; hydrolysis of other O-galloyl-D-hamameloses; | |
With tannase In water at 37℃; for 1.5h; | A n/a B 70 mg |
methyl 3,5-dihydroxy-4-methoxybenzoate
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogen iodide; acetic anhydride at 145℃; for 0.5h; |
(-)-shikimic acid 3-O-gallate
A
3,4,5-trihydroxybenzoic acid
B
shikimic acid
Conditions | Yield |
---|---|
tannase In water at 37℃; for 3h; Product distribution; | A 40 mg B 43 mg |
11-O-(3',4',5'-trihydroxygalloyl)bergenin
A
3,4,5-trihydroxybenzoic acid
B
bergenin
Conditions | Yield |
---|---|
With trifluoroacetic acid In water for 30h; Heating; |
Conditions | Yield |
---|---|
With trifluoroacetic acid In water for 30h; Heating; |
A
1,3,4,6-tetra-O-galloyl-β-D-glucose
B
3,4,5-trihydroxybenzoic acid
D
corilagin
Conditions | Yield |
---|---|
In water; acetone for 10h; Heating; | A 4 mg B 15 mg C 4 mg D 2 mg |
Conditions | Yield |
---|---|
enzymatic hydrolysis with tannase; |
Conditions | Yield |
---|---|
With sulfuric acid for 6h; Heating; | 100% |
With brominated modified sulfonic acid resin at 65℃; for 4h; Reagent/catalyst; | 99% |
With sulfuric acid for 1.5h; Heating / reflux; | 97% |
3,4,5-trihydroxybenzoic acid
tert-butyldimethylsilyl chloride
tert-butyldimethylsilyl 3,4,5-tri[(tert-butyldimethylsilyl)oxy]benzoate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; | 91.9% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Substitution; |
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With water-d2; hydrogen chloride for 6h; Inert atmosphere; Reflux; | 99% |
With Amberlyst 15; water-d2 at 90℃; for 24h; Substitution; | |
With nafion resin; water-d2 at 90℃; for 24h; |
Conditions | Yield |
---|---|
In methanol at 25℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With brominated modified sulfonic acid resin at 100℃; for 5h; | 98% |
With toluene-4-sulfonic acid at 107℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Sealed tube; Microwave irradiation; | 94% |
With cucurbit[6]uril-supported Keggin-type silicotungstic acid Q[6]-STA at 96.84℃; for 4h; Catalytic behavior; Time; Reagent/catalyst; | 94.7% |
Conditions | Yield |
---|---|
With brominated modified sulfonic acid resin at 80℃; for 5h; Reagent/catalyst; | 98% |
With toluene-4-sulfonic acid at 88℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Time; Sealed tube; Microwave irradiation; | 96% |
With sulfuric acid at 70℃; | 95% |
Conditions | Yield |
---|---|
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry; | 98% |
With Citrobacter sp at 28℃; for 24h; enzymatic synthesis by bacterium in a mixed medium containing: 0.5percent maltose, 0.2percent (NH4)2HPO4, 0.1percent KH2PO4, 0.05percent KCl, 0.05percentMgSO4.7H2Oand 0.05percent yeast, pH=4.5; | 97.4% |
With Cocos nucifera juice at 20℃; for 48h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation; | 98% |
With brominated hydrophobically modified sulfonic acid resin at 150℃; for 10h; | 92% |
Stage #1: 3,4,5-trihydroxybenzoic acid; hexan-1-ol With diisopropyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With dmap In tetrahydrofuran at 20℃; for 24h; | 72% |
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium carbonate In methanol at 20℃; Schlenk technique; Inert atmosphere; | 98% |
With sodium ethoxide In ethanol Inert atmosphere; Reflux; |
3,4,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With triethylamine sulfur trioxide; triethylamine In N,N-dimethyl-formamide at 86℃; for 1h; Microwave irradiation; Green chemistry; | 98% |
1-octadecanol
3,4,5-trihydroxybenzoic acid
octadecyl 3,4,5-trihydroxybenzoate
Conditions | Yield |
---|---|
With cation exchange resin 731 In ethyl acetate at 80 - 85℃; Dean-Stark; | 97.2% |
With toluene-4-sulfonic acid In 1,4-dioxane at 160℃; | 73% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 10h; | 61% |
With naphthalene-2-sulfonate; methoxybenzene; nitrobenzene unter Entfernen des entstehenden Wassers; | |
With toluene-4-sulfonic acid In toluene at 125℃; for 4h; Temperature; |
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation; | 97% |
With brominated modified sulfonic acid resin at 120℃; for 5h; | 96% |
With toluene-4-sulfonic acid at 128℃; under 9308.91 Torr; for 0.15h; Temperature; Wavelength; Sealed tube; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 0.5h; | 97% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 105℃; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 103℃; for 8h; Temperature; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation; | 96% |
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h; | 89% |
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h; | 89% |
3,4,5-trihydroxybenzoic acid
C6H10N2O3*C7H6O5
Conditions | Yield |
---|---|
In methanol for 24h; | 96% |
phosgene
3,4,5-trihydroxybenzoic acid
7-hydroxy-2-oxo-benzo[1,3]dioxole-5-carboxylic acid
Conditions | Yield |
---|---|
With sodium carbonate; triethylamine In dichloromethane; water at 12℃; for 1h; Temperature; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃; Concentration; Inert atmosphere; | 95.6% |
Conditions | Yield |
---|---|
With sulfuric acid at 80 - 120℃; for 5h; Autoclave; | 95% |
With sulfuric acid at 100℃; Inert atmosphere; | 92.2% |
With sulfuric acid for 0.025h; microwave irradiation; | 80% |
3,4,5-trihydroxybenzoic acid
acetic anhydride
3,4,5-triacetoxybenzoic acid
Conditions | Yield |
---|---|
at 130℃; for 4h; | 95% |
for 3h; Reflux; | 95% |
With sulfuric acid at 21 - 75℃; | 93% |
2,2'-biimidazole
3,4,5-trihydroxybenzoic acid
water
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
In water 2,2'-biimidazole added to a soln. of metal acetate in hot water, a soln.of 3,4,5-tris-hydroxy-benzoic acid in hot water added; concn., controlled evapn. at room temp. for 2-3 wk; elem. anal.; | 95% |
2-methyl-propan-1-ol
3,4,5-trihydroxybenzoic acid
isobutyl 3,4,5-trihydroxybenzoate
Conditions | Yield |
---|---|
With brominated hydrophobically modified sulfonic acid resin at 110℃; for 8h; | 94% |
With toluene-4-sulfonic acid at 118℃; under 9308.91 Torr; for 0.15h; Temperature; Wavelength; Sealed tube; Microwave irradiation; | 92% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 10h; | 87% |
3,4,5-trihydroxybenzoic acid
isopropyl alcohol
isopropyl 3,4,5-trihydroxybenzoate
Conditions | Yield |
---|---|
With brominated modified sulfonic acid resin at 85℃; for 7h; | 94% |
With sulfuric acid at 120℃; for 2h; | 94% |
With toluene-4-sulfonic acid at 92℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Sealed tube; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
With water In ethanol at 20℃; for 24h; | 94% |
Conditions | Yield |
---|---|
In methanol at 60℃; for 12h; Inert atmosphere; | 93.32% |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 2.5h; Cooling with ice; | 92.6% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 148℃; under 9308.91 Torr; for 0.166667h; Temperature; Wavelength; Sealed tube; Microwave irradiation; | 92% |
With brominated modified sulfonic acid resin at 135℃; for 8h; | 92% |
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation; | 83% |
Conditions | Yield |
---|---|
In diethyl ether byproducts: C5H6, H2; (vac. or Ar); addn. of acid to V-complex in ether (20°C, 48 h); filtration, washing (ether), drying; elem. anal.; | 92% |
Molecular Structure of Gallic acid (CAS NO.149-91-7):
IUPAC Name: 3,4,5-trihydroxybenzoic acid
Empirical Formula: C7H6O5
Molecular Weight: 170.1195
H bond acceptors: 5
H bond donors: 4
Freely Rotating Bonds: 4
Polar Surface Area: 53.99 ?2
Index of Refraction: 1.73
Molar Refractivity: 38.82 cm3
Molar Volume: 97.2 cm3
Surface Tension: 109.2 dyne/cm
Density: 1.749 g/cm3
Flash Point: 271 °C
Enthalpy of Vaporization: 81.07 kJ/mol
Boiling Point: 501.1 °C at 760 mmHg
Vapour Pressure: 7.32E-11 mmHg at 25°C
EINECS: 205-749-9
Melting point: 252 °C (dec.)(lit.)
Water Solubility: 12 g/L cold water
Merck: 14,4345
BRN: 2050274
Stability: Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides.
Product Categories: Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
InChI
InChI=1/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
Smiles
c1(cc(c(O)c(c1)O)O)C(O)=O
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 4300mg/kg (4300mg/kg) | Pharmacology and Toxicology Vol. 64, Pg. 247, 1989. | |
mouse | LD50 | intravenous | 320mg/kg (320mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02597, | |
rabbit | LD50 | oral | 5gm/kg (5000mg/kg) | LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: OTHER CHANGES LIVER: OTHER CHANGES | American Journal of Veterinary Research. Vol. 23, Pg. 1264, 1962. |
rat | LDLo | subcutaneous | 5gm/kg (5000mg/kg) | Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969. |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Poison by intravenous route. Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: LW7525000
F: 8-9-23
Gallic acid , with CAS number of 149-91-7, can be called 3,4,5-Trihydroxybenzoesäure ; 3,4,5-trihydroxy-Benzoic acid ; Acid, Gallic ; Acide 3,4,5-trihydroxybenzoïque ; benzoic acid, 3,4,5-trihydroxy- . It is a white powder, Gallic acid do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids. These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.
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