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Gallic acid

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Name

Gallic acid

EINECS 205-749-9
CAS No. 149-91-7 Density 1.749 g/cm3
PSA 97.99000 LogP 0.50160
Solubility 12 g/L in cold water Melting Point 252 °C (dec.)(lit.)
Formula C7H6O5 Boiling Point 501.1 °C at 760 mmHg
Molecular Weight 170.122 Flash Point 271 °C
Transport Information N/A Appearance white crystalline powder
Safety 24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 149-91-7 (Gallic acid) Hazard Symbols IrritantXi
Synonyms

Kyselina gallova [Czech];Gallate;Pyrogallol-5-carboxylic acid;Benzoic acid, 3,4,5-trihydroxy-;3,4,5-Trihydroxybenzoic acid;Kyselina 3,4,5-trihydroxybenzoova [Czech];3,4,5-Trihydroxybenzoate;Gallic acid, tech.;Benzoic acid,3,4,5-trihydroxy-;

Article Data 187

Gallic acid Synthetic route

tannic acid

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With water at 80℃; for 6h; Reagent/catalyst;96.99%

tannic acid

A

2280-44-6

D-Glucose

B

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With water at 60℃; for 6h; Reagent/catalyst;A n/a
B 91.5%
118-41-2

Eudesmic acid

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In xylene for 1.5h; Heating;75%
With hydrogen iodide
2922-42-1

(-)-3-dehydroshikimic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
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;
71-23-8

propan-1-ol

99-24-1

methyl galloate

A

121-79-9

Propyl gallate

B

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose at 25℃; pH=5; aq. acetate buffer; Enzymatic reaction;A 55%
B n/a
13677-79-7

gallaldehyde

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium bromate; hydrogenchloride; potassium bromide In water for 12h; Time;53%
555-44-2

glyceroltripalmitate

121-79-9

Propyl gallate

A

149-91-7

3,4,5-trihydroxybenzoic acid

B

3-((3',4',5'-trihydroxybenzoyl)oxy)propane-1,2-diyl dipalmitate

Conditions
ConditionsYield
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%

oolongtheanin 3'-O-gallate

A

149-91-7

3,4,5-trihydroxybenzoic acid

B

C36H24O16

C

C36H26O16

D

C43H32O21

Conditions
ConditionsYield
With water at 60℃; for 4h;A 24.7%
B 3.3%
C 5.6%
D 5.6%
99-50-3

3,4-Dihydroxybenzoic acid

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
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
2922-42-1

(-)-3-dehydroshikimic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

99-14-9

tricarallylic acid

C

149-91-7

3,4,5-trihydroxybenzoic acid

D

184105-29-1

dihydrogallic acid

E

87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
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.

Gallic acid Chemical Properties

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

Gallic acid Toxicity Data With Reference

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.

Gallic acid Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Gallic acid Safety Profile

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: IrritantXi
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 Specification

  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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