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149-91-7

Basic Information
CAS No.: 149-91-7
Name: Gallic acid
Article Data: 187
Cas Database
Molecular Structure:
Molecular Structure of 149-91-7 (Gallic acid)
Formula: C7H6O5
Molecular Weight: 170.122
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-;
EINECS: 205-749-9
Density: 1.749 g/cm3
Melting Point: 252 °C (dec.)(lit.)
Boiling Point: 501.1 °C at 760 mmHg
Flash Point: 271 °C
Solubility: 12 g/L in cold water
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25
Transport Information: N/A
PSA: 97.99000
LogP: 0.50160
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.
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    Product Name: Gallic acid CAS: 149-91-7 MF: C7H6O5 MW: 170.12 EINECS: 205-749-9 Mol File: 149-91-7.mol Gallic acid Structure Gallic acid Chemical Properties Melting point 251 °C (dec.) (lit.) Boiling point 259.73°C

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Chemistry

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

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.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

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

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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