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99-50-3

Basic Information
CAS No.: 99-50-3
Name: 3,4-Dihydroxybenzoic acid
Article Data: 289
Molecular Structure:
Molecular Structure of 99-50-3 (3,4-Dihydroxybenzoic acid)
Formula: C7H6O4
Molecular Weight: 154.122
Synonyms: 4-Carboxy-1,2-dihydroxybenzene;Protocatehuic acid;1/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11;4-10-00-01459 (Beilstein Handbook Reference);Benzoic acid, 3,4-dihydroxy- (9CI);Benzoic acid,3,4-dihydroxy-;3.4-Dihydroxy Benzoic Acid;Protocatechuate;3,4-Dihydroxy Benzoic Acid;Benzoic acid, 3,4-dihydroxy-;3,4-dihydroxybenzoic acid;protocatechuic acid;3,4-Dihydroxybenzoic Acid 98%;
EINECS: 202-760-0
Density: 1.559 g/cm3
Melting Point: 197-200 °C (dec.)(lit.)
Boiling Point: 410.7 °C at 760 mmHg
Flash Point: 216.3 °C
Solubility: Soluble in hot alcohol and ether. Slightly soluble in water.
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 77.76000
LogP: 0.79600
Synthetic route
121-34-6

3-methoxy-4-hydroxybenzoic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With 1,4-dithio-D,L-threitol; phosphite dehydrogenase; phosphite ion; iron(II) sulfate; NADH In dimethyl sulfoxide at 30℃; for 7h; pH=7.5; Catalytic behavior; Reagent/catalyst; Solvent; Enzymatic reaction;77%
121-33-5

vanillin

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 260℃; for 0.75h;94%
With potassium carbonate durch Schmelzen;
With potassium hydroxide durch Schmelzen;
With potassium hydroxide at 250℃;
6702-50-7

3-hydroxy-4-methoxybenzoate

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;89%
874-61-3

4-oxocyclohexanecarboxylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;84%
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; ethyl acetate; diisopropyl-carbodiimide In acetonitrile at 80℃; for 5h; Temperature;A 14%
B 72%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h; Temperature; Overall yield = 89 %; Overall yield = 0.684 g;A 64%
B 31%
619-12-5

4-formyl-3-hydroxybenzoic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 35℃; for 12h; Dakin Phenol Oxidation;71%
108-24-7

acetic anhydride

89475-36-5

3',4'-dihydroxy-7-dimethoxyflavylium chloride

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2237-36-7

4-methoxysalicylic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;A 70%
B 67%
6702-50-7

3-hydroxy-4-methoxybenzoate

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h;A 64%
B 31%
16205-98-4

3-oxo-cyclohexanecarboxylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;63%
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;
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    Basic Information Synonym 3,4-DIHYDROXYBENZOIC ACID/Protocatechuic acid/Protocatehuic acid/4-Carboxy-1,2-dihydroxybenzene CAS No. 99-50-3 Formula C7H6O4 Molecular Weight 154.12 g/mol Appa

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Chemistry

Molecular Formula: C7H6O4
Molecular Weight: 154.12 g/mol 
EINECS: 202-760-0 
Index of Refraction: 1.67
Density: 1.559 g/cm3
Flash Point: 216.3 °C
Enthalpy of Vaporization: 69.92 kJ/mol
Boiling Point: 410.7 °C at 760 mmHg
Vapour Pressure: 1.75E-07 mmHg at 25 °C
Melting point: 197-200 °C (dec.)(lit.)
Sensitive: Air Sensitive
Appearance: White to light yellow crystal powder
Structure of 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3):
                       
IUPAC Name: 3,4-Dihydroxybenzoic acid
Product Category of 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3): Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic Acid Derivative;Organic acids;API

Toxicity Data With Reference

1.    

dni-hmn:lyms 1 mmol/L

    BCPCA6    Biochemical Pharmacology. 29 (1980),1275.
2.    

msc-mus:lyms 300 mg/L

    EMMUEG    Environmental and Molecular Mutagenesis. 11 (1988),523.
3.    

cyt-ham:ovr 3 g/L

    CALEDQ    Cancer Letters (Shannon, Ireland). 14 (1981),251.
4.    

ipr-mus LD50:>800 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 196 (1976),478.

Safety Profile

Moderately toxic by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.

Specification

 3,4-Dihydroxybenzoic acid , its cas register number is 99-50-3. It also can be called Protocatechuic acid . 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3) has mixed effects on normal and cancer cells in in vitro and in vivo studies. It has been reported to induce apoptosis of human leukemia cells, as well as malignant HSG1 cells taken from human oral cavities,but it was found to have mixed effects on TPA-induced mouse skin tumours.