protocatechuic acid

Names

[ CAS No. ]:
99-50-3

[ Name ]:
protocatechuic acid

[Synonym ]:
MFCD00002509
3,4-dihydroxy-benzoic acid
4,5-Dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid
4-Carboxy-1,2-dihydroxybenzene
Protocatehuic acid
protocatechuate
EINECS 202-760-0
Benzoic acid, 3,4-dihydroxy-
protochatechuic acid
protocatechuic acid
3,4-dihydroxybenzoate
Benzoic acid,3,4-dihydroxy

Biological Activity

[Description]:

Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

Natural Products >> Phenols

[In Vitro]

Protocatechuic acid inhibits the aggregation of Aβ and αS and destabilizes their preformed fibrils. Protocatechuic acid prevents the death of PC12 cells triggered by Aβ- and αS-induced toxicity[3].

[In Vivo]

Protocatechuic acid is able to prevent stress induced immobility time in forced swim test without altering locomotor activity in mice. Further, Protocatechuic acid treatment attenuates the elevation of serum corticosterone, lipid peroxidation and restores enzymatic antioxidants in cerebral cortex and hippocampus in ARS mice[1]. Rat administered cadmium and treated with prostigmine and doses of Protocatechuic acid (10−20 mg/kg) has significantly reduced BChE activity. Cadmium and either prostigmine or Protocatechuic acid (10−20 mg/kg) treated rats shows significant reduction in MDA level[2].

[Kinase Assay]

AChE activity investigation is carried out in a reaction mixture containing 50 μL of tissue homogenate, 50 μL of 5, 5'-dithiobis-(2-nitrobenzoic) acid (DTNB), 1175 μL of 0.1 M phosphate-buffered solution, pH 8.0. After incubation for 20 min at 25°C, 25 μL of acetylthiocholine iodide solution is added as the substrate. The AChE activity is determined as changes in absorbance reading at 412 nm for 3 min at 25°C and using a UV/Visible spectrophotometer.

[Cell Assay]

Dilutions of Protocatechuic acid (2, 5, 10, 20, 50, and 100 μM) are prepared from stock solutions, with serum-free culture medium. Equal volumes of each solution are mixed with Aβ1-42 (10 μM), then incubated for 24 h on a thermoblock, with continuous agitation, and then exposed to PC12 cells for 24 h to test whether Protocatechuic acid can prevent cell death triggered by Aβ. Cell viability is determined by MTT reduction assay. Cells are treated with 200 μL per well of MTT solution (final concentration, 0.5 mg/mL in DMEM-Glutamax medium) for 3 h, at 37°C, with 5% CO2. The dark blue formazan crystals that formed are solubilized with 100 μL per well of DMSO, for 30 min. Absorbance is measured at 540 nm, with a microplate reader. Results are expressed as the percentage of MTT reduction in relation to the absorbance of control cells at 100%.

[References]

[1]. Thakare VN, et al. Attenuation of acute restraint stress-induced depressive like behavior and hippocampal alterations with protocatechuic acid treatment in mice. Metab Brain Dis. 2016 Oct 26.

[2]. Adefegha SA, et al. Alterations of Na+/K+-ATPase, cholinergic and antioxidant enzymes activity by protocatechuic acid in cadmium-induced neurotoxicity and oxidative stress in Wistar rats. Biomed Pharmacother. 2016 Oct;83:559-568.

[3]. Hornedo-Ortega R, et al. Protocatechuic Acid: Inhibition of Fibril Formation, Destabilization of Preformed Fibrils of Amyloid-β and α-Synuclein, and Neuroprotection. J Agric Food Chem. 2016 Oct 10.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
410.7±35.0 °C at 760 mmHg

[ Melting Point ]:
197-200 °C (dec.)(lit.)

[ Molecular Formula ]:
C₇H₆O₄

[ Molecular Weight ]:
154.120

[ Flash Point ]:
216.3±22.4 °C

[ Exact Mass ]:
154.026611

[ PSA ]:
77.76000

[ LogP ]:
1.16

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Stability ]:
Stable. Incompatible with strong oxidizing agents, strong bases.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UL0560000

CHEMICAL NAME :: Protocatechuic acid

CAS REGISTRY NUMBER :: 99-50-3

BEILSTEIN REFERENCE NO. :: 1448841

LAST UPDATED :: 199710

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C7-H6-O4

MOLECULAR WEIGHT :: 154.13

WISWESSER LINE NOTATION :: QVR CQ DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 3 gm/L

REFERENCE :: CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 14,251,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UL0560000

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

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