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Chemical Structure| 99-50-3 Chemical Structure| 99-50-3
Chemical Structure| 99-50-3

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Protocatechuic acid, a natural product isolated and purified from the herbs of Onychium japonicum, is a phenolic compound which exhibits neuroprotective effects.

Synonyms: 3,4-Dihydroxybenzoic acid; NSC 16631; PCA

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Product Details of protocatechuic acid

CAS No. :99-50-3
Formula : C7H6O4
M.W : 154.12
SMILES Code : C1=C(C=CC(=C1O)O)C(O)=O
Synonyms :
3,4-Dihydroxybenzoic acid; NSC 16631; PCA
MDL No. :MFCD00002509
InChI Key :YQUVCSBJEUQKSH-UHFFFAOYSA-N
Pubchem ID :72

Safety of protocatechuic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of protocatechuic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 99-50-3 ]

[ 99-50-3 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 99-50-3 ]
  • [ 100-44-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; (1) To a suspension of 3,4-dihydroxybenzoic acid (25.4 g, 0.17 mle) in ethanol (250 ml), 5N NaOH aq. (270 ml) and benzyl chloride (102 g, 0.81 mole) were added. The resulting mixture was reacted with stirring for 6 hours under reflux. The reaction mixture was cooled to room temperature, allowed to stand at same temperature overnight and acidified with conc. hydrochloric acid (40 ml). The precipitate was filtered, washed with hot ethanol and dried under reduced pressure to give 38.2 g of 3,4-dibenzyloxybenzoic acid as pale yellow crystals having a m.p. of 184°-186° C. 1 H-NMR delta ppm (DMSO-d6): 3.38 (1H, bs, OH), 5.18 and5.22 (each 2H, each s, each ARCH2 O-), 7.16(1H, d, J=8.8Hz, Ar 5-H), 7.30 - 7.57 (12H,m, ArH). IR (KBr-disk) nu cm-1: 1679 (C=O).
With sodium hydroxide; In ethanol; (1) To a suspension of 3,4-dihydroxybenzoic acid (25.4 g, 0.17 mole) in ethanol (250 ml), 5N NaOH aq. (270 ml) and benzyl chloride (102 g, 0.81 mole) were added, and the mixture was reacted with stirring for 6 hours under reflux. The reaction mixture was cooled to room temperature, allowed to stand at same temperature overnight and acidified with conc. hydrochloric acid (40 ml). The precipitate was filtered, washed with hot ethanol and dried under reduced pressure to give 38.2 g of 3,4-dibenzyloxybenzoic acid as pale yellow crystals having a m.p. of 184-186°C.
  • 2
  • [ 2922-42-1 ]
  • [ 99-50-3 ]
  • [ 99-14-9 ]
  • [ 149-91-7 ]
  • [ 184105-29-1 ]
  • [ 87-66-1 ]
  • 3
  • [ 99-50-3 ]
  • [ 32566-01-1 ]
  • [ 677297-13-1 ]
YieldReaction ConditionsOperation in experiment
54% 3,4-Dihydroxy-N-(2-(1H-indol-2-yl)-phenyl)-benzamide Prepared from 2-(2-aminophenyl) indole and 3,4-dihydroxybenzoic acid in 54% yield following procedure 1. The product was chromatographed on silica. 100% Purity by LC/MS (230 DAD), Mass-spec (M+H+)=345.83, 1H NMR (MeOH-d4): 6.645 s (1H), 6.80 d, 8 Hz (1H), 7.02 t, 8 Hz (1H), 7.12 td, 8, 1 Hz (1H), 7.23 dd, 8, 1 Hz (1H), 7.33-7.36 m (2H), 7.39-7.42 m (2H), 7.52 d, 7 Hz (1H), 7.65 dd, 8, 1 Hz (1H), 7.94 d, 8 Hz (1H).
  • 5
  • [ 99-50-3 ]
  • [ 100-39-0 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
Compound 12 was prepared according a procedure reported by Tranchimand et al.33 and spectral data were in accordance with literature. Briefly, benzyl bromide (14 mL, 117 mmol) and K2CO3 (10.7 g, 78 mmol) were added over a solution of 3,4-dihydroxybenzoic acid (11) (2.00 g, 13 mmol) in dry DMF (30 mL) under an argon atmosphere and heated to 60 °C for 20 h. The reaction mixture was cooled to room temperature, filtered and the solvent was removed under reduced pressure. The residue was dissolved in AcOEt (10 mL) and washed with 1 M HCl (3 x 5 mL) and brine (5 x 5 mL). The combined organic extracts were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residue was dissolved in CH3OH (38 mL), and treated with 2.3 MNaOH (14 mL) and the mixture was heated under reflux for 1 h. Then, solvents were evaporated under reduced pressure and the residue was treated with H2O (5 mL) and then extracted with Et2O (3 6 mL). The aqueous phase was made acidic (pH 1?2) with 1 M HCl and extracted with AcOEt (3 x 5 mL). The organic extracts were dried over MgSO4, filtered and the solvent was removed under reduced pressure. Mp 187?188 °C as reported inliterature.33
With potassium carbonate; In acetonitrile; for 18h;Reflux; Preparation of 3,4-bis(benzyloxy)benzoic acid (0175) 3,4-Dihydroxy benzoic acid, benzyl bromide, and potassium carbonate were dissolved in acetonitrile, and the solution was refluxed for 18 hours. The reaction solution was then cooled to room temperature and filtered. The solution was then concentrated and diluted with hexanes, resulting in a solid that was collected by filtration. The solid was then recrystallized in the mixture of THF and hexanes, giving rise to a pure product.
  • 6
  • [ 94-26-8 ]
  • [ 99-50-3 ]
  • [ 2474-72-8 ]
  • [ 89-86-1 ]
  • [ 149-91-7 ]
  • C7H6O5 [ No CAS ]
  • [ 123-31-9 ]
  • [ 106-51-4 ]
  • [ 108-95-2 ]
  • [ 99-96-7 ]
  • 7
  • [ 99-50-3 ]
  • [ 177429-27-5 ]
  • 8
  • [ 99-50-3 ]
  • [ 19387-91-8 ]
  • C8H13N3O4S*C7H6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; for 1.66667h; General procedure: The TN salts/molecular salts was preparedby grinding an equimolar mixture containing 200mg (1 mmol) of TN and 1mmol of correspondingcarboxylic acids/PTSA wetted with few drops of waterwas manually grounded in an agate mortar for 100minutes until a dried powder was obtained.
 

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