1034-01-1

Hazard Information

Chemical Properties

White powder

Definition

ChEBI: A gallate ester obtained by condensation of the carboxy group of gallic acid with the hydroxy group of octanol.

General Description

Octyl gallate is an ester of gallic acid which is generally used as an antioxidant in food and pharmaceutical industries. It can act against the oxidative damage caused by reactive oxygen species (ROS) in the form of hydroxyl radicals or hydrogen peroxides, and reactive sulfur species (RSS)

Synthesis

111-87-5

149-91-7

1034-01-1

Gallic acid (0.3 mmol, 50 mg), octanol (0.9 mmol) and concentrated sulfuric acid (0.07 mL) were added to the microwave reaction flask. After sealing the reaction bottle, it was placed in a microwave reactor and the reaction was radiated at 100 °C for 50 min. After completion of the reaction, it was cooled to room temperature and the volatile components of the reaction mixture were evaporated to dryness. The residue was dissolved with ethyl acetate (30 mL) and washed sequentially with saturated sodium bicarbonate solution (3 x 20 mL) and sodium chloride solution (1 x 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography with the eluent being a solvent mixture of hexane/ethyl acetate in the ratio of 3:7, v/v/v/v. The melting point and spectral data of the target compound octyl gallate were in agreement with those reported in literature [25d]. The isolated yield of octyl gallate was 70% under the present experimental conditions.

Material Safety Data Sheet(MSDS)

Questions And Answer

• Description

  Octyl gallate is the ester formed by 1-octanol and gallic acid. It can be used as an antioxidant and preservative to be supplemented to the food. It has been demonstrated to be an effective fungicide being capable of inhibiting the growth of S. cerevisiae and Z. bailii as it can inhibit the fluidity of the cell membrane through acting as a nonionic surface-active agent. It is also capable of killing both DNA and RNA viruses with a relatively moderate cytotoxicity. For example, it has the potential to treat influenza. Octyl gallate also has certain bactericidal activity, being capable of treating the infections associated with enterococci. ;

• References

  [1]Ken-Ichi, Fujita, and K. Isao. "Antifungal activity of octyl gallate. " International Journal of Food Microbiology 79.3(2002):1
  [2]Gutiérrez-Fernández, J, et al. "Antimicrobial activity of binary combinations of natural and synthetic phenolic antioxidants against Enterococcus faecalis. " Journal of Dairy Science 96.8(2013):4912-20.93.
  [3] Yamasaki, H, et al. "Antiviral effect of octyl gallate against influenza and other RNA viruses. " International Journal of Molecular Medicine 19.4(2007): 685-688. ;

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products