Description
Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits and has antioxidant and anti-inflammatory activities. It also acts as a protective agent against hypertension-associated cardiovascular remodeling. Veratric acid reduces upregulated COX-2 expression and levels of PGE2 and IL-6 after UVB irradiation. This compound could be reduced to veratrine aldehyde, and alcohol was performed with enzyme extracts from a wood-degrading basidiomycete, Polystictus (Trametes) versicolor[1].
Chemical Properties
white to slightly yellow powder
Uses
3,4-Dimethoxybenzoic acid is a derivative of Protocatechuic Acid.3,4-Dimethoxybenzoic acid is a reagent used in the production of antimicrobial agents, antifeedants, and a variety of other biologically active compounds.
Uses
Derivative of Protocatechuic Acid, and is a reagent used in the production of antimicrobial agents, antifeedants, and a variety of other biologically active compounds.
Definition
ChEBI: A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.
Synthesis
Veratric acid is prepared via a two-step synthesis starting with the methylation of acetovanillon using dimethylsulphate in alkaline media to obtain 3,4-dimethoxy acetophenone, followed by an oxidation based on the haloform reaction with sodium hypochlorite in alkaline media[2].
in vitro
Veratric acid (100, 200 μM) suppresses iNOS expression in LPS-stimulated RAW264.7 cells. Veratric acid (200 μM) inhibits LPS-induced activation of the PI3K/Akt pathway, HAT activation, and HDAC3 expression in RAW264.7 cells.
Veratric Acid (10-100 μg/mL) has anti-inflammatory activity, protects HaCaT cells against UVB-mediated phototoxicity, increases S-phase cells, and prevents UVB-mediated apoptosis.
Veratric acid reduces upregulated COX-2 expression and levels of PGE2, and IL-6 after UVB irradiation.
Purification Methods
Crystallise the acid from Et2O, H2O or aqueous acetic acid. It has m 180-181o after sublimation at 80o/1mm. [Beilstein 10 H 393, 10 I 188, 10 II 261, 10 III 1404, 10 IV 1406.]
References
[1] Gross, Georg G. “From lignins to tannins: Forty years of enzyme studies on the biosynthesis of phenolic compounds.” Phytochemistry 69 18 (2008): Pages 3018-3031.
