Veratric Acid Property

Melting point:

179-182 °C(lit.)

Boiling point:

275.56°C (rough estimate)

Density 

1.2481 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

0.5g/l

pka

4.35±0.10(Predicted)

form 

Crystalline Powder

color 

Almost white to beige or reddish

Water Solubility 

slightly soluble

Merck 

14,9953

BRN 

518285

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

DAUAQNGYDSHRET-UHFFFAOYSA-N

LogP

1.610

CAS DataBase Reference

93-07-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3,4-dimethoxy-(93-07-2)

EPA Substance Registry System

Benzoic acid, 3,4-dimethoxy- (93-07-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

DG8598750

TSCA 

Yes

HS Code 

29189090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Veratric Acid Chemical Properties,Usage,Production

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 plays an important role in producing antibiotics and various dyes. They are used as intermediates for pharmaceuticals (especially for antipyretic analgesic, antirheumatism) and other organic synthesis. It is used as matrix for ionization of peptides, proteins and carbohydrates.

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.

Definition

ChEBI: A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 26, p. 299, 1978 DOI: 10.1248/cpb.26.299
Tetrahedron Letters, 43, p. 4985, 2002 DOI: 10.1016/S0040-4039(02)00929-2

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.