Veratric acid

[Description]:

Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits, has antioxidant[1] and anti-inflammatory activities[3]. Veratric acid also acts as a protective agent against hypertension-associated cardiovascular remodelling[2]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3].

[Related Catalog]:

Natural Products >> Acids and Aldehydes

Research Areas >> Inflammation/Immunology

Research Areas >> Cardiovascular Disease

[Target]

COX-2[3]

[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[1]. 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[3]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3].

[In Vivo]

Veratric acid (40 mg/kg, p.o., b.w.) significantly promotes ventricular function, reduces lipid peroxidation and increases antioxidants in l-NAME-induced hypertensive rats[2].

[References]

[1]. Choi WS, et al. Veratric acid inhibits iNOS expression through the regulation of PI3K activation and histone acetylation in LPS-stimulated RAW264.7 cells. Int J Mol Med. 2015 Jan;35(1):202-10.

[2]. Saravanakumar M, et al. Oral administration of veratric acid, a constituent of vegetables and fruits, prevents cardiovascular remodelling in hypertensive rats: a functional evaluation. Br J Nutr. 2015 Nov 14;114(9):1385-94.

[3]. Shin SW, et al. Antagonist effects of veratric acid against UVB-induced cell damages. Molecules. 2013 May 10;18(5):5405-19.

[Related Small Molecules]

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
302.9±22.0 °C at 760 mmHg

[ Melting Point ]:
179-182 °C(lit.)

[ Molecular Formula ]:
C₉H₁₀O₄

[ Molecular Weight ]:
182.173

[ Flash Point ]:
120.9±15.8 °C

[ Exact Mass ]:
182.057907

[ PSA ]:
55.76000

[ LogP ]:
1.99

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.533

[ Storage condition ]:
Refrigerator

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

[ Water Solubility ]:
slightly soluble

Click to get detail MSDS

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DG8598750

CHEMICAL NAME :: Benzoic acid, 3,4-dimethoxy-

CAS REGISTRY NUMBER :: 93-07-2

BEILSTEIN REFERENCE NO. :: 0518285

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C9-H10-O4

MOLECULAR WEIGHT :: 182.19

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 :: DNA inhibition

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 1 mmol/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 29,1275,1980

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-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 ]:
DG8598750

[ HS Code ]:
2918990090

Click to get detail synthetic route

Precursor

DownStream

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Quantitative measurement of organic acids in tissues from gastric cancer patients indicates increased glucose metabolism in gastric cancer.

PLoS ONE 9(6) , e98581, (2014)

The levels of organic acids representing metabolic pathway end products are important indicators of physiological status, and may be associated with metabolic changes in cancer. The aim of this study ...

Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.

Bioorg. Med. Chem. 19 , 1381-9, (2011)

Carbonic anhydrases (CAs, EC 4.2.1.1) are inhibited by sulfonamides, inorganic anions, phenols, coumarins (acting as prodrugs) and polyamines. A novel class of CA inhibitors (CAIs), interacting with t...

The regulatory effect of veratric acid on NO production in LPS-stimulated RAW264.7 macrophage cells.

Cell. Immunol. 280(2) , 164-70, (2012)

Veratric acid, a simple benzoic acid derived from plants and fruits, has been reported to have anti-oxidant, anti-inflammation, and blood pressure-lowering effects. This study was designed to evaluate...

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CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

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Precursor & DownStream

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