Vanillic acid

Names

[ CAS No. ]:
121-34-6

[ Name ]:
Vanillic acid

[Synonym ]:
4-Hydroxy-3-methoxybenzoic acid
EINECS 204-466-8
4-hydroxy-m-Anisic acid
Benzoic acid, 4-hydroxy-3-methoxy-
4-Hydroxy-3-methoxy-benzoic acid
Vanillic acid
MFCD00002551
Acid, Vanillic

Biological Activity

[Description]:

Vanillic acid is a flavoring agent found in edible plants and fruits. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

[Related Catalog]:

Research Areas >> Infection

Natural Products >> Acids and Aldehydes

Research Areas >> Inflammation/Immunology

[Target]

p65

[In Vitro]

Vanillic acid inhibited lipopolysaccharide (LPS)-induced phosphorylation of IκB (cytoplasmatic NF-κB inhibitor) in the cytoplasm extract and NF-κB p65 subunit expression in the nuclear extract of macrophages in vitro as determined by Western blot[1]. Vanillic acid treatment reverses the Aβ1-42-induced elevated expression of IKK-β/NF-κB and reduces the activity of IKKβ/NF-κB. Vanillic acid is non-toxic to HT22 cells at all three concentrations (50, 100 and 200 μM); Vanillic acid co-treatment with Aβ1-42 significantly increases (1.5-, 1.9- and 2-fold respectively) cell viability. Aβ1-42 (5 μM) treatment results in a significant increase (1.6-fold) in ROS levels compared with the control cells. In contrast, Vanillic acid treatment at all three different concentrations (50, 100 and 200 μM) reduces (1.1-, 1.3- and 1.4-fold respectively) ROS levels, indicating that Vanillic acid is a potent antioxidant[2].

[In Vivo]

Vanillic acid (30 mg/kg, ip, 1 h) inhibits Carrageenan-induced NF-κB activation. Mice receive Vanillic acid (30 mg/kg, ip) 1 h before ipl injection of Carrageenan (300 μg/paw), and samples of the cutaneous plantar tissues are collected 3 h after stimulus injection. Carrageenan-induced activation of NF-κB is observed by a decrease in the ratio of total NF-κB/p-NF-κB, while treatment with Vanillic acid as well as the control drug Indomethacin (5 mg/kg, ip, diluted in Tris/HCl buffer, 40 min before stimulus) inhibits Carrageenan-induced activation of NF-κB[1].

[Cell Assay]

The viability of HT22 cells is assessed with the MTT assay. Cells are cultured in 96-well plates at a density of 1 × 104 cells per well in 100 μL of Dulbecco’s modified Eagle’s medium (DMEM). After 24 h, the medium is replaced with fresh medium containing Aβ1-42 (5 μM), with three different concentrations (50, 100 and 200 μM) of Vanillic acid either alone or in combination with Aβ1-42 (5 μM), and the cells are incubated for an additional 24 h. The control cells receive only DMEM. Following this, the cells are incubated with MTT solution for another 2-4 h at 37°C. Subsequently, the medium in each well is replaced with DMSO. Finally, the absorbance of the solution in each well at 570 nm is measured using an ApoTox instrument. All experiments are performed independently in triplicate[2].

[Animal admin]

Mice[1] During the experiments, Male Swiss mice (25-30 g) receive intraperitoneal (3, 10, or 30 mg/kg) treatment with Vanillic acid or vehicle (5% Tween 80 diluted in saline) 1 h before or 24 h after inflammatory stimuli injection[1].

[References]

[1]. Calixto-Campos C, et al. Vanillic acid Inhibits Inflammatory Pain by Inhibiting Neutrophil Recruitment, Oxidative Stress, Cytokine Production, and NFκB Activation in Mice. J Nat Prod. 2015 Aug 28;78(8):1799-808.

[2]. Amin FU, et al. Vanillic acid attenuates Aβ_1-42-induced oxidative stress and cognitive impairment in mice. Sci Rep. 2017 Jan 18;7:40753.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
353.4±27.0 °C at 760 mmHg

[ Melting Point ]:
208-210 °C(lit.)

[ Molecular Formula ]:
C₈H₈O₄

[ Molecular Weight ]:
168.147

[ Flash Point ]:
149.4±17.2 °C

[ Exact Mass ]:
168.042252

[ PSA ]:
66.76000

[ LogP ]:
1.33

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.586

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

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YW5300000

CHEMICAL NAME :: Vanillic acid

CAS REGISTRY NUMBER :: 121-34-6

BEILSTEIN REFERENCE NO. :: 2208364

LAST UPDATED :: 199710

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C8-H8-O4

MOLECULAR WEIGHT :: 168.16

WISWESSER LINE NOTATION :: QVR DQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5020 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2691 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 50 gm/L

REFERENCE :: CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 14,251,1981

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
YW5300000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ 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%

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