Vanillic acid

Modify Date: 2024-01-02 14:07:11

Vanillic acid Structure
Vanillic acid structure
 Common Name Vanillic acid
CAS Number 121-34-6 Molecular Weight 168.147
Density 1.4±0.1 g/cm3 Boiling Point 353.4±27.0 °C at 760 mmHg
Molecular Formula C8H8O4 Melting Point 208-210 °C(lit.)
MSDS Chinese USA Flash Point 149.4±17.2 °C

 Use of Vanillic acid


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].

 Names

Name vanillic acid
Synonym More Synonyms

 Vanillic acid 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
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 Aβ1-42-induced oxidative stress and cognitive impairment in mice. Sci Rep. 2017 Jan 18;7:40753.

 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.

 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

 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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 Synonyms

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
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