| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H8O3 |
| Molecular Weight | 152.1473 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(C=O)=CC=C1O
InChI
InChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
Vanillin (4-hydroxy-3-methoxybenzaldehyde), a pleasant smelling organic aromatic compound, is widely used as a flavoring additive in food, beverage, cosmetic and drug industries. It is reported to cross the blood brain barrier and also displayed antioxidant and neuroprotective activities. Vanillin is a natural substance widely found in many plant species and often used in beverages, foods, cosmetics, and pharmaceutical products. Antioxidant and anticancer potential have been described for this compound. Vanillin has been classified as
a bioantimutagen and is able to inhibit mutagenesis induced
by chemical and physical mutagens in various cell systems. Vanillin, a selective agonist of TRPV1, has been shown to attenuate i.c.v. STZ and AlCl3+d-galactose induced experimental Alzheime's disease (AD).
CNS Activity
Originator
Approval Year
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Drug as victim
Sourcing
PubMed
Patents
Sample Use Guides
Mice: In in vivo antioxidant assay, mice were orally given a
single dose (100 mg/kg) of vanillin. The highest activity in
the plasma ORAC assay was observed at 5 min, when the
concentrations of vanillin, vanillic acid, and protocatechuic
acid were high.
Route of Administration:
Oral
Vanillin at 2.5 mM
inhibited protein oxidation and lipid peroxidation induced by
photosensitization with methylene blue plus light in rat liver
mitochondria. It also exhibited hydroxyl radical and
2,2`-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) radical
cation (ABTS∙+) (IC50 value of 16.25 uM) scavenging
activities. Pretreatment of vanillin (100 nM) also reduced rotenone
induced mitochondrial dysfunction, oxidative stress, and
apoptosis in SH-SY5Y neuroblastoma cells
PARENT (METABOLITE)
SUBSTANCE RECORD
