Details
| 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
| Molecular Formula | C8H8O3 |
| Molecular Weight | 152.1473 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28077989 |
16.25 µM [IC50] | ||
Target ID: CHEMBL4357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25674660 |
81.5 µM [IC50] | ||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23715789 |
0.037 mM [IC50] | ||
Target ID: CHEMBL1781864 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27084583 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast. | 2003-03-20 |
|
| Colorimetric determination of gabapentin in pharmaceutical formulation. | 2003-02-05 |
|
| Probing suggested catalytic domains of glycosyltransferases by site-directed mutagenesis. | 2003-02 |
|
| Photo-Fenton treatment of water containing natural phenolic pollutants. | 2003-01 |
|
| Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys. | 2002-12-18 |
|
| Polymeric procyanidins as radical-scavenging components in red-hulled rice. | 2002-12-18 |
|
| Determination of available phenolic compounds in soils by liquid chromatography with solid-phase extraction. | 2002-12-13 |
|
| In vitro evaluation of thiazolyl and benzothiazolyl Schiff bases on pig cartilage. | 2002-12 |
|
| Protection against damaged DNA in the single cell by polyphenols. | 2002-12 |
|
| Vibrational analysis of substituted phenols: part I. Vibrational spectra, normal coordinate analysis and transferability of force constants of some formyl-, methoxy-, formylmethoxy-, methyl- and halogeno-phenols. | 2002-12 |
|
| Chromone and phenanthrene alkaloids from Dennettia tripetala. | 2002-12 |
|
| Properties of a laccase produced by Phanerochaete flavido-alba induced by vanillin. | 2002-12 |
|
| Infrared imaging of laser-induced heating during Raman spectroscopy of pharmaceutical solids. | 2002-11-07 |
|
| Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation. | 2002-11-06 |
|
| Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. | 2002-11 |
|
| A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran. | 2002-10-25 |
|
| Authentication of natural vanilla flavorings: isotopic characterization using degradation of vanillin into guaiacol. | 2002-10-23 |
|
| Mechanism of potent antiperoxidative effect of capsaicin. | 2002-10-10 |
|
| Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects. | 2002-10-09 |
|
| [Effect of vanillin and P-hydroxybenzoic acid on physiological characteristics of Chinese fir seedlings]. | 2002-10 |
|
| O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. | 2002-10 |
|
| Amperometric biosensors for detection of phenol using chemically modified electrodes containing immobilized bacteria. | 2002-10 |
|
| A novel strategy for the synthesis of benzofuran skeleton neolignans: application to ailanthoidol, XH-14, and obovaten. | 2002-09-20 |
|
| Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays. | 2002-09-11 |
|
| Changes in the HPLC phenolic profile of virgin olive oil from young trees (Olea europaea L. Cv. Arbequina) grown under different deficit irrigation strategies. | 2002-09-11 |
|
| [Do blind persons have a better sense of smell than normal sighted people?]. | 2002-09 |
|
| New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. | 2002-09 |
|
| Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits. | 2002-09 |
|
| Inhibitory effect of vanillin-like compounds on respiration and growth of adenocarcinoma TA3 and its multiresistant variant TA3-MTX-R. | 2002-09 |
|
| Odorant differentiated pattern of cerebral activation: comparison of acetone and vanillin. | 2002-09 |
|
| Quantitative determination of oleane derivatives in Terminalia arjuna by high performance thin layer chromatography. | 2002-08-20 |
|
| Asymmetry of pleasant vs. unpleasant odor processing during affective judgment in humans. | 2002-08-16 |
|
| Determination of minor and trace volatile compounds in wine by solid-phase extraction and gas chromatography with mass spectrometric detection. | 2002-08-09 |
|
| Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants. | 2002-08-01 |
|
| Bioactive constituents of the seeds of Brucea javanica. | 2002-08 |
|
| Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans. | 2002-07-26 |
|
| Application of pulsed field gradient NMR techniques for investigating binding of flavor compounds to macromolecules. | 2002-07-17 |
|
| Maturing wines in oak barrels. Effects of origin, volume, and age of the barrel on the wine volatile composition. | 2002-05-22 |
|
| In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum. | 2002-05 |
|
| Influence of oak wood on the aromatic composition and quality of wines with different tannin contents. | 2002-04-24 |
|
| Transformation of the Pseudonocardiaceae amycolatopsis sp. strain HR167 is highly dependent on the physiological state of the cells. | 2002-03 |
|
| Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS. | 2002-03 |
|
| Aspergillus flavus dose-response curves to selected natural and synthetic antimicrobials. | 2002-03 |
|
| Population dynamics of euglossinae bees (Hymenoptera, Apidae) in an early second-growth forest of Cajual Island, in the state of Maranhão, Brazil. | 2002-02 |
|
| Non-specific olfactory aversion induced by intrabulbar infusion of the GABA(A) receptor antagonist bicuculline in young rats. | 2002 |
|
| Purification and characterization of a microbial dehydrogenase: a vanillin:NAD(P)+ oxidoreductase. | 2002 |
|
| Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. | 2002 |
|
| Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001-11 |
|
| Production of oxychemicals from precipitated hardwood lignin. | 2001 |
|
| Detoxification of lignocellulose hydrolysates with ion-exchange resins. | 2001 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28077989
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28077989
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 13:29:58 GMT 2025
by
admin
on
Wed Apr 02 13:29:58 GMT 2025
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| Record UNII |
CHI530446X
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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EPA PESTICIDE CODE |
115801
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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JECFA EVALUATION |
VANILLIN
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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DTXSID0021969
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C45678
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CONCEPT | Industrial Aid | ||
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m11390
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PRIMARY | Merck Index | ||
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1711009
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819
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100000076965
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1027
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SUB15686MIG
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C100058
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403658
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CHI530446X
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48383
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CHI530446X
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121-33-5
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1710006
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1368176
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15351
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1183
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204-465-2
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VANILLIN
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C76737
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CHEMBL13883
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18346
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE |
MINOR
PLASMA
|