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=C(O)C=CC(C=O)=C1
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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: WP408 |
16.25 µM [IC50] | ||
Target ID: CHEMBL4357 |
81.5 µM [IC50] | ||
Target ID: CHEMBL220 |
0.037 mM [IC50] | ||
Target ID: CHEMBL1781864 |
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 |
|---|---|---|
| Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001 Nov |
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| Production of oxychemicals from precipitated hardwood lignin. | 2001 Spring |
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| Detoxification of lignocellulose hydrolysates with ion-exchange resins. | 2001 Spring |
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| Non-specific olfactory aversion induced by intrabulbar infusion of the GABA(A) receptor antagonist bicuculline in young rats. | 2002 |
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| Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. | 2002 |
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| Protective activities of some phenolic 1,3-diketones against lipid peroxidation: possible involvement of the 1,3-diketone moiety. | 2002 Apr 2 |
|
| Influence of oak wood on the aromatic composition and quality of wines with different tannin contents. | 2002 Apr 24 |
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| Bioactive constituents of the seeds of Brucea javanica. | 2002 Aug |
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| Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants. | 2002 Aug 1 |
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| Asymmetry of pleasant vs. unpleasant odor processing during affective judgment in humans. | 2002 Aug 16 |
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| Determination of minor and trace volatile compounds in wine by solid-phase extraction and gas chromatography with mass spectrometric detection. | 2002 Aug 9 |
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| In vitro evaluation of thiazolyl and benzothiazolyl Schiff bases on pig cartilage. | 2002 Dec |
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| Protection against damaged DNA in the single cell by polyphenols. | 2002 Dec |
|
| 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 Dec |
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| Chromone and phenanthrene alkaloids from Dennettia tripetala. | 2002 Dec |
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| Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys. | 2002 Dec 18 |
|
| Population dynamics of euglossinae bees (Hymenoptera, Apidae) in an early second-growth forest of Cajual Island, in the state of Maranhão, Brazil. | 2002 Feb |
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| Application of pulsed field gradient NMR techniques for investigating binding of flavor compounds to macromolecules. | 2002 Jul 17 |
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| Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans. | 2002 Jul 26 |
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| Quantitative determination of oleane derivatives in Terminalia arjuna by high performance thin layer chromatography. | 2002 Jul-Aug |
|
| A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran. | 2002 Jul-Dec |
|
| Transformation of the Pseudonocardiaceae amycolatopsis sp. strain HR167 is highly dependent on the physiological state of the cells. | 2002 Mar |
|
| Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS. | 2002 Mar |
|
| Aspergillus flavus dose-response curves to selected natural and synthetic antimicrobials. | 2002 Mar |
|
| Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. | 2002 Mar 27 |
|
| In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum. | 2002 May |
|
| Maturing wines in oak barrels. Effects of origin, volume, and age of the barrel on the wine volatile composition. | 2002 May 22 |
|
| Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. | 2002 Nov |
|
| Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation. | 2002 Nov 6 |
|
| Infrared imaging of laser-induced heating during Raman spectroscopy of pharmaceutical solids. | 2002 Nov 7 |
|
| Determination of available phenolic compounds in soils by liquid chromatography with solid-phase extraction. | 2002 Nov-Dec |
|
| [Effect of vanillin and P-hydroxybenzoic acid on physiological characteristics of Chinese fir seedlings]. | 2002 Oct |
|
| O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. | 2002 Oct |
|
| Amperometric biosensors for detection of phenol using chemically modified electrodes containing immobilized bacteria. | 2002 Oct |
|
| Mechanism of potent antiperoxidative effect of capsaicin. | 2002 Oct 10 |
|
| Authentication of natural vanilla flavorings: isotopic characterization using degradation of vanillin into guaiacol. | 2002 Oct 23 |
|
| Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects. | 2002 Oct 9 |
|
| [Do blind persons have a better sense of smell than normal sighted people?]. | 2002 Sep |
|
| New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. | 2002 Sep |
|
| 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 Sep |
|
| Inhibitory effect of vanillin-like compounds on respiration and growth of adenocarcinoma TA3 and its multiresistant variant TA3-MTX-R. | 2002 Sep |
|
| Odorant differentiated pattern of cerebral activation: comparison of acetone and vanillin. | 2002 Sep |
|
| Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays. | 2002 Sep 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 Sep 11 |
|
| A novel strategy for the synthesis of benzofuran skeleton neolignans: application to ailanthoidol, XH-14, and obovaten. | 2002 Sep 20 |
|
| Purification and characterization of a microbial dehydrogenase: a vanillin:NAD(P)+ oxidoreductase. | 2002 Spring |
|
| Probing suggested catalytic domains of glycosyltransferases by site-directed mutagenesis. | 2003 Feb |
|
| Colorimetric determination of gabapentin in pharmaceutical formulation. | 2003 Feb 5 |
|
| Photo-Fenton treatment of water containing natural phenolic pollutants. | 2003 Jan |
|
| Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast. | 2003 Mar 20 |
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
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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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ALTERNATIVE | |||
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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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PRIMARY | RxNorm | ||
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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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PARENT (METABOLITE)
SUBSTANCE RECORD
