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 |
|---|---|---|
| Mosaic chromosomal aberrations in synovial fibroblasts of patients with rheumatoid arthritis, osteoarthritis, and other inflammatory joint diseases. | 2001 |
|
| Human potency predictions for aldehydes using the local lymph node assay. | 2001 Aug |
|
| Phytochemical constituents of Artemisia stolonifera. | 2001 Aug |
|
| Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure. | 2001 Dec 27 |
|
| Neural mechanisms of anhedonia in schizophrenia: a PET study of response to unpleasant and pleasant odors. | 2001 Jul 25 |
|
| Enzymatic synthesis of vanillin. | 2001 Jun |
|
| Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents. | 2001 Jun |
|
| Multivariate calibration for the determination of total azadirachtin-related limonoids and simple terpenoids in neem extracts using vanillin assay. | 2001 Mar |
|
| A helical lid converts a sulfotransferase to a dehydratase. | 2001 May |
|
| Adverse reactions to foods. | 2001 May 25 |
|
| Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001 Nov |
|
| Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategies. | 2001 Nov |
|
| Enzymatic extraction and transformation of glucovanillin to vanillin from vanilla green pods. | 2001 Nov |
|
| The erosive effect of herbal tea on dental enamel. | 2001 Nov |
|
| The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. | 2001 Nov 27 |
|
| Influence of operating parameters on the use of the microwave-assisted process (MAP) for the extraction of azadirachtin-related limonoids from neem (Azadirachta indica) under atmospheric pressure conditions. | 2001 Oct |
|
| Functional consequences following infection of the olfactory system by intranasal infusion of the olfactory bulb line variant (OBLV) of mouse hepatitis strain JHM. | 2001 Oct |
|
| Characterization of the eugenol hydroxylase genes (ehyA/ehyB) from the new eugenol-degrading Pseudomonas sp. strain OPS1. | 2001 Sep |
|
| Determination of the active ingredients in Gastrodia rhizoma by capillary electrophoresis with electrochemical detection. | 2001 Sep |
|
| Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies. | 2001 Sep |
|
| Analysis of aromatic aldehydes in brandy and wine by high-performance capillary electrophoresis. | 2001 Sep 1 |
|
| The antimutagenic effect of vanillin and cinnamaldehyde on spontaneous mutation in Salmonella TA104 is due to a reduction in mutations at GC but not AT sites. | 2001 Sep 1 |
|
| Production of oxychemicals from precipitated hardwood lignin. | 2001 Spring |
|
| Non-specific olfactory aversion induced by intrabulbar infusion of the GABA(A) receptor antagonist bicuculline in young rats. | 2002 |
|
| Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. | 2002 |
|
| 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 |
|
| Population dynamics of euglossinae bees (Hymenoptera, Apidae) in an early second-growth forest of Cajual Island, in the state of Maranhão, Brazil. | 2002 Feb |
|
| Colorimetric and fluorimetric methods for determination of panthenol in cosmetic and pharmaceutical formulation. | 2002 Feb 1 |
|
| A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde. | 2002 Jan |
|
| Antioxidant activity of polyphenols in carob pods. | 2002 Jan 16 |
|
| Volatile components of Loureira, Dona Branca, and Treixadura wines. | 2002 Jan 30 |
|
| Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans. | 2002 Jul 26 |
|
| 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 |
|
| Characterization of degradation products from alkaline wet oxidation of wheat straw. | 2002 Mar |
|
| Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. | 2002 Mar 27 |
|
| 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 |
|
| 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 |
|
| [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 |
|
| Inhibitory effect of vanillin-like compounds on respiration and growth of adenocarcinoma TA3 and its multiresistant variant TA3-MTX-R. | 2002 Sep |
|
| Purification and characterization of a microbial dehydrogenase: a vanillin:NAD(P)+ oxidoreductase. | 2002 Spring |
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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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
