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
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 |
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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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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no | ||||
no | ||||
no | ||||
no | ||||
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yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
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yes |
PubMed
Title | Date | PubMed |
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In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation. | 2001 Dec |
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Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure. | 2001 Dec 27 |
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Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001 Nov |
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Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategies. | 2001 Nov |
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Enzymatic extraction and transformation of glucovanillin to vanillin from vanilla green pods. | 2001 Nov |
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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 |
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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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Influence of oak wood on the aromatic composition and quality of wines with different tannin contents. | 2002 Apr 24 |
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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 |
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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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Properties of a laccase produced by Phanerochaete flavido-alba induced by vanillin. | 2002 Dec |
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Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys. | 2002 Dec 18 |
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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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Colorimetric and fluorimetric methods for determination of panthenol in cosmetic and pharmaceutical formulation. | 2002 Feb 1 |
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A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde. | 2002 Jan |
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Antioxidant activity of polyphenols in carob pods. | 2002 Jan 16 |
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Volatile components of Loureira, Dona Branca, and Treixadura wines. | 2002 Jan 30 |
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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 |
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A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran. | 2002 Jul-Dec |
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Transformation of the Pseudonocardiaceae amycolatopsis sp. strain HR167 is highly dependent on the physiological state of the cells. | 2002 Mar |
|
The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities. | 2002 Mar |
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In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum. | 2002 May |
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Maturing wines in oak barrels. Effects of origin, volume, and age of the barrel on the wine volatile composition. | 2002 May 22 |
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Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. | 2002 Nov |
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Infrared imaging of laser-induced heating during Raman spectroscopy of pharmaceutical solids. | 2002 Nov 7 |
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Determination of available phenolic compounds in soils by liquid chromatography with solid-phase extraction. | 2002 Nov-Dec |
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[Effect of vanillin and P-hydroxybenzoic acid on physiological characteristics of Chinese fir seedlings]. | 2002 Oct |
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Amperometric biosensors for detection of phenol using chemically modified electrodes containing immobilized bacteria. | 2002 Oct |
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Mechanism of potent antiperoxidative effect of capsaicin. | 2002 Oct 10 |
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Authentication of natural vanilla flavorings: isotopic characterization using degradation of vanillin into guaiacol. | 2002 Oct 23 |
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[Do blind persons have a better sense of smell than normal sighted people?]. | 2002 Sep |
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Inhibitory effect of vanillin-like compounds on respiration and growth of adenocarcinoma TA3 and its multiresistant variant TA3-MTX-R. | 2002 Sep |
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Odorant differentiated pattern of cerebral activation: comparison of acetone and vanillin. | 2002 Sep |
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Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays. | 2002 Sep 11 |
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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 |
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Purification and characterization of a microbial dehydrogenase: a vanillin:NAD(P)+ oxidoreductase. | 2002 Spring |
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Probing suggested catalytic domains of glycosyltransferases by site-directed mutagenesis. | 2003 Feb |
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Colorimetric determination of gabapentin in pharmaceutical formulation. | 2003 Feb 5 |
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Photo-Fenton treatment of water containing natural phenolic pollutants. | 2003 Jan |
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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
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
Sat Dec 16 19:04:14 GMT 2023
by
admin
on
Sat Dec 16 19:04:14 GMT 2023
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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
Created by
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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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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
MINOR
PLASMA
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