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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8O3
Molecular Weight 152.1476
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VANILLIN

SMILES

COc1cc(ccc1O)C=O

InChI

InChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

HIDE SMILES / InChI

Molecular Formula C8H8O3
Molecular Weight 152.1476
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).

CNS Activity

Curator's Comment:: Vanillin is reported to cross the blood brain barrier and also displayed antioxidant and neuroprotective activities.

Originator

Curator's Comment:: Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil.
2001 Nov
Production of oxychemicals from precipitated hardwood lignin.
2001 Spring
Detoxification of lignocellulose hydrolysates with ion-exchange resins.
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
Influence of oak wood on the aromatic composition and quality of wines with different tannin contents.
2002 Apr 24
Bioactive constituents of the seeds of Brucea javanica.
2002 Aug
Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants.
2002 Aug 1
Asymmetry of pleasant vs. unpleasant odor processing during affective judgment in humans.
2002 Aug 16
Determination of minor and trace volatile compounds in wine by solid-phase extraction and gas chromatography with mass spectrometric detection.
2002 Aug 9
In vitro evaluation of thiazolyl and benzothiazolyl Schiff bases on pig cartilage.
2002 Dec
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
Chromone and phenanthrene alkaloids from Dennettia tripetala.
2002 Dec
Properties of a laccase produced by Phanerochaete flavido-alba induced by vanillin.
2002 Dec
Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys.
2002 Dec 18
Polymeric procyanidins as radical-scavenging components in red-hulled rice.
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
Application of pulsed field gradient NMR techniques for investigating binding of flavor compounds to macromolecules.
2002 Jul 17
Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans.
2002 Jul 26
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
Characterization of degradation products from alkaline wet oxidation of wheat straw.
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
Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.).
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:19:09 UTC 2021
Edited
by admin
on Fri Jun 25 21:19:09 UTC 2021
Record UNII
CHI530446X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VANILLIN
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   VANDF  
INCI  
Official Name English
VANILLALDEHYDE
Systematic Name English
VANILLIN [MART.]
Common Name English
4-HYDROXY-3-METHOXY-BENZYLDEHYDE
Common Name English
NSC-403658
Code English
VANILLIN, NATURAL [FHFI]
Common Name English
FEMA NO. 3107
Code English
METHYLPROTOCATECHUIC ALDEHYDE
Common Name English
BENZALDEHYDE, 4-HYDROXY-3-METHOXY-
Systematic Name English
VANILLIN [HSDB]
Common Name English
VANILLIN [VANDF]
Common Name English
VANILLIN [EP MONOGRAPH]
Common Name English
NPLC-0145
Code English
VANILLIN MELTING POINT STANDARD
USP-RS  
Common Name English
NSC-48383
Code English
NSC-15351
Code English
H-0264
Code English
VANILLIN [FCC]
Common Name English
VANILLIN [MI]
Common Name English
VANILLIC ALDEHYDE
Common Name English
VANILLIN [FHFI]
Common Name English
4-HYDROXY-M-ANISALDEHYDE
Systematic Name English
4-HYDROXY-3-METHOXYBENZALDEHYDE
Systematic Name English
VANILLIN [INCI]
Common Name English
LIOXIN
Brand Name English
RHOVANIL
Common Name English
VANILLIN [USP-RS]
Common Name English
P-HYDROXY-M-METHOXYBENZALDEHYDE
Common Name English
VANILLIN [II]
Common Name English
3-METHOXY-4-HYDROXYBENZALDEHYDE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 115801
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
JECFA EVALUATION VANILLIN
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
Code System Code Type Description
EPA CompTox
121-33-5
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
CONCEPT Industrial Aid
MERCK INDEX
M11390
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY Merck Index
HSDB
1027
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
EVMPD
SUB15686MIG
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
MESH
C100058
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
USP_CATALOG
1710006
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY USP-RS
FDA UNII
CHI530446X
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
CAS
121-33-5
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
USP_CATALOG
1711009
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY USP-RS
RXCUI
1368176
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY RxNorm
PUBCHEM
1183
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-465-2
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
WIKIPEDIA
VANILLIN
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
NCI_THESAURUS
C76737
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL13883
Created by admin on Fri Jun 25 21:19:09 UTC 2021 , Edited by admin on Fri Jun 25 21:19:09 UTC 2021
PRIMARY
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