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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
Structure of Vanillin

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

HIDE SMILES / InChI

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).

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
Mosaic chromosomal aberrations in synovial fibroblasts of patients with rheumatoid arthritis, osteoarthritis, and other inflammatory joint diseases.
2001
Changes in low molecular weight phenolic compounds in Spanish, French, and American oak woods during natural seasoning and toasting.
2001 Apr
Human potency predictions for aldehydes using the local lymph node assay.
2001 Aug
In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation.
2001 Dec
Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure.
2001 Dec 27
Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid.
2001 Feb 23
Using an ion-trap MS sensor to differentiate and identify individual components in grapefruit juice headspace volatiles.
2001 Jan
Neural mechanisms of anhedonia in schizophrenia: a PET study of response to unpleasant and pleasant odors.
2001 Jul 25
Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents.
2001 Jun
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil.
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
Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis.
2001 Oct
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
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
Protection against damaged DNA in the single cell by polyphenols.
2002 Dec
Polymeric procyanidins as radical-scavenging components in red-hulled rice.
2002 Dec 18
A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde.
2002 Jan
Antioxidant activity of polyphenols in carob pods.
2002 Jan 16
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
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
Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation.
2002 Nov 6
Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects.
2002 Oct 9
Odorant differentiated pattern of cerebral activation: comparison of acetone and vanillin.
2002 Sep
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
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 Sat Dec 16 19:04:14 GMT 2023
Edited
by admin
on Sat Dec 16 19:04:14 GMT 2023
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 [WHO-DD]
Common 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 Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
JECFA EVALUATION VANILLIN
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0021969
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
CONCEPT Industrial Aid
MERCK INDEX
m11390
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1711009
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
ALTERNATIVE
JECFA MONOGRAPH
819
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
SMS_ID
100000076965
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
HSDB
1027
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
EVMPD
SUB15686MIG
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
MESH
C100058
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
NSC
403658
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
DAILYMED
CHI530446X
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
NSC
48383
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
FDA UNII
CHI530446X
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
CAS
121-33-5
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
RS_ITEM_NUM
1710006
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
RXCUI
1368176
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY RxNorm
NSC
15351
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
PUBCHEM
1183
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-465-2
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
WIKIPEDIA
VANILLIN
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
NCI_THESAURUS
C76737
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL13883
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
CHEBI
18346
Created by admin on Sat Dec 16 19:04:14 GMT 2023 , Edited by admin on Sat Dec 16 19:04:14 GMT 2023
PRIMARY
Related Record Type Details
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