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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8O4
Molecular Weight 168.1467
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VANILLIC ACID

SMILES

COC1=C(O)C=CC(=C1)C(O)=O

InChI

InChIKey=WKOLLVMJNQIZCI-UHFFFAOYSA-N
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

HIDE SMILES / InChI

Molecular Formula C8H8O4
Molecular Weight 168.1467
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
On the occurence of vanillic acid in human brain and cerebrospinal fluid.
1976 Apr 23
Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma.
1979 Jul
Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure.
1993 Sep
Effect of low and very low doses of simple phenolics on plant peroxidase activity.
2004 Apr
Characterization of ligV essential for catabolism of vanillin by Sphingomonas paucimobilis SYK-6.
2007 Oct
[Studies on chemical constituents of leaves of Cassia angustifolia].
2007 Sep
A complete collection of single-gene deletion mutants of Acinetobacter baylyi ADP1.
2008
Two new phenolic water-soluble constituents from branch bark of Davidia involucrata.
2008 Apr 15
Preparation of lipophilic alkyl (hydroxy)benzoates by solvent-free lipase-catalyzed esterification and transesterification.
2008 Aug
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.
2008 Aug
Genetic and computational identification of a conserved bacterial metabolic module.
2008 Dec
A norsesquiterpene lactone and a benzoic acid derivative from the leaves of Cyclocarya paliurus and their glucosidase and glycogen phosphorylase inhibiting activities.
2008 Feb
Bacterial carbon processing by generalist species in the coastal ocean.
2008 Feb 7
Properties of the reversible nonoxidative vanillate/4-hydroxybenzoate decarboxylase from Bacillus subtilis.
2008 Jan
Crystal structure of the outer membrane protein OpdK from Pseudomonas aeruginosa.
2008 Jul
Complete genome sequence of the N2-fixing broad host range endophyte Klebsiella pneumoniae 342 and virulence predictions verified in mice.
2008 Jul 25
Screen for localized proteins in Caulobacter crescentus.
2008 Mar 12
Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification.
2008 Mar 12
Comparative analysis of Acinetobacters: three genomes for three lifestyles.
2008 Mar 19
Encapsulation of flavor molecules, 4-hydroxy-3-methoxy benzoic acid, into layered inorganic nanoparticles for controlled release of flavor.
2008 Oct
Aromatic degradative pathways in Acinetobacter baylyi underlie carbon catabolite repression.
2008 Oct
Carbon metabolism of the moderately acid-tolerant acetogen Clostridium drakei isolated from peat.
2008 Oct
Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.
2009 Apr 10
Serratene triterpenoids from Palhinhaea cernua var. sikkimensis.
2009 Dec
Cytoplasmic acidification and the benzoate transcriptome in Bacillus subtilis.
2009 Dec 14
Antioxidant and radical scavenging properties of Malva sylvestris.
2009 Jul
Antimicrobial phenolic compounds from Anabasis aphylla L.
2009 Mar
Biochemistry and occurrence of o-demethylation in plant metabolism.
2010
Premature terminator analysis sheds light on a hidden world of bacterial transcriptional attenuation.
2010
Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum.
2010 Apr 19
Global transcriptome analysis of spore formation in Myxococcus xanthus reveals a locus necessary for cell differentiation.
2010 Apr 26
Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols.
2010 Aug
The metabolic enzyme CTP synthase forms cytoskeletal filaments.
2010 Aug
Quinone-dependent D-lactate dehydrogenase Dld (Cg1027) is essential for growth of Corynebacterium glutamicum on D-lactate.
2010 Dec 15
Single-gene tuning of Caulobacter cell cycle period and noise, swarming motility, and surface adhesion.
2010 Dec 21
Enrichment of acetogenic bacteria in high rate anaerobic reactors under mesophilic and thermophilic conditions.
2010 Jul
Photoenhanced degradation of veratraldehyde upon the heterogeneous ozone reactions.
2010 Jul 21
Synthesis of bosutinib from 3-methoxy-4-hydroxybenzoic acid.
2010 Jun 11
Genomes of three tomato pathogens within the Ralstonia solanacearum species complex reveal significant evolutionary divergence.
2010 Jun 15
Fungi unearthed: transcripts encoding lignocellulolytic and chitinolytic enzymes in forest soil.
2010 Jun 4
YfiBNR mediates cyclic di-GMP dependent small colony variant formation and persistence in Pseudomonas aeruginosa.
2010 Mar 12
Nematicidal natural products from the aerial parts of Buddleja crispa.
2010 May
The beta-ketoadipate pathway of Acinetobacter baylyi undergoes carbon catabolite repression, cross-regulation and vertical regulation, and is affected by Crc.
2010 May
[Constituents of Gymnadenia conopsea].
2010 Nov
Ether cleaving methyltransferases of the strict anaerobe Acetobacterium dehalogenans: controlling the substrate spectrum by genetic engineering of the N-terminus.
2010 Oct
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Methylenebissantin: a rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase.
2012 Jan 1
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.
2013 Oct
Resveratrol and EGCG bind directly and distinctively to miR-33a and miR-122 and modulate divergently their levels in hepatic cells.
2014 Jan
Vanillic acid prevents altered ion pumps, ions, inhibits Fas-receptor and caspase mediated apoptosis-signaling pathway and cardiomyocyte death in myocardial infarcted rats.
2015 May 5
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:55:14 GMT 2025
Edited
by admin
on Mon Mar 31 19:55:14 GMT 2025
Record UNII
GM8Q3JM2Y8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VANILLIC ACID
MI  
Systematic Name English
4-HYDROXY-3-METHOXYBENZOIC ACID
FHFI  
Preferred Name English
NSC-674322
Code English
M-METHOXY-P-HYDROXY-BENZOIC ACID
Common Name English
VANILLIC ACID [MI]
Common Name English
FEMA NO. 3988
Code English
VA
Common Name English
BENZOIC ACID, 4-HYDROXY-3-METHOXY-
Common Name English
2-METHOXY-4-CARBOXYPHENOL
Systematic Name English
3-METHOXY-4-HYDROXYBENZOIC ACID
Systematic Name English
DROXIDOPA METABOLITE (VA)
Common Name English
4-HYDROXY-3-METHOXYBENZOIC ACID [FHFI]
Common Name English
NSC-3987
Code English
Code System Code Type Description
CHEBI
30816
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID6059522
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
PUBCHEM
8468
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
EVMPD
SUB129304
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
FDA UNII
GM8Q3JM2Y8
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
NSC
674322
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
JECFA MONOGRAPH
892
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
NSC
3987
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
SMS_ID
100000155284
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
MERCK INDEX
m11389
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB02130
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
WIKIPEDIA
VANILLIC ACID
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
CAS
121-34-6
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-466-8
Created by admin on Mon Mar 31 19:55:14 GMT 2025 , Edited by admin on Mon Mar 31 19:55:14 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
PARENT -> METABOLITE
In incubation medium and skin vanillic acid ranged from 0.11 to 7.97% of the radioactivity in each sample at all concentrations.
SKIN
PARENT -> METABOLITE