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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=CC(=CC=C1O)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 trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure.
1993 Sep
Comamonas testosteroni BR6020 possesses a single genetic locus for extradiol cleavage of protocatechuate.
2001 Aug
Clostridium uliginosum sp. nov., a novel acid-tolerant, anaerobic bacterium with connecting filaments.
2001 May
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Amperometric biosensors for detection of phenol using chemically modified electrodes containing immobilized bacteria.
2002 Oct
Alicycliphilus denitrificans gen. nov., sp. nov., a cyclohexanol-degrading, nitrate-reducing beta-proteobacterium.
2003 Jan
Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.
2004 Feb
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Phenyl methyl ethers: novel electron donors for respiratory growth of Desulfitobacterium hafniense and Desulfitobacterium sp. strain PCE-S.
2004 Mar
Functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway.
2005 Dec 15
[Studies on the chemical constituents from Fructus Rubi].
2005 Feb
Key enzymes of the protocatechuate branch of the beta-ketoadipate pathway for aromatic degradation in Corynebacterium glutamicum.
2005 Jun
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.
2005 Mar
Clostridium carboxidivorans sp. nov., a solvent-producing clostridium isolated from an agricultural settling lagoon, and reclassification of the acetogen Clostridium scatologenes strain SL1 as Clostridium drakei sp. nov.
2005 Sep
Antibacterial activity directed isolation of compounds from Onosma hispidum.
2006
[Study on the chemical constituents of Ardisia chinensis].
2006 Apr
Transcriptional regulation of catabolic pathways for aromatic compounds in Corynebacterium glutamicum.
2006 Dec 7
Structural analysis of ligand binding and catalysis in chorismate lyase.
2006 Jan 1
Transition metal-catalyzed nonoxidative decarboxylation reactions.
2006 Sep 5
Phenols and lignans from Chenopodium album.
2006 Sep-Oct
[Studies on chemical constituents from Serissa serissoides].
2007 Apr
Anaerobic oxalate consumption by microorganisms in forest soils.
2007 Apr
Reactivity of hydroxybenzoic acids in the hydrogen-isotope exchange reaction.
2007 May
Oxanthrone C-glycosides and epoxynaphthoquinol from the roots of Rumex japonicus.
2007 Oct
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
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
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
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
Antioxidant and radical scavenging properties of Malva sylvestris.
2009 Jul
Biochemistry and occurrence of o-demethylation in plant metabolism.
2010
Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum.
2010 Apr 19
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
Nematicidal natural products from the aerial parts of Buddleja crispa.
2010 May
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
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 Thu Jul 06 02:46:35 UTC 2023
Edited
by admin
on Thu Jul 06 02:46:35 UTC 2023
Record UNII
GM8Q3JM2Y8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VANILLIC ACID
MI  
Systematic Name English
NSC-674322
Code English
M-METHOXY-P-HYDROXY-BENZOIC ACID
Common Name English
VANILLIC ACID [MI]
Common Name English
VANILLIC ACID [INCI]
Common Name English
FEMA NO. 3988
Code English
VA
Common Name English
BENZOIC ACID, 4-HYDROXY-3-METHOXY-
Common Name English
4-HYDROXY-3-METHOXYBENZOIC ACID
FHFI  
Systematic 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 Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID6059522
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
PUBCHEM
8468
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
EVMPD
SUB129304
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
FDA UNII
GM8Q3JM2Y8
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
NSC
674322
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
NSC
3987
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
SMS_ID
100000155284
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
MERCK INDEX
M11389
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB02130
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
WIKIPEDIA
VANILLIC ACID
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
CAS
121-34-6
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-466-8
Created by admin on Thu Jul 06 02:46:35 UTC 2023 , Edited by admin on Thu Jul 06 02:46:35 UTC 2023
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