VANILLIC ACID

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 Search

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

Title	Date	PubMed
On the occurence of vanillic acid in human brain and cerebrospinal fluid.	1976 Apr 23	57225
Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure.	1993 Sep	8375048
Comamonas testosteroni BR6020 possesses a single genetic locus for extradiol cleavage of protocatechuate.	2001 Aug	11495993
Clostridium uliginosum sp. nov., a novel acid-tolerant, anaerobic bacterium with connecting filaments.	2001 May	11411680
Antiviral activity of Plantago major extracts and related compounds in vitro.	2002 Jul	12076751
Amperometric biosensors for detection of phenol using chemically modified electrodes containing immobilized bacteria.	2002 Oct	12243905
Alicycliphilus denitrificans gen. nov., sp. nov., a cyclohexanol-degrading, nitrate-reducing beta-proteobacterium.	2003 Jan	12661531
Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.	2004 Feb	14763983
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.	2004 Jul 2	15117964
Phenyl methyl ethers: novel electron donors for respiratory growth of Desulfitobacterium hafniense and Desulfitobacterium sp. strain PCE-S.	2004 Mar	14758469
Functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway.	2005 Dec 15	16242864
[Studies on the chemical constituents from Fructus Rubi].	2005 Feb	15981877
Key enzymes of the protocatechuate branch of the beta-ketoadipate pathway for aromatic degradation in Corynebacterium glutamicum.	2005 Jun	16092756
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
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	16166714
Antibacterial activity directed isolation of compounds from Onosma hispidum.	2006	16338589
[Study on the chemical constituents of Ardisia chinensis].	2006 Apr	16913485
Transcriptional regulation of catabolic pathways for aromatic compounds in Corynebacterium glutamicum.	2006 Dec 7	17183485
Structural analysis of ligand binding and catalysis in chorismate lyase.	2006 Jan 1	16343413
Transition metal-catalyzed nonoxidative decarboxylation reactions.	2006 Sep 5	16939193
Phenols and lignans from Chenopodium album.	2006 Sep-Oct	17019936
[Studies on chemical constituents from Serissa serissoides].	2007 Apr	17583202
Anaerobic oxalate consumption by microorganisms in forest soils.	2007 Apr	17350229
Reactivity of hydroxybenzoic acids in the hydrogen-isotope exchange reaction.	2007 May	17261367
Oxanthrone C-glycosides and epoxynaphthoquinol from the roots of Rumex japonicus.	2007 Oct	17603087
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.	2008 Aug	18511436
Genetic and computational identification of a conserved bacterial metabolic module.	2008 Dec	19096521
Crystal structure of the outer membrane protein OpdK from Pseudomonas aeruginosa.	2008 Jul	18611376
Complete genome sequence of the N2-fixing broad host range endophyte Klebsiella pneumoniae 342 and virulence predictions verified in mice.	2008 Jul 25	18654632
Comparative analysis of Acinetobacters: three genomes for three lifestyles.	2008 Mar 19	18350144
Encapsulation of flavor molecules, 4-hydroxy-3-methoxy benzoic acid, into layered inorganic nanoparticles for controlled release of flavor.	2008 Oct	19198382
Carbon metabolism of the moderately acid-tolerant acetogen Clostridium drakei isolated from peat.	2008 Oct	18710398
Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.	2009 Apr 10	19189963
Serratene triterpenoids from Palhinhaea cernua var. sikkimensis.	2009 Dec	19952448
Antioxidant and radical scavenging properties of Malva sylvestris.	2009 Jul	19731587
Biochemistry and occurrence of o-demethylation in plant metabolism.	2010	21423357
Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum.	2010 Apr 19	20419105
Single-gene tuning of Caulobacter cell cycle period and noise, swarming motility, and surface adhesion.	2010 Dec 21	21179017
Enrichment of acetogenic bacteria in high rate anaerobic reactors under mesophilic and thermophilic conditions.	2010 Jul	20554304
Photoenhanced degradation of veratraldehyde upon the heterogeneous ozone reactions.	2010 Jul 21	20502834
Nematicidal natural products from the aerial parts of Buddleja crispa.	2010 May	20461624
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011 Feb 8	21142015
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.	2013 Oct	23800587
Resveratrol and EGCG bind directly and distinctively to miR-33a and miR-122 and modulate divergently their levels in hepatic cells.	2014 Jan	24165878
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	25794854

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

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

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