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=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

Title	Date	PubMed
On the occurence of vanillic acid in human brain and cerebrospinal fluid.	1976 Apr 23	57225
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	455649
Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure.	1993 Sep	8375048
Effect of low and very low doses of simple phenolics on plant peroxidase activity.	2004 Apr	19330128
Characterization of ligV essential for catabolism of vanillin by Sphingomonas paucimobilis SYK-6.	2007 Oct	17928721
[Studies on chemical constituents of leaves of Cassia angustifolia].	2007 Sep	18236748
A complete collection of single-gene deletion mutants of Acinetobacter baylyi ADP1.	2008	18319726
Two new phenolic water-soluble constituents from branch bark of Davidia involucrata.	2008 Apr 15	18415854
Preparation of lipophilic alkyl (hydroxy)benzoates by solvent-free lipase-catalyzed esterification and transesterification.	2008 Aug	18542947
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
A norsesquiterpene lactone and a benzoic acid derivative from the leaves of Cyclocarya paliurus and their glucosidase and glycogen phosphorylase inhibiting activities.	2008 Feb	18300194
Bacterial carbon processing by generalist species in the coastal ocean.	2008 Feb 7	18223640
Properties of the reversible nonoxidative vanillate/4-hydroxybenzoate decarboxylase from Bacillus subtilis.	2008 Jan	18388975
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
Screen for localized proteins in Caulobacter crescentus.	2008 Mar 12	18335033
Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification.	2008 Mar 12	18275147
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
Aromatic degradative pathways in Acinetobacter baylyi underlie carbon catabolite repression.	2008 Oct	18832315
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
Cytoplasmic acidification and the benzoate transcriptome in Bacillus subtilis.	2009 Dec 14	20011599
Antioxidant and radical scavenging properties of Malva sylvestris.	2009 Jul	19731587
Antimicrobial phenolic compounds from Anabasis aphylla L.	2009 Mar	19413118
Biochemistry and occurrence of o-demethylation in plant metabolism.	2010	21423357
Premature terminator analysis sheds light on a hidden world of bacterial transcriptional attenuation.	2010	20920266
Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum.	2010 Apr 19	20419105
Global transcriptome analysis of spore formation in Myxococcus xanthus reveals a locus necessary for cell differentiation.	2010 Apr 26	20420673
Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols.	2010 Aug	22254058
The metabolic enzyme CTP synthase forms cytoskeletal filaments.	2010 Aug	20639870
Quinone-dependent D-lactate dehydrogenase Dld (Cg1027) is essential for growth of Corynebacterium glutamicum on D-lactate.	2010 Dec 15	21159175
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
Synthesis of bosutinib from 3-methoxy-4-hydroxybenzoic acid.	2010 Jun 11	20657439
Genomes of three tomato pathogens within the Ralstonia solanacearum species complex reveal significant evolutionary divergence.	2010 Jun 15	20550686
Fungi unearthed: transcripts encoding lignocellulolytic and chitinolytic enzymes in forest soil.	2010 Jun 4	20532045
YfiBNR mediates cyclic di-GMP dependent small colony variant formation and persistence in Pseudomonas aeruginosa.	2010 Mar 12	20300602
Nematicidal natural products from the aerial parts of Buddleja crispa.	2010 May	20461624
The beta-ketoadipate pathway of Acinetobacter baylyi undergoes carbon catabolite repression, cross-regulation and vertical regulation, and is affected by Crc.	2010 May	20110298
[Constituents of Gymnadenia conopsea].	2010 Nov	21322946
Ether cleaving methyltransferases of the strict anaerobe Acetobacterium dehalogenans: controlling the substrate spectrum by genetic engineering of the N-terminus.	2010 Oct	20923421
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011 Feb 8	21142015
Methylenebissantin: a rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase.	2012 Jan 1	22082562
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 `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

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Name

Type

Language

VANILLIC ACID

Systematic Name

English

4-HYDROXY-3-METHOXYBENZOIC ACID

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