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
Vanillic acid prevents altered ion pumps, ions, inhibits Fas-receptor and caspase mediated apoptosis-signaling pathway and cardiomyocyte death in myocardial infarcted rats.	2015-05-05	25794854
Resveratrol and EGCG bind directly and distinctively to miR-33a and miR-122 and modulate divergently their levels in hepatic cells.	2014-01	24165878
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.	2013-10	23800587
Methylenebissantin: a rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase.	2012-01-01	22082562
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011-02-08	21142015
Single-gene tuning of Caulobacter cell cycle period and noise, swarming motility, and surface adhesion.	2010-12-21	21179017
Quinone-dependent D-lactate dehydrogenase Dld (Cg1027) is essential for growth of Corynebacterium glutamicum on D-lactate.	2010-12-15	21159175
[Constituents of Gymnadenia conopsea].	2010-11	21322946
Ether cleaving methyltransferases of the strict anaerobe Acetobacterium dehalogenans: controlling the substrate spectrum by genetic engineering of the N-terminus.	2010-10	20923421
Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols.	2010-08	22254058
The metabolic enzyme CTP synthase forms cytoskeletal filaments.	2010-08	20639870
Photoenhanced degradation of veratraldehyde upon the heterogeneous ozone reactions.	2010-07-21	20502834
Enrichment of acetogenic bacteria in high rate anaerobic reactors under mesophilic and thermophilic conditions.	2010-07	20554304
Genomes of three tomato pathogens within the Ralstonia solanacearum species complex reveal significant evolutionary divergence.	2010-06-15	20550686
Synthesis of bosutinib from 3-methoxy-4-hydroxybenzoic acid.	2010-06-11	20657439
Fungi unearthed: transcripts encoding lignocellulolytic and chitinolytic enzymes in forest soil.	2010-06-04	20532045
Nematicidal natural products from the aerial parts of Buddleja crispa.	2010-05	20461624
The beta-ketoadipate pathway of Acinetobacter baylyi undergoes carbon catabolite repression, cross-regulation and vertical regulation, and is affected by Crc.	2010-05	20110298
Global transcriptome analysis of spore formation in Myxococcus xanthus reveals a locus necessary for cell differentiation.	2010-04-26	20420673
Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum.	2010-04-19	20419105
YfiBNR mediates cyclic di-GMP dependent small colony variant formation and persistence in Pseudomonas aeruginosa.	2010-03-12	20300602
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
Cytoplasmic acidification and the benzoate transcriptome in Bacillus subtilis.	2009-12-14	20011599
Serratene triterpenoids from Palhinhaea cernua var. sikkimensis.	2009-12	19952448
Antioxidant and radical scavenging properties of Malva sylvestris.	2009-07	19731587
Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.	2009-04-10	19189963
Antimicrobial phenolic compounds from Anabasis aphylla L.	2009-03	19413118
Genetic and computational identification of a conserved bacterial metabolic module.	2008-12	19096521
Encapsulation of flavor molecules, 4-hydroxy-3-methoxy benzoic acid, into layered inorganic nanoparticles for controlled release of flavor.	2008-10	19198382
Aromatic degradative pathways in Acinetobacter baylyi underlie carbon catabolite repression.	2008-10	18832315
Carbon metabolism of the moderately acid-tolerant acetogen Clostridium drakei isolated from peat.	2008-10	18710398
Preparation of lipophilic alkyl (hydroxy)benzoates by solvent-free lipase-catalyzed esterification and transesterification.	2008-08	18542947
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.	2008-08	18511436
Complete genome sequence of the N2-fixing broad host range endophyte Klebsiella pneumoniae 342 and virulence predictions verified in mice.	2008-07-25	18654632
Crystal structure of the outer membrane protein OpdK from Pseudomonas aeruginosa.	2008-07	18611376
Two new phenolic water-soluble constituents from branch bark of Davidia involucrata.	2008-04-15	18415854
Comparative analysis of Acinetobacters: three genomes for three lifestyles.	2008-03-19	18350144
Screen for localized proteins in Caulobacter crescentus.	2008-03-12	18335033
Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification.	2008-03-12	18275147
Bacterial carbon processing by generalist species in the coastal ocean.	2008-02-07	18223640
A norsesquiterpene lactone and a benzoic acid derivative from the leaves of Cyclocarya paliurus and their glucosidase and glycogen phosphorylase inhibiting activities.	2008-02	18300194
Properties of the reversible nonoxidative vanillate/4-hydroxybenzoate decarboxylase from Bacillus subtilis.	2008-01	18388975
A complete collection of single-gene deletion mutants of Acinetobacter baylyi ADP1.	2008	18319726
Characterization of ligV essential for catabolism of vanillin by Sphingomonas paucimobilis SYK-6.	2007-10	17928721
[Studies on chemical constituents of leaves of Cassia angustifolia].	2007-09	18236748
Effect of low and very low doses of simple phenolics on plant peroxidase activity.	2004-04	19330128
Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure.	1993-09	8375048
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.	1979-07	455649
On the occurence of vanillic acid in human brain and cerebrospinal fluid.	1976-04-23	57225

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