Page last updated: 2024-11-05

n-butyl gallate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

n-Butyl gallate (nBG) is an organic compound that is an ester of gallic acid and n-butanol. It is a white, crystalline solid that is soluble in organic solvents but insoluble in water. It is a common food additive used as an antioxidant to prevent oxidation of fats and oils. nBG is produced by the esterification of gallic acid with n-butanol. It has been shown to have several biological activities, including antioxidant, anti-inflammatory, and anticancer properties. nBG is also used in cosmetics as a preservative and in pharmaceuticals as an antioxidant. Studies on nBG have focused on its potential applications in food, cosmetics, and pharmaceuticals. It is being investigated for its use as a natural antioxidant alternative to synthetic antioxidants, and for its potential therapeutic effects. It is also being studied for its potential use in preventing oxidative stress and inflammation.'

Cross-References

ID SourceID
PubMed CID14128
CHEMBL ID494005
SCHEMBL ID35913
MeSH IDM0064039

Synonyms (37)

Synonym
HMS1577L19
benzoic acid, 3,4,5-trihydroxy-, butyl ester
butyl 3,4,5-trihydroxybenzoate
n-butyl gallate
butyl gallate
1083-41-6
gallic acid, butyl ester
nsc33956
benzoic acid,4,5-trihydroxy-, butyl ester
nsc-33956
progallin butyl
butylester kyseliny gallove [czech]
brn 3032709
nsc 33956
einecs 214-107-7
CBDIVE_013159
bdbm50280382
gallic acid butyl ester
G0186
CHEMBL494005
A801860
butyl 3,4,5-tris(oxidanyl)benzoate
3,4,5-trihydroxybenzoic acid butyl ester
unii-67hz41u710
67hz41u710 ,
butylester kyseliny gallove
4-10-00-02004 (beilstein handbook reference)
FT-0626597
AKOS015914064
SCHEMBL35913
gallic acid n-butyl ester
DTXSID40148490
mfcd00016432
CCG-305745
Q27264133
D90725
gallicacidn-butylester
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Estrogen receptorHomo sapiens (human)IC50 (µMol)8.97000.00000.723732.7000AID1505260
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
antral ovarian follicle growthEstrogen receptorHomo sapiens (human)
epithelial cell developmentEstrogen receptorHomo sapiens (human)
chromatin remodelingEstrogen receptorHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
signal transductionEstrogen receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEstrogen receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEstrogen receptorHomo sapiens (human)
androgen metabolic processEstrogen receptorHomo sapiens (human)
male gonad developmentEstrogen receptorHomo sapiens (human)
negative regulation of gene expressionEstrogen receptorHomo sapiens (human)
positive regulation of phospholipase C activityEstrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayEstrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptorHomo sapiens (human)
response to estradiolEstrogen receptorHomo sapiens (human)
regulation of toll-like receptor signaling pathwayEstrogen receptorHomo sapiens (human)
negative regulation of smooth muscle cell apoptotic processEstrogen receptorHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionEstrogen receptorHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
response to estrogenEstrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
fibroblast proliferationEstrogen receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEstrogen receptorHomo sapiens (human)
stem cell differentiationEstrogen receptorHomo sapiens (human)
regulation of inflammatory responseEstrogen receptorHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
RNA polymerase II preinitiation complex assemblyEstrogen receptorHomo sapiens (human)
uterus developmentEstrogen receptorHomo sapiens (human)
vagina developmentEstrogen receptorHomo sapiens (human)
prostate epithelial cord elongationEstrogen receptorHomo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesisEstrogen receptorHomo sapiens (human)
regulation of branching involved in prostate gland morphogenesisEstrogen receptorHomo sapiens (human)
mammary gland branching involved in pregnancyEstrogen receptorHomo sapiens (human)
mammary gland alveolus developmentEstrogen receptorHomo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongationEstrogen receptorHomo sapiens (human)
protein localization to chromatinEstrogen receptorHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptorHomo sapiens (human)
negative regulation of miRNA transcriptionEstrogen receptorHomo sapiens (human)
regulation of epithelial cell apoptotic processEstrogen receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (26)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
TFIIB-class transcription factor bindingEstrogen receptorHomo sapiens (human)
transcription coregulator bindingEstrogen receptorHomo sapiens (human)
transcription corepressor bindingEstrogen receptorHomo sapiens (human)
transcription coactivator bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
chromatin bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
nuclear receptor activityEstrogen receptorHomo sapiens (human)
steroid bindingEstrogen receptorHomo sapiens (human)
protein bindingEstrogen receptorHomo sapiens (human)
calmodulin bindingEstrogen receptorHomo sapiens (human)
beta-catenin bindingEstrogen receptorHomo sapiens (human)
zinc ion bindingEstrogen receptorHomo sapiens (human)
TBP-class protein bindingEstrogen receptorHomo sapiens (human)
enzyme bindingEstrogen receptorHomo sapiens (human)
protein kinase bindingEstrogen receptorHomo sapiens (human)
nitric-oxide synthase regulator activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor bindingEstrogen receptorHomo sapiens (human)
estrogen response element bindingEstrogen receptorHomo sapiens (human)
identical protein bindingEstrogen receptorHomo sapiens (human)
ATPase bindingEstrogen receptorHomo sapiens (human)
14-3-3 protein bindingEstrogen receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusEstrogen receptorHomo sapiens (human)
nucleoplasmEstrogen receptorHomo sapiens (human)
transcription regulator complexEstrogen receptorHomo sapiens (human)
cytoplasmEstrogen receptorHomo sapiens (human)
Golgi apparatusEstrogen receptorHomo sapiens (human)
cytosolEstrogen receptorHomo sapiens (human)
plasma membraneEstrogen receptorHomo sapiens (human)
membraneEstrogen receptorHomo sapiens (human)
chromatinEstrogen receptorHomo sapiens (human)
euchromatinEstrogen receptorHomo sapiens (human)
protein-containing complexEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID417968Antimicrobial activity against Trichophyton rubrum after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417967Antimicrobial activity against Epidermophyton floccosum after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197648Antiviral activity against feline herpesvirus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197623Antiviral activity against HCV genotype 1b I389luc-ubi-neo/NS3-3'/5.1 replicons infected in human Huh5-2 HCV subgenomic replicon-containing cells assessed as reduction in virus replication after 3 days by luciferase reporter gene assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID417962Antifungal activity against Cryptococcus neoformans after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417963Antimicrobial activity against Aspergillus fumigatus after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417960Antifungal activity against Candida tropicalis after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1505260Displacement of Fluor.ES2 Green from human ERalpha by TR-FRET competitive binding assay2018ACS medicinal chemistry letters, Jan-11, Volume: 9, Issue:1
Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution.
AID1505259Xenoestrogen activity in human MCF7 cells assessed as stimulation of estrogen production at 0.125 to 128 ug/ml incubated for 24 hrs by ELISA2018ACS medicinal chemistry letters, Jan-11, Volume: 9, Issue:1
Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution.
AID1505254Antibacterial activity against Staphylococcus aureus 155554A incubated for 16 hrs by microdilution assay2018ACS medicinal chemistry letters, Jan-11, Volume: 9, Issue:1
Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution.
AID417965Antimicrobial activity against Aspergillus niger after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197621Antiviral activity against HIV2 ROD infected in human CEM cells assessed as reduction in virus-induced cytopathicity after 4 to 5 days by microscopy based syncytium cell formation assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197649Antiviral activity against chikungunya virus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197638Antiviral activity against vesicular stomatitis virus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197642Antiviral activity against reovirus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID417964Antimicrobial activity against Aspergillus flavus after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197647Antiviral activity against feline coronavirus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197620Antiviral activity against HIV1 3B infected in human CEM cells assessed as reduction in virus-induced cytopathicity after 4 to 5 days by microscopy based syncytium cell formation assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197639Antiviral activity against human coxsackievirus B42015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID417961Antifungal activity against Saccharomyces cerevisiae after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197640Antiviral activity against RSV2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID417966Antimicrobial activity against Microsporum gypseum after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID417969Antimicrobial activity against Trichophyton mentagrophytes after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197622Cytotoxicity against human CEM cells assessed as inhibition of cell proliferation2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197646Antiviral activity against punta toro virus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197637Antiviral activity against vaccinia virus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197643Antiviral activity against sindbis virus2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID417959Antifungal activity against Candida albicans after 48 hrs by broth microdilution technique2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.
AID1197624Cytotoxicity against human Huh5-2 cells after 72 hrs by MTS assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197645Antiviral activity against influenza A virus (H1N1)2015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197644Antiviral activity against influenza A virus H3N22015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID1197641Antiviral activity against human parainfluenza virus 32015European journal of medicinal chemistry, Mar-06, Volume: 92Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's1 (10.00)18.2507
2000's3 (30.00)29.6817
2010's5 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.43 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]