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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O5
Molecular Weight 170.1198
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALLIC ACID

SMILES

c1c(cc(c(c1O)O)O)C(=O)O

InChI

InChIKey=LNTHITQWFMADLM-UHFFFAOYSA-N
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)

HIDE SMILES / InChI

Molecular Formula C7H6O5
Molecular Weight 170.1198
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Gallic acid is a polyphenol found in a variety of foods and herbs. Several studies have shown thta gallic acid has neuroprotective and anti-oxidant properties and can be a promising candidate for the treatment of cancer, cardiovascular diseases, neurodegenerative disorders, fatty liver disease and many others. Gallic acid acts by protecting cells against oxidative damage caused by reactive species often encountered in biological systems including, hydroxyl, superoxide and peroxyl and the non-radicals, hydrogen peroxide and hypochlorous acid. However, its ability to induce apoptosis, is mainly associated with its prooxidant, rather than antioxidant behavior.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.83 μM
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.09 μM
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.29 μM × h
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.55 μM × h
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.19 h
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.06 h
0.3 mmol single, oral
dose: 0.3 mmol
route of administration: Oral
experiment type: SINGLE
co-administered:
GALLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
yes (co-administration study)
Comment: No Ic50/Ki value given; Coadministration with linagliptin: increase in Cmax, AUC, AUMC, AUCtotal and t1/2 of linagliptin was found to be 1.89-fold, 2.45-fold, 1.76-fold, 1.54-fold and 0.5-fold, respectively
yes [IC50 394 uM]
yes [IC50 461 uM]
PubMed

PubMed

TitleDatePubMed
Reaction rate constants of superoxide scavenging by plant antioxidants.
2003 Dec 15
Effects of platelet inhibitors on propyl gallate-induced platelet aggregation, protein tyrosine phosphorylation, and platelet factor 3 activation.
2004 Apr
Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus.
2004 Dec
Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols.
2004 Dec 1
Gallium halide induced heterocycle expansion of dihalodiphosphadiaryldiazanes [(XPNR)2] to the corresponding triphosphatriazanes [(XPNR)3].
2004 Dec 27
Cellular toxicity of catechin analogues containing gallate in opossum kidney proximal tubular (OK) cells.
2004 Feb
Evaluation of epigallocatechin gallate and related plant polyphenols as inhibitors of the FabG and FabI reductases of bacterial type II fatty-acid synthase.
2004 Jul 23
Metal-mediated oxidative damage to cellular and isolated DNA by gallic acid, a metabolite of antioxidant propyl gallate.
2004 Mar 14
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.
2004 May
Protective effect of methyl gallate from Toona sinensis (Meliaceae) against hydrogen peroxide-induced oxidative stress and DNA damage in MDCK cells.
2004 May
Inhibition of fucosyltransferase VII by gallic acid and its derivatives.
2004 May 1
Apple phytochemicals and their health benefits.
2004 May 12
Lipoxygenase inhibitory activity of octyl gallate.
2004 May 19
HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea.
2004 May 19
Exobasidium vexans infection of Camellia sinensis increased 2,3-cis isomerisation and gallate esterification of proanthocyanidins.
2004 Nov
Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acyl-catechins.
2004 Oct
Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives.
2004 Oct 18
Two pyranocoumarins from the seeds of Calophyllum polyanthum.
2004 Sep
Phosphatidylinositol-3 kinase/Akt and GSK-3 mediated cytoprotective effect of epigallocatechin gallate on oxidative stress-injured neuronal-differentiated N18D3 cells.
2004 Sep
Protective effect of epigallocatechin gallate on brain damage after transient middle cerebral artery occlusion in rats.
2004 Sep 3
Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells.
2005 Apr
(-)-Epigallocatechin gallate and polyphenon E inhibit growth and activation of the epidermal growth factor receptor and human epidermal growth factor receptor-2 signaling pathways in human colon cancer cells.
2005 Apr 1
The intermediate filament protein vimentin is a new target for epigallocatechin gallate.
2005 Apr 29
Epigallocatechin-3-gallate suppresses galactose-alpha1,4-galactose-1beta,4-glucose ceramide expression in TNF-alpha stimulated human intestinal epithelial cells through inhibition of MAPKs and NF-kappaB.
2005 Aug
Examination of the anti-oxidative effect in renal tubular cells and apoptosis by oxidative stress.
2005 Aug
Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells.
2005 Aug 15
Synthesis of cyclo-2,4,6-triarsa-1,3,5-triazanes from cyclo-2,4-diarsa-1,3-diazanes demonstrating the general influence of substituent steric strain on the relative stability of pnictazane oligomers.
2005 Aug 8
Complexation of epigallocatechin gallate (a green tea extract, egcg) with Mn2+: nuclear spin relaxation by the paramagnetic ion.
2005 Feb
Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action.
2005 Feb
Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives.
2005 Feb 15
Oxidation of tea extracts and tea catechins by molecular oxygen.
2005 Jun 1
Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells.
2005 Jun 15
In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare.
2005 Jun 22
Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice.
2005 Nov
Bioflavonoids effectively inhibit smooth muscle cell-mediated contraction of collagen matrix induced by angiotensin II.
2005 Nov
cGMP-independent nitric oxide signaling and regulation of the cell cycle.
2005 Nov 3
In vivo treatment of acute Chlamydia pneumoniae infection with the flavonoids quercetin and luteolin and an alkyl gallate, octyl gallate, in a mouse model.
2005 Oct 15
Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases.
2005 Oct 21
[Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line].
2005 Sep
Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution.
2005 Sep 15
Anti-HIV protease activity from rosa family plant extracts and rosamultin from Rosa rugosa.
2005 Spring
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.
2006 Aug
A link between meiotic prophase progression and crossover control.
2006 Feb
(-)-Epigallocatechin gallate attenuates acute stress responses through GABAergic system in the brain.
2006 Feb 15
Epigallocatechin gallate increases the formation of cytosolic lipid droplets and decreases the secretion of apoB-100 VLDL.
2006 Jan
Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site.
2006 Jan
The effect of epigallocatechin gallate on suppressing disease progression of ALS model mice.
2006 Mar 6
Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas.
2006 May
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.
2006 May
Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes.
2006 Sep 28
Patents

Sample Use Guides

In a preclinical study rats were treated with galic acid at a dose of 100mg/kg, p.o. for 10 days (model of vascular dementia) or with 50, 100, and 200 mg/kg, p.o. for 10 days (model of Alzheimer disease). Mice were treated with 50 and 100 mg/kg/day, orally (nonalcoholic fatty liver disease model) or with 0.3% and 1% (w/v) gallic acid until 24 weeks of age (cancer model).
Route of Administration: Oral
In MTT assay human cervical cancer HeLa and HTB-35 cells were treated with varying concentrations (0, 10, 15, 20, 25, 30 and 40 ug/ml) of gallic acid for 24 h. Treatment of HeLa and HTB-35 human cancer cells with gallic acid decreased cell viability in a dose-dependent manner. Gallic acid reduced cell viability to 92, 84 and 66% of the control in the HeLa cells and to 94, 88 and 64% of the control in the HTB-35 cells at concentrations of 5, 10 and 15 ug/ml, respectively. At concentrations of 10, 15, and 20 ug/ml, gallic acid was able to dramatically inhibit cell migration to 73, 40 and 34% in the HeLa cells and to 45, 22 and 17% in the HTB-35 cells, respectively
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:49:40 UTC 2021
Edited
by admin
on Sat Jun 26 08:49:40 UTC 2021
Record UNII
632XD903SP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALLIC ACID
HSDB   INCI   MI   WHO-DD  
INCI  
Official Name English
3,4,5-TRIHYDROXYBENZOIC ACID
Systematic Name English
GALLIC ACID (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
GALLIC ACID [MI]
Common Name English
NSC-674319
Code English
BENZOIC ACID, 3,4,5-TRIHYDROXY-
Common Name English
GALLIC ACID [INCI]
Common Name English
GALLIC ACID [HSDB]
Common Name English
NSC-20103
Code English
GALLIC ACID [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
DSLD 1414 (Number of products:4)
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
NCI_THESAURUS C68539
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
Code System Code Type Description
CAS
149-91-7
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-749-9
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
RXCUI
1311389
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL288114
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
WIKIPEDIA
GALLIC ACID
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
HSDB
2117
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
FDA UNII
632XD903SP
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
PUBCHEM
370
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
MERCK INDEX
M5645
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY Merck Index
MESH
D005707
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
EPA CompTox
149-91-7
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
NCI_THESAURUS
C63648
Created by admin on Sat Jun 26 08:49:40 UTC 2021 , Edited by admin on Sat Jun 26 08:49:40 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL = 3.7 +/- 0.4.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Gallic acid exhibited a significant free radical scavenging effect against 1,1-diphenyl-2-picryl hydrazine (DPPH) radical generation and had an inhibitory effect on lipid peroxidation, as measured by the level of malondialdehyde (MDA) formation.
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY