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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O5
Molecular Weight 170.1195
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALLIC ACID

SMILES

OC(=O)C1=CC(O)=C(O)C(O)=C1

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 170.1195
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
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992 May
Production of hydrogen peroxide and methionine sulfoxide by epigallocatechin gallate and antioxidants.
2001 Jul-Aug
Tannic acid potently inhibits tumor cell proteasome activity, increases p27 and Bax expression, and induces G1 arrest and apoptosis.
2001 Oct
Protective activity of green tea against free radical- and glucose-mediated protein damage.
2002 Apr 10
Green tea catechins decrease apolipoprotein B-100 secretion from HepG2 cells.
2002 Jan
Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention.
2002 Jan
Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea.
2002 Jan 1
In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages.
2002 Jan 15
Antioxidant activity of dodecyl gallate.
2002 Jun 5
Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane.
2002 Mar 8
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2).
2002 May 20
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.
2002 Oct 11
Glucuronides of tea catechins: enzymology of biosynthesis and biological activities.
2003 Apr
Reaction rate constants of superoxide scavenging by plant antioxidants.
2003 Dec 15
Non-antibiotic antibacterial activity of dodecyl gallate.
2003 Feb 20
CP8668, a novel orally active nonsteroidal progesterone receptor modulator with tetrahydrobenzindolone skeleton.
2003 Feb 7
Propyl gallate is a superoxide dismutase mimic and protects cultured lens epithelial cells from H2O2 insult.
2003 Jan
Progressive resistance of BTK-143 osteosarcoma cells to Apo2L/TRAIL-induced apoptosis is mediated by acquisition of DcR2/TRAIL-R4 expression: resensitisation with chemotherapy.
2003 Jul 7
Use of double packaging and antioxidant combinations to improve color, lipid oxidation, and volatiles of irradiated raw and cooked turkey breast patties.
2003 May
A novel convenient process to obtain a raw decaffeinated tea polyphenol fraction using a lignocellulose column.
2003 May 7
Cellular uptake and efflux of the tea flavonoid (-)epicatechin-3-gallate in the human intestinal cell line Caco-2.
2003 Nov
(-)-Epigallocatechin gallate causes oxidative damage to isolated and cellular DNA.
2003 Nov 1
The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase.
2003 Nov 15
Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 activity by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose in murine macrophage cells.
2003 Oct
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
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
Inhibition of fucosyltransferase VII by gallic acid and its derivatives.
2004 May 1
Apple phytochemicals and their health benefits.
2004 May 12
HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea.
2004 May 19
Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acyl-catechins.
2004 Oct
Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells.
2005 Apr
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
Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells.
2005 Aug 15
Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress.
2005 Aug 31
Inhibitory effects of epigallocatechin gallate on compound 48/80-induced mast cell activation and passive cutaneous anaphylaxis.
2005 Aug 31
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
Structure-activity relationship of the tocopherol-regeneration reaction by catechins.
2005 May 1
Bioflavonoids effectively inhibit smooth muscle cell-mediated contraction of collagen matrix induced by angiotensin II.
2005 Nov
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
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
A link between meiotic prophase progression and crossover control.
2006 Feb
Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site.
2006 Jan
Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas.
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 Fri Dec 15 15:39:03 GMT 2023
Edited
by admin
on Fri Dec 15 15:39:03 GMT 2023
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 [WHO-DD]
Common Name English
GALLIC ACID [HSDB]
Common Name English
NSC-20103
Code English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
DSLD 1414 (Number of products:4)
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
NCI_THESAURUS C68539
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
Code System Code Type Description
CAS
149-91-7
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
NSC
674319
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-749-9
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
RXCUI
1311389
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL288114
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
CHEBI
30778
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
WIKIPEDIA
GALLIC ACID
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
HSDB
2117
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
FDA UNII
632XD903SP
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
PUBCHEM
370
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
DAILYMED
632XD903SP
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
SMS_ID
100000127361
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
MERCK INDEX
m5645
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY Merck Index
MESH
D005707
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID0020650
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
NSC
20103
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
PRIMARY
NCI_THESAURUS
C63648
Created by admin on Fri Dec 15 15:39:03 GMT 2023 , Edited by admin on Fri Dec 15 15:39:03 GMT 2023
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
SOLVATE->ANHYDROUS
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