GALLIC ACID

US Previously Marketed

First marketed in 1921

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 Search

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

Description
Sources: https://www.omicsonline.org/open-access/gallic-acid-a-promising-lead-molecule-for-drug-development-1920-4159-1000213.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24918580

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
amyloid fibril formation 8 Target ID: GO:1990000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8504
intrinsic apoptotic signaling pathway in response to oxidative stress 4 Target ID: GO:0008631 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Primary	Preclinical	Unknown Approved Use Unknown
Vascular dementia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726557	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24918580	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18445658	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.83 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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

Value	Dose	Co-administered	Analyte	Population
4.29 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11285327/	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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28766866/	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 Sources: https://pubmed.ncbi.nlm.nih.gov/28766866/
CYP3A4 2633	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4486538/	yes [IC50 394 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4486538/	yes [IC50 461 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:30778	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30778
ChemicalBook	CB0158671	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0158671
eMolecules	493996	https://www.emolecules.com/cgi-bin/more?vid=493996
MolPort	MolPort-000-881-260	https://www.molport.com/shop/molecule-link/MolPort-000-881-260
ZINC	ZINC000000001504	http://zinc15.docking.org/substances/ZINC000000001504

PubMed

Title	Date	PubMed
Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes.	2006-09-28	16303244
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.	2006-08	16443358
Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas.	2006-05	16423506
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.	2006-05	16308312
The effect of epigallocatechin gallate on suppressing disease progression of ALS model mice.	2006-03-06	16356650
(-)-Epigallocatechin gallate attenuates acute stress responses through GABAergic system in the brain.	2006-02-15	16457806
A link between meiotic prophase progression and crossover control.	2006-02	16462941
Epigallocatechin gallate increases the formation of cytosolic lipid droplets and decreases the secretion of apoB-100 VLDL.	2006-01	16227197
Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site.	2006-01	15943584
Activation of rat liver microsomal glutathione S-transferase by gallic acid.	2005-11-19	16125204
cGMP-independent nitric oxide signaling and regulation of the cell cycle.	2005-11-03	16269079
Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice.	2005-11	16300386
Bioflavonoids effectively inhibit smooth muscle cell-mediated contraction of collagen matrix induced by angiotensin II.	2005-11	16220062
Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases.	2005-10-21	16030014
In vivo treatment of acute Chlamydia pneumoniae infection with the flavonoids quercetin and luteolin and an alkyl gallate, octyl gallate, in a mouse model.	2005-10-15	16139801
Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution.	2005-09-15	16109305
[Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line].	2005-09	16304905
Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress.	2005-08-31	16155411
Inhibitory effects of epigallocatechin gallate on compound 48/80-induced mast cell activation and passive cutaneous anaphylaxis.	2005-08-31	16155406
Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells.	2005-08-15	16051220
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.	2005-08-08	16060645
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.	2005-08	16100442
Examination of the anti-oxidative effect in renal tubular cells and apoptosis by oxidative stress.	2005-08	16047215
In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare.	2005-06-22	15972098
Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells.	2005-06-15	15941307
Oxidation of tea extracts and tea catechins by molecular oxygen.	2005-06-01	15913321
Structure-activity relationship of the tocopherol-regeneration reaction by catechins.	2005-05-01	15808422
The intermediate filament protein vimentin is a new target for epigallocatechin gallate.	2005-04-29	15713670
(-)-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.	2005-04-01	15814656
Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells.	2005-04	15802789
Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives.	2005-02-15	15686878
Complexation of epigallocatechin gallate (a green tea extract, egcg) with Mn2+: nuclear spin relaxation by the paramagnetic ion.	2005-02	15621293
Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action.	2005-02	15569775
Anti-HIV protease activity from rosa family plant extracts and rosamultin from Rosa rugosa.	2005	15857219
Gallium halide induced heterocycle expansion of dihalodiphosphadiaryldiazanes [(XPNR)2] to the corresponding triphosphatriazanes [(XPNR)3].	2004-12-27	15606170
Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols.	2004-12-01	15563210
Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus.	2004-12	15643566
Exobasidium vexans infection of Camellia sinensis increased 2,3-cis isomerisation and gallate esterification of proanthocyanidins.	2004-11	15504433
Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives.	2004-10-18	15380225
Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acyl-catechins.	2004-10	15380264
Protective effect of epigallocatechin gallate on brain damage after transient middle cerebral artery occlusion in rats.	2004-09-03	15306237
Two pyranocoumarins from the seeds of Calophyllum polyanthum.	2004-09	15387670
Phosphatidylinositol-3 kinase/Akt and GSK-3 mediated cytoprotective effect of epigallocatechin gallate on oxidative stress-injured neuronal-differentiated N18D3 cells.	2004-09	15288510
Evaluation of epigallocatechin gallate and related plant polyphenols as inhibitors of the FabG and FabI reductases of bacterial type II fatty-acid synthase.	2004-07-23	15133034
Mechanisms of inhibition of tumor angiogenesis and vascular tumor growth by epigallocatechin-3-gallate.	2004-07-15	15269163
Lipoxygenase inhibitory activity of octyl gallate.	2004-05-19	15137872
HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea.	2004-05-19	15137818
Apple phytochemicals and their health benefits.	2004-05-12	15140261
Inhibition of fucosyltransferase VII by gallic acid and its derivatives.	2004-05-01	15081893
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.	2004-05	15120724

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 `Mon Mar 31 18:04:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:15 GMT 2025`
Record UNII	632XD903SP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALLIC ACID

Official Name

English

NSC-20103

Preferred 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 [WHO-DD]

Common Name

English

GALLIC ACID [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C275