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 6 Target ID: GO:1990000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8228
intrinsic apoptotic signaling pathway in response to oxidative stress 2 Target ID: GO:0008631 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 268 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Primary	Preclinical	Unknown Approved Use Unknown
Vascular dementia 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726557	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 29 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24918580	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 585 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 1579		inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1437

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
P-gp 1626	inhibitor 3240 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 1909	inhibitor 3240 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4486538/	yes [IC50 394 uM]
CYP2D6 1875	inhibitor 3240 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
MolPort	MolPort-000-881-260	https://www.molport.com/shop/molecule-link/MolPort-000-881-260
ZINC	ZINC000000001504	http://zinc15.docking.org/substances/ZINC000000001504
eMolecules	493996	https://www.emolecules.com/cgi-bin/more?vid=493996

PubMed

Title	Date	PubMed
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
Tea catechins inhibit cholesterol oxidation accompanying oxidation of low density lipoprotein in vitro.	2001 Feb	11239828
EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells.	2001 Mar 23	11259102
Inhibition by epigallocatechin gallate (EGCg) of conjugative R plasmid transfer in Escherichia coli.	2001 Sep	11810584
Green tea catechins decrease apolipoprotein B-100 secretion from HepG2 cells.	2002 Jan	11936850
Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1).	2002 Jan	11684313
Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea.	2002 Jan 1	11750019
Antioxidant activity of dodecyl gallate.	2002 Jun 5	12033824
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2).	2002 May 20	12085217
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.	2002 Oct 11	12270760
Use of double packaging and antioxidant combinations to improve color, lipid oxidation, and volatiles of irradiated raw and cooked turkey breast patties.	2003 May	12762410
Epigallocatechin gallate, the main component of tea polyphenol, binds to CD4 and interferes with gp120 binding.	2003 Nov	14610487
Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus.	2004 Dec	15643566
Cellular toxicity of catechin analogues containing gallate in opossum kidney proximal tubular (OK) cells.	2004 Feb	15018154
Metal-mediated oxidative damage to cellular and isolated DNA by gallic acid, a metabolite of antioxidant propyl gallate.	2004 Mar 14	15036124
Protective effect of methyl gallate from Toona sinensis (Meliaceae) against hydrogen peroxide-induced oxidative stress and DNA damage in MDCK cells.	2004 May	15046831
Inhibition of fucosyltransferase VII by gallic acid and its derivatives.	2004 May 1	15081893
Apple phytochemicals and their health benefits.	2004 May 12	15140261
Lipoxygenase inhibitory activity of octyl gallate.	2004 May 19	15137872
HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea.	2004 May 19	15137818
Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acyl-catechins.	2004 Oct	15380264
Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives.	2004 Oct 18	15380225
Examination of the anti-oxidative effect in renal tubular cells and apoptosis by oxidative stress.	2005 Aug	16047215
Inhibitory effects of epigallocatechin gallate on compound 48/80-induced mast cell activation and passive cutaneous anaphylaxis.	2005 Aug 31	16155406
Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action.	2005 Feb	15569775
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	15941307
In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare.	2005 Jun 22	15972098
Structure-activity relationship of the tocopherol-regeneration reaction by catechins.	2005 May 1	15808422
Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice.	2005 Nov	16300386
Activation of rat liver microsomal glutathione S-transferase by gallic acid.	2005 Nov 19	16125204
cGMP-independent nitric oxide signaling and regulation of the cell cycle.	2005 Nov 3	16269079
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	16139801
[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	16304905
Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution.	2005 Sep 15	16109305
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.	2006 Aug	16443358
A link between meiotic prophase progression and crossover control.	2006 Feb	16462941
(-)-Epigallocatechin gallate attenuates acute stress responses through GABAergic system in the brain.	2006 Feb 15	16457806
Epigallocatechin gallate increases the formation of cytosolic lipid droplets and decreases the secretion of apoB-100 VLDL.	2006 Jan	16227197
The effect of epigallocatechin gallate on suppressing disease progression of ALS model mice.	2006 Mar 6	16356650
Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes.	2006 Sep 28	16303244

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 `Wed Jul 05 23:08:13 UTC 2023` Edited by `admin` on `Wed Jul 05 23:08:13 UTC 2023`
Record UNII	632XD903SP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALLIC ACID

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