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 7 Target ID: GO:1990000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8297
intrinsic apoptotic signaling pathway in response to oxidative stress 3 Target ID: GO:0008631 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27303604	Primary	Preclinical	Unknown Approved Use Unknown
Vascular dementia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726557	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24918580	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 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 1587		inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
P-gp 1650	inhibitor 3277 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 1925	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4486538/	yes [IC50 394 uM]
CYP2D6 1891	inhibitor 3277 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
Reaction rate constants of superoxide scavenging by plant antioxidants.	2003 Dec 15	14680683
Application of isomorphous replacement in the structure determination of a cubic liquid crystal phase and location of counterions.	2003 Dec 24	14677989
Epigallocatechin gallate, the main component of tea polyphenol, binds to CD4 and interferes with gp120 binding.	2003 Nov	14610487
(-)-Epigallocatechin gallate causes oxidative damage to isolated and cellular DNA.	2003 Nov 1	14563487
The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase.	2003 Nov 15	14599562
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	14609132
Effects of platelet inhibitors on propyl gallate-induced platelet aggregation, protein tyrosine phosphorylation, and platelet factor 3 activation.	2004 Apr	15060414
Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus.	2004 Dec	15643566
Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols.	2004 Dec 1	15563210
Gallium halide induced heterocycle expansion of dihalodiphosphadiaryldiazanes [(XPNR)2] to the corresponding triphosphatriazanes [(XPNR)3].	2004 Dec 27	15606170
Exobasidium vexans infection of Camellia sinensis increased 2,3-cis isomerisation and gallate esterification of proanthocyanidins.	2004 Nov	15504433
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
Two pyranocoumarins from the seeds of Calophyllum polyanthum.	2004 Sep	15387670
Phosphatidylinositol-3 kinase/Akt and GSK-3 mediated cytoprotective effect of epigallocatechin gallate on oxidative stress-injured neuronal-differentiated N18D3 cells.	2004 Sep	15288510
Protective effect of epigallocatechin gallate on brain damage after transient middle cerebral artery occlusion in rats.	2004 Sep 3	15306237
Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells.	2005 Apr	15802789
(-)-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	15814656
The intermediate filament protein vimentin is a new target for epigallocatechin gallate.	2005 Apr 29	15713670
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	16100442
Examination of the anti-oxidative effect in renal tubular cells and apoptosis by oxidative stress.	2005 Aug	16047215
Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells.	2005 Aug 15	16051220
Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress.	2005 Aug 31	16155411
Inhibitory effects of epigallocatechin gallate on compound 48/80-induced mast cell activation and passive cutaneous anaphylaxis.	2005 Aug 31	16155406
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	16060645
Complexation of epigallocatechin gallate (a green tea extract, egcg) with Mn2+: nuclear spin relaxation by the paramagnetic ion.	2005 Feb	15621293
Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action.	2005 Feb	15569775
Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives.	2005 Feb 15	15686878
Oxidation of tea extracts and tea catechins by molecular oxygen.	2005 Jun 1	15913321
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
Bioflavonoids effectively inhibit smooth muscle cell-mediated contraction of collagen matrix induced by angiotensin II.	2005 Nov	16220062
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
Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases.	2005 Oct 21	16030014
[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
Anti-HIV protease activity from rosa family plant extracts and rosamultin from Rosa rugosa.	2005 Spring	15857219
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
Novel inhibitors of fatty-acid synthase from green tea (Camellia sinensis Xihu Longjing) with high activity and a new reacting site.	2006 Jan	15943584
The effect of epigallocatechin gallate on suppressing disease progression of ALS model mice.	2006 Mar 6	16356650
Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas.	2006 May	16423506
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.	2006 May	16308312
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 `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

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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