Showing Compound Gallic acid (FDB000662)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:39 UTC

Update date

2020-09-17 15:39:19 UTC

Primary ID

FDB000662

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gallic acid

Description

Gallic acid, also known as gallate or acid, gallic, belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. Gallic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gallic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Gallic acid is found, on average, in the highest concentration within a few different foods, such as mango, pomegranates, and cloves and in a lower concentration in red raspberries, cumins, and turnips. Gallic acid has also been detected, but not quantified in, several different foods, such as common walnuts, tarragons, gingers, fruit juices, and corns. This could make gallic acid a potential biomarker for the consumption of these foods. A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.

CAS Number

149-91-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3,4,5-Trihydroxybenzoic acid	ChEBI
Pyrogallol-5-carboxylic acid	ChEBI
3,4,5-Trihydroxybenzoate	Kegg
Pyrogallol-5-carboxylate	Generator
Gallate	Generator
Acid, gallic	MeSH
3,4,5-Trihydroxy-benzoate	HMDB
3,4,5-Trihydroxy-benzoic acid	HMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)	HMDB
Gallic acid polymer	HMDB
Gallic acid tech.	HMDB
Galop	HMDB
3,4,5-Hydroxybenzoic acid	PhytoBank
Gallic acid	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	4.94 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.26 m³·mol⁻¹	ChemAxon
Polarizability	14.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H6O5

IUPAC name

3,4,5-trihydroxybenzoic acid

InChI Identifier

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

InChI Key

LNTHITQWFMADLM-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

170.12

Monoisotopic Molecular Weight

170.021523293

Classification

Description

Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acids

Alternative Parents

Substituents

Gallic acid
Benzenetriol
Benzoic acid
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trihydroxybenzoic acid (CHEBI:30778 )
Gallotannins (C01424 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Fungi:

Aspergillus:

Aspergillus fischeri

Plant:

Biological location:

Biofluid and excreta:

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 49.42%; H 3.55%; O 47.02%	DFC
Melting Point	Mp 235-240° (225°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	11.9 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.70	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0fk9-2900000000-1949ca7ce1b8b610c278	2015-03-01	View Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0791200000-4d3e1baed2effb0bf15b	Spectrum
GC-MS	Gallic acid, 4 TMS, GC-MS Spectrum	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-0fk9-5900000000-6b43adb858d50b520ba7	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0791200000-4d3e1baed2effb0bf15b	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	Spectrum
GC-MS	Gallic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0691200000-8b11cbd28f656c4426b4	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fmi-1900000000-56bf9b5e0a68a9c0776a	Spectrum
Predicted GC-MS	Gallic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-4009300000-4326897e134d4856b180	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0umi-0900000000-e8e6e57cdaf8d518781a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-9600000000-8b3c3dc9e263c174a0ac	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-9000000000-da4704e31ba4de6b3aca	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0fk9-5900000000-425a258abda96a507ea0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-951aa8106825faaca3f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-46d7a232b169910da462	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9300000000-010429242e38b1b28c13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0ufr-0900000000-8e1ce790677a7c04e580	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-004i-0900000000-8999270f1e2b746047f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-880097b21bcd57ec8f77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-5900000000-bf4cb2a480d9abb570d4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9300000000-63bfcc112fc600a150de	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-6a9289e729e66d03cf50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-175241488c5f0956df1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kor-0900000000-1ceb76e12bc399878e0d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8e403dcee60bc20ba7b4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0900000000-20a78444c2179ed7730f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00os-9800000000-3011ae50626d9c15fadd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-bceef5d1a34c38d340ed	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00or-0900000000-bbec391317d064ab4d89	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-8900000000-049b564c5923498a6f3e	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

413

DrugBank ID

Not Available

HMDB ID

HMDB05807

CRC / DFC (Dictionary of Food Compounds) ID

BFL35-I:BFL35-I

EAFUS ID

Not Available

Dr. Duke ID

GALLIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002647

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Gallic_acid

Phenol-Explorer Metabolite ID

413

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti adenovirus	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti allergenic	50857	A drug used to treat allergic reactions.	DUKE
anti anaphylactic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti escherichic			DUKE
anti fibrinolytic			DUKE
anti flu	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leishmanic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti methicillin-resistant Staphylococcus aureus	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti mutagenic			DUKE
anti nitrosaminic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti periodontitic			DUKE
anti peroxidant			DUKE
anti polio	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti proteolytic			DUKE
anti radicular			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
apoptotic			DUKE
astringent	74783	A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.	DUKE
bacteristat	33282	A substance that kills or slows the growth of bacteria.	DUKE
bronchodilator	35523	An agent that causes an increase in the expansion of a bronchus or bronchial tubes.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
choleretic			DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
floral inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
Gram(+)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
Gram(-)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
hemostat			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
immunosuppressant	35705	An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.	DUKE
insulin-sparing			DUKE
myorelaxant			DUKE
nephrotoxic	50909	A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.	DUKE
nitric-oxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
styptic			DUKE
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	CHEBI