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Compound Summary

General Compound Information

gallic acid

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Description

Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor and an apoptosis inducer. It is a conjugate acid of a gallate.

Synonyms

Gallic acid; 3,4,5-Trihydroxybenzoic acid; 149-91-7; gallate; Benzoic acid, 3,4,5-trihydroxy-;

Gallic acid, tech.;GALOP;Pyrogallol-5-carboxylic acid;Kyselina gallova;HSDB 2117;3,4,5-Trihydroxybenzoate;MFCD00002510;CCRIS 5523;NSC 674319;CHEBI:30778;AI3-16412;Kyselina 3,4,5-trihydroxybenzoova;NSC-20103;NSC-674319;CHEMBL288114;3,4,5-trihydroxy-Benzoic acid;DTXSID0020650;632XD903SP;NSC20103;NSC674319;NCGC00091125-01;DTXCID60650;GALLIC ACID ANHYDROUS;Kyselina gallova [Czech];31387-49-2;CAS-149-91-7;Gallic acid [NF];SR-05000001537;EINECS 205-749-9;NSC 20103;BRN 2050274;gallic-acid;UNII-632XD903SP;Kyselina 3,4,5-trihydroxybenzoova [Czech];Gallic acid tech.;Gallic Acid, F;GDE;(?)-Gallic acid;Spectrum_000342;3,4,5-Trihydroxybenzoic acid, anhydrous;SpecPlus_000307;5-Trihydroxybenzoic acid;Spectrum2_000399;Spectrum3_000254;Spectrum4_001544;Spectrum5_000108;GALLIC ACID [MI];bmse000389;3,5-Trihydroxybenzoic acid;GALLIC ACID [HSDB];GALLIC ACID [INCI];WLN: QVR CQ DQ EQ;3,4,5-trihydroxy-Benzoate;Oprea1_087792;SCHEMBL15012;3,4,5-Trihydroxybenzoicacid;BSPBio_001668;KBioGR_002008;KBioSS_000822;SPECTRUM210369;3-10-00-02070 (Beilstein Handbook Reference);BIDD:ER0374;DivK1c_006403;GALLIC ACID [WHO-DD];SPBio_000617;3,4,5-Trihydroxybenzoate, X;Benzoic acid,4,5-trihydroxy-;GTPL5549;ZINC1504;3,4,5-Trihydroxybenzoic acid;;KBio1_001347;KBio2_000822;KBio2_003390;KBio2_005958;KBio3_001168;CPD-183;Gallic acid, puriss., 98.0%;HMS1923K07;HMS2091A07;Pharmakon1600-00210369;BCP18127;HY-N0523;NSC36997;Tox21_111089;Tox21_202515;BBL009937;BDBM50085536;CCG-38670;NSC-36997;NSC755825;s4603;STK298718;AKOS000119625;Tox21_111089_1;AC-1206;CS-8191;NSC-755825;PS-8710;SDCCGMLS-0066503.P001;NCGC00091125-02;NCGC00091125-03;NCGC00091125-04;NCGC00091125-05;NCGC00091125-07;NCGC00260064-01;DA-33612;SY038078;SBI-0052184.P002;Gallic acid, 97.5-102.5% (titration);FT-0626592;G0011;EN300-21542;C01424;D85056;3,4,5-trihydroxybenzoic acid (ACD/Name 4.0);AB00052697_03;Q375837;Q-201146;SR-05000001537-1;SR-05000001537-2;SR-05000001537-3;BRD-K77345217-001-01-9;F1908-0156;Gallic acid, certified reference material, TraceCERT(R);Z104501122;78563C7D-0E2D-4766-A8EA-670A03C78FCF;137657-43-3;

FlavorDB ID

828 PUBCHEM ID

Molecular Weight

170.12 Molecular Formula

C7H6O5

Openeye Can Smiles

C1=C(C=C(C(=C1O)O)O)C(=O)O

IUPAC Inchikey

LNTHITQWFMADLM-UHFFFAOYSA-N

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Similarity

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
taste	astringent	2.920e+2 µmol/L	red wine	details
taste	astringent	2.920e+2 µmol/L	red wine	details
taste	astringent	2.000e+2 µmol/L	green tea	details
taste	astringent	6.466e+1 µmol/L	whisky	details
taste	astringent	2.916e+2 µmol/L	whisky	details
taste	astringent	2.920e+2 µmol/L	whisky	details
taste	astringent	2.920e+2 µmol/L	whisky	details
taste	astringent	2.920e+2 µmol/L		details
taste	astringent	2.920e+2 µmol/L	red wine	details

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Gallic acid

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Output ID	SPECIES	Route	Duration Days	END POINT	QUALIFIER	VALUE	UNIT	EFFECT	Toxicity
607	Rat	oral: unspecified	91	NOAEL	=	119	mg/kg bw/day	organ weights	hepatotoxicity

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

OUTPUT ID	ASSESSMENT	QUALIFIER	VALUE	UNIT	POPULATION
2154	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
2313	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
2053	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
2101	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
2167	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
607	MSI/FC	=	20	mg/kg	Chicken for egg production
607	MSI/FC	=	20	mg/kg	Chicken for meat production
607	MSI/FC	=	24	mg/kg	Pigs - less than 1 year old
607	MSI/FC	=	36	mg/kg	Turkeys for meat production
607	MSI/FC	=	39	mg/kg	Cattle for milk production
607	MSI/FC	=	40	mg/kg	Pigs for meat production
607	MSI/FC	=	40	mg/kg	Pigs for reproduction
607	MSI/FC	=	42	mg/kg	Dogs as pet
607	MSI/FC	=	60	mg/kg	Cats as pet
607	MSI/FC	=	60	mg/kg	Cattle for meat production
607	MSI/FC	=	60	mg/kg	Cattle for meat production - less than 1 year old
607	critical study not identified		0		Workers

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA AFC	2006	2154	Negative
EFSA AFC	2009	2313	Negative
EFSA CEF	2010	2053	Negative
EFSA CEF	2011	2101	Negative
EFSA CEF	2012	2167	Negative
EFSA FEEDAP	2012	607	No data

EFSA Outputs

Output ID	Title	DOI	Published
607	Scientific Opinion on the safety and efficacy of benzyl alcohols, aldehydes, acids, esters and acetals (chemical group 23) when used as flavourings for all animal species	doi:10.2903/j.efsa.2012.2785	24Jul2012
2053	Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30	doi:10.2903/j.efsa.2010.1405	02Jul2010
2101	Scientific Opinion on Flavouring Group Evaluation 20, Revision 3 (FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30	doi:10.2903/j.efsa.2011.2176	12Jul2011
2154	Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to Flavouring Group Evaluation 20: Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)	doi:10.2903/j.efsa.2006.296	09Jan2006
2167	Scientific Opinion on Flavouring Group Evaluation 20, Revision 4 (FGE.20Rev4): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30	doi:10.2903/j.efsa.2012.2994	07Dec2012
2313	Flavouring Group Evaluation 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23 Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)	doi:10.2903/j.efsa.2009.976	12Feb2009

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R4	details	Activated

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative

Content

Compound Summary

gallic acid

Description

Synonyms

Gallic acid; 3,4,5-Trihydroxybenzoic acid; 149-91-7; gallate; Benzoic acid, 3,4,5-trihydroxy-;

FlavorDB ID

828

PUBCHEM ID

370

Molecular Weight

170.12

Molecular Formula

C7H6O5

Openeye Can Smiles

C1=C(C=C(C(=C1O)O)O)C(=O)O

IUPAC Inchikey

LNTHITQWFMADLM-UHFFFAOYSA-N

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Content

Compound Summary

gallic acid

Description

Synonyms

Gallic acid; 3,4,5-Trihydroxybenzoic acid; 149-91-7; gallate; Benzoic acid, 3,4,5-trihydroxy-;

FlavorDB ID

828

PUBCHEM ID

370

Molecular Weight

170.12

Molecular Formula

C7H6O5

Openeye Can Smiles

C1=C(C=C(C(=C1O)O)O)C(=O)O

IUPAC Inchikey

LNTHITQWFMADLM-UHFFFAOYSA-N

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Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

OpenFoodTox: component Gallic acid

Reference Details

GC-MS Spectrum

GC-MS Spectrum

GC-MS Spectrum