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Record Information
Version	2.0
Creation Date	2012-05-31 13:56:21 -0600
Update Date	2015-09-13 12:56:12 -0600
Secondary Accession Numbers	ECMDB02260
Identification
Name:	Gallic acid
Description	Gallic acid (GA) is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. Plants, bacteria and fungi are capable of synthesizing gallic acid. Shikimate dehydrogenase (SDH), a shikimate pathway enzyme essential for aromatic amino acid synthesis, is required for gallic acid production in Escherichia coli. SDH catalyzes NADPH-dependent reduction of 3-DHS (3-dehydroshikimate) to shikimic acid (SA), which is ultimately used to produce the aromatic amino acids l-tyrosine, l-tryptophan, and l-phenylalanine. SDH also catalyzes NADP+-dependent dehydrogenation of SA to 3-DHS, but also the dehydrogenation of 3-DHS to GA.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa92ee2cc> Close
Synonyms:	3,4,5-Trihydroxy-Benzoate 3,4,5-Trihydroxy-Benzoic acid 3,4,5-Trihydroxybenzoate 3,4,5-Trihydroxybenzoate (acd/name 4.0) 3,4,5-Trihydroxybenzoic acid 3,4,5-trihydroxybenzoic acid (ACD/Name 4.0) Gallate Gallate polymer Gallate tech. Gallic acid Gallic acid polymer Gallic acid tech. Galop Pyrogallol-5-carboxylate Pyrogallol-5-carboxylic acid
Chemical Formula:	C7H6O5
Weight:	Average: 170.1195 Monoisotopic: 170.021523302
InChI Key:	LNTHITQWFMADLM-UHFFFAOYSA-N
InChI:	InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
CAS number:	149-91-7
IUPAC Name:	3,4,5-trihydroxybenzoic acid
Traditional IUPAC Name:	galop
SMILES:	OC(=O)C1=CC(O)=C(O)C(O)=C1
Chemical Taxonomy
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	Pyrogallols and derivatives Benzoic acids Benzoyl derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
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 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	258-265 °C
Experimental Properties:	Property Value Source Water Solubility: 11.9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: 0.70 [HANSCH,C ET AL. (1995)] PhysProp
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 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 39.26 m³·mol⁻¹ ChemAxon Polarizability 14.75 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-001i-0791200000-4d3e1baed2effb0bf15b View in MoNA GC-MS GC-MS Spectrum - GC-MS (4 TMS) splash10-053r-0491700000-68a1d17dd1d0bb6c5354 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0fk9-5900000000-6b43adb858d50b520ba7 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-001i-0791200000-4d3e1baed2effb0bf15b View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-053r-0491700000-68a1d17dd1d0bb6c5354 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-001i-0691200000-8b11cbd28f656c4426b4 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0fmi-1900000000-56bf9b5e0a68a9c0776a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-00xu-4009300000-4326897e134d4856b180 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0umi-0900000000-e8e6e57cdaf8d518781a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0a59-9600000000-8b3c3dc9e263c174a0ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0ue9-9000000000-da4704e31ba4de6b3aca View in MoNA LC-MS/MS LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive splash10-0fk9-5900000000-425a258abda96a507ea0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-014i-0900000000-951aa8106825faaca3f9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-004i-0900000000-bdedf4b4b4fd922ec704 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-004i-5900000000-46d7a232b169910da462 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-004i-9300000000-010429242e38b1b28c13 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0g29-9100000000-fb4dc241b26c248950f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - DI-ESI-qTof , Positive splash10-0ufr-0900000000-8e1ce790677a7c04e580 View in MoNA LC-MS/MS LC-MS/MS Spectrum - DI-ESI-qTof , Negative splash10-004i-0900000000-8999270f1e2b746047f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-014i-0900000000-880097b21bcd57ec8f77 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-0900000000-bdedf4b4b4fd922ec704 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-5900000000-bf4cb2a480d9abb570d4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-9300000000-63bfcc112fc600a150de View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0g29-9100000000-fb4dc241b26c248950f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-00di-0900000000-6a9289e729e66d03cf50 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-00di-0900000000-175241488c5f0956df1f View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0kor-0900000000-1ceb76e12bc399878e0d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-0900000000-8e403dcee60bc20ba7b4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fb9-0900000000-20a78444c2179ed7730f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00os-9800000000-3011ae50626d9c15fadd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-0900000000-bceef5d1a34c38d340ed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00or-0900000000-bbec391317d064ab4d89 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00or-8900000000-049b564c5923498a6f3e View in MoNA MS Mass Spectrum (Electron Ionization) splash10-0fk9-2900000000-1949ca7ce1b8b610c278 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Cheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 30778 HMDB ID HMDB05807 Pubchem Compound ID 370 Kegg ID C01424 ChemSpider ID 361 Wikipedia Gallic acid BioCyc ID CPD-183 EcoCyc ID CPD-183

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