Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:56:21 -0600 |
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Update Date | 2015-09-13 12:56:12 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Gallic acid |
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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. |
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Structure | |
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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
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Chemical Formula: | C7H6O5 |
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Weight: | Average: 170.1195 Monoisotopic: 170.021523302 |
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InChI Key: | LNTHITQWFMADLM-UHFFFAOYSA-N |
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InChI: | InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) |
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CAS number: | 149-91-7 |
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IUPAC Name: | 3,4,5-trihydroxybenzoic acid |
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Traditional IUPAC Name: | galop |
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SMILES: | OC(=O)C1=CC(O)=C(O)C(O)=C1 |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Gallic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | 258-265 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 11.9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | 0.70 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - 1,4-Dichlorobenzene degradation ec00627
- Microbial metabolism in diverse environments ec01120
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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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 |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-053r-0491700000-68a1d17dd1d0bb6c5354 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fk9-5900000000-6b43adb858d50b520ba7 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-001i-0791200000-4d3e1baed2effb0bf15b | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-053r-0491700000-68a1d17dd1d0bb6c5354 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-001i-0691200000-8b11cbd28f656c4426b4 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fmi-1900000000-56bf9b5e0a68a9c0776a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-00xu-4009300000-4326897e134d4856b180 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0umi-0900000000-e8e6e57cdaf8d518781a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a59-9600000000-8b3c3dc9e263c174a0ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ue9-9000000000-da4704e31ba4de6b3aca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-0fk9-5900000000-425a258abda96a507ea0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-951aa8106825faaca3f9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-bdedf4b4b4fd922ec704 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-5900000000-46d7a232b169910da462 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9300000000-010429242e38b1b28c13 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0g29-9100000000-fb4dc241b26c248950f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-0ufr-0900000000-8e1ce790677a7c04e580 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-004i-0900000000-8999270f1e2b746047f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-880097b21bcd57ec8f77 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-bdedf4b4b4fd922ec704 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-5900000000-bf4cb2a480d9abb570d4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9300000000-63bfcc112fc600a150de | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0g29-9100000000-fb4dc241b26c248950f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00di-0900000000-6a9289e729e66d03cf50 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00di-0900000000-175241488c5f0956df1f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0kor-0900000000-1ceb76e12bc399878e0d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-8e403dcee60bc20ba7b4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fb9-0900000000-20a78444c2179ed7730f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00os-9800000000-3011ae50626d9c15fadd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-bceef5d1a34c38d340ed | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00or-0900000000-bbec391317d064ab4d89 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00or-8900000000-049b564c5923498a6f3e | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0fk9-2900000000-1949ca7ce1b8b610c278 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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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
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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 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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