Record Information |
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Version | 2.0 |
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Created at | 2007-01-23 13:04:37 UTC |
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Updated at | 2024-09-03 04:16:56 UTC |
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NP-MRD ID | NP0000524 |
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Natural Product DOI | https://doi.org/10.57994/0863 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Gallic acid |
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Description | Gallic acid 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. The chemical formula is C6H2(OH)3CO2H. Gallic acid is widely distributed in plants and is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine. Salts and esters of gallic acid are termed gallates. Gallic acid has been found to be s metabolite of Aspergillus (PMID:24031294 ). |
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Structure | OC(=O)C1=CC(O)=C(O)C(O)=C1 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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Synonyms | Value | Source |
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3,4,5-Trihydroxybenzoic acid | ChEBI | Pyrogallol-5-carboxylic acid | ChEBI | 3,4,5-Trihydroxybenzoate | Kegg | Pyrogallol-5-carboxylate | Generator | Gallate | Generator | 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 | Acid, gallic | HMDB | 3,4,5-Hydroxybenzoic acid | HMDB |
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Chemical Formula | C7H6O5 |
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Average Mass | 170.1200 Da |
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Monoisotopic Mass | 170.02152 Da |
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IUPAC Name | 3,4,5-trihydroxybenzoic acid |
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Traditional Name | galop |
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CAS Registry Number | 149-91-7 |
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SMILES | OC(=O)C1=CC(O)=C(O)C(O)=C1 |
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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) |
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InChI Key | LNTHITQWFMADLM-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-07 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-25 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-09-05 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-09-05 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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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Experimental Properties | Property | Value | Reference |
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Melting Point | 258 - 265 °C | Not Available | Boiling Point | 501.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 11.9 mg/mL at 20 °C | Not Available | LogP | 0.70 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - Bajpai B, Patil S: A new approach to microbial production of gallic acid. Braz J Microbiol. 2008 Oct;39(4):708-11. doi: 10.1590/S1517-838220080004000021. Epub 2008 Dec 1. [PubMed:24031294 ]
- Yoshioka K, Kataoka T, Hayashi T, Hasegawa M, Ishi Y, Hibasami H: Induction of apoptosis by gallic acid in human stomach cancer KATO III and colon adenocarcinoma COLO 205 cell lines. Oncol Rep. 2000 Nov-Dec;7(6):1221-3. doi: 10.3892/or.7.6.1221. [PubMed:11032918 ]
- Sohi KK, Mittal N, Hundal MK, Khanduja KL: Gallic acid, an antioxidant, exhibits antiapoptotic potential in normal human lymphocytes: A Bcl-2 independent mechanism. J Nutr Sci Vitaminol (Tokyo). 2003 Aug;49(4):221-7. doi: 10.3177/jnsv.49.221. [PubMed:14598907 ]
- Mennen LI, Sapinho D, Ito H, Galan P, Hercberg S, Scalbert A: Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake. Eur J Clin Nutr. 2008 Apr;62(4):519-25. doi: 10.1038/sj.ejcn.1602744. Epub 2007 Apr 4. [PubMed:17426744 ]
- Nam SH, Park J, Jun W, Kim D, Ko JA, Abd El-Aty AM, Choi JY, Kim DI, Yang KY: Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent. AMB Express. 2017 Dec 22;7(1):224. doi: 10.1186/s13568-017-0523-x. [PubMed:29273963 ]
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