Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:39 UTC |
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Update date | 2019-11-26 02:55:10 UTC |
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Primary ID | FDB000663 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Methyl gallate |
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Description | Methyl gallate, also known as methyl 3 or methyl galloic acid, is a member of the class of compounds known as galloyl esters. Galloyl esters are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. Methyl gallate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Methyl gallate can be found in peach and pomegranate, which makes methyl gallate a potential biomarker for the consumption of these food products. Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid . |
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CAS Number | 99-24-1 |
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Structure | |
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Synonyms | Synonym | Source |
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Methyl gallic acid | Generator | Methyl 3 | ChEMBL | 45-Trihydroxybenzoate | ChEMBL | Methyl galloate | ChEMBL | 345-Trihydroxy-benzoic acid methyl ester | ChEMBL | 45-Trihydroxybenzoic acid | Generator | Methyl galloic acid | Generator | 345-Trihydroxy-benzoate methyl ester | Generator | Gallic acid, methyl ester | MeSH | Methyl 3,4,5-trihydroxybenzoate | MeSH | 3,4,5-Trihydroxy-benzoic acid methyl ester | biospider | Benzoic acid, 3,4,5-trihydroxy-, methyl ester | biospider | Gallic acid methyl ester | biospider | Gallicin? | db_source | Methyl gallate | db_source | Methylgallate | biospider |
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Predicted Properties | |
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Chemical Formula | C8H8O5 |
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IUPAC name | methyl 3,4,5-trihydroxybenzoate |
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InChI Identifier | InChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3 |
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InChI Key | FBSFWRHWHYMIOG-UHFFFAOYSA-N |
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Isomeric SMILES | COC(=O)C1=CC(O)=C(O)C(O)=C1 |
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Average Molecular Weight | 184.1461 |
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Monoisotopic Molecular Weight | 184.037173366 |
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Classification |
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Description | Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. |
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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 | Galloyl esters |
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Alternative Parents | |
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Substituents | - Galloyl ester
- P-hydroxybenzoic acid alkyl ester
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid ester
- Benzoate ester
- Benzenetriol
- Pyrogallol derivative
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Methyl ester
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Polyol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 52.18%; H 4.38%; O 43.44% | DFC |
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Melting Point | Mp 157° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 10.6 mg/mL | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 0.86 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa1 7.88 (25°, 0.1M KNO3) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 283 () (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Methyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ufr-0900000000-72baa95f31204513dc9d | Spectrum | Predicted GC-MS | Methyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Methyl gallate, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0006-9700000000-11744c62170a98354cbc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00di-1900000000-d6261b21dc9a9fd566b9 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-401d71dbf57a34ddc235 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f79-0900000000-51202d68563eee1bdab2 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvj-5900000000-b7c5629192d45e0d9cb1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-90389cc7f792df061dc3 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-50a11e1df989b937ae23 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uk9-5900000000-59e6084d7e7bb182a1a7 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-fc79f14d18e4e34433ab | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fc0-1900000000-16bd999e2e402d7a0912 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-067l-9300000000-e54d0ca66a63d30da4f1 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-366cfe98e3457a4b68f3 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-1900000000-5526e088c3d9034b9235 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gds-9300000000-b3fffc0f1194e7adbb93 | 2021-10-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 7428 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 551062 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | BFL35-I:BFL36-J |
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EAFUS ID | Not Available |
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Dr. Duke ID | METHYL-GALLATE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00030754 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-allergenic | 50857 | An agent that reduces or blocks allergic reactions, commonly used to treat conditions such as hay fever, asthma, and skin allergies, by inhibiting the release of histamine and other inflammatory mediators, providing relief from symptoms like itching, sneezing, and congestion. | DUKE | Anti-asthmatic | 49167 | An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health. | DUKE | Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti-bronchitic | 52217 | An agent that relieves bronchial congestion and inflammation, commonly used in managing respiratory disorders such as bronchitis, asthma, and chronic obstructive pulmonary disease (COPD), to reduce coughing, wheezing, and shortness of breath. | DUKE | Anti-herpetic | 22587 | An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles. | DUKE | Anti leukemic | 35610 | An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti septic | 33281 | An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management. | DUKE | Anti-staphylococcic | 33282 | An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Anti-viral | 22587 | An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19. | DUKE | Gram(+)icide | 33282 | An agent that targets and kills Gram-positive bacteria, playing a crucial role in treating bacterial infections. Therapeutically, it is used to combat infections caused by Gram-positive microorganisms, with key medical applications including treating skin infections, pneumonia, and sepsis. | DUKE | Gram(-)icide | 33282 | An agent that kills Gram-negative bacteria, playing a crucial role in treating infections. Therapeutically, it is used to combat bacterial infections, particularly those resistant to other antibiotics. Key medical uses include treating sepsis, pneumonia, and urinary tract infections caused by Gram-negative bacteria. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | Reverse transcriptase inhibitor | 59897 | An agent that blocks the activity of reverse transcriptase, an enzyme used by retroviruses to replicate. Therapeutically, it prevents viral replication, commonly used in managing HIV/AIDS and other retroviral infections, such as hepatitis B. | DUKE | Xanthine oxidase inhibitor | 35634 | An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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