methyl 3,4,5-trihydroxy benzoate
Methyl gallate
CAS: 99-24-1
Molecular Formula: C8H8O5
methyl 3,4,5-trihydroxy benzoate - Names and Identifiers
| Name | Methyl gallate |
| Synonyms | METHYGALLATE Methyl gallate METHYLGALLATE(RG) Methyl 3,4,5-trihydroxybenzoate methyl 3,4,5-trihydroxy benzoate 3,4,5-trihydroxy-benzoic acidd methyl ester METHYL GALLATE(METHYL 3,4,5-TRIHYDROXYBENZOATE ) 2-diazo-1-naphthol-5-sulfonic acid, ester with novolac Gallic acid methyl ester, Methyl 3,4,5-trihydroxybenzoate 3,4,5-trihydroxybenzoic acid methyl ester (intermediate of bifendate) |
| CAS | 99-24-1 |
| EINECS | 202-741-7 |
| InChI | InChI=1/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3 |
| InChIKey | FBSFWRHWHYMIOG-UHFFFAOYSA-N |
methyl 3,4,5-trihydroxy benzoate - Physico-chemical Properties
| Molecular Formula | C8H8O5 |
| Molar Mass | 184.15 |
| Density | 1.3840 (rough estimate) |
| Melting Point | 201-204°C |
| Boling Point | 278.08°C (rough estimate) |
| Flash Point | 190.8°C |
| Water Solubility | SOLUBLE IN HOT WATER |
| Solubility | Soluble in hot water, ethanol, ether and methanol |
| Vapor Presure | 1.02E-08mmHg at 25°C |
| Appearance | monoclinic prismatic crystal (methanol) |
| Color | White to slightly beige |
| Merck | 14,4345 |
| BRN | 2113180 |
| pKa | 8.04±0.23(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5690 (estimate) |
| MDL | MFCD00002194 |
| Physical and Chemical Properties | Melting point 199-203°C WATER-SOLUBLE IN HOT WATER |
| Use | Used as an intermediate for biphenyl bisphenol and other drugs |
| In vitro study | The growth of A. viscosus is inhibited completely by a low dose of Methyl gallate (MIC=1 mg/mL). S. mutans and . sobrinus show intermediate sensitivity to Methyl gallate (MIC=2-4 mg/mL), whereas the growth of Lactobacillus spp. is inhibited completely at a relatively high concentration (MIC=8 mg/mL). Methyl gallate, in a concentration of 100 mM, could alleviate lipid peroxidation of the cells exposed to a short-term H 2 O 2 treatment. In addition, Methyl gallate-treated cells could prevent intracellular glutathione (GSH) from being depleted following an exposure of H 2 O 2 (8.0 mM) for a 3 h period. Methyl gallate inhibits Treg cell-suppressive effects on effector CD4+ T cells and Treg migration toward tumor environment. Furthermore, forkhead box P3 (Foxp3) expression is also significantly decreased by methyl gallate. |
methyl 3,4,5-trihydroxy benzoate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R43 - May cause sensitization by skin contact |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LW8000000 |
| TSCA | Yes |
| HS Code | 29182900 |
methyl 3,4,5-trihydroxy benzoate - Reference
| Reference Show more | 1. Zhou Kun, Jian Ping, Liang Wenyi, et al. Analysis of chemical composition of Tibetan medicine Terminalia and Terminalia Terminalia based on UPLC-Q-Exactive Orbitrap-MS [J]. Chinese Journal of Mass Spectrometry, 2020, 041(003):254-267. 2. Liang Wenyi, Yi Qi, Liang Lin Jin, etc. High performance liquid chromatographic fingerprint of Terminalia chebulae based on Chemometrics analysis [J]. World Science and Technology-modernization of traditional Chinese medicine, 2018, 20(09):167-171. 3. Liang Linjin, Yi qi, Ye Ting, etc. Study on quality control of Terminalia based on simultaneous determination of total tannins and seven components [J]. World Science and Technology: modernization of traditional Chinese medicine, 2018, 20(09):1638-1644. 4. Li-Mei Feng, Yan-Yan Chen, Ding-Qiao Xu, Rui-Jia Fu, Shi-Jun Yu, Qi Zhao, Yu-Xi Huang, Xue Bai, Mei Wang, Li-Ming Xing, Yu-Ping Tang, Jin-Ao Duan,An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropa 5. Li-Mei Feng, Yan-Yan Chen, Ding-Qiao Xu, Rui-Jia Fu, Shi-Jun Yue, Qi Zhao, Yu-Xi Huang, Xue Bai, Mei Wang, Li-Ming Xing, Yu-Ping Tang Jin-Ao Duan,An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropa 6. [IF=4.952] Ren-You Gan et al."Pigmented edible bean coats as natural sources of polyphenols with antioxidant and antibacterial effects."Lwt Food Sci Technol. 2016 Nov;73:168 7. [IF=3.935] Li Li et al."Rapid identification of urokinase plasminogen activator inhibitors from Traditional Chinese Medicines based on ultrafiltration, LC-MS and in silico docking."J Pharmaceut Biomed. 2019 Feb;164:241 8. [IF=6.312] Yue Zhou et al."Optimization of Ultrasound-Assisted Extraction of Antioxidant Polyphenols from the Seed Coats of Red Sword Bean (Canavalia gladiate (Jacq.) DC.)."Antioxidants-Basel. 2019 Jul;8(7):200 9. [IF=5.645] Zhang-Zhen Bai et al."Comparative investigation on metabolites and biological activities of Paeonia ostii stamens from different geographical regions of China."Ind Crop Prod. 2021 Nov;172:114038 10. [IF=4.36] Li-Mei Feng et al."An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropathic pain by the combination of partial least-squares regression and multi-index comprehensive method."J Ethnopharmacol. 2020 Oc 11. [IF=5.246] Wei Gu et al."Investigation of Tannins Transformation in Sanguisorbae Radix Over Carbonizing by Stir-Frying."Front Mol Biosci. 2022; 9: 762224 |
methyl 3,4,5-trihydroxy benzoate - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| reagent use | Methyl gallate exhibits potent anti-tumor activity by inhibiting infiltration of CD4 CD25 regulatory T cells. |
| biological activity | Methyl gallate is a plant phenol with antioxidant, anticancer and anti-inflammatory activity. Methyl gallate can also inhibit bacterial activity. Methyl gallate also has inhibitory activity against HIV-1 and HIV-1 enzymes. |
| Target | Bacterial |
| Use | an intermediate of bifendate. It is also a rubber antioxidant. used as intermediate for biphenyl bisphenol and other drugs |
| production method | is prepared by esterification of Gallic acid with methanol under sulfuric acid catalysis. |
Last Update：2024-04-09 15:16:52
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View History
methyl 3,4,5-trihydroxy benzoate
14233-53-5
5-hydroxy-3-(hydroxymethyl)pentyl hydrogen cyclohex-4-ene-1,2-dicarboxylate
Borane dimethyl sulfide
5-Amino-4-bromobenzothiazole
Trifluoroanisole
METHYL M-METHOXYPHENYLACETATE
2-Aminomethylazetidine
(2-AMINO-BENZOTHIAZOL-6-YL)-MORPHOLIN-4-YL-METHANONE
3-Pyrrolidinol, 1-(phenylmethyl)-, 3-(4-methylbenzenesulfonate)
14233-53-5
5-hydroxy-3-(hydroxymethyl)pentyl hydrogen cyclohex-4-ene-1,2-dicarboxylate
Borane dimethyl sulfide
5-Amino-4-bromobenzothiazole
Trifluoroanisole
METHYL M-METHOXYPHENYLACETATE
2-Aminomethylazetidine
(2-AMINO-BENZOTHIAZOL-6-YL)-MORPHOLIN-4-YL-METHANONE
3-Pyrrolidinol, 1-(phenylmethyl)-, 3-(4-methylbenzenesulfonate)