3-O-Methylgallic acid
(Synonyms: 3-O-甲基没食子酸,3,4-Dihydroxy-5-methoxybenzoic acid) 目录号 : GC60507
3-O-Methylgallicacid(3,4-Dihydroxy-5-methoxybenzoicacid)是一种花青素代谢产物，具有强大的抗氧化能力。3-O-Methylgallicacid能抑制Caco-2细胞增殖，IC50值为24.1μM。3-O-Methylgallicacid还诱导细胞凋亡(apoptosis)并具有抗癌作用。
Cas No.:3934-84-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-O-Methylgallic acid (3,4-Dihydroxy-5-methoxybenzoic acid) is an anthocyanin metabolite and has potent antioxidant capacity. 3-O-methylgallic acid inhibits Caco-2 cell proliferation with an IC50 value of 24.1 μM. 3-O-methylgallic acid also induces cell apoptosis and has anti-cancer effects[1][2].
[1]. Forester SC, et al. Gut metabolites of anthocyanins, gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde, inhibit cell proliferation of Caco-2 cells. J Agric Food Chem. 2010 May 12;58(9):5320-7. [2]. Forester SC, The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals. Mol Carcinog. 2014 Jun;53(6):432-9.
| Cas No. | 3934-84-7 | SDF | |
| 别名 | 3-O-甲基没食子酸,3,4-Dihydroxy-5-methoxybenzoic acid | ||
| Canonical SMILES | O=C(O)C1=CC(OC)=C(O)C(O)=C1 | ||
| 分子式 | C8H8O5 | 分子量 | 184.15 |
| 溶解度 | DMSO: 50 mg/mL (271.52 mM); Water: 2.2 mg/mL (11.95 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.4304 mL | 27.1518 mL | 54.3036 mL |
| 5 mM | 1.0861 mL | 5.4304 mL | 10.8607 mL |
| 10 mM | 0.543 mL | 2.7152 mL | 5.4304 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthesis of 3-O-Methylgallic acid a powerful antioxidant by electrochemical conversion of syringic acid
Biochim Biophys Acta 2013 Jun;1830(6):3643-9.PMID:23434437DOI:10.1016/j.bbagen.2013.02.012.
Background: A kinetic study of the electrochemical oxidation of syringic acid (3,5-dimethoxy-4-hydroxybenzoic acid) by cyclic voltammetry at treated gold disk was combined with results of electrolyses at Ta/PbO2 anode in order to convert it into potentially high-added-value product. Methods: The electrochemical oxidation of syringic acid was carried out in order to convert this compound to 3-O-Methylgallic acid. This latter was identified by mass spectrophotometry using LC-MS/MS apparatus. The 3-O-Methylgallic acid synthesis was controlled by cyclic volammetry, Ortho-diphenolicdeterminations and DPPH radical-scavenging activity. Results: The proposed mechanism is based on the hypothesis of a bielectronic discharge of syringic acid molecule under free and adsorbed form involving two intermediate cation mesomers. Hydrolysis of the more stable of this last one leads to the formation of the 3,4-dihydroxy-5-methoxybenzoic acid (3-O-Methylgallic acid) as a major product. The latter aromatic compound was synthesized by anodic oxidation of syringic acid at PbO2 electrode. The cyclic voltammogram of the electrolysis bath of syringic acid shows that the anodic peak potential of 3-O-Methylgallic acid was lower (Epa=128mV) than that of SA (Epa=320mV). And the strongest antiradical activity was detected when the 3-O-Methylgallic acid concentration was higher". Conclusion: The electrochemical oxidation using PbO2 anode is a rapid, simple and efficient method tool for a conversion of SA into 3-O-Methylgallic acid, a potent antioxidant derivative General significance: The electrochemical process consists in a simple transformation of the syringic acid into 3-O-Methylgallic acid having a better antioxidant capacity. This result has been justified by cyclic voltametry which shows that anodic peak of 3-O-Methylgallic acid is reversible. Furthermore, its potential is lower than that of the irreversible anodic peak of syringic acid to 3-O-Methylgallic acid.
Gut metabolites of anthocyanins, gallic acid, 3-O-Methylgallic acid, and 2,4,6-trihydroxybenzaldehyde, inhibit cell proliferation of Caco-2 cells
J Agric Food Chem 2010 May 12;58(9):5320-7.PMID:20373763DOI:10.1021/jf9040172.
Gut microflora metabolize anthocyanins to phenolic acids and aldehydes. These metabolites may explain the relationship between anthocyanin consumption and reduced incidence of colon cancer. Here, all six major metabolites, along with a Cabernet Sauvignon anthocyanin extract, were incubated with Caco-2 cells at concentrations of 0-1000 microM over 72 h to determine effects on cell proliferation and for 24 h to assess cytotoxicity effects and at 140 microM for 24 h to measure induction of apoptosis. These measurements were based on colorimetric methods. Gallic acid and 3-O-Methylgallic acid inhibited cell proliferation and lacked cytotoxicity at low concentrations. The aldehyde metabolite and anthocyanin extract also inhibited cell proliferation at low concentrations and had low cytotoxicity at a wide range of concentrations. Of the four substances that effectively reduced cell proliferation, the aldehyde was the best inducer of apoptosis. In addition, these same four treatments degraded quickly in growth media, suggesting the involvement of subsequent oxidation products in the reduction of cell viability. These results indicate that the anthocyanin microfloral metabolites gallic acid, 3-O-Methylgallic acid, and 2,4,6-trihydroxybenzaldehyde reduce cell proliferation in Caco-2 cells more effectively than anthocyanins and may offer protection against colon cancer after their formation in the gut.
The anthocyanin metabolites gallic acid, 3-O-Methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals
Mol Carcinog 2014 Jun;53(6):432-9.PMID:23124926DOI:10.1002/mc.21974.
Anthocyanins are a class of polyphenols abundant in the skins of red grapes, and have been shown to have anti-cancer effects in models of colon cancer [Cooke et al. Int J Cancer 2006;119:2213-2220; Jing et al. J Agric Food Chem 2008;56:9391-9398]. Gut microflora metabolize anthocyanins to phenolic acids and aldehydes. These metabolites may explain the relationship between anthocyanin consumption and reduced incidence of colorectal cancer (CRC). Previously, gallic acid (Gal), 3-O-Methylgallic acid (Megal), and 2,4,6-trihydroxybenzaldehyde (THBA) were found to decrease Caco-2 cell viability to a larger extent than other anthocyanin metabolites. To better understand the potential anti-CRC action of these compounds, this paper investigated their capacity to modulate the cell cycle, and induce apoptotic cell death. Dividing Caco-2 cells were incubated for 24-72 h in the presence of 10-100 µM Gal, Megal, THBA, and malvidin-3-glucoside (M3g). THBA reduced cell viability only at 100 µM, while Gal and Megal (10-100 µM) caused a time- and dose-dependent decrease in cell viability. After 72 h incubation, the metabolites caused cell cycle arrest at G0 /G1 . The activation of the apoptotic pathway by Megal, Gal, and THBA was evidenced by the activation of caspase-3. However, only Megal and Gal caused DNA fragmentation and nuclear condensation. Megal, Gal, and THBA inhibited transcription factors NF-κB, AP-1, STAT-1, and OCT-1 which are known to be activated in CRC. In conclusion, the anti-cancer effects of Megal and Gal occurs as a consequence of both the inhibition of cell proliferation and induction of apoptosis. The inhibition of transcription factors that promote cell proliferation and survival can in part underlie the observed effects.
Production of methanol from aromatic acids by Pseudomonas putida
J Bacteriol 1980 Jun;142(3):916-24.PMID:7380811DOI:10.1128/jb.142.3.916-924.1980.
When grown at the expense of 3,4,5-trimethoxybenzoic acid, a strain of Pseudomonas putida oxidized this compound and also 3,5-dimethoxy-4-hydroxybenzoic (syringic) and 3,4-dihydroxy-5-methoxybenzoic (3-O-methylgallic) acids; but other hydroxy- or methoxy-benzoic acids were oxidized slowly or not at all. Radioactivity appeared exclusively in carbon dioxide when cells were incubated with [4-methoxyl-14C]trimethoxybenzoic acid, but was found mainly in methanol when[methoxyl-14C]3-O-Methylgallic acid was metabolized. The identity of methanol was proved by analyzing the product from [methoxyl-13C]3-O-Methylgallic acid by nuclear magnetic resonance spectroscopy and by isolating the labeled 3,5-dinitrobenzoic acid methyl ester, which was examined by mass spectrometry. These results, together with measurements of oxygen consumed in demethylations catalyzed by cell extracts, showed that two methoxyl groups of 3,4,5-trimethoxybenzoate and one of syringate were oxidized to give carbon dioxide and 3-O-methylgallate. This was then metabolized to pyruvate; the other product was presumed to be the 4-methyl ester of oxalacetic acid, for which cell extracts contained an inducible, specific esterase. P. putida did not metabolize the methanol released from this compound by hydrolysis. Support for the proposed reaction sequence was obtained by isolating mutants which, although able to convert 3,4,5-trimethoxybenzoic acid into 3-O-Methylgallic acid, were unable to use either compound for growth.
Gallic acid metabolites are markers of black tea intake in humans
J Agric Food Chem 2000 Jun;48(6):2276-80.PMID:10888536DOI:10.1021/jf000089s.
Gallic acid is one of the main phenolic components of black tea. The objective of this study was to identify urinary gallic acid metabolites with potential for use as markers of black tea intake. In an initial study, nine compounds, assessed by using gas chromatography-mass spectrometry, were found to increase in concentration in urine after 3 cups of black tea over 3 h. A subsequent study employed a controlled crossover design in which 10 subjects consumed 5 cups per day of black tea or water for 4 weeks in random order. Twenty-four hour urine samples were collected at the end of each period. Of the 9 candidate compounds identified in the initial study, only 3 were present at higher concentrations in urine of all 10 subjects during tea-drinking in comparison to water-drinking periods. These compounds were identified as 4-O-methylgallic acid, 3-O-Methylgallic acid, and 3, 4-O-dimethylgallic acid, all methyl ether derivatives of gallic acid. It is suggested that these compounds have the potential to be used as markers of black tea intake.