2,4,6-Trihydroxybenzaldehyde
(Synonyms: 2,4,6-三羟基苯甲醛) 目录号 : GC680442,4,6-Trihydroxybenzaldehyde 是一种具有口服活性的 NF-?B 抑制剂。2,4,6-Trihydroxybenzaldehyde 具有抗肿瘤活性、抗癌细胞增殖活性和抗肥胖活性。
Cas No.:487-70-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2,4,6-Trihydroxybenzaldehyde is an orally active NF-?B inhibitor. 2,4,6-Trihydroxybenzaldehyde shows anti-tumor activity, anti-cancer cell proliferative activity and anti-obesity activity[1][2][3].
2,4,6-Trihydroxybenzaldehyde inhibits adipocyte differentiation and lipid accumulation in 3T3-L1 cells[1].
2,4,6-Trihydroxybenzaldehyde down-regulates PPARγ, C/EBPα, SREBP-1c, and FAS protein expression levels[1].
2,4,6-Trihydroxybenzaldehyde (oral administration; 5 and 25 mg/kg for 13 weeks) reduces the HFD-induced increase in weight gain, reduces serum levels of glucose, triglycerides, and total cholesterol[1].
[1]. Kim KN, et al. 2,4,6-Trihydroxybenzaldehyde, a potential anti-obesity treatment, suppressed adipocyte differentiation in 3T3-L1 cells and fat accumulation induced by high-fat diet in C57BL/6 mice. Environ Toxicol Pharmacol. 2015 Mar;39(2):962-8.
[2]. Marton A, et al. Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NF?B Activation and Suppress Growth of A375 Human Melanoma. Anticancer Res. 2016 Nov;36(11):5743-5750.
[3]. 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.
| Cas No. | 487-70-7 | SDF | Download SDF |
| 别名 | 2,4,6-三羟基苯甲醛 | ||
| 分子式 | C7H6O4 | 分子量 | 154.12 |
| 溶解度 | 储存条件 | 4°C, stored under nitrogen | |
| 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 | 6.4885 mL | 32.4423 mL | 64.8845 mL |
| 5 mM | 1.2977 mL | 6.4885 mL | 12.9769 mL |
| 10 mM | 0.6488 mL | 3.2442 mL | 6.4885 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。
Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NFĸB Activation and Suppress Growth of A375 Human Melanoma
Anticancer Res 2016 Nov;36(11):5743-5750.PMID:27793895DOI:10.21873/anticanres.11157.
Background/aim: Constitutive activation of nuclear factor kappa-B (NFĸB) is a hallmark of various cancer types, including melanoma. Chemotherapy may further increase tumour NFĸB activity, a phenomenon that, in turn, exacerbates drug resistance. This study aimed at preliminary screening of a panel of aromatic aldehydes, including vanillin, for cytotoxicity and suppression of tumour cell NFĸB activity. Materials and methods: The cytotoxic and NFĸB-inhibitory effects of 10 aromatic aldehydes, including vanillin, were investigated in cultured A375 human melanoma cells. Each compound was assayed alone and in combination with the model NFĸB-activating drug doxorubicin. The most promising analogues were then tested alone and in combination with 4-hydroperoxycyclophosphamide in vitro, and with cyclophosphamide in mice bearing A375 xenografts. Results: The vanillin analogues o-vanillin and 2,4,6-Trihydroxybenzaldehyde exhibited cytotoxicity against cultured A375 cells, and inhibited doxorubicin- and 4-hydroperoxycyclophosphamide-induced NFĸB activation. They also suppressed A375 cell growth in mice. Conclusion: o-vanillin and 2,4,6-Trihydroxybenzaldehyde deserve further evaluation as potential anticancer drugs.
2,4,6-Trihydroxybenzaldehyde, a potential anti-obesity treatment, suppressed adipocyte differentiation in 3T3-L1 cells and fat accumulation induced by high-fat diet in C57BL/6 mice
Environ Toxicol Pharmacol 2015 Mar;39(2):962-8.PMID:25812771DOI:10.1016/j.etap.2015.02.007.
In the present study, 2,4,6-Trihydroxybenzaldehyde (THB) was evaluated for inhibitory effects on adipocyte differentiation in 3T3-L1 cells and anti-obesity effects in mice with high-fat diet (HFD)-induced obesity. Lipid accumulation measurement indicated that THB markedly inhibited adipogenesis, and this involved down-regulation of the expression of the adipogenesis-related proteins, CCAAT/enhancer-binding protein α (C/EBPα), peroxisome proliferator-activated receptor γ (PPARγ), fatty acid synthase (FAS) and sterol regulatory element-binding protein-1c (SREBP-1c), in 3T3-L1 pre-adipocyte cells. In a mouse model of HFD-induced obesity, oral administration of THB (5 and 25mg/kg for 13 weeks) reduced the HFD-induced increase in weight gain. THB administration also reduced serum levels of glucose, triglycerides, and total cholesterol. A reduction in the hypertrophy of white adipose tissue was also observed. Furthermore, THB administration inhibited HFD-induced hepatic steatosis. These results provided evidence that administration of THB alleviated HFD-induced obesity in C57BL/6 mice and revealed the potential of THB as a nutraceutical to help prevent or treat obesity and the associated metabolic disorders.
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.
A synthetically benign one-pot construction of enamino-xanthene dyes
Org Biomol Chem 2022 Oct 26;20(41):8108-8119.PMID:36214790DOI:10.1039/d2ob01358d.
Polyhydroxylated phenols are components of biomass and precursors of pigments in plants. This paper reports a novel entry to xanthene dyes, involving the reaction of 2,4,6-Trihydroxybenzaldehyde with primary aliphatic amines. This catalyst-free synthesis exhibits a high atom economy and can be conducted under eco-friendly conditions and operational simplicity.