(Ethoxymethyl)benzene
(Synonyms: 苄基乙醚) 目录号 : GC60404
(Ethoxymethyl)benzene是一种内源性代谢产物。
Cas No.:539-30-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(Ethoxymethyl)benzene is an endogenous metabolite.
| Cas No. | 539-30-0 | SDF | |
| 别名 | 苄基乙醚 | ||
| Canonical SMILES | CCOCC1=CC=CC=C1 | ||
| 分子式 | C9H12O | 分子量 | 136.19 |
| 溶解度 | 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 | 7.3427 mL | 36.7134 mL | 73.4268 mL |
| 5 mM | 1.4685 mL | 7.3427 mL | 14.6854 mL |
| 10 mM | 0.7343 mL | 3.6713 mL | 7.3427 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。
3‑Bromo‑5‑(Ethoxymethyl)‑1,2‑benzenediol inhibits LPS-induced pro-inflammatory responses by preventing ROS production and downregulating NF-κB in vitro and in a zebrafish model
Int Immunopharmacol 2019 Feb;67:98-105.PMID:30537636DOI:10.1016/j.intimp.2018.11.021.
The anti-inflammatory effects of 3‑bromo‑5‑(Ethoxymethyl)‑1,2‑benzenediol (BEMB) from Polysiphonia morrowii were evaluated in lipopolysaccharide (LPS)-induced RAW264.7 cells and zebrafish embryo. BEMB showed anti-inflammatory effects by inhibiting the production of nitric oxide (NO) and reactive oxygen species (ROS), and the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in the LPS-activated RAW264.7 cells and zebrafish embryo without cytotoxicity. Moreover, BEMB suppressed the protein and mRNA expression levels of nuclear factor (NF)-κB (p65 and inhibitor of NF-κB [IκB]-A) in RAW264.7 cells and zebrafish embryo, respectively. Collectively, the results of this study indicate that BEMB suppressed the production of pro-inflammatory mediators such as NO, iNOS, and COX-2 as well as their regulation in LPS-induced RAW264.7 cells and zebrafish embryos by inhibiting ROS production and NF-κB expression. Therefore, this study suggests that BEMB could be a potential anti-inflammatory agent for the treatment of inflammatory diseases.
Synthesis and biological evaluation of novel bromophenol derivatives as carbonic anhydrase inhibitors
Arch Pharm (Weinheim) 2013 Jun;346(6):447-54.PMID:23649517DOI:10.1002/ardp.201300054.
Here, we provide an alternative synthesis of the natural bromophenol 3,4-dibromo-5-(2,3-dibromo-4,5-dihydroxybenzyl)-6-(Ethoxymethyl)benzene-1,2-diol (3) and the first synthesis of (4,5-dihydroxy-2-methylphenyl)(3,4-dihydroxyphenyl)methanone (18) and its brominated derivatives 19-21. The compounds were characterized and tested against the two most studied members of the pH regulatory enzyme family, carbonic anhydrase (CA). The inhibitory potencies of the novel compounds and two natural bromophenols 2, 3 were analyzed at the human isoforms hCA I and hCA II as targets and the KI values were calculated. The KI values of the novel compounds were measured in the range of 13.7-32.7 mM for the hCA I isozyme and 0.65-1.26 mM for the hCA II isozyme. The structurally related compound 14 was also tested in order to understand the structure–activity relationship, and the clinically used sulfonamide acetazolamide (AZA)was tested for comparison reasons. All of the compounds exhibited competitive inhibition with 4-nitrophenylacetate as substrate. The compounds showed strong inhibitory activity against hCA I, being more effective as compared to the clinically used AZA (KI: 36.2 mM), but rather less activity against hCA II.
HPN, a synthetic analogue of bromophenol from red alga Rhodomela confervoides: synthesis and anti-diabetic effects in C57BL/KsJ-db/db mice
Mar Drugs 2013 Jan 30;11(2):350-62.PMID:23364683DOI:10.3390/md11020350.
3,4-Dibromo-5-(2-bromo-3,4-dihydroxy-6-(isopropoxymethyl)benzyl)benzene-1,2-diol (HPN) is a synthetic analogue of 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(Ethoxymethyl)benzyl)benzene-1,2-diol (BPN), which is isolated from marine red alga Rhodomela confervoides with potent protein tyrosine phosphatase 1B (PTP1B) inhibition (IC(50) = 0.84 μmol/L). The in vitro assay showed that HPN exhibited enhanced inhibitory activity against PTP1B with IC(50) 0.63 μmol/L and high selectivity against other PTPs (T cell protein tyrosine phosphatase (TCPTP), leucocyte antigen-related tyrosine phosphatase (LAR), Src homology 2-containing protein tyrosine phosphatase-1 (SHP-1) and SHP-2). The results of antihyperglycemic activity using db/db mouse model demonstrated that HPN significantly decreased plasma glucose (P < 0.01) after eight weeks treatment period. HPN lowered serum triglycerides and total cholesterol concentration in a dose-dependent manner. Besides, both of the high and medium dose groups of HPN remarkably decreased HbA1c levels (P < 0.05). HPN in the high dose group markedly lowered the insulin level compared to the model group (P < 0.05), whereas the effects were less potent than the positive drug rosiglitazone. Western blotting results showed that HPN decreased PTP1B levels in pancreatic tissue. Last but not least, the results of an intraperitoneal glucose tolerance test in Sprague-Dawley rats indicate that HPN have a similar antihyperglycemic activity as rosiglitazone. HPN therefore have potential for development as treatments for Type 2 diabetes.
Effects of a natural PTP1B inhibitor from Rhodomela confervoides on the amelioration of fatty acid-induced insulin resistance in hepatocytes and hyperglycaemia in STZ-induced diabetic rats
RSC Adv 2020 Jan 21;10(6):3429-3437.PMID:35497760DOI:10.1039/c9ra10660j.
PTP1B is a key negative regulator of insulin signaling transduction, and the inhibition of PTP1B has emerged as a potential therapeutic strategy to treat T2DM. 3,4-Dibromo-5-(2-bromo-6-(Ethoxymethyl)-3,4-dihydroxybenzyl)benzene-1,2-diol (BPN), a natural bromophenol isolated from marine red alga Rhodomela confervoides, was found to inhibit PTP1B activity in our previous study. Herein, we identified that BPN functioned as a competitive PTP1B inhibitor and enhanced phosphorylation of IRβ, IRS-1 and Akt in palmitate acid-induced insulin-resistant HepG2 cells. Moreover, 2-deoxyglucose uptake technology-based characterization demonstrated that BPN could stimulate glucose uptake in HepG2 cells. Furthermore, the effects of BPN against oxidative stress were investigated and showed that BPN attenuated oxidative stress by attenuating ROS generation. Finally, long-term oral administration of BPN at dose of 20 mg kg-1 significantly reduced blood glucose levels in streptozotocin-induced diabetic mice and no visible toxic effects were observed. Our work is thus expected to provide a natural uncharged PTP1B inhibitor that could be used as a potential lead compound for further research.
Design, synthesis, and biological evaluation of 2-benzylpyrroles and 2-benzoylpyrroles based on structures of insecticidal chlorfenapyr and natural pyrrolomycins
Mol Divers 2014 Aug;18(3):593-8.PMID:24664285DOI:10.1007/s11030-014-9515-9.
Based on structures of insecticidal chlorfenapyr and antibiotic natural pyrrolomycins, a series of new 2-benzylpyrroles and 2-benzoylpyrroles (with or without Ethoxymethyl group on the nitrogen of pyrrole) were designed and synthesized. These compounds or their parent compounds possess weak acidity and high lipophilicity, the two characteristic properties for uncouplers of oxidative phosphorylation; therefore, they are expected to have insecticidal and acaricidal activity. The bioassay result verified that both 2-benzylpyrroles 17 and 2-benzoylpyrroles 19 had varied degrees of insecticidal activity against oriental armyworm depending on the substituents on the benzene ring, but they did not give any acaricidal activity. Conversely, most N-alkylated compounds 18 and 20 exhibited both insecticidal activity and acaricidal activity, of which compound 18i [4-bromo-2-(2,4-dichlorobenzyl)-1-(Ethoxymethyl) -5-(trifluoromethyl) -1H-pyrrole-3-carbonitrile] has IC50 as low as 10-20 mg L(-1) on both activities.