Diethyl succinate
(Synonyms: 丁二酸二乙酯,Diethyl Butanedioate) 目录号 : GC38771
Diethyl succinate (Butanedioic acid diethyl ester) is the diethyl ester of succinate and acts as an irritant.
Cas No.:123-25-1
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
Diethyl succinate (Butanedioic acid diethyl ester) is the diethyl ester of succinate and acts as an irritant.
| Cas No. | 123-25-1 | SDF | |
| 别名 | 丁二酸二乙酯,Diethyl Butanedioate | ||
| Canonical SMILES | O=C(OCC)CCC(OCC)=O | ||
| 分子式 | C8H14O4 | 分子量 | 174.19 |
| 溶解度 | DMSO: ≥ 250 mg/mL (1435.21 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 | 5.7409 mL | 28.7043 mL | 57.4086 mL |
| 5 mM | 1.1482 mL | 5.7409 mL | 11.4817 mL |
| 10 mM | 0.5741 mL | 2.8704 mL | 5.7409 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。
Diethyl succinate Modulates Microglial Polarization and Activation by Reducing Mitochondrial Fission and Cellular ROS
Metabolites 2021 Dec 8;11(12):854.PMID:34940612DOI:10.3390/metabo11120854.
Succinate is a metabolite in the tricarboxylic acid cycle (TCA) which plays a central role in mitochondrial activity. Excess succinate is known to be transported out of the cytosol, where it activates a succinate receptor (SUCNR1) to enhance inflammation through macrophages in various contexts. In addition, the intracellular role of succinate beyond an intermediate metabolite and prior to its extracellular release is also important to the polarization of macrophages. However, the role of succinate in microglial cells has not been characterized. Lipopolysaccharide (LPS) stimulates the elevation of intracellular succinate levels. To reveal the function of intracellular succinate associated with LPS-stimulated inflammatory response in microglial cells, we assessed the levels of ROS, cytokine production and mitochondrial fission in the primary microglia pretreated with cell-permeable Diethyl succinate mimicking increased intracellular succinate. Our results suggest that elevated intracellular succinate exerts a protective role in the primary microglia by preventing their conversion into the pro-inflammatory M1 phenotype induced by LPS. This protective effect is SUCNR1-independent and mediated by reduced mitochondrial fission and cellular ROS production.
Succinate Is a Natural Suppressor of Antiviral Immune Response by Targeting MAVS
Front Immunol 2022 Mar 2;13:816378.PMID:35309330DOI:10.3389/fimmu.2022.816378.
Succinate is at the crossroads of multiple metabolic pathways and plays a role in several immune responses acting as an inflammation signal. However, whether succinate regulates antiviral immune response remains unclear. Here, we found that the production of succinate was reduced in RAW264.7 cells during vesicular stomatitis virus (VSV) infection. Using Diethyl succinate to pretreat the mouse peritoneal macrophages and RAW264.7 cells before VSV infection, the production of interferon-β (IFN-β), chemokine (C-X-C motif) ligand 10 (CXCL-10), and IFN-stimulated genes 15 (ISG15) was significantly decreased, following which the VSV replication in diethyl succinate-pretreated cells was obviously increased. Moreover, succinate decreased the expression of IFN-β in serum, lung, and spleen derived from the VSV-infected mice. The overall survival rate in the VSV-infected mice with Diethyl succinate pretreatment was also remarkably downregulated. Furthermore, we identified that succinate inhibited the activation of MAVS-TBK1-IRF3 signaling by suppressing the formation of MAVS aggregates. Our findings provide previously unrecognized roles of succinate in antiviral immune response and establish a novel link between metabolism and innate immune response.
[2,5-Bis(di-propyl-amino)-4-(hy-droxy-meth-yl)phen-yl]methanol
IUCrdata 2021 Apr 30;6(Pt 4):x210443.PMID:36339103DOI:10.1107/S2414314621004430.
The centrosymmetric title compound, C22H36N2O2, was prepared in five steps from Diethyl succinate. The di-propyl-amino groups are almost orthogonal to the central phenyl-enedi-methanol ring [dihedral angle = 87.62 (9)°]. In the crystal, the mol-ecules are connected by O-H⋯N hydrogen bonds, forming (101) layers separated by the propyl chains.
Real-time molecular imaging of tricarboxylic acid cycle metabolism in vivo by hyperpolarized 1-(13)C Diethyl succinate
J Am Chem Soc 2012 Jan 18;134(2):934-43.PMID:22146049DOI:10.1021/ja2040865.
The Krebs tricarboxylic acid cycle (TCA) is central to metabolic energy production and is known to be altered in many disease states. Real-time molecular imaging of the TCA cycle in vivo will be important in understanding the metabolic basis of several diseases. Positron emission tomography (PET) with FDG-glucose (2-[(18)F]fluoro-2-deoxy-d-glucose) is already being used as a metabolic imaging agent in clinics. However, FDG-glucose does not reveal anything past glucose uptake and phosphorylation. We have developed a new metabolic imaging agent, hyperpolarized diethyl succinate-1-(13)C-2,3-d(2) , that allows for real-time in vivo imaging and spectroscopy of the TCA cycle. Diethyl succinate can be hyperpolarized via parahydrogen-induced polarization (PHIP) in an aqueous solution with signal enhancement of 5000 compared to Boltzmann polarization. (13)C magnetic resonance spectroscopy (MRS) and magnetic resonance imaging (MRI) were achieved in vivo seconds after injection of 10-20 μmol of hyperpolarized Diethyl succinate into normal mice. The downstream metabolites of hyperpolarized Diethyl succinate were identified in vivo as malate, succinate, fumarate, and aspartate. The metabolism of Diethyl succinate was altered after exposing the animal to 3-nitropropionate, a known irreversible inhibitor of succinate dehydrogenase. On the basis of our results, hyperpolarized Diethyl succinate allows for real-time in vivo MRI and MRS with a high signal-to-noise ratio and with visualization of multiple steps of the TCA cycle. Hyperpolarization of Diethyl succinate and its in vivo applications may reveal an entirely new regime wherein the local status of TCA cycle metabolism is interrogated on the time scale of seconds to minutes with unprecedented chemical specificity and MR sensitivity.
Chemoenzymatic resolution of rac-malathion
Tetrahedron Asymmetry 2014 Apr 15;25(6-7):529-533.PMID:24839353DOI:10.1016/j.tetasy.2014.02.013.
Malathion, diethyl 2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate, is an organophosphate used to control insect pests. Malathion contains a Diethyl succinate moiety that is a known functional group susceptible to desymmetrizing enzymes such as esterases that selectively react with a single enantiomer. Purified rac-malathion was subjected to hydrolysis at the Diethyl succinate moiety of malathion under various conditions using wild type pig liver esterase to form (S)-malathion (12 % ee) and ~ 3:2 mixture of α- and β-monoacids of (R)-malathion. Technical malathion could not be enriched due to the presence of esterase inhibitors. Further investigation of this resolution using a panel of six PLE isoenzymes also demonstrated formation of (S)-malathion, however, an improvement of up to 56 % ee was obtained.