Diolein
(Synonyms: 二油酸甘油酯9C18:1) 目录号 : GC45432
A diacylglycerol
Cas No.:25637-84-7
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
Diolein is a diacylglycerol that contains the monounsaturated 18-carbon fatty acid oleic acid at two positions.
References
| Cas No. | 25637-84-7 | SDF | |
| 别名 | 二油酸甘油酯9C18:1 | ||
| Canonical SMILES | OC(COC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O | ||
| 分子式 | C39H72O5 | 分子量 | 621 |
| 溶解度 | DMF: 10 mg/ml,Ethanol: 10 mg/ml,Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml | 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 | 1.6103 mL | 8.0515 mL | 16.1031 mL |
| 5 mM | 0.3221 mL | 1.6103 mL | 3.2206 mL |
| 10 mM | 0.161 mL | 0.8052 mL | 1.6103 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。
Diolein Based Nanostructures as Targeted Theranostics
J Biomed Nanotechnol 2016 May;12(5):1076-88.PMID:27305827DOI:10.1166/jbn.2016.2212.
Diolein based non-targeted theranostic nanoparticles (DO-NPs) containing 10%wt of the amphiphilic Gadolinium complex (C18)2DTPA(Gd), and targeted NPs, obtained by introducing growing amounts (3% wt, 6% wt or 10% wt) of (C18)2-Peg3000- FA in the sample composition, have been studied for their in vitro and in vivo properties. Cellular binding was studied by lCP-MS analysis of the Gadolinium content and by Surface Plasmon Resonance (SPR) assays. The best formulation in terms of selectivity towards IGROV-1 cells with respect to non-targeted DO-NPs, was that containing 3% (C18)2Peg3000- FA (P < 0.01). Cytotoxic studies and confocal microscopy analysis of IGROV-1 cells indicate high selective properties of the targeted doxorubicin (DOX) loaded NPs. Nanoparticles described here represent the first example in which a targeted carrier characterized by a stable foamy mesophase, provided by the Diolein component, combine the therapeutic effect due to the anticancer drug doxorubicin, with the imaging properties provided by paramagnetic gadolinium complexes for MRI. As evidenced by T(1w), and T(2w) MRI images and by the in vivo antitumor effect in IGROV-1 tumor-bearing mice, DO-NP3-FA/DOX provides very high therapeutic efficacy with a tumor growth regression of 80% and 50% higher as compared to the mice treated with saline solution and with Doxil, respectively.
Rational synthesis of 1,3-diolein by enzymatic esterification
J Biotechnol 2012 May 31;159(1-2):44-9.PMID:22370538DOI:10.1016/j.jbiotec.2012.02.006.
t-Butanol was an excellent reaction medium for enzyme-mediated esterification of oleic acid with glycerol for 1,3-diolein preparation which has been proved by our group. Herein, to achieve the rational synthesis of 1,3-diolien, response surface methodology was applied to examine the effects of the significant variables and their reciprocal effects on the product synthesis. Under the optimal conditions (62.4°C, 0.75g Novozym 435, substrate molar ratio (oleic acid/glycerol) 2.4 and 4.8g t-butanol), the Diolein yield of 87.4% could be achieved, and the value of 1,3-diolien/Diolein was as high as 87.8%, which were quite close to the predicted values. Compared with the results of our previous single factor experiment, although the values of Diolein yield and 1,3-diolien/Diolein could not be improved markedly, the enzyme dosage and the reaction medium were spared by 25% and 20%, respectively, which was a remarkable improvement of the enzymatic process.
Kinetics and Mechanism of Solvent Influence on the Lipase-Catalyzed 1,3-Diolein Synthesis
ACS Omega 2020 Sep 15;5(38):24708-24716.PMID:33015488DOI:10.1021/acsomega.0c03284.
1,3-Diacylglycerol preparation has roused increasing attention in recent years as the 1,3-diacylglycerol-rich oils can suppress the deposition of visceral fat and prevent the body weight increasing. Lipozyme TL IM-mediated esterification of oleic acid with monoolein was effective for 1,3-diacylglycerol production. During the esterification process, the solvent shows obvious influence on the Diolein synthesis as well as the 1,3-diolein production. This work investigated the related kinetics and mechanism of the solvent effect on the esterification and Lipozyme TL IM performance. The results indicated that both the esterification rate constant and the acyl migration rate constant positively correlated with the logP of the solvent, while the site specificity of lipase has negative correlation with solvent logP. The acylation toward the 2-position of 1-monoolein was more sensitive to the solvent logP compared to the 1-position of glycerides. Molecular dynamics simulation revealed that solvents with different logP influenced the structure of Lipozyme TL IM including RMSD, hydrogen bond, and radial distribution function to a large extent, which subsequently led to the catalytic activity and selectivity variation of the lipase.
Evaluation of the Candida sp. 99-125 Lipase Positional Selectivity for 1,3-Diolein Synthesis
Biomed Res Int 2019 May 20;2019:4318631.PMID:31236406DOI:10.1155/2019/4318631.
In this study, comparative experiments were carried out to investigate the positional selectivity of Candida sp. 99-125 lipase in preparing 1,3-diolein by using medium engineering strategy. The results indicated that the Diolein yield was markedly enhanced from 56.5% to 86.7% with increasing logP values of the solvents, while the selectivity of the examined lipase for the sn-1 over the sn-2 hydroxyl of glycerol was decreased, thus leading to a reduced 1,3-diolein to 1,2-diolein ratio. To evaluate the possibility of industrial enzymatic production of 1,3-diolein, larger-scale experiments were assessed. After being used repeatedly for eight batches, the Diolein content reached 95.1%, while the 1,3-diolein to 1,2-diolein ratio was 7:1 following purification. Results of the kg level experiments significantly demonstrated the practicability of the enzymatic process and the efficiency of the purification strategy for the product.
Characterization of a novel diolein-based LPDII vector for gene delivery
J Control Release 2002 Sep 18;83(1):121-32.PMID:12220844DOI:10.1016/s0168-3659(02)00167-0.
LPDII vectors are non-viral vehicles for gene delivery comprised of polycation-condensed plasmid DNA (polyplexes) complexed with anionic pH-sensitive liposomes. Here, we describe a novel LPDII formulation containing polyethylenimine (PEI) polyplexes complexed with anionic pH-sensitive liposomes composed of Diolein/cholesteryl hemisuccinate (CHEMS) (6:4 mol/mol). The pH-sensitivity of Diolein/CHEMS liposomes was evaluated through quantitative fluorescence measurements of calcein release and particle size analysis. The results indicated that Diolein/CHEMS liposomes are stable at physiological pH, but undergo rapid aggregation and fluorescence dequenching at pH values < or =5.0. Using a luciferase reporter gene, in vitro transfection of KB oral cancer cells showed that the transfection efficiency of LPDII vectors was superior to other well-characterized polyplexes and lipoplexes. Results further showed that gene delivery using diolein-containing LPDII vectors was dependent on the PEI nitrogen/DNA phosphate (N/P) ratio, the lipid/DNA weight ratio and the cell line being transfected. Replacing PEI with poly-L-lysine as the DNA condensing agent resulted in only a moderate reduction in transfection activity. Moreover, in contrast to LPDII formulations incorporating dioleoylphosphatidylethanolamine (DOPE), the transfection efficiency of diolein-based LPDII vectors was sustained in media containing up to 50% fetal bovine serum. Since diolein-based LPDII vectors mediate efficient gene transfer and retain their transfection activity in the presence of serum, Diolein may be a promising alternative to DOPE for the construction of non-viral vectors for in vivo gene delivery.