Docosahexaenoic Acid ethyl ester
(Synonyms: (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-二十二碳六烯酸乙酯,Ethyl docosahexaenoate) 目录号 : GC45438
An ω-3 fatty acid ethyl ester
Cas No.:81926-94-5
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
Fish oils in the diet have anti-inflammatory and cardiovascular benefits due to an abundance of ω-3 polyunsaturated fatty acids (PUFAs), including docosahexaenoic acid (DHA).1 DHA is the most abundant ω-3 PUFA in neural tissues, especially in the retina and brain. DHA ethyl ester is the stabilized ethyl ester form of the ω-3 22:6 fatty acid. Dietary intake of DHA ethyl ester enhances maze-learning ability in old mice.2 In rats, dietary DHA ethyl ester increases plasma and erythrocyte membrane DHA levels without altering the content of the ω-6 arachidonic acid.3 Dietary DHA ethyl ester increases fatty acid oxidation enzymes in rats and, in humans with peroxisomal disorders, improves vision, liver function, muscle tone, and social contact.4,5 The ω-3 fatty acid eicosapentaenoic acid competitively inhibits the metabolism of arachidonic acid by COX enzymes, suggesting that DHA ethyl ester may also directly modulate the actions of enzymes involved in fatty acid metabolism.6
References
1. von Schacky, C. A review of omega-3 ethyl esters for cardiovascular prevention and treatment of increased blood triglyceride levels. Vascular Health and Risk Management 2(3), 251-262 (2006).
2. Lim, S.Y., and Suzuki, H. Intakes of dietary docosahexaenoic acid ethyl ester and egg phosphatidylcholine improve maze-learning ability in young and old mice. Journal of Nutrition 130, 1629-1632 (2000).
3. Valenzuela, A., Valenzuela, V., Sanhueza, J., et al. Effects of supplementation with docosahexaenoic acid ethyl ester and sn-2 docosahexaenyl monoacylglyceride on plasma and erythrocyte fatty acids in rats. Annuals of Nutrition and Metabolism 49, 49-53 (2005).
4. Hong, D.D., Takahashi, Y., Kushiro, M., et al. Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat. Biochimica et Biophysica Acta 1635, 29-36 (2003).
5. Martinez, M., VÁzquez, E., GarcÍa-Silva, M.T., et al. Therapeutic effects of docosahexaenoic acid ethyl ester in patients with generalized peroxisomal disorders. American Journal of Clinical Nutrition 71, 376S-385S (2000).
6. Wada, M., DeLong, C.J., Hong, Y.H., et al. Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. J. Biol. Chem. 282(31), 22254-22266 (2007).
| Cas No. | 81926-94-5 | SDF | |
| 别名 | (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-二十二碳六烯酸乙酯,Ethyl docosahexaenoate | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(OCC)=O | ||
| 分子式 | C24H36O2 | 分子量 | 356.5 |
| 溶解度 | DMF: 100 mg/ml,DMSO: 100 mg/ml,Ethanol: 500 mg/ml,PBS (pH 7.2): 0.15 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 | 2.805 mL | 14.0252 mL | 28.0505 mL |
| 5 mM | 0.561 mL | 2.805 mL | 5.6101 mL |
| 10 mM | 0.2805 mL | 1.4025 mL | 2.805 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。
Kinetics of Docosahexaenoic Acid ethyl ester accumulation in dog plasma and brain
Prostaglandins Leukot Essent Fatty Acids 2016 Oct;113:1-8.PMID:27720035DOI:10.1016/j.plefa.2016.08.001.
This study explores dog plasma and brain fatty acid composition achieved after long-term supplementation at high DHA doses. A 90% concentrate of DHA Ethyl Ester (DHA-EE) administered by oral gavage to Beagle dogs at doses of 100, 500, 1000, and 2000mg/kg bw/day for 8 weeks resulted in DHA increases in both plasma and brain. In a subsequent 9-month study, DHA-EE was administered at 150, 1000 and 2000mg/kg bw/day. Plasma DHA increased between 150 and 1000mg/kg bw/day but not between 1000 and 2000mg/kg bw/day and there were increases from Day 1to 92 but not between days 92 and 273. Doses >500mg/kg bw/day in the 8-week and all doses in the 9-month study resulted in DHA increases in the brain. The dose of 150mg/k gbw/day is sufficient to achieve maximal brain concentrations if DHA is administered chronically. For shorter than 6 months of supplementation, higher doses are required.
A biphasic system based on guanidinium ionic liquid: Preparative separation of eicosapentaenoic acid ethyl ester and Docosahexaenoic Acid ethyl ester by countercurrent chromatography
J Chromatogr A 2020 May 10;1618:460872.PMID:31959458DOI:10.1016/j.chroma.2020.460872.
Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are high nutritional components. Evidence for unique effects of them is increasing. Further understanding of their independent biological functions urgently needs more efficient separation techniques. Nowadays, most of the commercially available fish oil products are the mixture of eicosapentaenoic acid ethyl ester (EPAEE) and Docosahexaenoic Acid ethyl ester (DHAEE). It will be convenient to directly separate esterified EPA and DHA without saponification pretreatment. However, it is of great challenge to separate EPAEE and DHAEE because of their extremely fat-soluble nature and the equivalent chain length rule. In this research, the suitability of green guanidinium ionic liquid (IL) in countercurrent chromatography (CCC) solvent system for the separation of them was evaluated for the first time. Compared with imidazolium IL and phosphonium IL, guanidinium IL based non-aqueous biphasic system showed more outstanding separation performance. The separation mechanism was elucidated in depth through quantum mechanical calculations. It was found that guanidinium IL acted a crucial role in the CCC separation, which resulted in difference of partition behavior of EPAEE and DHAEE via different hydrogen-bonding affinity. EPAEE and DHAEE were successfully separated by solvent system (n-heptane/methanol/propylguanidinium chloride ([C3Gun]Cl, 1:1:5%, v/v/m)) with high purity (>95%) in one step, which was not achieved beforehand. Moreover, an easy recycling procedure of IL had also been devised, which significantly reduced waste generated. It opens up a new way for reasonable design water-free two-phase solvent system for efficient separation of very non-polar lipid compounds.
[Separation of eicosapentaenoic acid ethyl ester and Docosahexaenoic Acid ethyl ester by simulated moving bed chromatography]
Se Pu 2018 Sep 8;36(9):858-865.PMID:30251513DOI:10.3724/SP.J.1123.2018.04018.
Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are important ω -3 polyunsaturated fatty acids. Their physiological effects on humans are not exactly the same; therefore, the production of products with high-purity EPA or DHA monomers is significant. In this work, EPA ethyl ester (EPA-EE) and DHA ethyl ester (DHA-EE) were first separated using HPLC with poly(styrene-co-divinylbenzene) (PS/DVB) as the stationary phase. The effects of the mobile phase, PS/DVB particle diameter, and column temperature were systematically evaluated. The results showed that methanol is a suitable mobile phase, having a resolution of 2.75. By comparing resolutions, a PS/DVB particle diameter of 10 μ m was chosen; however, when the pressure drop of PS/DVB is considered, PS/DVB with a particle diameter of 20 μ m is more favorable for large-scale preparations. A column temperature of 40℃ was found to be the most feasible for maintaining efficient separation. Second, eight semi-preparative columns (150 mm×10 mm) of PS/DVB polymer were prepared for the simulated moving bed (SMB) chromatography; the homogeneity of these columns was perfect, with a relative total column porosity error of less than 1%. Finally, an EPA-EE and DHA-EE mixture was separated using the SMB chromatography, and the contents of the extract and the raffinate were determined using GC-FID. The effects of the flow rate of Zone Ⅱ and Zone Ⅲ, the flow rate of the feed, and the feed concentration were investigated. Under optimal conditions, EPA-EE and DHA-EE with favorable purities of 91.6% and 93.6%, respectively, were achievable. The recovery of the EPA-EE was 97.0% and the recovery of the DHA-EE was 91.6%. The productivity and solvent requirements were 5.97 g/(L\5h) and 1.52 L/g, respectively. Therefore, SMB chromatography is an attractive technology for the production of high-value products.
Docosahexaenoic Acid ethyl ester enhances 6-hydroxydopamine-induced neuronal damage by induction of lipid peroxidation in mouse striatum
Neurochem Res 2009 Jul;34(7):1299-303.PMID:19219632DOI:10.1007/s11064-008-9909-0.
Superoxide and hydroxyl radicals are implicated in the pathogenesis of Parkinson disease, and induction of lipid peroxidation is an important factor in progression of this disease. Docosahexaenoic acid (DHA) is a key component of the cell membrane, and its peroxidation is inducible due to the double-bond chemical structure. However, DHA has neuroprotective effects. In this study, we examined the effects of intraperitoneal injection (ipi) of DHA ethyl ester (DHA-Et) on 6-hydroxydopamine (6-OHDA)-induced dopamine (DA) reduction in the mouse striatum. DHA-Et ipi for 7 days before and 7 days after a single intracerebroventricular injection of 6-OHDA enhanced 6-OHDA-induced reduction of striatal DA level. On the other hand, ipi of DHA-Et for 7 days increased its concentration in the striatum. Co-injection of DHA-Et and 6-OHDA increased the levels of thiobarbituric acid-reactive substances (a marker of lipid peroxidation) in the striatum. Our results suggest that DHA-Et enhances 6-OHDA-induced DA depression by increasing lipid peroxidation, and that excessive use of DHA-Et may increase the susceptibility of Parkinson disease in animal model.
Effect of supplementation with Docosahexaenoic Acid ethyl ester and sn-2 docosahexaenyl monoacylglyceride on plasma and erythrocyte fatty acids in rats
Ann Nutr Metab 2005 Jan-Feb;49(1):49-53.PMID:15735367DOI:10.1159/000084177.
Background/aims: Docosahexaenoic acid (C22:6, DHA) is an omega-3 fatty acid required for the normal development of the mammalian nervous and visual system. DHA is provided by the mother during pregnancy and lactating period. Mother's DHA supplementation during pregnancy, and even before pregnancy, has been suggested. DHA can be provided by marine oils, egg's yolk phospholipids, single cell algae oils, the pure fatty acid, or by the ethyl ester derivative (DHA-EE). Another way to provide DHA can be by sn-2 docosahexaenyl monoacylglyceride (DHA-MG), obtained by the treatment of fish oil with stereospecific lipases. sn-2 Fatty acid monoacylglycerides can be more easily absorbed at the intestine than other fatty acid derivatives. Methods: Female rats fed with a synthetic, which provided essentially no DHA, received a 40-day supplementation of either DHA-EE or DHA-MG. Plasma and erythrocyte fatty acid composition were assessed by gas chromatography at day 0 and 40 of supplementation. Results: DHA-EE increased plasma and erythrocyte DHA by 15 and 11.9%, respectively, with no modification of arachidonic acid (AA) content. DHA-MG supplementation increased plasma and erythrocyte DHA by 24 and 23.8%, respectively, but reduced AA by 5.5 and 3%, respectively. Conclusions: We conclude that in the rat, DHA-MG supplementation allows a higher plasma and erythrocyte DHA content than DHA-EE with minor modification of AA content.