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Eicosapentaenoic acid

CAS# 10417-94-4

Eicosapentaenoic acid

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Chemical structure

Eicosapentaenoic acid

3D structure

Chemical Properties of Eicosapentaenoic acid

Cas No. 10417-94-4 SDF Download SDF
PubChem ID 446284.0 Appearance Powder
Formula C20H30O2 M.Wt 302.46
Type of Compound Aliphatics Storage Desiccate at -20°C
Synonyms Timnodonic acid;
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
SMILES CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Standard InChIKey JAZBEHYOTPTENJ-JLNKQSITSA-N
Standard InChI InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Eicosapentaenoic acid Dilution Calculator

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Eicosapentaenoic acid Molarity Calculator

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Preparing Stock Solutions of Eicosapentaenoic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3062 mL 16.5311 mL 33.0622 mL 66.1244 mL 82.6556 mL
5 mM 0.6612 mL 3.3062 mL 6.6124 mL 13.2249 mL 16.5311 mL
10 mM 0.3306 mL 1.6531 mL 3.3062 mL 6.6124 mL 8.2656 mL
50 mM 0.0661 mL 0.3306 mL 0.6612 mL 1.3225 mL 1.6531 mL
100 mM 0.0331 mL 0.1653 mL 0.3306 mL 0.6612 mL 0.8266 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Eicosapentaenoic acid

Dual stress factors adaptive evolution for high EPA production in Schizochytrium sp. and metabolomics mechanism analysis.[Pubmed:38687387]

Bioprocess Biosyst Eng. 2024 Apr 30.

Eicosapentaenoic acid (EPA) is a vital ɷ-3 polyunsaturated fatty acid (PUFA) for human body with various physiological functions. In this study, we proposed an adaptive evolutionary strategy based on high-temperature and high-oxygen two-factor stress to increase the EPA production capacity of Schizochytrium. High-temperature stress was used to increase EPA yield, and high oxygen was implemented to continuously stimulate cell growth and lipid accumulation. The biomass and EPA production of ALE-D50 reached 35.33 g/L and 1.54 g/L, which were 43.85% and 71.11% higher than that of the original strain, respectively. Lower in vivo reactive oxygen species levels indicated that the evolved strain possessed stronger antioxidant activity. Liquid chromatography-mass spectrometry metabolomics showed that enhanced glucose consumption and glycolysis metabolism, as well as a weakened tricarboxylic acid cycle and reduced amino acid metabolic tributaries in the evolved strain, might be associated with increased growth and EPA synthesis. Finally, the lipid production and EPA production in a fed-batch fermentation were further increased to 48.93 g/L and 3.55 g/L, improving by 54.30% and 90.86%, respectively. This study provides a novel pathway for promoting EPA biosynthesis in Schizochytrium.

Higher Plasma Omega-3 Levels are Associated With Improved Exacerbation Risk and Respiratory-Specific Quality of Life in COPD.[Pubmed:38687147]

Chronic Obstr Pulm Dis. 2024 Apr 22.

BACKGROUND: Omega-3 polyunsaturated fatty acids (PUFAs) have been associated with systemic anti-inflammatory responses. Dietary intake of omega-3 PUFAs Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) has also been associated with lower COPD morbidity using self-report food frequency questionnaires. OBJECTIVE: To investigate the relationship between measured PUFA intake using plasma EPA+DHA levels and COPD morbidity. METHODS: Former smokers with moderate-severe COPD living in low-income communities were enrolled in a 6-month prospective cohort study. Participants completed standardized questionnaires, spirometry, and plasma samples at 3-month intervals. Total plasma PUFAs were analyzed using gas chromatography/ mass spectrometry for DHA and EPA concentrations. Linear or logistic mixed model regression was used to evaluate EPA+DHA's and COPD morbidity's association, accounting for demographics, lung function, pack years, comorbidities, and neighborhood poverty. RESULTS: 133 plasma EPA+DHA samples from 57 participants were available. Participants exhibited average plasma EPA and DHA levels of 14.7+/-7.3 microg/mL and 40.2+/-17.2 microg/mL, respectively, across the three clinic visits. Each standard deviation increase in EPA+DHA levels was associated with 2.7 points lower SGRQ score (95% CI -5.2, -0.2) and lower odds of moderate exacerbation (OR 0.4; 95% CI 0.2, 0.9) but lacked significant association with CAT score (95% CI -2.4, 0.8), mMRC (95% CI -02, 0.2), or severe exacerbations (95% CI 0.3, 1.4). CONCLUSION: Plasma EPA+DHA levels are associated with better respiratory-specific quality of life and lower odds of moderate exacerbations in patients with moderate-to-severe COPD. Further research is warranted to investigate the efficacy of an omega-3 dietary intervention in the management of COPD morbidities.

Application of Goat and Lamb Lipases on the Development of New Immobilized Biocatalysts Aiming at Fish Oil Hydrolysis.[Pubmed:38683451]

Appl Biochem Biotechnol. 2024 Apr 29.

The use of lipases from animal sources for the synthesis of new biocatalysts is barely studied in the literature. The present work focused on the immobilization of lipases from kid goat's and lamb's epiglottis in different ionic supports. For this, anionic supports (monoaminoethyl-N-aminoethyl-agarose (MANAE) and diethylaminoethyl-agarose (DEAE)) and cationic supports (carboxymethyl-agarose and sulfopropyl-agarose) were used. The immobilization parameters were evaluated, as well as the thermal stability of the immobilized enzymes and their stability at different values of pH. Then, the performance of the biocatalysts was evaluated in hydrolysis reactions for obtaining omega-3 fatty acids from fish oil (Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)). Values of 100% of recovered activity were obtained for lipase from goats, indicating that it was possible to maintain all the enzymatic activities of the immobilized enzymes on the supports. The immobilized enzymes were more stable in different pH conditions and at a temperature of 50 degrees C, reaching values of stabilization factor of 12.17 and t(1/2) of 9.86 h(-1), for lamb lipase immobilized in sulfopropyl agarose. In general, the anionic supports led to lower Km values and the cationic ones to a higher Vmax. Lamb lipase showed the highest selectivity values for EPA/DHA, reaching values of 6.43 using MANAE. Thus, the high potential for using such biocatalysts from animal sources in the food or pharmaceutical industries is observed.

Contribution of phospholipase B to the formation of characteristic flavor in steamed sturgeon meat.[Pubmed:38681231]

Food Chem X. 2024 Apr 13;22:101391.

Sensory analysis and untargeted lipidomics were employed to study the impact of phospholipase B (PLB) on lipid oxidation and flavor in steamed sturgeon meat, revealing the inherent relationship between lipid oxidation and flavor regulation. The research verified that PLB effectively suppresses fat oxidation and improves the overall taste of steamed sturgeon meat. Furthermore, the PLB group identified 52 compounds, and the content of odor substances such as isoamyl alcohol and hexanal was reduced compared with other groups. Finally, lipid substances containing Eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) were screened out from 32 kinds of differential phospholipids. Through Pearson correlation analysis, it was observed that certain differential phospholipids such as PC (22:6) and PC (22:5) exhibited varying correlations with odor substances like hexanal and isovaleraldehyde. These findings suggest that PLB specifically affects certain phospholipids, leading to the production of distinct volatile substances through oxidative degradation.

Eicosapentaenoic acid activates the P62/KEAP1/NRF2 pathway for the prevention of diabetes-associated cognitive dysfunction.[Pubmed:38680120]

Food Funct. 2024 Apr 29.

Diabetes-associated cognitive dysfunction (DCD) is a severe complication of diabetes mellitus (DM), threatening the life quality of the diabetic population. However, there is still a lack of effective approaches for its intervention. Eicosapentaenoic acid (EPA) is an omega-3 polyunsaturated fatty acid that was not previously investigated for its effect on DCD. In this study, EPA was found to improve DCD in a mouse model of type 2 DM (T2DM) induced by streptozotocin and a high-fat diet, exhibiting profound protective effects on cognitive dysfunction, neuronal loss, and cerebral oxidative stress and inflammation. While EPA did not attenuate advanced glycation end product-induced neuron injury, we hypothesized that EPA might protect neurons by regulating microglia polarization, the effect of which was confirmed by the co-culture of neurons and lipopolysaccharide-stimulated microglia. RNA sequencing identified nuclear factor-erythroid-2-related factor 2 (NRF2) antioxidant signaling as a major target of EPA in microglia. Mechanistically, EPA increased sequestosome-1 (SQSTM1 or P62) levels that might structurally inhibit Kelch-like ECH associated protein 1 (KEAP1), leading to nuclear translocation of NRF2. P62 and NRF2 predominantly mediated EPA's effect since the knockdown of P62 or NRF2 abolished EPA's protective effect on microglial oxidative stress and inflammation and sequential neuron injuries. Moreover, the regulation of P62/KEPA1/NRF2 axes by EPA was confirmed in the hippocampi of diabetic mice. The present work presents EPA as an effective nutritional approach and microglial P62/KEAP1/NRF2 as molecular targets for the intervention of DCD.

The Antimicrobial and Antibiofilm Abilities of Fish Oil Derived Polyunsaturated Fatty Acids and Manuka Honey.[Pubmed:38674722]

Microorganisms. 2024 Apr 11;12(4):778.

Both honey and fish oil have been historically used in medicine and identified as having antimicrobial properties. Although analyses of the substances have identified different components within them, it is not fully understood how these components interact and contribute to the observed effect. With the increase in multi-drug resistant strains of bacteria found in infections, new treatment options are needed. This study aimed to assess the antimicrobial abilities of fish oil components, including docosahexaenoic acid (DHA), Eicosapentaenoic acid (EPA), and derived resolvins (RvE1, RvD2, and RvD3), as well as two varieties of manuka honey, against a panel of medically relevant microorganisms and antimicrobial resistant organisms, such as Methicillin Resistant Staphylococcus aureus (MRSA) and carbapenem-resistant Escherichia coli. Minimum inhibitory concentrations (MIC) and minimum bactericidal concentrations (MBC) were identified; further minimum biofilm eradication concentrations (MBEC) were investigated for responsive organisms, including S. aureus, E. coli, Staphylococcus epidermidis, Klebsiella pneumoniae, and Pseudomonas aeruginosa. Concurrent with the existing literature, manuka honey was found to be a broad-spectrum antimicrobial with varied potency according to methylglyoxal content. DHA and EPA were both effective against Gram-positive and negative bacteria, but some drug-resistant strains or pathogens were not protected by a capsule. Only E. coli was inhibited by the resolvins.

Nutritional Composition and Safety Aspects of Deep-Sea Whelks (Buccinum tenuissimum Kuroda).[Pubmed:38672842]

Foods. 2024 Apr 11;13(8):1169.

The deep-sea whelk Buccinum tenuissimum Kuroda is highly sought-after as food in East Asian countries, notably, Korea and Japan. However, it lacks official recognition as a food product in Korea. This study aimed to assess its nutritional composition and safety for the potential development of seafood products. The nutritional analysis revealed high protein (13.54-20.47 g/100 g whelk), fat (0.85-8.59 g/100 g whelk), carbohydrate (1.55-12.81 g/100 g whelk), and dietary fiber (1.25-1.95 g/100 g whelk) contents in both muscle and gut samples, with energy contents ranging from 339.11 +/- 1.64 to 692.00 +/- 3.21 kJ/100 g. Key minerals, including iron, potassium, calcium, and sodium, and essential fatty acids, including Eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid, omega-3, and omega-6 fatty acids, were abundant, making it a potential supplementary food. Notably, heavy metal levels met the Korean standards for seafood safety. No trans fats, radioactivity concerning the radioactive isotopes (134)Cs/(137)Cs and (131)I, or pathogenic bacteria were detected. This confirms the safety and nutritional value of deep-sea whelks, suggesting their potential for developing seafood products rich in beneficial components, which could enhance nutrition and food security while contributing to economic growth.

Atherosclerosis Residual Lipid Risk-Overview of Existing and Future Pharmacotherapies.[Pubmed:38667744]

J Cardiovasc Dev Dis. 2024 Apr 21;11(4):126.

Patients with atherosclerotic disease remain at increased risk of future events despite receiving optimal medical treatment. This residual risk is widely heterogeneous, but lipoprotein particles and their content play a major role in determining future cardiovascular events. Beyond low-density lipoprotein cholesterol (LDL-c), other lipoprotein particles have not demonstrated similar contribution to the progression of atherosclerosis. Statins, ezetimibe, and more recently, proprotein convertase subtilisin kexin 9 (PCSK9) inhibitors and bempedoic acid have confirmed the causal role of LDL-c in the development of atherosclerosis. Data on high-density lipoprotein cholesterol (HDL-c) suggested a possible causal role for atherosclerosis; nonetheless, HDL-c-raising treatments, including cholesteryl-ester transfer protein (CETP) inhibitors and niacin, failed to confirm this relationship. On the other hand, mendelian randomisation revealed that triglycerides are more implicated in the development of atherosclerosis. Although the use of highly purified Eicosapentaenoic acid (EPA) was associated with a reduction in the risk of adverse cardiovascular events, this beneficial effect did not correlate with the reduction in triglycerides level and has not been consistent across large phase 3 trials. Moreover, other triglyceride-lowering treatments, such as fibrates, were not associated with a reduction in future cardiovascular risk. Studies assessing agents targeting angiopoietin-like 3 (lipoprotein lipase inhibitor) and apolipoprotein C3 antisense will add further insights into the role of triglycerides in atherosclerosis. Emerging lipid markers such as lipoprotein (a) and cholesterol efflux capacity may have a direct role in the progression of atherosclerosis. Targeting these biomarkers may provide incremental benefits in reducing cardiovascular risk when added to optimal medical treatment. This Review aims to assess available therapies for current lipid biomarkers and provide mechanistic insight into their potential role in reducing future cardiovascular risk.

Metabolic engineering of omega-3 long chain polyunsaturated fatty acids in plants using different ∆6- and ∆5-desaturases co-expressed with LPCAT from the marine diatom Phaeodactylum tricornutum.[Pubmed:38664593]

Sci Rep. 2024 Apr 25;14(1):9512.

Continuous research on obtaining an even more efficient production of very long-chain polyunsaturated fatty acids (VLC-PUFAs) in plants remains one of the main challenges of scientists working on plant lipids. Since crops are not able to produce these fatty acids due to the lack of necessary enzymes, genes encoding them must be introduced exogenously from native organisms producing VLC-PUFAs. In this study we reported, in tobacco leaves, the characterization of three distinct ∆(6)-desaturases from diatom Phaeodactylum tricornutum, fungi Rhizopus stolonifer and microalge Osterococcus tauri and two different ∆(5)-desaturases from P. tricornutum and single-celled saprotrophic eukaryotes Thraustochytrium sp. The in planta agroinfiltration of essential ∆(6)-desaturases, ∆(6)-elongases and ∆(5)-desaturases allowed for successful introduction of Eicosapentaenoic acid (20:5(∆5,8,11,14,17)) biosynthesis pathway. However, despite the desired, targeted production of omega3-fatty acids we detected the presence of omega6-fatty acids, indicating and confirming previous results that all tested desaturases are not specifically restricted to neither omega3- nor omega6-pathway. Nevertheless, the additional co-expression of acyl-CoA:lysophosphatidylcholine acyltransferase (LPCAT) from Phaeodactylum tricornutum boosted the proportion of omega3-fatty acids in newly synthesized fatty acid pools. For the most promising genes combinations the EPA content reached at maximum 1.4% of total lipid content and 4.5% of all fatty acids accumulated in the TAG pool. Our results for the first time describe the role of LPCAT enzyme and its effectiveness in alleviating a bottleneck called 'substrate dichotomy' for improving the transgenic production of VLC-PUFAs in plants.

Efficacy of dietary supplements on mortality and clinical outcomes in adults with sepsis and septic shock: A systematic review and network meta-analysis.[Pubmed:38663051]

Clin Nutr. 2024 Apr 10;43(6):1299-1307.

AIM: The aim of this network meta-analysis (NMA) was to investigate the effects of different dietary supplements on the mortality and clinical status of adults with sepsis. METHODS: We searched PubMed, EMBASE, and the Cochrane Library Central Register of Controlled Trials until February 2023. The inclusion criteria were: 1) randomized controlled trials (RCT)s; 2) adults suffering sepsis or septic shock; 3) evaluation of short- or long-mortality; and 4) publications between 1994 and 2023. The general information of studies and details of interventions were extracted. The primary outcome was short-term mortality (<90 days), and the secondary outcomes were long-term mortality (>/=90 days), length of ICU and hospital stays, and duration of mechanical ventilation (MV). The risk of bias of RCTs was assessed using the Cochrane risk of bias tool 2 (ROB2). A random effect NMA was performed to rank the effect of each intervention using a frequentist approach. RESULTS: Finally, 56 RCTs with 5957 participants met the criteria. Approximately, one-third of RCTs were low risk of bias. NMA analysis revealed that there was no treatment more effective in short- or long-term mortality than control or other interventions, except for magnesium (RR: 0.33, 95% CI: 0.14, 0.79; GRADE = low) and vitamin C (RR: 0.81, 95% CI: 0.67, 0.99; low certainty evidence), which had beneficial effects on short-term mortality. Moreover, Eicosapentaenoic acid, gamma-linolenic acid, and antioxidants (EPA + GLA + AOs) combination was the most effective, and magnesium, vitamin D and vitamin C were the other effective approaches in terms of duration of MV, and ICU length of stay. There was no beneficial dietary supplement for hospital stay in these patients. CONCLUSIONS: In septic patients, none of the dietary supplements had a substantial effect on mortality except for magnesium and vitamin C, which were linked to lower short-term mortality with low certainty of evidence. Further investigation into high-quality studies with the use of dietary supplements for sepsis should be highly discouraged.

Risk predictors of glycaemic control in children and adolescents with type 1 diabetes: A systematic review and meta-analysis.[Pubmed:38661073]

J Clin Nurs. 2024 Apr 25.

OBJECTIVES: To conduct systematic evaluation of the risk predictors of glycaemic control in children and adolescents with type 1 diabetes mellitus. METHODS: Cohort studies on risk predictors of glycaemic control in children and adolescents with type 1 diabetes were retrieved from CNKI, PubMed, Web of Science, Embase databases, etc. from the construction of the repository to 3 February 2023. Literature screening was conducted according to inclusion and exclusion criteria, then data extraction of region, sample size, age, follow-up time, risk predictors, outcome indicators, etc., and quality evaluation of The Newcastle-Ottawa Scale were conducted by two researchers while the third researcher makes decisions if there are disagreements. Finally, Revman5.4 and StataMP17 were used for meta-analysis. RESULTS: A total of 29 studies were included, and the results showed that insulin pump [Weighed mean difference (WMD) = -.48, 95% CI (-.73, -.24), p < .01], high-frequency sensor monitoring, early use of insulin pumps, prospective follow-up male, white race, large body mass index-standardised scoring, conscientiousness, agreeableness of mothers, Eicosapentaenoic acid, leucine and protein (p < .05) were beneficial for reducing HbA1c levels in children and adolescents with diabetes. Ketoacidosis [WMD = .39, 95% CI (.28, .50), p < .01], selective admission, higher HbA1c level at one time (p < .01), higher glutamate decarboxylase antibody at 1 month after diagnosis, lower socio-economic status, non-living with biological parents, non-two-parent family, family disorder, family history of diabetes and high carbohydrate intake (p < .05) increased HbA1c levels in children and adolescents with diabetes. CONCLUSION: For children and adolescents with type 1 diabetes mellitus, the use of insulin pump, high-frequency sensor monitoring, prospective follow-up, good family support and reasonable diet are conducive to blood glucose control, while selective admission and DKA are not. Disease characteristics and demographic characteristics of children are closely related to subsequent blood glucose control, and the relationship between diagnosis age and blood glucose control needs to be further explored.

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