Melting point	208-213 ºC (分解)***
Boiling point	200 ºC (0.3 Torr)****
Flash point	125.6±39.1 ºC, 计算值*
Density	1.901 g/cm3 (25 ºC)**
Refractive index	1.4270 (20 ºC)*****

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Source	SDS/MSDS Samples
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Synthetic Route

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Articles

Peer-Reviewed Papers

Omega-3 Polyunsaturated Fatty Acids Inhibit IL-17A Secretion through Decreased ICAM-1 Expression in T Cells Co-Cultured with Adipose-Derived Stem Cells Harvested from Adipose Tissues of Obese Subjects.Marwa Chehimi et al.Molecular nutrition & food research, 63(11), e1801148-e1801148 (2019-03-09) Eicosapentaenoic acid protects against palmitic acid-induced endothelial dysfunction via activation of the AMPK/eNOS pathway.Che-Hsin Lee et al.International journal of molecular sciences, 15(6), 10334-10349 (2014-06-12) Curcumin induces human cathelicidin antimicrobial peptide gene expression through a vitamin D receptor-independent pathway.Chunxiao Guo et al.The Journal of nutritional biochemistry, 24(5), 754-759 (2012-07-31) A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C.Tatsuya Ide et al.International journal of molecular medicine, 11(6), 729-732 (2003-05-09) The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes.S Sipka et al.Clinical immunology and immunopathology, 79(3), 224-228 (1996-06-01) Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients.Richard J Woodman et al.Atherosclerosis, 166(1), 85-93 (2002-12-17) Altered release of cytochrome p450 metabolites of arachidonic acid in renovascular disease.Pietro Minuz et al.Hypertension (Dallas, Tex. : 1979), 51(5), 1379-1385 (2008-04-02) Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension.A Surdacki et al.Journal of cardiovascular pharmacology, 33(4), 652-658 (1999-04-28) The cirrhotic liver is depleted of docosahexaenoic acid (DHA), a key modulator of NF-κB and TGFβ pathways in hepatic stellate cells.Mónica Enguita et al.Cell death & disease, 10(1), 14-14 (2019-01-10) Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid.C Calzada et al.Biochimica et biophysica acta, 1127(2), 147-152 (1992-07-29) Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells.R C Gillis et al.The Journal of surgical research, 107(1), 145-153 (2002-10-18) Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells.Vigdis Aas et al.Journal of lipid research, 47(2), 366-374 (2005-11-23) Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid.M Takenaga et al.Thrombosis research, 41(3), 373-384 (1986-02-01) Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response.Sayako Maruo et al.Bioorganic & medicinal chemistry, 19(19), 5803-5812 (2011-09-10) Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis.I Hafström et al.Arthritis and rheumatism, 31(5), 585-592 (1988-05-01) Effects of small concentrations of eicosapentaenoic acid on platelets.M Lagarde et al.Journal of internal medicine. Supplement, 731, 177-179 (1989-01-01) Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study.Saleh Abdelhamid et al.American journal of hypertension, 16(7), 522-530 (2003-07-10) A high omega-3 fatty acid diet has different effects on early and late stage myeloid progenitors.Melinda E Varney et al.Lipids, 46(1), 47-57 (2010-11-03) The human serum metabolome.Nikolaos Psychogios et al.PloS one, 6(2), e16957-e16957 (2011-03-02) HMDB: a knowledgebase for the human metabolome.David S Wishart et al.Nucleic acids research, 37(Database issue), D603-D610 (2008-10-28) Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients.Shun Wang et al.Hypertension research : official journal of the Japanese Society of Hypertension, 31(4), 623-632 (2008-07-18) [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet].W Herrmann et al.Zeitschrift fur die gesamte innere Medizin und ihre Grenzgebiete, 42(5), 117-122 (1987-03-01) Canned bluefin tuna, an in vitro cardioprotective functional food potentially safer than commercial fish oil based pharmaceutical formulations.Gian Carlo Tenore et al.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 71, 231-235 (2014-06-28) The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition.J A Dunstan et al.Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 34(8), 1237-1242 (2004-08-10) Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay.Marcy J Balunas et al.Journal of natural products, 69(4), 700-703 (2006-04-29) Protection from drug-induced hepatocellular changes by pretreatment with conjugating enzyme inhibitors in rats.G Sato et al.Life sciences, 68(24), 2665-2673 (2001-06-13) Omega-3 fatty acids eicosapentaenoic acid and docosahexaenoic acid and their mechanisms of action on apolipoprotein B-containing lipoproteins in humans: a reviewOscarsson J and Hurt-Camejo E Lipids in Health and Disease, 16(1), 149-149 (2017) Docosahexaenoic acid enhances methylmercury-induced endoplasmic reticulum stress and cell death and eicosapentaenoic acid potentially attenuates these effects in mouse embryonic fibroblastsTakanezawa Y, et al. Toxicology Letters, 306(15), 35-42 (2019) Lipidomics reveals a remarkable diversity of lipids in human plasma.Oswald Quehenberger et al.Journal of lipid research, 51(11), 3299-3305 (2010-07-31) Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration.H Miwa et al.Journal of chromatography. B, Biomedical applications, 677(2), 217-223 (1996-03-03) Docosahexaenoic acid enhances methylmercury-induced endoplasmic reticulum stress and cell death and eicosapentaenoic acid potentially attenuates these effects in mouse embryonic fibroblasts.Yasukazu Takanezawa et al.Toxicology letters, 306, 35-42 (2019-02-16) Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts.Hyeon Ho Kim et al.Journal of lipid research, 46(8), 1712-1720 (2005-06-03) Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo.Hyeon Ho Kim et al.Journal of lipid research, 47(5), 921-930 (2006-02-10) A new antiangiogenic C24 oxylipin from the soft coral Sinularia numerosa.Takahiro Yamashita et al.Bioorganic & medicinal chemistry, 17(6), 2181-2184 (2008-11-28) Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients.Keisuke Hino et al.Journal of gastroenterology and hepatology, 21(8), 1269-1275 (2006-07-29) Dietary lipids fuel GPX4-restricted enteritis resembling Crohn's disease.Lisa Mayr et al.Nature communications, 11(1), 1775-1775 (2020-04-15) omega-3 Fatty acids reverse lipotoxity through induction of autophagy in nonalcoholic fatty liver diseaseChen Y, et al. Nutrition, 31(11-12), 1423-1429 (2015) Analysis of biogenic amines in plasma of hypertensive patients and a control group.R Andrew et al.Neurochemical research, 18(11), 1179-1182 (1993-11-01) Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.Denis Fourches et al.Chemical research in toxicology, 23(1), 171-183 (2009-12-18) Nutrition and traumatic brain injury: improving acute and subacute health outcomes in military personnel (2011) Angiogenesis-a crucial step in breast cancer growth, progression and dissemination by Raman imagingKopec M and Abramczyk H Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 198, 338-345 (2018) [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis].V I Hereliuk Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994), 46(6), 112-115 (2001-06-27) Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk.Cindy A Francois et al.The American journal of clinical nutrition, 77(1), 226-233 (2002-12-25) A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty AcidsCholewski M, et al. Nutrients, 10(11), 1662-1662 (2018) A high-fat meal enriched with eicosapentaenoic acid reduces postprandial arterial stiffness measured by digital volume pulse analysis in healthy men.Wendy L Hall et al.The Journal of nutrition, 138(2), 287-291 (2008-01-22) Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release.R Luostarinen et al.Prostaglandins, leukotrienes, and essential fatty acids, 55(3), 167-172 (1996-09-01) Effect of eicosapentaenoic acid and docosahexaenoic acid on myogenesis and mitochondrial biosynthesis during murine skeletal muscle cell differentiationHsueh TY, et al. Frontiers in nutrition, 5, 15-15 (2018) Metabolic switching of human myotubes is improved by n-3 fatty acids.N P Hessvik et al.Journal of lipid research, 51(8), 2090-2104 (2010-04-07) Resveratrol enhances palmitate-induced ER stress and apoptosis in cancer cells.Cristina Rojas et al.PloS one, 9(12), e113929-e113929 (2014-12-02) Microsomal prostaglandin E2 synthase-1 (mPGES-1): a novel anti-inflammatory therapeutic target.Richard W Friesen et al.Journal of medicinal chemistry, 51(14), 4059-4067 (2008-05-08) Angiotensins in plasma of hypertensive rats and human.M K Sim et al.Regulatory peptides, 111(1-3), 179-182 (2003-03-01)

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