Docosahexaenoic acid - CAS 6217-54-5
Catalog number:
6217-54-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
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Description:
Docosahexaenoic acid (DHA) is an omega-3 fatty acid. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end. Its trivial name is cervonic acid, its systematic name is all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid, and its shorthand name is 22:6(n-3) in the nomenclature of fatty acids. Fish oils are rich in DHA. Most of the DHA in fish and more complex organisms originates in photosynthetic and heterotrophic microalgae, and becomes increasingly concentrated in organisms as it moves up the food chain. DHA is also commercially manufactured from microalgae; Crypthecodinium cohnii and another of the genus Schizochytrium. DHA manufactured using microalgae is vegetarian. Most animals make very little DHA through metabolism; however small amounts are manufactured internally through the consumption of α-linolenic acid, an omega-3 fatty acid found in plants, animals, and milk. DHA is metabolized to form the docosanoids, which comprise several families of potent hormones. DHA is a major fatty acid in sperm and brain phospholipids, particularly in the retina. Dietary DHA may reduce the risk of heart disease by reducing the level of blood triglycerides in humans. Low levels of DHA have been associated with Alzheimer's disease.
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Synonyms:
DHA; Doconexent; cervonic acid,;
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1.Essentiality of arachidonic acid intake in murine early development.
Hatanaka E1, Harauma A1, Yasuda H1, Watanabe J1, Nakamura MT2, Salem N Jr3, Moriguchi T4. Prostaglandins Leukot Essent Fatty Acids. 2016 May;108:51-7. doi: 10.1016/j.plefa.2016.03.007. Epub 2016 Mar 28.
We previously reported the importance of long-chain polyunsaturated fatty acid (LC-PUFA (>C20)) intake, including arachidonic acid (ARA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), for growth. This follow-up study focuses on ARA using a novel artificial rearing model during the lactation period in delta-6-desaturase knockout (D6D-KO) mice. Newborn D6D-KO male mouse pups were separated from dams within 48 hours and fed artificial milks containing 18-C essential fatty acids (EFAs) (16-17% LA, 3.8-4.1% ALA) with or without 1.2% ARA. After weaning, mice were maintained on similar diets: 15% LA, 2.3-2.4% ALA with or without 1.9% ARA. As a reference group, new born wild type (WT) male mouse pups were maintained by artificial milk and diet containing LA and ALA without ARA. Aspects of brain function were measured behaviorally (motor activity and rota-rod test) when mice were age 9 weeks. Body weight in the KO-Cont group was significantly lower (approximately 30%) than in the WT-Cont group, but this decrease was ameliorated by providing ARA in the KO-ARA group.
2.In vitro and in vivo bimodal effects of docosahexaenoic acid supplements on redox status and platelet function.
Lagarde M1, Calzada C1, Guichardant M1, Véricel E1. Prostaglandins Leukot Essent Fatty Acids. 2016 May;108:1-4. doi: 10.1016/j.plefa.2016.03.008. Epub 2016 Mar 23.
Docosahexaenoic acid (DHA) is a prominent nutrient of marine lipids. Together with eicosapentaenoic acid, it is recognized as a protective molecule against atherosclerosis and thrombosis through the regulation of blood cell functions, especially platelets. Its high unsaturation index may however make it prone to peroxidation, which is usually considered as deleterious. This short review takes into consideration this possibility related to DHA concentrations both in vitro and in vivo. It is suggested that protective effects of DHA on platelet activation depend on the reduction of oxidative stress, and appear bimodal with the abolishment of such a protection when DHA is used at relatively high concentrations.
3.The clinical benefits of long-term supplementation with omega-3 fatty acids in cystic fibrosis patients - A pilot study.
Hanssens L1, Thiébaut I2, Lefèvre N2, Malfroot A3, Knoop C4, Duchateau J5, Casimir G2. Prostaglandins Leukot Essent Fatty Acids. 2016 May;108:45-50. doi: 10.1016/j.plefa.2016.03.014. Epub 2016 Mar 28.
Effectiveness of omega-3 supplementation in cystic fibrosis (CF) remains controversial. This study sought to evaluate clinical status, exercise tolerance, inflammatory parameters, and erythrocyte fatty acid profile after 1 year of oral omega-3 supplementation in CF patients. Fifteen ΔF508-homozygous patients undergoing chronic azithromycin were randomized to receive omega-3 fish oil supplementation at a dose of 60mg/Kg/day or placebo. In comparison with the previous year, in the supplemented group, the number of pulmonary exacerbations decreased at 12 months (1.7 vs. 3.0, p<0.01), as did the duration of antibiotic therapy (26.5 days vs. 60.0 days, p<0.025). Supplementation significantly increased the levels of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) as early as <3 months of administration, with concomitant decreases in arachidonic acid (AA) levels. This pilot study suggests that long-term omega-3 supplementation offers several clinical benefits as to the number of exacerbations and duration of antibiotic therapy in CF patients.
4.Bioavailability of long chain omega-3 polyunsaturated fatty acids from phospholipid-rich herring roe oil in men and women with mildly elevated triacylglycerols.
Cook CM1, Hallaråker H2, Sæbø PC2, Innis SM3, Kelley KM4, Sanoshy KD4, Berger A2, Maki KC4. Prostaglandins Leukot Essent Fatty Acids. 2016 Mar 4. pii: S0952-3278(15)30011-9. doi: 10.1016/j.plefa.2016.01.007. [Epub ahead of print]
This randomized, single-blind, crossover trial assessed the bioavailability of eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), and docosapentaenoic acid (DPA) from two different sources, each examined over a 12h period following consumption of a single serving and after 2-weeks of daily supplementation. Thirty-two adults with fasting triacylglycerol (TAG) concentrations between 100 and 399mg/dL were randomly assigned, with stratification by sex and age, to receive 12 capsules/day containing either phospholipid (PL)-rich herring roe oil (Romega® 30, 628mg/day EPA; 1810mg/day DHA; 137mg/day DPA) or TAG-rich fish oil (575mg/day EPA; 1843mg/day DHA; 259mg/day DPA) each for a 2-week period separated by a 4 week washout. The net incremental area under the curve from 0 to 12h for EPA, DHA, and EPA+DHA in plasma phosphatidylcholine (PC) were significantly higher (p<0.01 for all) after Romega 30 supplementation compared to fish oil. Similar results were observed when the data for the Romega 30 condition were normalized to fish oil EPA and DHA intakes (p<0.
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CAS 6217-54-5 Docosahexaenoic acid

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