Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. Chemically, 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. Image File history File links Download high resolution version (1499x173, 5 KB) Summary Chemical structure of Docosahexaenoic acid created with ChemDraw. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... In chemistry, a trivial name (also common or vernacular name) is a non-systematic name. ... It has been suggested that Fish oil, Oily fish be merged into this article or section. ... Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... CIS usually refers to: Commonwealth of Independent States, a modern-day political entity consisting of 11 former Soviet Union Republics CIS is also an acronym for: Canadian Interuniversity Sport Cancer Information Service Carcinoma in situ Centre for Independent Studies Center for Immigration Studies Chinese International School Cisalpino Citizenship & Immigration Services...

DHA is most often found in fish oil. Most of the DHA in fish and other more complex organisms originates in microalgae of the genus Schizochytrium, and concentrates in organisms as it moves up the food chain. DHA is also commercially manufactured from Crypthecodinium cohnii.^[1] Most animals make very little DHA metabolically, however small amounts are manufactured internally through the consumption of α-linolenic acid, an omega-3 fatty acid found in chia, flax, and many other seeds and nuts. Fish Oil is oil derived from fishes. ... Linolenic acid Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid with the molecular formula C18H30O2 and molar mass 278. ... Binomial name Salvia hispanica L. Chia (Salvia hispanica) is a plant of the genus Salvia of the mint family. ... Binomial name Linum usitatissimum L. Linnaeus, 17?? Common flax (also known as linseed) is a member of the Linaceae family, which includes about 150 plant species widely distributed around the world. ...

DHA is a major fatty acid in sperm and brain phospholipids, and especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease. Low levels of DHA cause reduction of brain serotonin levels^[2] and have been associated with ADHD, Alzheimer's disease, and depression, among other diseases, and there is mounting evidence that DHA supplementation may be effective in combating such diseases (see external links at the end of this article). Phospholipid Two schematic representations of a phospholipid. ... Human blood smear: a - erythrocytes; b - neutrophil; c - eosinophil; d - lymphocyte. ... Example of an unsaturated fat triglyceride. ... Heart disease is an umbrella term for a number of different diseases which affect the heart and as of 2007 it is the leading cause of death in the United States. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... Attention-Deficit/Hyperactivity Disorder (ADHD) previously known as Attention Deficit Disorder (ADD), is generally considered to be a developmental disorder, largely neurological in nature, affecting about 5% of the worlds population. ... Clinical depression (also called major depressive disorder, or unipolar depression when compared to bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ...

Metabolic synthesis

In the human body, DHA is either present in the diet or it is derived from eicosapentaenoic acid (EPA, 20:5, ω-3) via docosapentaenoic acid (DPA, 22:5 ω-3) as an intermediate. This is done with an elongation step followed by the action of Δ4-desaturase. Another pathway has also been described in peroxysomes and mitochondria. EPA is twice elongated yielding 24:5 ω-3, then desaturated to 24:6 ω-3, then shortened to DHA (22:6 ω-3) via beta oxidation. This pathway is known as Sprecher's shunt.^[3][4] Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. ... Docosapentaenoic acid designates any straight chain 22:5 fatty acid. ... A Desaturase is an enzyme which removes two hydrogen atoms from an organic compound, creating a carbon/carbon double bond. ... Peroxisomes are ubiquitous organelles in eukaryotes. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Schematic demonstrating mitochondrial fatty acid beta-oxidation and effects of LCHAD deficiency Beta oxidation is the process by which fatty acids, in the form of Acetyl-CoA molecules, are broken down in the mitochondria to generate Acetyl-CoA, the entry molecule for the Krebs Cycle. ...

DHA in Alzheimer's Disease

A large NIH drug trial is currently recruiting patients for evaluating DHA in Alzheimer's disease. ^[5] This is the first human trial of DHA. Animal studies in TG3 transgenic mouse model of Alzheimer's disease have shown decrease in amyloid plaques and tau by DHA. Animal studies also show that when combined with Arachidonic acid (another fatty acid present in fish oil) the effectiveness of DHA in preventing plaques was lesser than when used alone.

DHA Inhibiting Human Carcinoma in Mice

Researchers at the University of Nevada conducted a study on the effects of DHA supplementation on the growth of human colon adeno carcinoma in mice. The animals received one of four specialized diets: low fat with corn oil (omega-6 linoleic acid), high fat with corn oil (omega-6 linoleic acid), high fat with fish oil (omega-3 EPA and DHA), and high fat with algae-derived DHA (omega-3 DHA). At completion, the mice receiving a diet supplemented with algae-derived DHA had tumors that were smaller than those of mice receiving diets supplemented with omega-3 from fish oil as well as those fed both the high and low fat corn oil (omega-6) diets. These results indicate that algae-derived DHA possesses greater tumor suppressing properties than do corn or fish oil. ^[6] Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ...

DHA in breast milk and infant formula

DHA concentrations in breast milk range from 0.07% to greater than 1.0% of total fatty acids, with a mean of about 0.34%. DHA levels in breast milk are higher if a mother's diet is high in fish. It has been suggested that the section Benefits for the infant from the article Breastfeeding be merged into this article or section. ...

DHA has been an ingredient in several brands of premium infant formula sold in North America since 2001 after Mead Johnson, the first infant formula manufacturer to add DHA and ARA (arachidonic acid) to its Enfamil Lipil product, received approval by the Food and Drug Administration and Health Canada. Both DHA and ARA are permitted in infant formula as both are components of human breast milk. The addition of DHA at dose effective levels has been shown to improve congitive function in both term and preterm infants. An infant being fed by bottle. ... North America North America is a continent[1] in the Earths northern hemisphere and (chiefly) western hemisphere. ... Year 2001 (MMI) was a common year starting on Monday (link displays the 2001 Gregorian calendar). ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). ... hi “FDA” redirects here. ... The Department of Health, also referred to as Health Canada, is the department of the government of Canada with responsibility for national public health. ...

DHA makes infant formula more like human milk than "conventional" formula containing linolenic acid and linoleic acid, which are precursors to DHA. Formula sold in North America uses lipids from microorganisms grown in bioreactors as sources of DHA.^[7][1] Linolenic acid Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid with the molecular formula C18H30O2 and molar mass 278. ... Linoleic acid (LA) is an unsaturated omega-6 fatty acid. ... A bioreactor may refer to any device or system that supports a biologically active environment. ...

Superiority of Algae Derived DHA in Infant Nutrition

A study^[8] found that preterm infants fed baby formulas fortified with DHA derived directly from algae gained weight faster than infants fed formula fortified with DHA from fish oil. Additionally, there are no risks of harmful contaminants such as methyl mercury or dioxins, which may be present in fish and fish oils.^{[citation needed]} This is especially important for pregnant and nursing women and young children.

DHA Studies of Vegans and Vegetarians

Vegans and vegetarians have markedly lower stores of DHA. Their bodily DHA levels do not rise much even with high dietary levels of linolenate. This, and features of the production and distribution of DHA in pregnant and lactating women, indicates that DHA per se is an essential nutrient.^[9] Hens kept in cramped conditions — the avoidance of animal suffering is the primary motivation of people who become vegans A vegan is a person who avoids the ingestion or use of animal products. ... For animals adapted to eat primarily plants, sometimes referred to as vegetarian animals, see Herbivore. ...

Promotion of DHA as a food additive

DHA is actively promoted by its major manufacturers, Martek Biosciences and Ocean Nutrition Canada, as a food additive. Until recently sales other than to makers of infant formula have been minimal; however, in 2007 several DHA-fortified dairy items (milk, yogurt) began selling in grocery stores. In anticipation of demand Martek had by 2007 increased its manufacturing capacity to three times the amount which was able to sell. Martek Biosciences is based in Columbia, MD, you might know them best for the DHA and ARA found in Infant Formula. ... Ocean Nutrition Canada, a subsidiary of Clearwater Fine Foods, is a global supplier of Omega-3 EPA/DHA fatty acids. ... Food additives are substances added to food to preserve flavor or improve its taste and appearance. ...

There is less DHA available in the average diet than formerly due to cattle being taken off grass and fed grain before butchering; likewise there is less in eggs due to factory farming. DHA is widely believed to be helpful to people with a history of heart disease, for premature infants, and to support healthy brain development especially in young children. Some manufactured DHA is a vegetarian product extracted by a patented process from algae, but costs approximately twice as much as fish oil. Both are odorless and tasteless after processing.^[10] Heart disease is an umbrella term for a number of different diseases which affect the heart and as of 2007 it is the leading cause of death in the United States. ... For animals adapted to eat primarily plants, sometimes referred to as vegetarian animals, see Herbivore. ...

See also

fat whores

• List of omega-3 fatty acids
• Polyunsaturated fatty acids

Essential fatty acid Essential nutrient (note: not all listed above are classified as essential nutrients) Categories: | | ... A polyunsaturated fatty acid (PUFA) is a class of unsaturated fat that contains more than one double bond. ...

References