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Docosahexaenoic acid is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, sperm, testicles and retina.
Docosahexaenoic acid can be synthesized from alphalinolenic acid or obtained directly from maternal milk or fish oil.
Docosahexaenoic acid's structure is a carboxylic acid(~oic acid) with a 22-carbon chain (docosa- is Greek for 22) and six (Greek "hexa") cis double bonds (-en~); the first double bond is located at the third carbon from the omega end.
CAS: 6217-54-5
MF: C22H32O2
MW: 328.49
EINECS: 612-950-9
Synonyms
doconexent;Docosahexaenoicacid,97;DOCOSAHEXAENOIC ACID(DHA);cis-4,7,10,13,16,19-DocosahexaenoicAcid(stabiliz;CIS-4,7,10,13,16,19-DOCOSA-PENTAENOIC ACID;4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-;CIS-4,7,10,13,16,19-DOCOSAHEXAENOICACID(OIL);CIS-4,7,10,13,16,19-DOCOSAHEXAENOICACID(POWDER)
Docosahexaenoic acid's 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.
Docosahexaenoic acid is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils.
Docosahexaenoic acid comprises approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes.
Docosahexaenoic acid typically represents 0.52-7.5% of human total plasma fatty acids.
Docosahexaenoic acid is produced from α-linolenic acid (ALA; Item Nos. 90210 | 21910) via a series of desaturase- and elongase-catalyzed reactions, resulting in a docosapentaenoic acid (DPA; ) intermediate, which is elongated, desaturated, and β-oxidized to produce DHA.
Docosahexaenoic acid can be liberated from cellular membranes by phospholipase A2 (PLA2) and converted to numerous oxylipins, including specialized pro-resolving mediators (SPMs), which are produced by lipoxygenases and include D-series protectins and resolvins, as well as maresins, that regulate host defense and the resolution of inflammation.
Docosahexaenoic acid has roles in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation.
A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.
cis-4,7,10,13,16,19-Docosahexaenoic acid (also known as DHA or cervonic acid) is one of the omega-3 fatty acids (a group of highly unsaturated fatty acids).
As for most omega-3 fatty acids, good sources of Docosahexaenoic acid include fish oils and other seafoods.
Docosahexaenoic acid plays a key role in human brain development and function and is also found in high concentration in the retina, central nervous system and skin.
As such Docosahexaenoic acid is a key nutrient which is widely used as a dietary supplement, particularly for infants and pregnant women, with its potential health benefits currently being investigated across a number of different disease areas.
Docosahexaenoic acid is one of the omega-3 fatty acids and is produced from linolenic acid.
Docosahexaenoic Acid can be found in fish oils and is also found in high concentration in the retina, central nervous system and skin.
Docosahexaenoic Acid Chemical Properties
Melting point: -44°C
Boiling point: 446.7±24.0 °C(Predicted)
Density: 0.943±0.06 g/cm3(Predicted)
Refractive index: 1.5030-1.5060
Fp: 62°C
Storage temp.: -20°C
Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated, Sonicated)
Pka: 4.58±0.10(Predicted)
Form: Oil
Color: Clear colorless to light yellow
Biological source: algae
Merck: 14,3398
BRN: 1715505
Stability: Light and Air Sensitive
InChIKey: MBMBGCFOFBJSGT-UAYLQDFESA-N
LogP: 6.778 (est)
CAS DataBase Reference: 6217-54-5(CAS DataBase Reference)
NIST Chemistry Reference: Doconexent(6217-54-5)
EPA Substance Registry System: Docosahexaenoic acid (6217-54-5)
Application
Docosahexaenoic acid is used as a supplement for premature babies and as an ingredient in baby formula during the first year of life to promote better mental development.
Docosahexaenoic acid is also used in infant formula to prevent lung diseases, allergic diseases such as eczema or hay fever, and diarrhea.
This practice probably started because Docosahexaenoic acid is found naturally in breast milk.
In some cases, Docosahexaenoic acid is used in combination with arachidonic acid.
Docosahexaenoic acid is also taken by mouth alone or along with EPA to improve mental function in healthy people or those with mental impairment.
Docosahexaenoic acid is also used to improve mental function in people with dementia or age-related mental decline.
Docosahexaenoic acid is also taken by mouth for attention deficit-hyperactivity disorder (ADHD), depression, aggressive behavior, Alzheimer's disease, autism, and to prevent relapse in schizophrenic patients who stop taking antipsychotic medication.
Docosahexaenoic acid is also taken by mouth for diabetes, coronary artery disease (CAD), stroke, high levels of cholesterol and fats in the blood, high blood pressure, and cancer including breast and prostate cancer.
Docosahexaenoic acid is also used for a type of fatty liver not related to drinking alcohol, obesity, ear infections, and learning problems in children.
Some people use Docosahexaenoic acid is for improving vision, preventing an eye disease called age-related macular degeneration (AMD), treating an eye condition called retinitis pigmentosa, and increasing Docosahexaenoic acid levels in people with cystic fibrosis.
Docosahexaenoic acid is taken by mouth in combination with eicosapentaenoic acid (EPA) for a variety of conditions, including the prevention and reversal of heart disease, stabilizing heart rhythm, preventing abnormal heart beats after heart surgery, painful menstrual periods, lupus, and certain kidney diseases.
EPA and Docosahexaenoic acid are also used in combination for preventing migraine headaches in teenagers, Behcet's syndrome, psoriasis, Raynaud's syndrome, rheumatoid arthritis, bipolar disorder, and ulcerative colitis.
Docosahexaenoic acid is found in fish oils in nature.
Docosahexaenoic acid is also commercially manufactured from microalgae; Crypthecodinium cohnii and Schizochytrium.
Omega-3 fatty acid found in marine fish oils and in many phospholipids.
Major structural component of excitable membranes of the retina and brain; synthesized in the liver from a-linolenic acid.
