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CAS NUMBER: 6217-54-5
EC NUMBER: 612-950-9
MOLECULAR FORMULA: C22H32O2
MOLECULAR WEIGHT: 328.5
IUPAC NAME: (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Docosahexaenoic Acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina.
In physiological literature, Docosahexaenoic Acid is given the name 22:6(n-3).
Docosahexaenoic Acid can be synthesized from alpha-linolenic acid or obtained directly from maternal milk (breast milk), fatty fish, fish oil, or algae oil.
Docosahexaenoic Acid (DHA) is an omega-3 fatty acid that is found along with eicosapentaenoic acid (EPA) in cold-water fish, including tuna and salmon.
Docosahexaenoic Acid plays a key role in the development of eye and nerve tissues.
Docosahexaenoic Acid might also reduce the risk of heart and circulatory disease by decreasing the thickness of the blood, reducing swelling (inflammation), and lowering blood levels of triglycerides.
People commonly use Docosahexaenoic Acid for high levels of cholesterol or other fats in the blood.
Docosahexaenoic Acid is also used for boosting memory and thinking skills, for helping infant and child development, for certain eye disorders, and many other conditions, but there is no good scientific evidence to support many of these uses.
Docosahexaenoic Acid's structure is a carboxylic acid (-oic acid) with a 22-carbon chain (docosa- derives from the Ancient Greek for 22) and six (hexa-) cis double bonds (-en-); with the first double bond located at the third carbon from the omega end.
Docosahexaenoic Acid's trivial name is cervonic acid (from the Latin word cerebrum for "brain"), 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.
Most of the Docosahexaenoic Acid in fish and multi-cellular organisms with access to cold-water oceanic foods originates from photosynthetic and heterotrophic microalgae, and becomes increasingly concentrated in organisms the further they are up the food chain.
Docosahexaenoic Acid is also commercially manufactured from microalgae: Crypthecodinium cohnii and another of the genus Schizochytrium.
Docosahexaenoic Acid manufactured using microalgae is vegetarian.
In organisms that do not eat algae containing Docosahexaenoic Acid nor animal products containing Docosahexaenoic Acid, Docosahexaenoic Acid is instead produced internally from α-linolenic acid, a shorter omega-3 fatty acid manufactured by plants (and also occurring in animal products as obtained from plants).
Limited amounts of eicosapentaenoic and docosapentaenoic acids are possible products of α-linolenic acid metabolism in young women and men.
Docosahexaenoic Acid in breast milk is important for the developing infant.
Rates of Docosahexaenoic Acid production in women are 15% higher than in men.
Docosahexaenoic Acid is a major fatty acid in brain phospholipids and the retina.
Research into the potential role or benefit of Docosahexaenoic Acid in various pathologies is ongoing, with significant focus on its mechanism in Alzheimer's disease and cardiovascular disease.
Forms:
Triglyceride is the natural form. Basically, all supplements sold at present are in triglyceride form and some in ethyl ester and phospholipid form. However, some bioavailability of DHA or EPA in the lysophosphatidylcholine (LPC) form is more efficient than triglyceride and phosphatidylcholines (PC) according to a 2020 study.
Central nervous system constituent:
Docosahexaenoic Acid is the most abundant omega-3 fatty acid in the brain and retina.
Docosahexaenoic Acid comprises 40% of the polyunsaturated fatty acids (PUFAs) in the brain and 60% of the PUFAs in the retina.
Fifty percent of a neuronal plasma membrane is composed of Docosahexaenoic Acid.
Docosahexaenoic Acid modulates the carrier-mediated transport of choline, glycine, and taurine, the function of delayed rectifier potassium channels, and the response of rhodopsin contained in the synaptic vesicles.
Phosphatidylserine (PS) – which contains high Docosahexaenoic Acid content – has roles in neuronal signaling and neurotransmitter synthesis, and DHA deficiency is associated with cognitive decline.
Docosahexaenoic Acid levels are reduced in the brain tissue of severely depressed people.
Metabolic Synthesis:
In humans, Docosahexaenoic Acid is either obtained from the diet or may be converted in small amounts from eicosapentaenoic acid (EPA, 20:5, ω-3) via docosapentaenoic acid (DPA, 22:5 ω-3) as an intermediate.
This synthesis had been thought to occur through an elongation step followed by the action of Δ4-desaturase.
It is now considered more likely that Docosahexaenoic Acid is biosynthesized via a C24 intermediate followed by beta oxidation in peroxisomes.
Thus, 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".
In organisms such as microalgae, mosses and fungi, biosynthesis of Docosahexaenoic Acid usually occurs as a series of desaturation and elongation reactions, catalyzed by the sequential action of desaturase and elongase enzymes.
One known pathway in these organisms involves:
*a desaturation at the sixth carbon of alpha-linolenic acid by a Δ6 desaturase to produce stearidonic acid,
*elongation of the stearidonic acid by a Δ6 elongase to produce to eicosatetraenoic acid,
*desaturation at the fifth carbon of eicosatetraenoic acid by a Δ5 desaturase to produce eicosapentaenoic acid,
*elongation of eicosapentaenoic acid by a Δ5 elongase to produce docosapentaenoic acid, and
*desaturation at the fourth carbon of docosapentaenoic acid by a Δ4 desaturase to produce DHA
Metabolism: Docosahexaenoic Acid can be metabolized into DHA-derived specialized pro-resolving mediators (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others.
The enzyme CYP2C9 metabolizes Docosahexaenoic Acid to epoxydocosapentaenoic acids (EDPs; primarily 19,20-epoxy-eicosapentaenoic acid isomers.
Docosahexaenoic Acid is widely used as a food supplement.
Docosahexaenoic Acid was first used primarily in infant formulas.
In 2019, the US Food and Drug Administration published qualified health claims for Docosahexaenoic Acid.
Some manufactured Docosahexaenoic Acid is a vegetarian product extracted from algae, and it competes on the market with fish oil that contains Docosahexaenoic Acid and other omega-3s such as EPA.
Both fish oil and Docosahexaenoic Acid are odorless and tasteless after processing as a food additive.
Docosahexaenoic Acid and EPA in fish oils:
Fish oil is widely sold in capsules containing a mixture of omega-3 fatty acids, including EPA and Docosahexaenoic Acid.
Oxidized fish oil in supplement capsules may contain lower levels of EPA and Docosahexaenoic Acid.
Light, oxygen exposure, and heat can all contribute to oxidation of fish oil supplements.
Docosahexaenoic Acid, or DHA, is a type of omega-3 fat.
Like the omega-3 fat eicosapentaenoic acid (EPA), Docosahexaenoic Acid is plentiful in oily fish, such as salmon and anchovies.
Docosahexaenoic Acid (DHA) is an omega-3 fatty acid found in cold-water, fatty fish, such as salmon.
Docosahexaenoic Acid is also found in fish oil supplements, along with eicosapentaenoic acid (EPA).
Vegetarian sources of Docosahexaenoic Acid come from seaweed.
Omega-3 fatty acids are good for your heart, and your body needs Docosahexaenoic Acid for a healthy brain.
Infants need Docosahexaenoic Acid, especially during the first 6 months of their lives, so their brains, eyes, and nervous systems can develop as they should.
Docosahexaenoic Acid is found in breast milk and is added to some infant formula.
Our bodies naturally make small amounts of Docosahexaenoic Acid, but we must get the amounts we need from food or supplements.
Most people in the Western world do not get enough omega-3 fatty acids in their diet.
USES:
Attention-Deficit Hyperactivity Disorder (ADHD):
Because children need omega-3 fatty acids for their brains to develop properly, researchers have examined whether fish oil might reduce ADHD symptoms.
Depression:
Although some studies show that fish oil reduces symptoms of depression, it is not clear whether DHA by itself has the same effect.
Other studies suggest EPA improves depression.
Heart Disease:
Fish oil appears to help improve outcomes for people who already have heart disease.
Docosahexaenoic Acid may also lower the risk for developing heart disease.
Omega-3 fatty acids found in fish oil help lower triglycerides (fats in the blood), lower blood pressure, reduce the risk of blood clots, improve the health of arteries, and reduce the amount of arterial plaque, which narrows arteries and causes heart disease.
The American Heart Association recommends eating fish, particularly fatty fish, at least 2 times per week.
Fatty fish include salmon, herring, lake trout, sardines and albacore tuna.
People who already have heart disease may need fish oil supplements in addition to adding more fish to their diet.
Infant Development:
Docosahexaenoic Acid plays a crucial role in the growth and development of the central nervous system, as well as visual functioning in infants.
Breastfed babies with healthy mothers should get enough DHA in breast milk.
Rheumatoid Arthritis:
Several small studies found that fish oil may help reduce symptoms and inflammation linked with rheumatoid arthritis.
However, Docosahexaenoic Acid does not stop joint damage from getting worse.
Docosahexaenoic Acid (DHA) is a long-chain, highly unsaturated omega-3 (n-3) fatty acid.
Docosahexaenoic Acid has a structure that gives it unique physical and functional properties.
Docosahexaenoic Acid is metabolically related to other n-3 fatty acids: it can be synthesised from the plant essential fatty acid α-linolenic acid (ALA).
However, this pathway does not appear to be very efficient in many individuals, although the conversion of ALA to DHA is much better in young women than in young men.
Furthermore, young infants may be more efficient converters of ALA to Docosahexaenoic Acid than many adults, although the conversion rate is variable among infants.
Many factors have been identified that affect the rate of conversion.
The implication of poor conversion is that preformed Docosahexaenoic Acid needs to be consumed.
Docosahexaenoic Acid is found in fairly high amounts in seafood, especially fatty fish, and in various forms of n-3 supplements.
The amount of Docosahexaenoic Acid in seafood and in supplements varies.
Breast milk contains Docosahexaenoic Acid .
Docosahexaenoic Acid is found esterified into complex lipids within the bloodstream, in adipose stores and in cell membranes.
Docosahexaenoic Acid's concentration in different compartments varies greatly.
The brain and eye have high Docosahexaenoic Acid contents compared to other organs.
Docosahexaenoic Acid is especially concentrated in the grey matter of the brain and in the rod outer segments of the retina.
In the brain Docosahexaenoic Acid is involved in neuronal signalling, while in the eye it is involved in the quality of vision.
Docosahexaenoic Acid is accumulated in the brain and eye late in pregnancy and in early infancy.
A lower Docosahexaenoic Acid content is linked to poorer cognitive development and visual function.
Docosahexaenoic Acid affects cell and tissue physiology and function through numerous mechanisms, including alterations in membrane structure and function, in membrane protein function, in cellular signalling and in lipid mediator production.
• Docosahexaenoic Acid (DHA) is a bioactive omega-3 polyunsaturated fatty acid that influences membrane structure and function, cell signalling and communication mechanisms, gene expression and lipid mediator production.
• Docosahexaenoic Acid is found in high concentrations in the human brain and eye, where it is linked to better development and function.
• Maintenance of Docosahexaenoic Acid concentration is important throughout the life course, but pregnancy, lactation and infancy are vulnerable periods, where insufficient DHA supply can impact mental and visual development and performance.
Docosahexaenoic Acid (DHA) is an omega-3 fatty acid essential for brain development during pregnancy and early childhood.
Docosahexaenoic Acid is also linked to improved heart health, better vision, and reduced inflammatory response.
Docosahexaenoic Acid is naturally produced in small quantities by our bodies, but to achieve adequate amounts, DHA needs to be taken in through dietary sources such as cold-water fish, grass-fed meat, dairy, or omega-3 enriched or pasture-raised eggs.
Docosahexaenoic Acid is also available as supplements, such as fish oil.
The long-chain omega-3 fatty acid is found in cell membranes throughout the body and helps to transmit messages between nerves.
Docosahexaenoic Acid is essential for brain development and accounts for 97% of the omega-3 fatty acids found in the brain and 25% of the brain’s total fat content.
All-cis-docosa-4,7,10,13,16,19-hexaenoic acid is a docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.
Docosahexaenoic Acid has a role as a nutraceutical, an antineoplastic agent, a human metabolite, a Daphnia tenebrosa metabolite, a mouse metabolite and an algal metabolite.
Docosahexaenoic Acid is a docosahexaenoic acid and an omega-3 fatty acid.
Docosahexaenoic Acid is a conjugate acid of a (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate.
A mixture of fish oil and primrose oil, doconexent is used as a high-docosahexaenoic acid (DHA) supplement.
Docosahexaenoic Acid is a 22 carbon chain with 6 cis double bonds with anti-inflammatory effects.
Docosahexaenoic Acid can be biosythesized from alpha-linolenic acid or commercially manufactured from microalgae.
Docosahexaenoic Acid is an omega-3 fatty acid and primary structural component of the human brain, cerebral cortex, skin, and retina thus plays an important role in their development and function.
The amino-phospholipid Docosahexaenoic Acid is found at a high concentration across several brain subcellular fractions, including nerve terminals, microsomes, synaptic vesicles, and synaptosomal plasma membranes.
Doconexent is a polyunsaturated very long-chain fatty acid with a 22-carbon backbone and 6 double bonds, originating from the 3rd, 6th, 9th, 12th, 15th and 18th positions from the methyl end.
PHYSICAL PROPERTIES:
-Molecular Weight: 328.5
-XLogP3-AA: 6.2
-Exact Mass: 328.240230259
-Monoisotopic Mass: 328.240230259
-Topological Polar Surface Area: 37.3 Ų
-Physical Description: Liquid
-Collision Cross Section: 184.62 Ų
Docosahexaenoic Acid (DHA) is a member of a group of natural compounds known to many as omega-3 fatty acids.
The designation omega-3 (or ω-3) means that there is a double bond at the third carbon atom from the far end of the hydrocarbon chain.
All six double bonds in Docosahexaenoic Acid have a cis (Z) configuration, unlike fatty acids with trans double bonds.
Docosahexaenoic Acid is widely found in the human body, especially in the brain, skin, and retina.
Therefore, Docosahexaenoic Acid is not considered an "essential" fatty acid such as α-linolenic acid (ALA) or linoleic acid, which the body cannot synthesize.
However, many dietitians recommend consuming external sources of DHA, such as fish, algae, and dietary supplements.
The supplement is especially desirable for vegetarians and vegans.
The recommended initial use of Docosahexaenoic Acid as a supplement is for pregnant and lactating women.
CHEMICAL PROPERTIES:
-Hydrogen Bond Donor Count: 1
-Hydrogen Bond Acceptor Count: 2
-Rotatable Bond Count: 14
-Heavy Atom Count: 24
-Formal Charge: 0
-Complexity: 462
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 0
-Defined Bond Stereocenter Count: 6
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
Docosahexaenoic Acid (DHA) is essential for the growth and functional development of the brain in infants.
Docosahexaenoic Acid is also essential for maintaining normal brain function in adults.
Adding plenty of Docosahexaenoic Acid to the diet improves learning ability, while DHA deficiencies are associated with deficits in learning.
Docosahexaenoic Acid is taken up by the brain preferentially to other fatty acids.
The turnover of Docosahexaenoic Acid in the brain is much faster than is generally thought.
Healthy, full-term, formula-fed babies have improved visual acuity when their formula contains DHA.
SYNONYMS:
Docosahexaenoic acid
Doconexent
Cervonic acid
cis-4,7,10,13,16,19-Docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
all-cis-DHA
Doconexento
Doconexentum
Doxonexent
Docosahexaenoate
Martek DHA HM
Ropufa 60
all-cis-4,7,10,13,16,19-Docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
Docosahexaenoic acid (all-Z)
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid
DOCOSA-4,7,10,13,16,19-HEXAENOIC ACID
4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)-
docosahexaenoic acid(DHA)
delta4,7,10,13,16,19-Docosahexaenoic acid
4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid
4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid
(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid
OMEGA-3 MARINE TRIGLYCERIDES
efalex
DOCOSAHEXAENOIC ACID (22:6 n-3)
cis-4,7,10,13,16,19-Docosahexanoic acid
4,7,10,13,16,19-Docosahexaenoic acid
C22:6n-3,6,9,12,15,18
Monolife 50
Doconexent [INN]
Marinol D 50TG
4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-
Doconexentum [INN-Latin]
Doconexento [INN-Spanish]
DHA-[21,21,22,22,22-d5]
Cervonate
FA 22:6
Algal DHA
Docosahexanenoic acid
Omega 3 fatty acid
all-Z-Docosahexaenoate
Cervonic acid|||DHA
Docoshexaenoic Acid (Powder)
Retriacyl (proposed trade name)
4,7,10,13,16,19-Docosahexaenoate
all cis- Docosahexaenoic acid (cis-DHA)
M355
SMR001881493
cis-4,7,10,13,16,19-Docosahexanoate
4,7,10,13,16,19-Docosahexaenoic acid, (all cis)-
A320050000
cis-4,7,10,13,16,19-Docosahexaenoic acid, >=98%
z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid
(all-Z)-4,7,10,13,16,19-Docosahexaenoic Acid, DHA
4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)- (8CI)
cis-4,7,10,13,16,19-Docosahexaenoic acid, analytical standard
(4Z,7Z,10Z,13Z,16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4, 7,10,13,16,19-hexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19- hexaenoic acid
cis-4,7,13,16,19-Docosahexaenoic acid (stabilized with vitamine E)
4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)- (9CI)
1024594-51-1
cis-4,7,10,13,16,19-Docosahexaenoic acid, 500 mug/mL in ethanol, certified reference material
