Docosahexaenoic Acid CAS NO.6217-54-5

Product Name:	Docosahexaenoic Acid
Synonyms:	Docosahexaenoic acid DHA 6217-54-5;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)
CAS:	6217-54-5
MF:	C22H32O2
MW:	328.49
EINECS:	612-950-9
Product Categories:	-;Biological and chemical;Biochemistry;Higher Fatty Acids & Higher Alcohols;Unsaturated Higher Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
Mol File:	6217-54-5.mol

Docosahexaenoic Acid Chemical Properties

Melting point	-44°C
refractive index	1.5030-1.5060
Fp	62°C
storage temp.	−20°C
form	Oil
color	Clear colorless to light yellow
Merck	14,3398
BRN	1715505
Stability:	Light and Air Sensitive
InChIKey	MBMBGCFOFBJSGT-UAYLQDFESA-N
CAS DataBase Reference	6217-54-5(CAS DataBase Reference)
NIST Chemistry Reference	Doconexent(6217-54-5)

Safety Information

Safety Statements	23-24/25
RIDADR	UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany	3
F	8-10-23
HS Code	29161900

MSDS Information

Docosahexaenoic Acid Usage And Synthesis

Description	Docosa Hexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, sperm, testicles and retina. It can be synthesized from alphalinolenic acid or obtained directly from maternal milk or fish oil. DHA'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.[3] 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. Cold-water oceanic fish oils are rich in DHA. Most of the DHA 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. DHA is also commercially manufactured from microalgae; Crypthecodinium cohnii and another of the genus Schizochytrium. DHA manufactured using microalgae is vegetarian. Some animals with access to seafood make very little DHA through metabolism, but obtain it in the diet. How ever, in strict herbivores, and carnivores that do not eat seafood, DHA is manufactured internally from α-linolenic acid, a shorter omega -3 fatty acid manufactured by plants (and also occurring in animal products as obtained from plants). Eicosa pentaenoic and docosa pentaenoic acids are the principal products of α-linolenic acid metabolism in young men and illustrates the importance of DHA production for the developing fetus and healthy breast milk. Giltay, Gooren, Toorians, and Katan (2004) found rates of conversion 15% higher for women, and that those taking oral contraceptives demonstrated 10 % higher DHA levels. Administration of testosterone or the aromatase inhibitor anastrozole, which blocks conversion of testosterone to estradiol, reduces DHA conversion. DHA is a major fatty acid in sperm and brain phospholipids and in the retina. Dietary DHA may reduce the risk of heart disease by reducing the level of blood triglycerides in humans. Below- normal levels of DHA have been associated with Alzheimer's disease. A low level of DHA is also spotted in patients with retinitis pigmentosa.
Chemical Properties	Clear Colourless Liquid
Occurrence	Ordinary types of cooked salmon contain 500 – 1500 mg DHA and 300–1000 mg EPA per 100 grams.(USDA) Additional top fish sources of DHA are: tuna, bluefish, mackerel, swordfish, anchovies, herring, sardines, and caviar. The discovery of algae - based DHA In the early 1980s, NASA sponsored scientific research in search of a plant-based food source that could generate oxygen and nutrition on long-duration space flights. The researchers discovered that certain species of marine algae produced rich nutrients. This research led to the development of an algae-based, vegetable-like oil that contains two essential polyunsaturated fatty acids: DHA and ARA (Arachidonic acid). Use as a food additive DHA is widely used as a food supplement. It was first used primarily in infant formulas. In 2004, the US Food and Drug Administration endorsed qualified health claims for DHA , and by 2007 DHA - fortified dairy items (milk, yogurt, cooking oil) started to appear in grocery stores. DHA is 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 along with supporting retinal development. Some manufactured DHA is a vegetarian product extracted from algae, and it competes on the market with fish oil that contains DHA and other omega-3's such as EPA. Both fish oil and DHA are odorless and tasteless after processing as a food additive. Studies of vegetarians and vegans Vegetarian diets typically contain limited amounts of DHA, and vegan diets typically contain no DHA. Vegetarians and vegans have substantially lower levels of DHA in their bodies, and short-term supplemental ALA has been shown to increase EPA, but not DHA. However, supplemental preformed DHA, available in algae-derived oils or capsules, has been shown to increase DHA levels. While there is little evidence of adverse health or cognitive effects due to DHA deficiency in adult vegetarians or vegans, fetal and breast milk levels remain a concern. DHA and EPA in fish oils Fish oil is widely sold in gelatin capsules containing a mixture of omega-3 fatty acids including EPA and smaller quantities of DHA. One study found fish oil higher in DHA than EPA lowered inflammatory cytokines, such as IL-6 and IL-1β, associated with neurodegenerative and autoimmune diseases. They note the brain normally contains DHA, but not EPA, though both DHA and EPA plasma concentrations increased significantly for participants.
Uses	Nutritional supplement.
Uses	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 α-linolenic acid. Nutritional supplement.
Uses	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. Nutritional supplement.
Definition	ChEBI: A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.
Biological Activity	Endogenous omega-3 fatty acid. Acts as a selective retinoid X receptor (RXR) agonist that displays no activity at RAR, thyroid hormone receptor or the vitamin D receptor (VDR). Activates all three RXR isoforms. Also shown to inhibit A β 1-42 fibrillation and toxicity in vitro .
Purification Methods	Its solubility in CHCl3 is 5%. It has been purified from fish oil by GLC using Ar as mobile phase and EGA as stationary phase with an ionisation detector [UV: Stoffel & Ahrens J Lipid Res 1 139 1959], and via the ester by evaporative "molecular" distillation using a 'continuous molecular still' at 10-4 mm with the highest temperature being 110o and a total contact time with the hot surface being 60sec [Farmer & van den Heuvel J Chem Soc 427 1938]. The methyl ester has b 208-211o/2mm, d4 0.9398, 20 1.5035. nD With Br2 it forms a dodecabromide m ca 240o(dec). Also, the acid was converted to the methyl ester and purified through a three-stage molecular still [as described by Sutton Chem Ind (London) 11383 1953] at 96o, and the rate was adjusted so that one-third of the material was removed each cycle of three distillations. The distillate (numbered 4) (13g) was dissolved in EtOH (100mL containing 8g of KOH) at -70o and set aside for 4hours at 30o with occasional shaking under a vacuum. Water (100mL) was added and the solution was extracted with pentane, washed with HCl, dried (MgSO4), filtered and evaporated to give a clear oil (11.5g) m -44.5o to -44.1o. In the catalytic hydrogenation of the oil six mols of H2 are absorbed and docosanoic acid (behenic acid) is produced with m 79.0-79.3o undepressed with an authentic sample (see docosanoic acid below) [Whitcutt Biochem J 67 60 1957]. [Beilstein 2 IV 1812.]

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