6217-54-5 Usage
Description
cis-4,7,10,13,16,19-Docosahexaenoic acid, also known as Docosahexaenoic 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 is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils, comprising approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes. DHA's structure is a carboxylic acid with a 22-carbon chain and six cis double bonds, with the first double bond located at the third carbon from the omega end. Its trivial name is cervonic acid, and its shorthand name is 22:6(n-3) in the nomenclature of fatty acids.
Uses
Used in Pharmaceutical Industry:
cis-4,7,10,13,16,19-Docosahexaenoic acid is used as a pharmaceutical ingredient for its role in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation. It is also used in the production of specialized pro-resolving mediators (SPMs), which regulate host defense and the resolution of inflammation.
Used in Nutritional Supplements:
cis-4,7,10,13,16,19-Docosahexaenoic acid is used as a nutritional supplement to support brain health, cognitive function, and overall well-being. It is commonly found in fish oil supplements and is also commercially manufactured from microalgae, such as Crypthecodinium cohnii and Schizochytrium.
Used in Food Industry:
cis-4,7,10,13,16,19-Docosahexaenoic acid is used as a food additive to enrich products with omega-3 fatty acids, which are essential for maintaining a healthy diet and supporting various bodily functions.
Used in Cosmetics Industry:
cis-4,7,10,13,16,19-Docosahexaenoic acid is used in cosmetics and skincare products for its beneficial effects on skin health, including moisturization and anti-inflammatory properties.
Used in Research and Development:
cis-4,7,10,13,16,19-Docosahexaenoic acid is used as a research compound in the development of new drugs and therapies targeting various health conditions, as well as in studies investigating the role of omega-3 fatty acids in human health and disease.
Biosynthesis of DHA
ALA is an essential fatty acid. It is synthesised in plants and in many lower organisms and is found in the human diet mainly as a component of green leaves, some nuts, seeds and vegetable oils, and foods made from or containing those ingredients. There is a metabolic pathway that links ALA to DHA. This pathway involves a series of enzyme-catalysed elongation and desaturation reactions. Elongation enzymes, called elongases, add pairs of carbon atoms to the growing acyl chain, in this case converting an 18-carbon fatty acid into a 22-carbon one, while desaturase enzymes insert double bonds into the acyl chain, in this case converting a fatty acid with 3 double bonds in its acyl chain into one with 6 double bonds. These reactions occur predominantly within the endoplasmic reticulum. The pathway is believed to mainly occur within the liver, but there is some evidence that other tissues, including brain and testis, have high expression of the genes encoding the relevant enzymes.
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 .
Biochem/physiol Actions
Docosahexaenoic acid, DHA, is an omega-3 polyunsaturated fatty acid with 22 carbons and six double bonds, the first double bond occuring at position three from the methyl terminus (22:6 n-3). DHA is a component of lipid membranes and the myelin sheath. DHA also serves as a precursor for signaling molecules such as prostaglandins and eicosanoids.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 6217-54-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,1 and 7 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 6217-54:
(6*6)+(5*2)+(4*1)+(3*7)+(2*5)+(1*4)=85
85 % 10 = 5
So 6217-54-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3+,7-6+,10-9+,13-12+,16-15+,19-18-
6217-54-5Relevant articles and documents
Synthesis of all-Z-1,6,9,12,15-octadecapenten-3-one, a vinyl ketone polyunsaturated marine natural product isolated from callysponga sp
Langseter, Anne Marie,Stenstroom, Yngve,Skattebool, Lars
, p. 3804 - 3812 (2014)
The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z- octadecapentaen- 3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield.
PROCESSES IN THE PREPARATION OF POLYUNSATURATED KETONE COMPOUNDS
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Page/Page column 36-37, (2019/12/04)
A process comprising the following steps: a-i) treating a polyunsaturated ester with a base in a solvent of lower alcohol and water to form the corresponding polyunsaturated acid; a-ii) treating the product from step a-i), especially the crude product, with a halolactonization agent in the solvent of lower alcohol and water, to form the corresponding polyunsaturated halolactone; and a-iii) treating the product from step a-ii), especially the crude product, with a reagent in the solvent of lower alcohol and water to convert the polyunsaturated halolactone to the corresponding polyunsaturated epoxide lower alkyl ester.
PROCESS FOR THE PREPARATION OF A POLYUNSATURATED KETONE COMPOUND
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Page/Page column 21; 22, (2015/02/19)
The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acccptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.