Цис-4,7,10,13,16,19-докосагексаeновая кислота

Химические свойства

Clear Colourless Liquid

Использование

Docosahexaenoic acid is found in fish oils in nature. It is also commercially manufactured from microalgae; Crypthecodinium cohnii and Schizochytrium.

Определение

ChEBI: A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.

Общее описание

An omega-3 fatty acid essential for normal brain growth and

function, docosahexaenoic acid (DHA) plays an important role as a signaling factor in cells for both anti- and pro-inflammatory processes. Levels of docosahexaenoic acid as well as other fatty acids are analyzed by GC/MS or LC-MS/MS methods to monitor patients undergoing diet therapy for mitochondrial or peroxisomal disorders. This Certified Spiking Solution^? is suitable for use as starting material in the

preparation of linearity standards, calibrators, or controls in mass spectrometry-based DHA testing applications such as assessment of cardiovascular disease risk and fatty acid deficiency, and detection and quantification of DHA in nutraceuticals and dietary supplements.

Биологическая активность

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 .

Методы очистки

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.]