ドコサヘキサエン酸

外観

無色～うすい黄赤色～黄色透明液体

定義

本品は、次の化学式で表される直鎖高度不飽和脂肪酸である。

解説

ドコサヘキサエン酸,EPAとともに血栓性疾患および動脈硬化性疾患の発症を予防する高度不飽和脂肪酸として注目されている．α-リノレン酸の代謝産物である．融点－44.5 ℃．

森北出版「化学辞典（第2版）

化粧品の成分用途

皮膚コンディショニング剤

製造

ドコサヘキサエン酸,略称DHA．セルボン酸ともいう．エイコサペンタエン酸(EPA)とともに魚油やリン脂質に多く含まれている．

化学的特性

Clear Colourless Liquid

使用

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

定義

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

一般的な説明

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.

生物活性

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 .

純化方法

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.]