Arachidonic acid

Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.

Liquid

Arachidonic acid is a long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite. It is an icosa-5,8,11,14-tetraenoic acid, an omega-6 fatty acid and a long-chain fatty acid. It is a conjugate acid of an arachidonate. It derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.|Arachidonic Acid is an unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.(ChemID Plus)|An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Method one: Preparation of brominated debrominated oil ether solution Weigh 40 kg of minced pig adrenal gland, add equal volume of 95% ethanol and 2.5 kg of potassium hydroxide, adjust pH 10, mix well, heat and reflow with nitrogen until the saponification is complete, Get saponified liquid. Cool the saponification solution to 50°C, add equal volume of hydrochloric acid, adjust pH 3, separate the layers, extract the emulsified layer with ether, combine the ether extract and the oil layer, concentrate to half, put in a -20°C cold storage overnight, filter at 0°C, filter residue Wash with ether, combine the filtrates, concentrate to half, then put in a cold store at -20°C overnight. After repeated treatment in this way, oil ether liquid is obtained. Preparation of porcine adrenal gland [ethanol] → [KOH, pH10] saponification solution [HCl, pH3] → [ether] oil ether liquid debromination solution Preparation of bromine ether solution (prepared below 0°C, V bromine: V ether = 1: 2) Add to the oil ether solution, stir vigorously while adding, until the bromination is complete, an orange precipitate is deposited, the bromine ether solution is poured out, the precipitate is washed with ether until the washing liquid is colorless, the precipitate is white, and the precipitate is white, and the bromide is obtained. Grind the bromide, add 100g of zinc powder, 750-1000ml of methanol, 2-4ml of hydrochloric acid to 100g of bromide, put nitrogen in a water bath at 75-80 ℃ and reflux for 8h, filter, the filter residue is washed with an appropriate amount of methanol, and the filtrate and washing liquid are combined. Get debrominated liquid. Oil ether liquid [bromine, ether] → [<0℃] bromide [zinc, methanol] → [8h] Preparation of debromination liquid arachidonic acid methyl ester Concentrate the debromination liquid to 1/3 volume, plus 3 times Amount of water, add 4mol/L hydrochloric acid to adjust pH3, add ether to extract 3-4 times, combine ether extracts, add anhydrous sodium sulfate, concentrate with nitrogen to remove ether to obtain crude oil. Add 2-3 times methanol (containing saturated hydrogen chloride), and place in a water bath at 70-80°C to reflux for 6h. Add 2mol/L sodium hydroxide to adjust pH5-6, filter, wash the precipitate with diethyl ether, combine the filtrates, concentrate to remove the organic solvent to obtain the methyl ester liquid, and then conduct high vacuum distillation, take 190-200 ℃ fractions to obtain arachidonic acid Methyl ester. Debromination liquid [ether] → [Na2SO4, pH3] refined oil [methanol] → [70-80℃, 6h] methyl ester liquid [190-200℃, 0.3kPa] → arachidonic acid methyl ester arachidonic acid finished product Preparation of methyl arachidonic acid, add 10 times the amount of 1mol/L KOH methanol solution, in a 40-80 ℃ water bath filled with nitrogen and reflux for 0.5h, concentrated to remove part of the methanol, add 3 times the amount of water, add 4mol/L hydrochloric acid to adjust pH 3. Diethyl ether was added for extraction, and the ether layer was washed with water to pH 5-6, anhydrous sodium sulfate was added, and nitrogen was concentrated under reduced pressure to remove diethyl ether to obtain arachidonic acid. Arachidonic acid methyl ester [diethyl ether]→[KOH, 40-80℃, 0.5h] arachidonic acid finished product method 2. Preparation of mixed fatty acid diethyl ether solution by urea inclusion method Take pig adrenal homogenate, add 95% ethanol (3 Double amount, double amount) Extract twice, filter to obtain filtrate, concentrate to remove ethanol, add ether to extract, concentrate to remove ether to obtain lipid. Add 1.5 times ethanol to dissolve, add 500g/L potassium hydroxide to adjust the pH to above 10, and fill with nitrogen to reflux to obtain mixed fatty acid potassium salt. Add acid to adjust pH3 and extract with ether to obtain mixed fatty acid ether solution. Pig adrenal gland homogenate [ethanol, ether] → [KOH, HCl, pH10, pH3] Preparation of mixed fatty acid ether solution Mixed unsaturated fatty acid Take mixed fatty acid ether solution, concentrate to remove ether, add 10 times the amount of acetone to dissolve, then in order -5 ℃, -25 ℃, -45 ℃, -72 ℃ frozen crystallization, 2h each time, filtered, the filtrate was concentrated to remove acetone, mixed unsaturated fatty acids were obtained. Mixed fatty acid ether liquid [acetone, 2h]→[-5℃, -25℃, -45℃, -72℃] Preparation of mixed unsaturated fatty acid arachidonic acid finished product Dissolve mixed unsaturated fatty acid with appropriate amount of methanol, add urea And methanol, after the urea is dissolved, the crystals are frozen at -3 ℃, -20 ℃ and -75 ℃ in sequence, filtered, the filtrate is dried over anhydrous sodium sulfate, and methanol is distilled off to obtain the finished product of arachidonic acid. Mixed unsaturated fatty acids [urea, methanol, anhydrous sodium sulfate] → [-3℃, -20℃, -75℃] Finished arachidonic acid Method 3. Preparation of linoleic acid with oleic acid as raw material The raw material is desaturated to produce linoleic acid. Oleic acid [desaturation] → Preparation of linoleic linolenic acid Linoleic acid produces α-linolenic acid under the action of ω-3 dehydrogenase; γ-linolenic acid is produced under the action of ω-6 dehydrogenase. Preparation of arachidonic acid α-linolenic acid grows through the C2 chain to obtain eicosapentaenoic acid. Arachidonic acid is prepared by desaturating eicosapentaenoic acid. α-linolenic acid [C2 chain growth] → eicosapentaenoic acid [desaturation] → arachidonic acid method 4. Microbial fermentation method Ion beam bioengineering center, Institute of Plasma Physics, Chinese Academy of Sciences Change the technology, inject and improve the AA starting bacteria NT, and successfully select a high-yield fungus bead. Shinmen et al. used fermented beads of Mortierella alpina and Mortierella multicephalus to obtain AA, and screened the high-yield bacteria of A. multifida.

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.

Molecular Weight:304.5
XLogP3:6.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:14
Exact Mass:304.240230259
Monoisotopic Mass:304.240230259
Topological Polar Surface Area:37.3
Heavy Atom Count:22
Complexity:362
Defined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes