55726-28-8

Basic information

• Product Name: Arachidonicacidanhydride
• Synonyms: ARACHIDONIC ANHYDRIDE
• CAS NO: 55726-28-8
• Molecular Formula: C₄₀H₆₂O₃
• Molecular Weight: 590.91848
• Mol File: 55726-28-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Arachidonicacidanhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Arachidonicacidanhydride(55726-28-8)
• EPA Substance Registry System: Arachidonicacidanhydride(55726-28-8)

Safety Data

• Hazardous Substances Data: 55726-28-8(Hazardous Substances Data)

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 

Downstream Products

• 1338939-14-2 2,4-diisopropylphenol arachidonic acid 
• 187224-29-9 N-arachidonoyl serine 
• 18892-74-5 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine 
• 128201-89-8 arachidonamide of γ-amino-n-butyric acid 

Relevant articles and documents

Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

Polyunsaturated fatty acids (PUFAs) have been reported to play a regulatory role in tumour growth progression. In the present study, we have synthesized ester derivatives of two important PUFA viz., linoleic acid (LA) and arachidonic acid (AA) with propof

The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1′-13C3 and -2,1′-13C2 by a novel chemoenzymatic method

2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A2 was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies.

Mead ethanolamide, a novel eicosanoid, is an agonist for the central (CB1) and peripheral (CB2) cannabinoid receptors

The recently discovered endogenous agonist for the cannabinoid receptor, anandamide (arachidonylethanolamide), can be formed enzymatically by the condensation of arachidonic acid with ethanolamine. 5Z,8Z,11Z-Eicosatrienoic acid (mead acid) has been found to substitute for arachidonic acid in the sn- 2 position of phospholipids and accumulate during periods of dietary fatty acid deprivation in rats. In the present study, the chemically synthesized ethanolamide of mead acid was evaluated as a potential agonist at the two known subtypes of cannabinoid receptor: CB1 (central) and CB2 (peripheral). This compound was equipotent to anandamide in competing with [3H]CP55,940 binding to plasma membranes prepared from L cells expressing the human CB1 receptor and from ATt-20 cells expressing the human CB2 receptor. Mead ethanolamide was also equipotent to anandamide in inhibiting forskolin- stimulated cAMP accumulation in cells expressing the CB1 receptor. It inhibited N-type calcium currents with a lower potency than anandamide. Mead and arachidonic acid were equally efficacious as substrates for the enzymatic synthesis of their respective ethanolamides in rat and adult human hippocampal P2 membranes. Palmitic acid was not an effective substrate for the enzymatic synthesis of palmitoyl ethanolamide. Mead ethanolamide exhibits several characteristics of a novel agonist to CB1 and CB2 receptors and may represent another candidate endogenous ligand for the CB1 receptor. Due to the anticonvulsant properties of GABA and the positional similarity of L- serine to ethanolamine in membrane phospholipids, these compounds were synthetically coupled to arachidonic acid, and their resulting arachidonamides were tested as potential cannabinoid agonists. The arachidonamides of GABA and L-serine were inactive in both binding and functional assays at the CB1 receptor.