ARACHIDONOYL CHLORIDE

Base Information

• Chemical Name: ARACHIDONOYL CHLORIDE
• CAS No.: 57303-04-5
• Molecular Formula: C20H31ClO
• Molecular Weight: 322.919
• Hs Code.: 2916190090
• Mol file: 57303-04-5.mol

Synonyms:DELTA 5-8-11-14 CIS-EICOSATETRAENOYL CHLORIDE;ARACHIDONOYL CHLORIDE;5,8,11,14-EICOSATETRAENOIC ACID CHLORIDE

Chemical Property of ARACHIDONOYL CHLORIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 410.824°C at 760 mmHg
• Flash Point: 201.009°C
• PSA: 17.07000
• Density: 0.92 g/mL at 25 °C(lit.)
• LogP: 6.89750
• Storage Temp.: −20°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

ArachidonoylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Arachidonoyl Chloride is a derivative of Arachidonic Acid (A765000), an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, depot fats of animals, in small amounts in human depot fats, and is also a constituent of animal phosphatides.

Technology Process of ARACHIDONOYL CHLORIDE

There total 4 articles about ARACHIDONOYL CHLORIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → arachidonoyl chloride (57303-04-5)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; Ambient temperature;

DOI:10.1016/S0040-4020(01)85980-9

Reference yield:

oxalyl dichloride (79-37-8) + all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → arachidonoyl chloride (57303-04-5)

Guidance literature:

With N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.lfs.2012.06.040

Reference yield:

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester (119520-63-7) → arachidonoyl chloride (57303-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature

2: oxalyl chloride, DMF / benzene / Ambient temperature

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In ethanol; benzene;

DOI:10.1016/S0040-4020(01)85980-9

upstream raw materials:

all cis 5,8,11,14-eicosatetraenoic acid

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester

N-(p-nitrophenyl)-arachidonamide

oxalyl dichloride

Downstream raw materials:

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (3-hydroxy-phenyl)-amide

N-methylarachidonamide

arachidonic acid pyrrolidide

methyl arachidonate

Refernces

• 1、 Corey, E. J.,Cashman, John R.,Kantner, Steven S.,Wright, Stephen W.. "Rationally Designed, Potent Competitive Inhibitors of Leukotriene Biosynthesis". . p. 1503 - 1504. Retrieved 1984.
• 2、 Xing, Qi,Chan, Chun-Ming,Yeung, Yiu-Wai,Yu, Wing-Yiu. "Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones". supporting information. . Retrieved 2019/03/11.
• 3、 Miceli, Matteo,Casati, Silvana,Ottria, Roberta,Di Leo, Simone,Eberini, Ivano,Palazzolo, Luca,Parravicini, Chiara,Ciuffreda, Pierangela. "Set-up and validation of a high throughput screening method for human monoacylglycerol lipase (MAGL) based on a new red fluorescent probe". . . Retrieved 2019/06/20.