5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER

Base Information

• Chemical Name: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER
• CAS No.: 390824-17-6
• Molecular Formula: C₂₅H₃₆O₂S
• Molecular Weight: 400.626
• Mol file: 390824-17-6.mol

Synonyms:

Chemical Property of 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER

Chemical Property:

• PSA: 54.54000
• LogP: 7.93700

Purity/Quality:

CAY10412 ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Anandamide (arachidonoyl ethanolamide; AEA) is an endogenous lipid with cannabinergic activity; along with 2-arachidonoyl glycerol, it forms part of the endocannabinoid system. AEA undergoes reuptake into neurons by a facilitated process. Controversy exists as to whether there is a specific AEA transporter, or instead the uptake process is simply driven by hydrolysis of AEA by intracellular fatty acyl amide hydrolase (FAAH). CAY10412 is an analog of AEA that has no intrinsic binding affinity for either CB1 or CB2 receptors. It is a potent inhibitor of AEA reuptake in U937 lymphoma cells, with an IC50 of 3 μM. CAY10412 could be a useful tool for distinguishing the competing transporter theories. The pharmacology of CAY10412 is largely unexplored; it may enhance endocannabinoid signalling by augmenting endocannabinoid concentrations.

Technology Process of 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER

There total 3 articles about 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER 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: 89.0%

3-hydroxymethyl-thiophene (71637-34-8) + arachidonoyl chloride (57303-04-5) → 5Z,8Z,11Z,14Z-eicosatetraenoic acid 3-thienylmethyl ester (390824-17-6)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1021/jm0210818

Reference yield: 65.0%

3-hydroxymethyl-thiophene (71637-34-8) + all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 5Z,8Z,11Z,14Z-eicosatetraenoic acid 3-thienylmethyl ester (390824-17-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -20 - 20 ℃;

DOI:10.1016/S0223-5234(03)00045-X

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 5Z,8Z,11Z,14Z-eicosatetraenoic acid 3-thienylmethyl ester (390824-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 1 h / 20 °C

2: CH₂Cl₂ / 20 °C

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/S0223-5234(03)00045-X

upstream raw materials:

3-hydroxymethyl-thiophene

arachidonoyl chloride

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

Refernces

• 1、 López-Rodríguez,Viso,Ortega-Gutiérrez,Lastres-Becker,González,Fernández-Ruiz,Ramos. "Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors". . p. 4505 - 4508. Retrieved 2001.