390824-17-6

Basic information

• Product Name: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER
• Synonyms: CAY10412;5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER;YOPBWSZRYHDZAA-DOFZRALJSA-N
• CAS NO: 390824-17-6
• Molecular Formula: C25H36O2S
• Molecular Weight: 400.62
• Mol File: 390824-17-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(390824-17-6)
• EPA Substance Registry System: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(390824-17-6)

Safety Data

• Hazardous Substances Data: 390824-17-6(Hazardous Substances Data)

Usage

Description

5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER is a complex lipid molecule with a unique structure, characterized by the presence of four double bonds at the 5, 8, 11, and 14 positions. It is an ester derivative of eicosatetraenoic acid, with a thiophene ring attached to the methyl group. 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER has potential applications in various fields due to its unique chemical properties and interactions with biological systems.

Uses

Used in Pharmaceutical Industry:
5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER is used as a potential therapeutic agent for modulating the endocannabinoid system. It acts as an inhibitor of anandamide reuptake, which may enhance endocannabinoid signaling and potentially provide therapeutic benefits in various conditions.
Used in Research Applications:
In the field of scientific research, 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER can be used as a valuable tool for studying the endocannabinoid system and its role in various physiological processes. It may help researchers distinguish between competing transporter theories and better understand the mechanisms of anandamide uptake and metabolism.
Used in Drug Development:
5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER may also be utilized in the development of new drugs targeting the endocannabinoid system, which is involved in various physiological processes, including pain, mood, and appetite regulation. By enhancing endocannabinoid signaling, 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER could potentially be used to develop novel therapeutics for a range of conditions, such as chronic pain, anxiety, and obesity.
Used in Drug Delivery Systems:
Similar to gallotannin, 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER could be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes. By using various organic and metallic nanoparticles as carriers, the compound's delivery and efficacy could be enhanced, potentially leading to more effective treatments.

Upstream product

• 71637-34-8 3-hydroxymethyl-thiophene 
• 57303-04-5 arachidonoyl chloride 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of new endocannabinoid transporter inhibitors

In the present work we describe the synthesis and the in vitro evaluation of a series of arachidonic acid derivatives of general structure I as endocannabinoid transporter inhibitors. In addition, we report the first in vivo studies of the most potent derivative (4, UCM707) within this series. The majority of compounds studied are highly potent (IC50=24-0.8 μM) and selective endocannabinoid uptake inhibitors with very low affinities for either the enzyme fatty acid amide hydrolase (IC50=30-113 μM) or for cannabinoid receptor subtype 1 (CB1), cannabinoid receptor subtype 2 (CB2) and vanilloid receptor subtype 1 (VR1) (Ki=1000-10000 nM). Among them, (5Z,8Z,11Z,14Z)-N-(fur-3-ylmethyl)icosa-5,8,11,14-tetraenamide (UCM707) behaves as the most potent endocannabinoid transporter inhibitor described to date (IC50=0.8 μM) and exhibits improved potency for the anandamide transporter, high selectivity for CB1 and VR1 receptors, and modest selectivity for CB2. In vivo it enhances the analgesia and hypokinetic effects induced by a subeffective dose of anandamide.

Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: Comparison with effects on fatty acid amidohydrolase

A new series of arachidonic acid derivatives were synthesized and evaluated as inhibitors of the endocannabinoid uptake. Most of them are able to inhibit anandamide uptake with IC50 values in the low micromolar range (IC50 = 0.8-24 μM). ln general, the compounds had only weak effects upon CB1, CB2, and VR1 receptors (Ki > 1000-10000 nM). In addition, there was no obvious relationship between the abilities of the compounds to affect anandamide uptake and to inhibit anandamide metabolism by fatty acid amidohydrolase (FAAH; IC50 = 30-113 μM). This indicates that the compounds do not exert their effects secondarily to FAAH inhibition. It is hoped that these compounds, particularly the most potent in this series (compound 5, UCM707, with IC50 values for anandamide uptake and FAAH of 0.8 and 30 μM, respectively), will provide useful tools for the elucidation of the role of the anandamide transporter system in vivo.