98770-65-1

Basic information

• Product Name: (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride
• Synonyms: (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride
• CAS NO: 98770-65-1
• Molecular Weight: 320.903
• Mol File: 98770-65-1.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride(98770-65-1)
• EPA Substance Registry System: (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride(98770-65-1)

Safety Data

• Hazardous Substances Data: 98770-65-1(Hazardous Substances Data)

Usage

Description

(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride, also known as arachidonyl chloride, is a long-chain fatty acid derivative with 20 carbon atoms and five double bonds. It is derived from arachidonic acid, a polyunsaturated omega-6 fatty acid present in the phospholipids of cell membranes. (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl chloride is widely utilized in chemical synthesis and research as a reagent for creating various derivatives and compounds. Additionally, arachidonyl chloride serves as a precursor for the synthesis of bioactive compounds, such as endocannabinoids, which are lipid signaling molecules with diverse physiological and pharmacological effects.

Uses

Used in Chemical Synthesis:
Arachidonyl chloride is used as a reagent in chemical synthesis for the production of various derivatives and compounds. Its unique structure with multiple double bonds allows for versatile chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in Research:
In research, arachidonyl chloride is employed as a tool to study the properties and functions of arachidonic acid and its related compounds. It aids in understanding the roles of polyunsaturated fatty acids in cellular processes and their potential applications in medicine and pharmacology.
Used in the Production of Endocannabinoids:
Arachidonyl chloride is used as a precursor in the synthesis of endocannabinoids, which are lipid signaling molecules that play a crucial role in various physiological and pharmacological processes in the body. These endocannabinoids have been linked to the regulation of mood, appetite, pain sensation, and immune response, among other functions.
Used in Pharmaceutical Development:
Due to its role in the synthesis of endocannabinoids and other bioactive compounds, arachidonyl chloride is utilized in the development of pharmaceuticals targeting a wide range of conditions, including pain management, inflammation, and neurological disorders.
Used in the Cosmetics Industry:
Arachidonyl chloride may also find applications in the cosmetics industry, where it could be used in the formulation of products designed to promote skin health and address various skin conditions by leveraging the properties of endocannabinoids and related compounds.

Upstream product

• 86227-47-6 eicosapentaenoic acid ethyl ester 
• 10417-94-4 all cis-5,8,11,14,17-eicosapentaenoic acid 

Downstream Products

• 1204318-01-3 2-hydroxy-5-(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamidobenzoic acid 

Relevant articles and documents

Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives

In this research, we studied the antioxidative properties and chemical changes of quercetin in fish oil during accelerated storage at 60 °C for 5 days. Gas chromatography (GC) analysis showed that quercetin inhibited aldehyde formation and unsaturated fatty acid oxidation in fish oil significantly; however, the inhibitory effects decreased gradually with prolonged heating time. Moreover, quercetin was consumed with increasing heating time. Some new phenolic derivatives were discovered in the fish oil with quercetin, with their structures fully elucidated by LC-MS/MS and comparison with newly synthesized ones (characterized by MS and NMR spectroscopy). Based on their chemical structures, we proposed that quercetin reacted with EPA and DHA to form the corresponding quercetin fatty acid esters in fish oil. In addition, the newly formed quercetin-3-O-eicosapentaenoate and quercetin-3-O-docosahexaenoate showed weaker DPPH and ABTS radical cation scavenging activity but much improved lipophilicity, higher cell membrane affinity, and hence enhanced cellular antioxidant activity compared with the parent quercetin. Overall, quercetin could be used as a safe dietary polyphenol to inhibit lipid oxidation. The newly formed quercetin-polyunsaturated fatty acid esters may render improved bioactivity to humans, which needs further investigation.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF IRRITABLE BOWEL SYNDROME

The disclosures herein provide compounds of formula I, formula II, formula III, formula IV, formula V, formula VI, formula VII, formula VIII, formula IX, formula X, formula XI, formula XII, formula XIII, formula XIV and formula XV or its pharmaceutical acceptable salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral administration, suppository, transdermal, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of irritable bowel syndrome (IBS), inflammatory bowel diseases or its associated complications.

Lipophilization of resveratrol and effects on antioxidant activities

Resveratrol (R), a polyphenol, was structurally modified via esterification with selected fatty acids to expand its potential application in lipophilic foods, drugs, and cosmetics. The esterification was carried out using 12 different fatty acids with varying chain lengths and degrees of unsaturation (C3:0-C22:6). Two monoesters, two diesters, and one triester were identified by high-performance liquid chromatography-mass spectrometry, and the monoesters (R-3-O-monodocosahexaenoate and R-4'-O-monodocosahexaenoate) were structurally confirmed by nuclear magnetic resonance. The lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging assay, whereas short-chain fatty acid (C3:0, C4:0, and C6:0) showed higher antioxidant activity in the ABTS radical cation scavenging assay. The results may imply that resveratrol derivatives could be used in lipophilic media as health beneficial antioxidants.