72059-45-1

Usage

Uses

Used in Pharmaceutical Industry:
4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoic acid is used as a pharmaceutical agent for its potential therapeutic effects. 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoic acid's unique structure and properties may allow it to interact with specific biological targets, such as receptors or enzymes, which could be relevant for the treatment of various diseases or conditions.
Used in Research and Development:
In the field of research and development, 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoic acid can be used as a starting material or a tool compound for the synthesis of other complex molecules with potential biological activities. Its unique structural features may also make it a valuable probe for studying the mechanisms of action of various biological processes.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoic acid could potentially be incorporated into drug delivery systems to improve its bioavailability and therapeutic efficacy. By using carriers such as organic or metallic nanoparticles, the compound's delivery to specific target cells or tissues could be enhanced, leading to improved treatment outcomes.

InChI:InChI=1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11-,15-13+/t18-,19-/m0/s1

Upstream product

• 74448-21-8 rac-trans-(2E,4E)-3-(1,3-tetradecadiene-5,8-diynyl)oxiranebutanoic acid methyl ester 
• 18495-27-7 1-bromooct-2-yne 
• 74448-16-1 rac-(E)-4-methyl-3,5-dioxa-7-decen-9-yne 
• 74454-36-7 (E)-2-tridecene-4,7-diyn-1-ol 
• 74448-17-2 (E)-4-methyl-3,5-dioxa-7-octadecene-9,12-diyne 
• 74448-19-4 rac-(E)-1,4-pentadecadiene-6,9-diyn-3-ol 
• 74448-18-3 (E)-2-tridecene-4,7-diynal 
• 74448-20-7 (2E,4E)-1-bromo-2,4-pentadecadiene-6,9-diyne 
• 81019-26-3 (E,E)-2,4-pentadecadien-6,9-diyn-1-yl tetrahydrothiophenium bromide 
• 71774-08-8 5(S)-HPETE 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 73466-12-3 Leukotriene A₄ methyl ester 

Downstream Products

• 73466-12-3 Leukotriene A₄ methyl ester 
• 76738-49-3 5S,6R-6-epi-Leukotriene A₄ methyl ester 
• 79356-68-6 5R,6S-6-epi-Leukotriene A₄ methyl ester 
• 79356-65-3 5-epi-6-epi-leukotriene A₄ methyl ester 

Relevant academic research and scientific papers

Human leukocytes selectively convert 4S,5S-epoxy-resolvin to resolvin D3, resolvin D4, and a cys-resolvin isomer

Human phagocytes have key functions in the resolution of inflammation. Here, we assessed the role of the proposed 4S,5S-epoxy-resolvin intermediate in the biosynthesis of both resolvin D3 and resolvin D4. We found that human neutrophils converted this synthetic intermediate to resolvin D3 and resolvin D4. M2 macrophages transformed this labile epoxide intermediate to resolvin D4 and a previously unknown cysteinyl-resolvin isomer without appreciable amounts of resolvin D3. M2 macrophages play critical roles in the resolution of inflammation and in wound healing. Human M2 macrophages also converted leukotriene A4 to lipoxins. The cysteinyl-resolvin isomer significantly accelerated tissue regeneration of surgically injured planaria. In a model of human granuloma formation, the cysteinyl-resolvin isomer significantly inhibited granuloma development by human peripheral blood leukocytes. Together, these results provide evidence for a human cell type–specific role of 4S,5S-epoxy-resolvin in the biosynthesis of resolvin D3 by neutrophils, resolvin D4 by both M2 macrophages and neutrophils, and a unique cysteinyl-resolvin isomer produced by M2 macrophages that carries potent biological activities in granuloma formation and tissue regeneration.

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

The n-3 polyunsaturated fatty acids act as substrates during the resolution phase of acute inflammation for the biosynthesis of specialized pro-resolving lipid mediators. One premier example is the C22-dihydroxy-polyunsaturated fatty acid protectin D1 (1). The human 15-lipoxygenase type I, via stereoselective processes and with docosahexaenoic acid as the substrate, enables the formation of this specialized pro-resolving lipid mediator. Herein, based on results from LC/MS-MS metabololipidomics, support is presented for the apprehended biosynthesis of 1 in human macrophages occurring via the intermediate 16S,17S-epoxyprotectin (5). Stereochemically pure 5 was obtained using the Katsuki-Sharpless epoxidation protocol, establishing the chirality at the C16 and C17 atoms, one Z-selective reduction, and E- and Z-stereoselective Wittig reactions. In addition, information on the nonenzymatic aqueous hydrolysis products and the half-life of 16S,17S-epoxyprotectin (5) is presented.

Leukotriene antagonists

Leukotriene antagonists are disclosed comprising compounds having the general formula represented by the formula shown below, esters, amides and physio-logically acceptable salts thereof. These compounds retain the natural 5(S) 6(R) configuration, the 5-hydroxyl group and the natural unsaturated tail with the peptide replaced by a substituted aromatic nucleus linked via a sulfur or oxygen substituent linking a substituent to the 6 position.

Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate

The pathway of biosynthesis of leukotriene A4 (LTA4, 2) from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-S-HPETE, 1) has been explored by the comparative study of (S)- and (R)-lipoxygenase (LO) enzymes as catalysts.The purified LO from potato, an S-lipoxygenase, converts (anaerobically) 1 to 2 (determined as the characteristic hydrolysis mixture of two epimeric 5,6-diols and two epimeric 5,12-diols), as previously reported by Samuelsson et al.However, the 8-R-LO from the coral Plexaura homomalla transforms 1 (anaerobically) into 6-epi-LTA4 (6).Theobserved divergence of stereopathways agrees with predictions based on the intermediacy of organoiron intermediates in enzymic lipoxygenation (Scheme I) and detailed in Schemes II and III.Further evidence for the intervention of such intermediates has been obtained by trapping experiments under pure O2 at pressures of 1-60 atm.Under O2 pressure 1 is converted by the potato LO to a new product, the bis(hydroperoxide) 7, whereas the coral LO converts 1 to the diastereomeric bis(hydroperoxide) 9.