105304-92-5

Basic information

• Product Name: 14(R),15(S)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID
• Synonyms: 14[R],15[S]-EET;14(R),15(S)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID;14(R),15(S)-epoxy-(5Z,8Z,11Z)-*eicosatrienoic aci
• CAS NO: 105304-92-5
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 105304-92-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 464.5°C at 760 mmHg
• Flash Point: 155.7°C
• Appearance: /
• Density: 0.983g/cm³
• Vapor Pressure: 6.48E-10mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: −20°C
• CAS DataBase Reference: 14(R),15(S)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 14(R),15(S)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(105304-92-5)
• EPA Substance Registry System: 14(R),15(S)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(105304-92-5)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• WGK Germany: 3
• Hazardous Substances Data: 105304-92-5(Hazardous Substances Data)

Usage

Chemical group

Eicosanoids
Eicosanoids are signaling molecules derived from arachidonic acid.

Function

Potent inflammatory mediator
The compound exhibits pro-inflammatory effects and plays a role in various physiological processes.

Involvement in physiological processes

Inflammation, immune response, and blood flow regulation
The compound is involved in these processes and helps coordinate the body's response to challenges such as tissue injury or infection.

Production

In response to tissue injury or infection
The compound is typically produced as a response to these conditions.

Potential target for drug development

Anti-inflammatory drugs
Due to its inflammatory properties, it has been studied as a potential target for the development of anti-inflammatory medications.

Structural features

Contains epoxy and triene groups
The compound has a unique structure with an epoxy group at the 14(R),15(S) position and three conjugated double bonds (5Z,8Z,11Z) in the eicosatrienoic acid chain.

Molecular weight

Approximately 316.47 g/mol
The molecular weight is an estimate of the mass of one mole of the compound.

Chemical structure

A polyunsaturated fatty acid derivative
The compound is derived from a polyunsaturated fatty acid, specifically arachidonic acid, with additional functional groups.

InChI:InChI=1/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m1/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 97589-09-8 (2R,3R)-2,3-epoxy-1-octanol 
• 110822-67-8 (S)-2-((S)-1-Chloro-hexyl)-oxirane 
• 110901-52-5 14(S),15(R)-epoxyeicosatrienoic acid methyl ester 

Downstream Products

• 110901-52-5 14(S),15(R)-epoxyeicosatrienoic acid methyl ester 

Relevant articles and documents

Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: A potential P450 and lipoxygenase interaction

Herein, we characterize a generally applicable transformation of fatty acid epoxides by lipoxygenase (LOX) enzymes that results in the formation of a five-membered endoperoxide ring in the end product. We demonstrated this transformation using soybean LOX-1 in the metabolism of 15,16-epoxy-α-linolenic acid, and murine platelet-type 12-LOX and human 15-LOX-1 in the metabolism of 14,15-epoxyeicosatrienoic acid (14,15-EET). A detailed examination of the transformation of the two enantiomers of 15,16-epoxy-α-linolenic acid by soybean LOX-1 revealed that the expected primary product, a 13 S-hydroperoxy-15,16-epoxide, underwent a nonenzymatic transformation in buffer into a new derivative that was purifi ed by HPLC and identified by UV, LC-MS, and 1H-NMR as a 13,15-endoperoxy-16-hydroxy-octadeca-9,11-dienoic acid. The configuration of the endoperoxide (cis or trans side chains) depended on the steric relationship of the new hydroperoxy moiety to the enantiomeric configuration of the fatty acid epoxide. The reaction mechanism involves intramolecular nucleophilic substitution (SNi) between the hydroperoxy (nucleophile) and epoxy group (electrophile). Equivalent transformations were documented in metabolism of the enantiomers of 14,15-EET by the two mammalian LOX enzymes, 15-LOX-1 and platelet-type 12-LOX. We conclude that this type of transformation could occur naturally with the co-occurrence of LOX and cytochrome P450 or peroxygenase enzymes, and it could also contribute to the complexity of products formed in the autoxidation reactions of polyunsaturated fatty acids.

Enzymatic synthesis and chemical inversion provide both enantiomers of bioactive epoxydocosapentaenoic acids

Epoxy PUFAs are endogenous cytochrome P450 (P450) metabolites of dietary PUFAs. Although these metabolites exert numerous biological effects, attempts to study their complex biology have been hampered by difficulty in obtaining the epoxides as pure regioi

ASYMMETRIC TOTAL SYNTHESIS OF 14(R),15(S)-, 14(S),15(R)-, 14(R),15(R)-, AND 14(S),15(S)-EPOXYEICOSATRIENOIC ACIDS

The four chiral stereoisomers of 14,15-oxido-5Z,8Z,11Z-eicosatrienoic acid were synthesized.The absolute stereochemistry in each case was derived from an asymmetric epoxidation of E-2-octen-1-ol.