98103-48-1

Basic information

• Product Name: 14(S),15(R)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID
• Synonyms: 14[S],15[R]-EET;14(S),15(R)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID;14(S) 15(R)-EPOXY-(5Z 8Z 11Z)- &;(5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid;14R,15S-EpETrE
• CAS NO: 98103-48-1
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 98103-48-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 464.5°Cat760mmHg
• 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(S),15(R)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 14(S),15(R)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(98103-48-1)
• EPA Substance Registry System: 14(S),15(R)-EPOXY-(5Z,8Z,11Z)-EICOSATRIENOIC ACID(98103-48-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1170 3/PG 2
• Hazardous Substances Data: 98103-48-1(Hazardous Substances Data)

Usage

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+/m0/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 90080-09-4 14(R),15(S)-epoxyeicosatrienoic acid methyl ester 
• 110901-52-5 14(S),15(R)-epoxyeicosatrienoic acid methyl ester 
• 358621-02-0 (5Z,8Z,11Z)-(14S,15S)-14-Hydroxy-15-(2-phenylsulfanyl-ethoxy)-icosa-5,8,11-trienoic acid methyl ester 
• 358621-03-1 (5Z,8Z,11Z)-(14S,15S)-15-(2-Benzenesulfonyl-ethoxy)-14-(toluene-4-sulfonyloxy)-icosa-5,8,11-trienoic acid methyl ester 
• 89461-51-8 [(2S,3S)-3-pentyloxiran-2-yl]methanol 
• 110822-65-6 (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-chloro-octan-2-ol 
• 110822-57-6 (2R,3R)-3-Chloro-1-[1,3]dithian-2-yl-octan-2-ol 
• 110822-59-8 (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-chloro-nonanal 
• 110822-62-3 (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-15-chloro-icosa-5,8,11-trienoic acid methyl ester 
• 108682-84-4 (2S,3S)-3-chloro-1,2-octanediol 
• 110822-56-5 (R)-2-((R)-1-Chloro-hexyl)-oxirane 

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.

Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.

Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450

Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs).Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis.Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.