80234-67-9

Basic information

• Product Name: 8(R),15(S)-DIHETE
• Synonyms: 8(R),15(S)-DIHETE;8(R),15(S)-DIHYDROXYEICOSA-5Z,9E,11E,13E-TETRAENOIC ACID;8R,15S-diHETE (8(R),15(S)-Dihydroxyeicosa-5Z,9E,11E,13E-tetraenoic acid)
• CAS NO: 80234-67-9
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 80234-67-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8(R),15(S)-DIHETE(CAS DataBase Reference)
• NIST Chemistry Reference: 8(R),15(S)-DIHETE(80234-67-9)
• EPA Substance Registry System: 8(R),15(S)-DIHETE(80234-67-9)

Safety Data

• Hazardous Substances Data: 80234-67-9(Hazardous Substances Data)

Upstream product

• 70981-96-3 (5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 93292-46-7 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid methyl ester 
• 93292-44-5 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid 
• 93292-48-9 (Z)-(8R,9S)-8-(tert-Butyl-diphenyl-silanyloxy)-9,10-dihydroxy-dec-5-enoic acid methyl ester 
• 93292-56-9 (5Z,9E,11E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-trideca-5,9,11-trienoic acid methyl ester 
• 93292-51-4 (5Z,9E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-undeca-5,9-dienoic acid methyl ester 
• 93292-50-3 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-oxo-non-5-enoic acid methyl ester 
• 93292-60-5 [(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-12-methoxycarbonyl-dodeca-2,4,8-trienyl]-triphenyl-phosphonium; bromide 
• 93292-70-7 (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester 
• 39968-97-3 (4-carboxybutylene)triphenylphosphorane 
• 93292-62-7 (2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-octane-1,2-diol 
• 93292-63-8 (S)-2-(tert-butyldiphenylsilyloxy)heptanal 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 

Downstream Products

• 93292-75-2 (5Z,9E,11Z,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester 
• 93292-70-7 (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester 
• 93381-40-9 (5Z,9E,11Z,13E)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester 
• 93292-69-4 (5Z,9E,11E,13E)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester 

Relevant articles and documents

Formation of a cyclopropyl epoxide via a leukotriene A synthase-related pathway in an anaerobic reaction of soybean lipoxygenase-1 with 15S-hydroperoxyeicosatetraenoic acid: Evidence that oxygen access is a determinant of secondary reactions with fatty acid hydroperoxides

The further conversion of an arachidonic acid hydroperoxide to a leukotriene A (LTA) type epoxide by specific lipoxygenase (LOX) enzymes constitutes a key step in inflammatory mediator biosynthesis. Whereas mammalian 5-LOX transforms its primary product (5S-hydroperoxyeicosatetraenoic acid; 5S-HPETE) almost exclusively to LTA4, the model enzyme, soybean LOX-1, normally produces no detectable leukotrienes and instead further oxygenates its primary product 15S-HPETE to 5,15- and 8,15-dihydroperoxides. Mammalian 15-LOX-1 displays both types of activity. We reasoned that availability of molecular oxygen within the LOX active site favors oxygenation, whereas lack of O2 promotes LTA epoxide synthesis. To test this, we reacted 15S-HPETE with soybean LOX-1 under anaerobic conditions and identified the products by high pressure liquid chromatography, UV, mass spectrometry, and NMR. Among the products, we identified a pair of 8,15-dihydroxy diastereomers with all-trans-conjugated trienes that incorporated 18O from H 218O at C-8, indicative of the formation of 14,15-LTA4. A pair of 5,15-dihydroxy diastereomers containing two trans,trans-conjugated dienes (6E,8E,11E,13E) and that incorporated 18O from H 218O at C-5 was deduced to arise from hydrolysis of a novel epoxide containing a cyclopropyl ring, 14,15-epoxy-[9,10,11-cyclopropyl]- eicosa-5Z,7E,13E-trienoic acid. Also identified was the δ-lactone of the 5,15-diol, a derivative that exhibited no 18O incorporation due to its formation by intramolecular reaction of the carboxyl anion with the proposed epoxide intermediate. Our results support a model in which access to molecular oxygen within the active site directs the outcome from competing pathways in the secondary reactions of lipoxygenases.