87984-82-5

Basic information

• Product Name: 13(S)-HOTRE
• Synonyms: 13(S)-HOT;13(S)-HOTE;13(S)-HOTRE;13(S)-HOTRE(GAMMA);13S-HYDROXY-6Z,9Z,11E-OCTADECATRIENOIC ACID;13(S)-HYDROXY-9(Z),11(E),15(Z)-OCTADECATRIENOIC ACID;13(S)-HYDROXYOCTADECA-6Z,9Z,11E-TRIENOIC ACID;KLLGGGQNRTVBSU-FQSPHKRJSA-N
• CAS NO: 87984-82-5
• Molecular Formula: C18H30O3
• Molecular Weight: 294.43
• Mol File: 87984-82-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 13(S)-HOTRE(CAS DataBase Reference)
• NIST Chemistry Reference: 13(S)-HOTRE(87984-82-5)
• EPA Substance Registry System: 13(S)-HOTRE(87984-82-5)

Safety Data

• Hazardous Substances Data: 87984-82-5(Hazardous Substances Data)

Usage

Description

13(S)-HOTrE is the 15-lipoxygenase (15-LO) product of linolenic acid. It has been detected in cell membranes and as the cholesteryl ester associated with the lesions of atherosclerosis, and in the biomembranes of soybeans exposed to 15-LO.

Upstream product

• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 90080-97-0 (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester 
• 67597-26-6 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid 
• 1642-49-5 dec-9-ynoic acid 
• 62285-66-9 methyl dec-9-ynoate 
• 17643-36-6 9-decyn-1-ol 
• 67548-36-1 (2E,5Z)-Octa-2,5-dien-1-ol 
• 133575-33-4 (2S-trans)-3-<(Z)-pent-2-enyl>oxirane methanol 
• 142795-87-7 (1E,3S,5Z)-1-chloro-1,5-octadien-3-ol 
• 142795-86-6 (2R-trans)-3-<(Z)-pent-2-enyl>oxiranemethylchloride 
• 142748-78-5 (1E,3S,5Z)-1-chloro-3-t-butyldimethylsilyloxy-1,5-octadiene 
• 142748-83-2 methyl (9Z,11E,13S,15Z)-13-t-butyldimethylsilyloxyoctadeca-9,11,15-trienoate 
• 142748-81-0 methyl (11E,13S,15Z)-13-t-butyldimethylsilyloxyoctadec-11,15-dien-9-ynoate 

Relevant articles and documents

Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA

We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E , Z , E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from α-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX. Copyright

Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways

Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p

Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants

Configurationally pure 9-oxo-10E,12Z,15Z- and 13-oxo-9Z,11E,15E-octadecatrienoic acid are available from linolenic acid via regioselective functionalisation using lipoxygenases from soybean or tomato at specific pH conditions. Reduction of the resulting hydroperoxides followed by oxidation of the resulting allylic alcohols with Bobbitt's reagent yields the configurationally pure but labile ketotrienoic acids 4 and 5 without concomitant isomerisation.