82337-46-0

Usage

Uses

Used in Pharmaceutical Industry:
12(R)-HETE is used as a pharmaceutical agent for its potential role in modulating inflammatory responses and other biological processes. Its specific structure allows it to interact with cellular receptors and signaling pathways, making it a promising candidate for the development of new drugs targeting various diseases.
Used in Research Applications:
In the field of scientific research, 12(R)-HETE is used as a biochemical marker for studying the role of eicosanoids in various physiological and pathological conditions. Its presence can help researchers understand the underlying mechanisms of inflammation, pain, and other related processes, ultimately contributing to the advancement of medical knowledge.
Used in Drug Development:
12(R)-HETE is utilized in drug development as a lead compound for the synthesis of new therapeutic agents. Its unique chemical structure provides a foundation for the design and optimization of novel drugs with improved efficacy, selectivity, and safety profiles, addressing unmet medical needs in various therapeutic areas.

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 100428-45-3 (R)-methyl (5Z,8Z,10Z,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate 
• 116012-52-3 (2E,4R)-4-<(tert-butyldiphenylsilyl)oxy>-2-dodecen-6-ynal 
• 90108-26-2 (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal 
• 100311-77-1 (Z)-8-(Triphenyl-λ⁵-phosphanylidene)-oct-5-enoic acid 
• 135236-80-5 Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester 
• 110065-97-9 (5Z,8Z,10E)-11-((2S,4R)-4,5-Dihydroxy-tetrahydro-furan-2-yl)-undeca-5,8,10-trienoic acid methyl ester 
• 110065-98-0 (5Z,8Z,10E)-12-Formyloxy-14-oxo-tetradeca-5,8,10-trienoic acid methyl ester 
• 128888-95-9 Methyl (5Z,8Z)-9-iodo-5,8-nonadienoate 
• 6026-86-4 methyl 4-formylbutanoate 
• 291755-32-3 Methanesulfonic acid (2R,3R)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester 
• 291755-34-5 (4R,5R)-4-Hydroxy-5-((Z)-oct-2-enyl)-dihydro-furan-2-one 
• 291755-30-1 methyl dodec-3-en-6-ynoate 
• 291755-29-8 (E)-1-bromoundec-2-en-5-yne 

Relevant academic research and scientific papers

12-LIPOXYGENASE ACTIVITY IN THE RED MARINE ALGA GRACILARIOPSIS LEMANEIFORMIS

The temperate red alga Gracilariopsis lemaneiformis is a rich source of polyunsaturated fatty acids that are regio-specifically oxidized at C-12.In this in vitro study, we demonstrate the existence of a highly active lipoxygenase-type activity in Gracilariopsis.GC-MS of the methyl ester, trimethylsilyl ether derivatives of the crude reaction mixture identified the production of 12-hydroxyicosatetraenoic acid, a 12-lipoxygenase product previously isolated from this alga.This is the first report of 12-lipoxygenase-type activity from the plant kingdom.

Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase

Lipoxygenases (LOX) play critical roles in mammalian biology in the generation of potent lipid mediators of the inflammatory response; consequently, they are targets for the development of isoform-specific inhibitors. The regio- and stereo-specificity of the oxygenation of polyunsaturated fatty acids by the enzymes is understood in terms of the chemistry, but structural observation of the enzyme-substrate interactions is lacking. Although several LOX crystal structures are available, heretofore the rapid oxygenation of bound substrate has precluded capture of the enzyme-substrate complex, leaving a gap between chemical and structural insights. In this report, we describe the 2.0 ? resolution structure of 8R-LOX in complex with arachidonic acid obtained under anaerobic conditions. Subtle rearrangements, primarily in the side chains of three amino acids, allow binding of arachidonic acid in a catalytically competent conformation. Accompanying experimental work supports a model in which both substrate tethering and cavity depth contribute to positioning the appropriate carbon at the catalytic machinery.

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

Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution

The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.

A short catalytic enantioselective synthesis of the proinflammatory eicosanoid 12(R)-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid (12(R)-HETE)

(equation presented) A new and effective pathway is described for the synthesis of 12(R)-HETE and the 12(S)-enantiomer from the common intermediates 4 and 8.

A CONCISE SYNTHESIS OF (R)-HYDROXY-E,Z-DIENE FATTY ACIDS: PREPARATION OF 12(R)-HETE, TETRANOR-12(R)-HETE, AND 13(R)-HODE

Chiral E-enals derived from functionalized 2-deoxy-D-ribofuranoses by ylide-induced β-elimination were exploited for the synthesis of fatty acid metabolites containing (R)-hydroxy-E,Z-diene subunit.

TOTAL ENANTIOSPECIFIC SYNTHESIS OF 12(R)-HETE

A total synthesis of 12(R)-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid was accomplished via a short, efficient, enantiospecific route.

ENANTIOSPECIFIC TOTAL SYNTHESIS OF 8- and 12-HYDROXYEICOSATETRAENOIC ACID

The R- and S-isomers of 8- and 12-hidroxyeicosatetraenoic acid (8- and 12-HETE) were synthesized from dimethyl malate derived precursors.