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Usage

Uses

Used in Pharmaceutical Industry:
12-EPI LEUKOTRIENE B4 is used as a research compound for studying its biological effects and potential therapeutic applications. Due to its less affinity than LTB4 at LTB4 receptors, it can be used to investigate the role of leukotrienes in various diseases and conditions, such as asthma, inflammatory bowel disease, and cardiovascular disorders.
Used in Research Applications:
12-EPI LEUKOTRIENE B4 is used as a research tool for understanding the molecular mechanisms of leukotriene signaling pathways and their involvement in immune and inflammatory processes. This knowledge can help in the development of new drugs and therapies targeting these pathways for the treatment of related diseases.
Used in Drug Development:
12-EPI LEUKOTRIENE B4 can be used in the development of drugs that modulate leukotriene activity, either by enhancing or inhibiting their effects. This can lead to the creation of novel therapeutic agents for the treatment of various inflammatory and immune-related disorders.

InChI:InChI=1/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19+/m0/s1

Upstream product

• 71160-24-2 Leukotriene B 
• 73466-14-5 (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 156764-08-8 (6E,8E,10E,14Z,5S,12R)-1,5,12-trishydroxy-6,8,10,14-eicosatetraene 
• 149130-15-4 (-)-2(S)-2,6-bis(t-butyldimethylsilyloxy)-1-hexanal 
• 78606-79-8 Benzoic acid (S)-4-methoxycarbonyl-1-(R)-oxiranyl-butyl ester 
• 76745-27-2 (2S,3R)-2-((E)-Buta-1,3-dienyl)-3-((Z)-oct-2-enyl)-oxirane 
• 76745-26-1 (R)-1-[(2S,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-ethane-1,2-diol 
• 82493-58-1 ethyl 2-O benzoyl-3,4,5-trideoxy-L-glycero-hexuronate 
• 42017-07-2 1-heptynyllithium 
• 1053634-06-2 (R)-1-[(4R,5R)-5-((R)-1-Hydroxy-non-3-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-non-3-yn-1-ol 
• 109420-89-5 diethyl 5(S),8(S)-bis(benzoyloxy)-6(S),7(S)-dihydroxydodecanedioate 
• 119392-29-9 diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate 
• 109458-67-5 diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate 
• 109420-88-4 9(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-6-(Z),14(Z)-icosadiene-10(S),11(S)-diol 

Downstream Products

• 79065-10-4 (6E,8Z,10Z,14Z)-(5S,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester 
• 79389-19-8 LTB_x methyl ester 
• 79065-10-4 (6E,8Z,10Z,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester 
• 90529-28-5 (6E,8Z,10E,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester 

Relevant academic research and scientific papers

COX-2-dependent and -independent biosynthesis of dihydroxy-arachidonic acids in activated human leukocytes

Biosynthesis of 5,15-dihydroxyeicosatetraenoic acid (5,15-diHETE) in leukocytes involves consecutive oxygenation of arachidonic acid by 5-lipoxygenase (LOX) and 15-LOX in either order. Here, we analyzed the contribution of cyclooxygenase (COX)-2 to the biosynthesis of 5,15-di-HETE and 5,11-diHETE in isolated human leukocytes activated with lipopolysaccharide and calcium ionophore A23187. Transformation of arachidonic acid was initiated by 5-LOX providing 5 S -HETE as a substrate for COX-2 forming 5 S,15 S -diHETE, 5 S,15 R -diHETE, and 5 S,11 R -di-HETE as shown by LC/MS and chiral phase HPLC analyses. The levels of 5,15-diHETE were 0.45 ± 0.2 ng/106 cells (mean ± SEM, n = 6), reaching about half the level of LTB 4 (1.3 ± 0.5 ng/106 cells, n = 6). The COX-2 specific inhibitor NS-398 reduced the levels of 5,15-diHETE to below 0.02 ng/106 cells in four of six samples. Similar reduction was achieved by MK-886, an inhibitor of 5-LOX activating protein but the above differences were not statistically significant. Aspirin treatment of the activated cells allowed formation of 5,15-diHETE (0.1 ± 0.05 ng/106 cells, n = 6) but, as expected, abolished formation of 5,11-diHETE. The mixture of activated cells also produced 5 S,12 S -diHETE with the unusual 6 E,8 Z,10 E double bond configuration, implicating biosynthesis by 5-LOX and 12-LOX activity rather than by hydrolysis of the leukotriene A 4 -epoxide. Exogenous octadeuterated 5 S -HETE and 15 S -HETE were converted to 5,15-diHETE, implicating that multiple oxygenation pathways of arachidonic acid occur in activated leukocytes. The contribution of COX-2 to the biosynthesis of dihydroxylated derivatives of arachidonic acid provides evidence for functional coupling with 5-LOX in activated human leukocytes. Copyright

Preparation of high specific activity tritium-labelled leukotriene B 4 suitable for radioligand binding assay

We describe a method of preparation of high specific activity tritium-labelled leukotriene (LT) B4 from [5,6,8,9,11,12, 14,15- 3H] arachidonic acid (AA; 6.66 TBq/mmol) utilizing a LTB 4-synthesizing enzyme system from rat basophilic leukemia (RBL-1) cells. It was shown that both cyclooxygenase inhibitor indomethacin and adenosine 5′-triphosphate induced [3H] AA transformation to [3H] LTB4. In optimized conditions up to 15% of total radioactivity of the incubation mixture was present in [3H] LTB 4. A separation of [3H] LTB4 from other labelled C20:4 products was achieved by a three-step reverse phase-high-performance liquid chromatography in methanol- and acetonitrile-based solvent systems. [3H] LTB4 was confirmed to be identical to the naturally occurring LTB4 by a radioligand binding assay using a culture of HF1 cells that express a BLT1 receptor. Copyright

Application of the low-valent titanium reductive elimination of 1,6-dibenzoate-2,4-dienes to the total synthesis of 6(E)-5(S)-12(R)-leukotriene B4

A stereoselective synthesis of 6(E)-5(S)-12(R)-leukotriene B4 is described in this paper, using a novel reaction, the low-valent titanium induced reductive elimination of a 1,6-dibenzoate-2,4-diene, for the selective synthesis of the trans-trie

Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues

A highly stereocontrolled and practical new method for synthesis of LTB4 (1), 20-OH-LTB4 (2), and LTB3 (3) has been developed, which uses the palladium catalyzed coupling reaction of the vinylborane 5, derived from the C(1)-C(9) fragment 4, with the corresponding C(10)-C(20) fragments 6a-c.The acetylene 4 was synthesized by palladium-copper-catalyzed coupling reaction of (trimethylsilyl)acetylene with the bromide 12, which was prepared from γ-(trimethylsilyl)allylic alcohol (S)-10 by bromination followed by debromosilylation.The alcohol (S)-10 was obtained by the kinetic resolution of the racemate dl-10 using the Sharpless reagent.The vinyl iodides 6a and 6b were prepared from racemic γ-(trimethylsilyl)allylic alcohols dl-17 and dl-28, respectively, by the Sharpless kinetic resolution followed by the reactions taking advantage of the reactivity of vinylsilane moiety, while the segment 6c was prepared by the Sharpless kinetic resolution of racemic γ-iodoallylic alcohol dl-34 followed by protection.By using this method, precursors of the radiolabeled LTB4, and 20-OH-LTB4, i.e., 14,15-didehydro-LTB4 (40) and 14,15-didehydro-20-OH-LTB4 (41), respectively, were also synthesized.Similarly the novel structural analogue of LTB 42-44 were prepared.

SYNTHESIS OF 5S,12S-diHETE (LTBx)

The total synthesis of 5S,12S-diHETE (LTBx) was completed.The Wittig reaction of phosphorane 8 and chiral aldehyde 9 provided the key step to form the C-20 chain.

STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE B4 (LTB4)

A stereospecific and chirally economical synthesis of LTB4 starting from 2-deoxy-D-ribose is reported as part of a comprehensive and efficient approach to the Leukotrienes (A, B, C, D, E).The process includes a novel approach to chiral dienic synthons.

SIMPLE EFFICIENT SYNTHESIS OF LTB4 AND 12-epi-LTB4

Using L- and D-arabinose respectively as the source of chirality at C-12 in LTB4, efficient new syntheses of LTB4 and 12-epi-LTB4 have been realized.

STEREOSPECIFIC TOTAL SYNTHESIS OF 12-(R)- AND 12-(S) FORMS OF 6-TRANS LEUKOTRIENE B

Non enzyamatic hydration of leukotriene A (1), the biogenetic precursor of leukotriene B (2) affords among other products two diastereomeric 6-trans-isomers of 2, the first stereospecific and efficient syntheses of which are recorded herein.