83709-73-3

Basic information

• Product Name: 12-EPI LEUKOTRIENE B4
• Synonyms: 12-EPI LEUKOTRIENE B4;5S,12S-DIHYDROXY-6Z,8E,10E,14Z-EICOSATETRAENOIC ACID;(5S,6Z,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;12(S)-Leukotriene B4;VNYSSYRCGWBHLG-CBBLYLIKSA-N
• CAS NO: 83709-73-3
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 83709-73-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 536.4°C at 760 mmHg
• Flash Point: 292.3°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 9.63E-14mmHg at 25°C
• Refractive Index: 1.527
• PKA: 4.66±0.10(Predicted)
• CAS DataBase Reference: 12-EPI LEUKOTRIENE B4(CAS DataBase Reference)
• NIST Chemistry Reference: 12-EPI LEUKOTRIENE B4(83709-73-3)
• EPA Substance Registry System: 12-EPI LEUKOTRIENE B4(83709-73-3)

Safety Data

• Hazardous Substances Data: 83709-73-3(Hazardous Substances Data)

Usage

Description

12-EPI LEUKOTRIENE B4, also known as 12S-LEUKOTRIENE B4, is a leukotriene that is the 12S-isomer of leukotriene B4. It is a bioactive molecule derived from the metabolism of arachidonic acid and plays a role in various biological processes, including inflammation and immune responses.

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

• 42017-07-2 1-heptynyllithium 
• 82493-56-9 <6(R)-<(tert-butyldiphenylsilyl)oxy>-2(E),4(E),8(Z)-tetradecatrien-1-yl>triphenylphosphonium bromide 
• 100428-42-0 2(R)-<(tert-butyldiphenylsilyl)oxy>dec-4(Z)-enal 
• 82493-61-6 ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(E),8(E),10(E),14(Z)-icosatetraenoate 
• 79389-19-8 LTB_x methyl ester 
• 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 
• 82493-60-5 Benzoic acid (2Z,4E,6E,10Z)-(1S,8R)-1-(3-ethoxycarbonyl-propyl)-8-hydroxy-hexadeca-2,4,6,10-tetraenyl ester 
• 83685-95-4 [(2E,4E,8Z)-6-(tert-Butyl-dimethyl-silanyloxy)-tetradeca-2,4,8-trienyl]-triphenyl-phosphonium; bromide 
• 79308-40-0 (E)-(5R,6S)-5,6,7-Trihydroxy-hept-2-enoic acid ethyl ester 
• 79308-52-4 ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate 
• 82493-51-4 ethyl tetrahydro-4(S)-<(tert-butyldimethylsilyl)oxy>-5(S)-(iodomethyl)-2-furanacetate 
• 92007-81-3 Benzoic acid (R)-1-((S)-1,2-dihydroxy-ethyl)-4-ethoxycarbonyl-butyl ester 
• 82493-58-1 6-ethoxy-1,6-dioxohexan-2-yl benzoate 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 

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 articles and documents

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

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

Total synthesis of leukotriene (+)-LTB4 from D-mannitol

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