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

Uses

12-epi Leukotriene B4 is a leukotriene with less affinity than LTB4 at LTB4 receptors.

Definition

ChEBI: A leukotriene that is the 12S-isomer of leukotriene B4.

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 
• 78815-98-2 Benzoic acid (2E,4E)-(S)-1-(3-methoxycarbonyl-propyl)-6-oxo-hexa-2,4-dienyl 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 
• 76745-31-8 methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate 
• 149199-32-6 (6E, 8E, 10E, 14Z, 5S, 12R)-12-hydroxy-6, 8,10,14-eicosatetraene-(1,5)-lactone 
• 87729-38-2 5-(tert-butyldimethylsilanyloxy)pentanoic acid methyl ester 
• 149130-20-1 (2S)-2,6-bis(t-butyldimethylsilyloxy)-hexan-1-ol 
• 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 
• 149130-13-2 6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 156764-06-6 1-[(R)-(S)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexane-1-sulfinyl]-4-methyl-benzene 
• 149130-17-6 (6E,8E,10E,14Z)-(5S,12R)-1,5,12-Tris-(tert-butyl-dimethyl-silanyloxy)-icosa-6,8,10,14-tetraene 
• 149130-14-3 (S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-ol 
• 16666-79-8 hexylidenetriphenylphosphoran 

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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