73151-67-4

Basic information

• Product Name: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID
• Synonyms: 6-TRANS-12-EPI-LTB4;6-TRANS-12-EPI LEUKOTRIENE B4;6E-12-EPI-LEUKOTRIENE B4;(5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID;5(S), 12(S)-DIHETE;5(S),12(S)-DIHYDROXYEICOSA-6E,8E,10E,14Z-TETRAENOIC ACID;(5S,12S)-dihydroxy-(6E,8E,10E,14Z)-*eicosatetraen;(5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOS ATETRAENOI
• CAS NO: 73151-67-4
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• EINECS: 200-578-6
• Mol File: 73151-67-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 536.4°C at 760 mmHg
• Flash Point: 14℃
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 9.63E-14mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: −20°C
• PKA: 4.68±0.10(Predicted)
• CAS DataBase Reference: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID(73151-67-4)
• EPA Substance Registry System: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID(73151-67-4)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-7
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 73151-67-4(Hazardous Substances Data)

Usage

Uses

5(S),12(S)-DiHETE is a compound that acts as a potent eicosanoid lipid mediator.

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+

Upstream product

• 149130-13-2 6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 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 
• 109420-87-3 9(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-10(S),11(S)-O-(1-methylethylidene)-6(Z),14(Z)-icosadiene-10,11-diol 
• 119414-22-1 9(R),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-10(S),11(S)-O-(1-methylethylidene)-6,14-icosadiyne-10,11-diol 
• 82493-61-6 ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(E),8(E),10(E),14(Z)-icosatetraenoate 
• 628-71-7 1-Heptyne 
• 6026-86-4 methyl 4-formylbutanoate 
• 115418-85-4 methyl 5(S)-<(tert-butyldimethylsilyl)oxy>-6(Z)-nonen-8-ynoate 
• 115418-81-0 methyl 5-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate 
• 115461-52-4 methyl 5(S)-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate 

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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