71548-19-1

Basic information

• Product Name: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID
• Synonyms: (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;6-TRANS-12-EPI LEUKOTRIENE B4;6-TRANS-12-EPI-LTB4;6E-12-EPI-LEUKOTRIENE B4;(5S,6E,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;6-trans-12-epi Leukotriene B4 Lipid Maps MS Standard
• CAS NO: 71548-19-1
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 71548-19-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 536.4 °C at 760 mmHg
• Flash Point: 292.3 °C
• Appearance: /
• Density: 1.04 g/cm³
• Vapor Pressure: 9.63E-14mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: −20°C
• 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(71548-19-1)
• EPA Substance Registry System: (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID(71548-19-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 71548-19-1(Hazardous Substances Data)

Usage

Description

(5S,12S)-Dihydroxy-(6E,8E,10E,14Z)-eicosatetraenoic acid, also known as 6-trans-12-epi Leukotriene B4 (LTB4), is a non-enzymatic hydrolysis product of LTA4. It is a leukotriene that is the 6-trans,12S-isomer of leukotriene B4, originally isolated from glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNL). (5S,12S)-DIHYDROXY-(6E,8E,10E,14Z)-EICOSATETRAENOIC ACID possesses weak chemotactic properties for PMNL, with approximately 20 times less potency than LTB4, and has no effect on the aggregation response.

Uses

Used in Pharmaceutical Industry:
(5S,12S)-Dihydroxy-(6E,8E,10E,14Z)-eicosatetraenoic acid is used as a research compound for studying its chemotactic properties and potential applications in the development of therapeutic agents targeting leukocyte migration and inflammation. Its weak chemotactic potency compared to LTB4 makes it a valuable tool for understanding the mechanisms of leukocyte recruitment and related inflammatory processes.
Used in Research Applications:
In the field of biomedical research, (5S,12S)-Dihydroxy-(6E,8E,10E,14Z)-eicosatetraenoic acid is used as a reference compound to compare the chemotactic and inflammatory effects of other leukotrienes and related compounds. This helps researchers to identify potential therapeutic targets and develop new drugs for the treatment of various inflammatory diseases.
Used in Drug Development:
(5S,12S)-Dihydroxy-(6E,8E,10E,14Z)-eicosatetraenoic acid can be used as a starting material for the synthesis of novel leukotriene analogs with improved chemotactic properties or other therapeutic effects. These analogs may have potential applications in the development of new drugs for the treatment of inflammatory disorders and other related conditions.

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

• 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 
• 79389-19-8 LTB_x methyl ester 
• 76745-16-9 4-[(4S,5R)-2,2-Dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-butyric acid methyl ester 
• 76745-24-9 Toluene-4-sulfonic acid (Z)-(1S,2R)-1-((S)-1,2-dihydroxy-ethyl)-2-hydroxy-dec-4-enyl ester 
• 76745-22-7 (Z)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-dec-4-en-1-ol 
• 76745-25-0 (R)-4-[(2R,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-[1,3]dioxolan-2-one 
• 76745-14-7 (E)-4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester 
• 76745-26-1 (R)-1-[(2S,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-ethane-1,2-diol 
• 76745-27-2 (2S,3R)-2-((E)-Buta-1,3-dienyl)-3-((Z)-oct-2-enyl)-oxirane 
• 78606-79-8 Benzoic acid (S)-4-methoxycarbonyl-1-(R)-oxiranyl-butyl ester 
• 76745-15-8 4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 76745-18-1 (+)-(S,R)-δ-hydroxyoxiranepentanoic acid methyl ester 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 149130-14-3 (S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-ol 

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

-