6-trans-12-epi-Leukotriene B4

Base Information

• Chemical Name: 6-trans-12-epi-Leukotriene B4
• CAS No.: 71548-19-1
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• DSSTox Substance ID: DTXSID101315522
• Nikkaji Number: J381.084D
• Wikidata: Q27132948
• Metabolomics Workbench ID: 2572
• Mol file: 71548-19-1.mol

Synonyms:6-trans-12-epi-Leukotriene B4;71548-19-1;6-trans-12-epi-LTB4;(5S,6E,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;5S,12S-dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acid;Delta(6)-trans-12-epi-leukotriene B4;6,8,10,14-Eicosatetraenoicacid, 5,12-dihydroxy-, (5S,6E,8E,10E,12S,14Z)-;5(S),12(S)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoic acid;6-trans-12-Epileukotriene B4;starbld0009754;D6-trans-12-epi-LTB4;BML1-D06;SCHEMBL2522613;CHEBI:63982;D6-trans-12-Epileukotriene B4;12-epi-D6-trans-Leukotriene B4;DTXSID101315522;5(S),12(S)-DIHETE all trans;LMFA03020014;12-epi-Delta(6)-trans-leukotriene B4;NCGC00161263-01;PD018248;HY-113442;CS-0059552;Q27132948;5S,12S-dihydroxy-6E,8E,10E,14Z-icosatetraenoic acid;6-trans-12-epi Leukotriene B4 Lipid Maps(R) MS Standard;[S-[R*,R*-(E,E,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoate;[S-[R*,R*-(E,E,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoic acid;5(S),12(S)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoate;(5S,6E,8E,10E,12S,14Z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid;6,8,10,14-Eicosatetraenoicacid,5,12-dihydroxy-,(5S,6E,8E,10E,12S,14Z)-

Chemical Property of 6-trans-12-epi-Leukotriene B4

Chemical Property:

• Vapor Pressure: 9.63E-14mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 536.4 °C at 760 mmHg
• Flash Point: 292.3 °C
• PSA: 77.76000
• Density: 1.04 g/cm³
• LogP: 4.15830
• Storage Temp.: −20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 421

Purity/Quality:

99% ^*data from raw suppliers

6-trans-12-epiLeukotrieneB4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Isomeric SMILES: CCCCC/C=C\C[C@@H](/C=C/C=C/C=C/[C@H](CCCC(=O)O)O)O
• Uses: 6-trans-12-epi Leukotirene B4 (LTB4) is a non-enzymatic hydrolysis product of LTA4. It was originally isolated from glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNL). 6-trans-12-epi LTB4 is weakly chemotactic for PMNL, with approximately 20 times less potency than LTB4, and has no effect on the aggregation response. 6-trans-12-epi Leukotriene B4 is a product of the non-enzymatic hydrolysis of LTA4.

Technology Process of 6-trans-12-epi-Leukotriene B4

There total 124 articles about 6-trans-12-epi-Leukotriene B4 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

<5,6,8,9,11,12,14,15-3H8>arachidonic acid (66753-05-7) → Leukotriene B (71160-24-2) + 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9) + 5(S)-HETE (61641-47-2,70608-72-9,71030-39-2,71774-09-9,72255-35-7,73307-52-5,74080-72-1,88588-79-8) + (5S,12S,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (70578-51-7,71160-24-2,71548-19-1,71652-82-9,73151-67-4,77367-60-3,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,79056-01-2)

Guidance literature:

With ATP; calcium(II) nitrate; edetate disodium; In phosphate buffer; water; at 30 ℃; for 0.25h; pH=7.4; Further byproducts.;

DOI:10.1002/jlcr.1488

Reference yield:

<5,6,8,9,11,12,14,15-3H8>arachidonic acid (66753-05-7) → Leukotriene B (71160-24-2) + 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9) + 5(S)-HETE (61641-47-2,70608-72-9,71030-39-2,71774-09-9,72255-35-7,73307-52-5,74080-72-1,88588-79-8) + (5S,12S,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (70578-51-7,71160-24-2,71548-19-1,71652-82-9,73151-67-4,77367-60-3,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,79056-01-2)

Guidance literature:

With ATP; calcium(II) nitrate; edetate disodium; In phosphate buffer; water; at 30 ℃; for 0.25h; pH=7.4; Further byproducts.;

DOI:10.1002/jlcr.1488

Reference yield:

(E)-4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester (76745-14-7) → 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen / 10percent palladium-on-charcoal / ethyl acetate / 4 h / 23 °C

2: pyridine / 12 h / 23 °C

3: 1.) 2percent methanolic HCl, 2.) potassium carbonate / 1.) 23 deg C, 7 h, 2.) methanol, 23 deg C, 30 min

4: pyridine / 1 h / 23 °C

5: 1.) 70percent perchloric acid, dimethyl carbonate, 2.) lead tetracetate, sodium carbonate / 1.) water, 23 deg C, 4 h, 2.) methylene chloride, -40 deg C, 10 min

6: 32 percent / n-butyllithium, HMPA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> -20 deg C, 30 min, 3.) -20 deg C -> 0 deg C, 30 min

7: 1.) potassium carbonate, 2.) lithium hydroxide / 1.) methanol, 25 deg C, 6.5 h, 2.) methanol-water (2:1) 23 deg C, 1 h

With lead(IV) acetate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; perchloric acid; hydrogen; sodium carbonate; potassium carbonate; carbonic acid dimethyl ester; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate;

DOI:10.1021/ja00547a051

upstream raw materials:

Leukotriene B

Benzoic acid (2E,4E)-(S)-1-(3-methoxycarbonyl-propyl)-6-oxo-hexa-2,4-dienyl ester

(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

methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Downstream raw materials:

(6E,8Z,10Z,14Z)-(5S,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

LTB_x methyl ester

(6E,8Z,10Z,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

(6E,8Z,10E,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

Refernces

• 1、 Schramm, Stanislav I.,Nagaev, Igor Yu.,Sabirsh, Alan,Shevchenko, Valeriy P.,Arkhipova, Anastasiya S.,Haeggstroem, Jesper Z.,Myasoedov, Nikolay F.. "Preparation of high specific activity tritium-labelled leukotriene B 4 suitable for radioligand binding assay". . p. 101 - 105. Retrieved 2008/09/20.
• 2、 Kobayashi, Yuichi,Shimazaki, Toshiyuki,Taguchi, Hideki,Sato, Fumie. "Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues". . p. 5324 - 5335. Retrieved 2007/10/02.