12-epi-LTB4

Base Information

• Chemical Name: 12-epi-LTB4
• CAS No.: 83709-73-3
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID601017288
• Nikkaji Number: J2.203.607F
• Wikidata: Q27070760
• Pharos Ligand ID: VGZUNTFJFUZ9
• Metabolomics Workbench ID: 2573
• Mol file: 83709-73-3.mol

Synonyms:12-epi-LTB4;12-epi-Leukotriene B4;12(S)-Leukotriene B4;12-epi LTB4;83709-73-3;12-Epi leukotriene B4;(5S,6Z,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;5S,12S-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid;6,8,10,14-Eicosatetraenoicacid, 5,12-dihydroxy-, (5S,6Z,8E,10E,12S,14Z)-;2-epi-LTB4;D0F7XM;12S-LTB4;GTPL6160;SCHEMBL3125900;CHEBI:72795;DTXSID601017288;LMFA03020015;AKOS040756146;5(S),12(S)-Dihydroxyeicosatetraenoate;PD021027;5(S),12(S)-Dihydroxyeicosatetraenoic acid;SR-01000946891;5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoate;SR-01000946891-1;Q27070760;5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acid;[S-[R*,R*-(E,Z,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoate;[S-[R*,R*-(E,Z,E,Z)]]-5,12-dihydroxy-6,8,10,14-Eicosatetraenoic acid

Chemical Property of 12-epi-LTB4

Chemical Property:

• Vapor Pressure: 9.63E-14mmHg at 25°C
• Boiling Point: 536.4°C at 760 mmHg
• PKA: 4.66±0.10(Predicted)
• Flash Point: 292.3°C
• PSA: 77.76000
• Density: 1.04g/cm³
• LogP: 4.15830
• 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

12-epiLeukotrieneB4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of 12-epi-LTB4

There total 133 articles about 12-epi-LTB4 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.