12-oxo-ETE

Base Information

• Chemical Name: 12-oxo-ETE
• CAS No.: 108437-64-5
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• DSSTox Substance ID: DTXSID00390599
• Nikkaji Number: J1.453.622A
• Wikidata: Q27115848
• Metabolomics Workbench ID: 2643
• ChEMBL ID: CHEMBL3310737
• Mol file: 108437-64-5.mol

Synonyms:12-KETE;12-keto-5,8,11,13-eicosatetraenoic acid

Chemical Property of 12-oxo-ETE

Chemical Property:

• Vapor Pressure: 3.82E-11mmHg at 25°C
• Boiling Point: 494.9°Cat760mmHg
• Flash Point: 267.2°C
• PSA: 54.37000
• Density: 0.98g/cm³
• LogP: 5.39570
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

12-OxoETE ≥90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(=O)C=CC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\CC(=O)/C=C/C=C\C/C=C\CCCC(=O)O
• Uses: 12-OxoETE is synthesized by human platelets and Aplysia nervous tissue after incubation with arachidonic acid. Microsomal fractions of various tissues will reduce 12-oxoETE to 12(S)-HETE or a mixture of 12(S)- and 12(R)-HETE. 12-OxoETE induces a rapid, dose dependent increase of cytoplasmic free calcium via an Leukotriene B4 receptor or a common activation sequence.

Technology Process of 12-oxo-ETE

There total 19 articles about 12-oxo-ETE 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: 80.0%

(5Z,8Z,10E)-11-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-undeca-5,8,10-trienoic acid (158359-25-2) → 12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid (108437-64-5)

Guidance literature:

With N-chloro-succinimide; silver perchlorate; In water; acetone;

DOI:10.1016/S0040-4039(00)73109-1

Reference yield:

1-bromooct-2-yne (18495-27-7) → 12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid (108437-64-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / 1.) n-BuLi / tetrahydrofuran / 1.) -78 deg C to -20 deg C, 2 h; 2.) -78 deg C to rt.

2: 94 percent / H₂ / Ni(AcO)2*4H₂O, NaBH₄ / aq. ethanol

3: 77 percent / 1.) n-BuLi / tetrahydrofuran / 1.) -30 deg C, 2 h; 2.) -78 deg C, rt.

4: 91 percent / LDA / tetrahydrofuran / -78 - 20 °C

5: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 76 percent / PCC-SiO₂ / CH₂Cl₂

7: 62 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

8: 92 percent / LiOH / tetrahydrofuran; H₂O

9: 80 percent / NCS, AgClO₄ / acetone; H₂O

With lithium hydroxide; N-chloro-succinimide; n-butyllithium; pyridinium chlorochromate on silica gel; hydrogen; silver perchlorate; diisobutylaluminium hydride; lithium hexamethyldisilazane; lithium diisopropyl amide; sodium tetrahydroborate; nickel diacetate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)73109-1

Reference yield:

2-Oct-2-ynyl-[1,3]dithiane (158359-18-3) → 12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid (108437-64-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / H₂ / Ni(AcO)2*4H₂O, NaBH₄ / aq. ethanol

2: 77 percent / 1.) n-BuLi / tetrahydrofuran / 1.) -30 deg C, 2 h; 2.) -78 deg C, rt.

3: 91 percent / LDA / tetrahydrofuran / -78 - 20 °C

4: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

5: 76 percent / PCC-SiO₂ / CH₂Cl₂

6: 62 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

7: 92 percent / LiOH / tetrahydrofuran; H₂O

8: 80 percent / NCS, AgClO₄ / acetone; H₂O

With lithium hydroxide; N-chloro-succinimide; n-butyllithium; pyridinium chlorochromate on silica gel; hydrogen; silver perchlorate; diisobutylaluminium hydride; lithium hexamethyldisilazane; lithium diisopropyl amide; sodium tetrahydroborate; nickel diacetate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)73109-1

upstream raw materials:

(5Z,8Z,10E)-11-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-undeca-5,8,10-trienoic acid

1-bromooct-2-yne

methyl 4-formylbutanoate

(Z)-8-hydroxyoct-5-enoic acid methyl ester

Refernces

• 1、 Belyaeva, Olga V.,Boeglin, William E.,Brash, Alan R.,Goggans, Kelli R.,Karki, Suman,Kedishvili, Natalia Y.,Popov, Kirill M.,Wendell, Stacy G.,Wirth, Samuel E.. "Dehydrogenase reductase 9 (SDR9C4) and related homologs recognize a broad spectrum of lipid mediator oxylipins as substrates". . . Retrieved 2022/01/31.