(5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid

Base Information

• Chemical Name: (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid
• CAS No.: 845673-74-7
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.478
• Mol file: 845673-74-7.mol

Synonyms:

Chemical Property of (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid

Chemical Property:

Purity/Quality:

≥90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid

There total 4 articles about (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid 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: 26.0%

(5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid (90906-40-4) → (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid (845673-74-7)

Guidance literature:

With Dess-Martin periodane; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmc.2005.07.074

Reference yield:

docosahexaenoic acid (6217-54-5) → (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid (845673-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / I2; γ-collidine / acetonitrile / 1 h / 20 °C

2: 85 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / 20 °C

3: 93 percent / aq. KOH / methanol / 5 h / 20 °C

4: 26 percent / Dess-Martin periodinane; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With 2,4,6-trimethyl-pyridine; potassium hydroxide; iodine; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/j.bmc.2005.07.074

Reference yield:

5-[(3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone (78144-19-1) → (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid (845673-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / 20 °C

2: 93 percent / aq. KOH / methanol / 5 h / 20 °C

3: 26 percent / Dess-Martin periodinane; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With potassium hydroxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; benzene;

DOI:10.1016/j.bmc.2005.07.074

upstream raw materials:

(5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid

docosahexaenoic acid

5-[(3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone

5-((1E,3Z,6Z,9Z,12Z,15Z)-Octadeca-1,3,6,9,12,15-hexaen-1-yl)dihydrofuran-2(3H)-one