12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid

Base Information

• Chemical Name: 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid
• CAS No.: 117346-20-0
• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.488
• Wikidata: Q76293823
• Metabolomics Workbench ID: 2619
• ChEMBL ID: CHEMBL329415
• Mol file: 117346-20-0.mol

Synonyms:12(R)DH-HETE;12-hydroxy-5,8,14-eicosatrienoic acid;12-hydroxy-5,8,14-eicosatrienoic acid, (S-(Z,Z,Z))-isomer;12-hydroxy-5,8,14-eicosatrienoic acid, (Z,Z,Z)-isomer

Chemical Property of 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid

Chemical Property:

• Vapor Pressure: 4.13E-11mmHg at 25°C
• Boiling Point: 477.2°Cat760mmHg
• Flash Point: 256.5°C
• PSA: 57.53000
• Density: 0.971g/cm³
• LogP: 5.41150
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 322.25079494
• Heavy Atom Count: 23
• Complexity: 356

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C[C@@H](CC/C=C\C/C=C\CCCC(=O)O)O

Technology Process of 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid

There total 8 articles about 12R-hydroxy-5Z,8Z,12Z-eicosatrienoic 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:

methyl 12(R)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoate (127251-16-5) → 12(R)-Hydroxy-5,8,14-(Z,Z,Z)-eicosatrienoic acid (117346-20-0)

Guidance literature:

With lithium hydroxide; In methanol; water; at 23 ℃; for 6h;

DOI:10.1016/S0040-4039(00)99285-2

Reference yield:

(Z)-1-iodohept-1-ene (63318-29-6) → 12(R)-Hydroxy-5,8,14-(Z,Z,Z)-eicosatrienoic acid (117346-20-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) CuCN / 1.) Et₂O, -60 deg C, 20 min, 2.) -78 deg C to -45 deg C, 30 min, 3.) -50 deg C, 30 min

2: diisobutylaluminum hydride / toluene / 3 h / -78 °C

3: tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 deg C to -24 deg C

4: Ph₃P, DEAD / tetrahydrofuran / 2 h / 0 °C

5: NaOMe / methanol / 6 h / 23 °C

6: LiOH / methanol; H₂O / 6 h / 23 °C

With lithium hydroxide; n-butyllithium; sodium methylate; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; toluene;

DOI:10.1016/S0040-4039(00)99285-2

Reference yield:

(Z)-5-(oct-2-en-1-yl)dihydrofuran-2(3H)-one. (63357-98-2) → 12(R)-Hydroxy-5,8,14-(Z,Z,Z)-eicosatrienoic acid (117346-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminum hydride / toluene / 3 h / -78 °C

2: tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 deg C to -24 deg C

3: Ph₃P, DEAD / tetrahydrofuran / 2 h / 0 °C

4: NaOMe / methanol / 6 h / 23 °C

5: LiOH / methanol; H₂O / 6 h / 23 °C

With lithium hydroxide; sodium methylate; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; toluene;

DOI:10.1016/S0040-4039(00)99285-2

upstream raw materials:

methyl 12(R)-hydroxyeicosa-5(Z),8(Z),14(Z)-trienoate

(Z)-1-iodohept-1-ene

(Z)-5-(oct-2-en-1-yl)dihydrofuran-2(3H)-one.

(S)-γ-6-Z-n-octen-γ-butirrolattolo

Refernces