5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid

Base Information

• Chemical Name: 5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid
• CAS No.: 92950-25-9
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Nikkaji Number: J138.389B
• Wikipedia: Lipoxin
• Metabolomics Workbench ID: 1092
• Mol file: 92950-25-9.mol

Synonyms:5,14,15-THET;5,14,15-trihydroxy-6,8,10,12-eicosatetraenoic acid;5-methyl-LXB4;5D,14,15L-trihydroxy-6,8,10,12-eicosatetraenoic acid;lipoxin B4;LXB4

Chemical Property of 5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 2.39E-16mmHg at 25°C
• Boiling Point: 589.4°Cat760mmHg
• Flash Point: 324.3°C
• PSA: 97.99000
• Density: 1.096g/cm³
• LogP: 3.12910
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C(C=CC=CC=CC=CC(CCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCCC(C(/C=C/C=C/C=C/C=C/C(CCCC(=O)O)O)O)O

Technology Process of 5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid

There total 11 articles about 5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic 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:

4-[(2S,3S)-3-((1E,3E,5Z,7E)-(R)-9-Hydroxy-tetradeca-1,3,5,7-tetraenyl)-oxiranyl]-butyric acid (94235-42-4,99529-21-2,105615-96-1,123878-03-5) → Lipoxin A (89663-86-5,94292-80-5,94292-82-7,94292-83-8,94292-84-9,94292-86-1,95341-55-2,119720-62-6,120442-99-1,121842-52-2,171030-11-8) + Lipoxin B (92950-25-9,98049-68-4,98049-69-5,98049-79-7,98049-80-0,103001-19-0,103001-21-4,103001-22-5,106062-83-3,121786-22-9,121842-51-1,136781-63-0)

Guidance literature:

Mechanism;

DOI:10.1016/S0040-4039(00)98692-1

Reference yield:

(2S,3R)-Octane-1,2,3-triol (135068-38-1) → (6E,8E,10E,12E)-(5S,14S,15R)-5,14,15-Trihydroxy-icosa-6,8,10,12-tetraenoic acid (92950-25-9,98049-68-4,98049-69-5,98049-79-7,98049-80-0,103001-19-0,103001-21-4,103001-22-5,106062-83-3,121786-22-9,121842-51-1,136781-63-0)

Guidance literature:

Multi-step reaction with 13 steps

1: pyridine / CH₂Cl₂ / 14 h / Ambient temperature

2: imidazole / dimethylformamide / 16 h / 25 °C

3: (i-C₄H₉)2AlH / CH₂Cl₂; hexane / 0.5 h / -78 °C

4: pyridinium chlorochromate / CH₂Cl₂ / 6 h / 25 °C

5: 1.) n-C₄H₉Li / 1.) THF, -78 deg C, 1 h, 2.) room temp., 3 h

6: iodine / benzene / 1 h / Ambient temperature

7: AgNO₃ / aq. ethanol; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temp., 1 h

8: 1.) n-C₃H₇NH₂, / 1.) Pd6H₅)3>4, 2.) CuI / 1.) benzene, room temp., 45 min, 2.) benzene, 25 deg C, 2 h

9: HF/pyridine complex / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 0 - 25 deg C

10: aq. LiOH / tetrahydrofuran / 0 °C

11: diethyl ether / 0 °C

12: H₂ / Lindlar catalyst / CH₂Cl₂ / 25 °C

13: aq. LiOH / methanol / 25 °C

With pyridine; 1H-imidazole; propylamine; lithium hydroxide; n-butyllithium; hydrogen fluoride; hydrogen; iodine; diisobutylaluminium hydride; silver nitrate; pyridinium chlorochromate; Lindlar's catalyst; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1986-31673

Reference yield:

2,2-Dimethyl-propionic acid (2S,3R)-2,3-dihydroxy-octyl ester (106031-55-4) → (6E,8E,10E,12E)-(5S,14S,15R)-5,14,15-Trihydroxy-icosa-6,8,10,12-tetraenoic acid (92950-25-9,98049-68-4,98049-69-5,98049-79-7,98049-80-0,103001-19-0,103001-21-4,103001-22-5,106062-83-3,121786-22-9,121842-51-1,136781-63-0)

Guidance literature:

Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 16 h / 25 °C

2: (i-C₄H₉)2AlH / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: pyridinium chlorochromate / CH₂Cl₂ / 6 h / 25 °C

4: 1.) n-C₄H₉Li / 1.) THF, -78 deg C, 1 h, 2.) room temp., 3 h

5: AgNO₃ / aq. ethanol; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temp., 1 h

6: 1.) n-C₃H₇NH₂, / 1.) Pd6H₅)3>4, 2.) CuI / 1.) benzene, room temp., 45 min, 2.) benzene, 25 deg C, 2 h

7: HF/pyridine complex / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 0 - 25 deg C

8: aq. LiOH / tetrahydrofuran / 0 °C

9: diethyl ether / 0 °C

10: H₂ / Lindlar catalyst / CH₂Cl₂ / 25 °C

11: iodine / CH₂Cl₂ / 4 h / Ambient temperature

12: aq. LiOH / methanol / 25 °C

With pyridine; 1H-imidazole; propylamine; lithium hydroxide; n-butyllithium; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; silver nitrate; pyridinium chlorochromate; Lindlar's catalyst; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1986-31673

upstream raw materials:

4-[(2S,3S)-3-((1E,3E,5Z,7E)-(R)-9-Hydroxy-tetradeca-1,3,5,7-tetraenyl)-oxiranyl]-butyric acid

(2S,3R)-Octane-1,2,3-triol

2,2-Dimethyl-propionic acid (2S,3R)-2,3-dihydroxy-octyl ester

(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-octan-1-ol

Refernces

• 1、 Fitzsimmons,Rokach. "On the biosynthesis and the structure of lipoxin B". . p. 3939 - 3942. Retrieved 2007/10/02.