5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoic acid

Base Information

• Chemical Name: 5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoic acid
• CAS No.: 80445-66-5
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• European Community (EC) Number: 632-877-6
• Mol file: 80445-66-5.mol

Synonyms:5,12-dihydroxy-6,8,10,14,17-eicosapentaenoic acid;leukotriene B5;LTB 5

Chemical Property of 5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoic acid

Chemical Property:

• Vapor Pressure: 7.47E-14mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 538.7 °C at 760 mmHg
• Flash Point: 293.7 °C
• PSA: 77.76000
• Density: 1.054 g/cm³
• LogP: 3.93430
• Storage Temp.: −70°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

LeukotrieneB5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Uses: Leukotriene B5 is a derivative of Arachidonic Acid (A765000), which is an essential fatty acid. It is an inflammatory mediator produced by human neutrophils that is less potent but similar to Leukotriene B4 (L473510).

Technology Process of 5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoic acid

There total 18 articles about 5,12-Dihydroxyicosa-6,8,10,14,17-pentaenoic 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:

(5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one (41976-28-7) → (6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid (80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / zinc amalgum, anhydrous hydrogen chloride / diethyl ether / 2 h / 0 °C

2: 1.) LiOH; 2.) H₂ / 2.) 10percent Pd-C / 1.) DME, 25 deg C, 2 h; 2.) 1 atm, ethylacetate

3: 78 percent / pyridinium dichromate, anhydrous magnesium sulfate, 4A mol.siev. / CH₂Cl₂ / 1.5 h / 23 °C

5: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis

With hydrogenchloride; lithium hydroxide; amalgamated zinc; dipyridinium dichromate; 4A mol.siev; hydrogen; potassium isopropoxide; magnesium sulfate; palladium on activated charcoal; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(01)99801-6

Reference yield:

octa-2,5-diyn-1-ol (35378-76-8) → (6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid (80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / tetrahydrofuran / 12 h / 65 °C

2: 91 percent / LiAlH₄ / diethyl ether / 5 h / 25 °C

3: 76 percent / dimethyl(S,S)(-)-tartarate

4: 90 percent / H₂ / Lindlar / tetrahydrofuran / 760 Torr

5: 84 percent / O₂ / oxidation with Collins reagent

6: 94 percent / tetrahydrofuran / -78 deg C, 10 min,; and then from -78 deg Cto 0 deg C over 1 h.

7: 84 percent / acetic acid; acetonitrile; H₂O / 6 h / 25 °C

8: triphenylphosphine, imidazole, I₂, diisopropylamine / diethyl ether; acetonitrile / 0.67 h / 25 °C

9: acetonitrile / 16 h / 60 °C

11: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis

With 1H-imidazole; lithium aluminium tetrahydride; Dimethyl D-tartrate; hydrogen; iodine; oxygen; potassium isopropoxide; diisopropylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; water; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(01)99801-6

Reference yield:

pent-2-yn-1-ol (6261-22-9) → (6Z,8Z,10E,14Z,17Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14,17-pentaenoic acid (80445-66-5,88763-91-1,88763-92-2,92008-52-1,109958-18-1,109958-19-2,109958-20-5,126721-43-5,126721-44-6,144489-46-3,150447-94-2)

Guidance literature:

Multi-step reaction with 13 steps

1: triphenyl phosphite, I₂, imidazol / diethyl ether; acetonitrile / 0.67 h / 25 °C

2: Cu(I)

3: 90 percent / tetrahydrofuran / 12 h / 65 °C

4: 91 percent / LiAlH₄ / diethyl ether / 5 h / 25 °C

5: 76 percent / dimethyl(S,S)(-)-tartarate

6: 90 percent / H₂ / Lindlar / tetrahydrofuran / 760 Torr

7: 84 percent / O₂ / oxidation with Collins reagent

8: 94 percent / tetrahydrofuran / -78 deg C, 10 min,; and then from -78 deg Cto 0 deg C over 1 h.

9: 84 percent / acetic acid; acetonitrile; H₂O / 6 h / 25 °C

10: triphenylphosphine, imidazole, I₂, diisopropylamine / diethyl ether; acetonitrile / 0.67 h / 25 °C

11: acetonitrile / 16 h / 60 °C

13: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis

With 1H-imidazole; triphenyl phosphite; lithium aluminium tetrahydride; Dimethyl D-tartrate; hydrogen; iodine; oxygen; potassium isopropoxide; diisopropylamine; triphenylphosphine; Lindlar's catalyst; copper; In tetrahydrofuran; diethyl ether; water; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(01)99801-6

upstream raw materials:

(R)-6-{(1Z,4Z)-5-[(2R,3R)-((2Z,5Z)-3-Octa-2,5-dienyl)-oxiranyl]-penta-1,4-dienyl}-tetrahydro-pyran-2-one

(5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one

octa-2,5-diyn-1-ol

pent-2-yn-1-ol

Refernces