5,12-Dihydroxyicosa-6,8,10-trienoic acid

Base Information

• Chemical Name: 5,12-Dihydroxyicosa-6,8,10-trienoic acid
• CAS No.: 88099-35-8
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488
• European Community (EC) Number: 632-968-0
• Mol file: 88099-35-8.mol

Synonyms:leukotriene B3;leukotriene B3, (S-(R*,R*-(E,E,Z)))-isomer;LTB3

Chemical Property of 5,12-Dihydroxyicosa-6,8,10-trienoic acid

Chemical Property:

• Vapor Pressure: 2.94E-13mmHg at 25°C
• Boiling Point: 525.9°C at 760 mmHg
• Flash Point: 285.9°C
• PSA: 77.76000
• Density: 1.025g/cm³
• LogP: 4.38230
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 338.24570956
• Heavy Atom Count: 24
• Complexity: 385

Purity/Quality:

98%Min ^*data from raw suppliers

LTB3(LeukotrieneB3) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Uses: LTB3 (Leukotriene B3) is found in leukocytes with proinflammatory properties similar to those of LTA4.

Technology Process of 5,12-Dihydroxyicosa-6,8,10-trienoic acid

There total 19 articles about 5,12-Dihydroxyicosa-6,8,10-trienoic 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: 75.0%

methyl 5ζ,12ζ-dihydroxy-6(E),8(E),10(E)-eicosatrienoate (111037-21-9,130121-31-2,130121-32-3,135570-16-0,135570-17-1,142760-34-7) → (+/-)-LTB3 (88020-87-5,88099-35-8,96283-44-2,110771-27-2,127776-70-9,130194-11-5,130194-12-6,135637-50-2,135637-51-3)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; for 1h; Ambient temperature;

DOI:10.1021/jo00312a031

Reference yield:

Nonanoyl chloride (764-85-2) → (+/-)-LTB3 (88020-87-5,88099-35-8,96283-44-2,110771-27-2,127776-70-9,130194-11-5,130194-12-6,135637-50-2,135637-51-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) AlCl₃, 2) AlCl₃ / 1) CH₂Cl₂, 0 deg C, 1 h, 2) r.t., 1.5 h

2: 87 percent / NaBH₄ / methanol / 0 °C

3: 46 percent / aq.LiOH / methanol / 0 °C

With lithium hydroxide; sodium tetrahydroborate; aluminium trichloride; In methanol;

DOI:10.1021/jo00021a056

Reference yield:

2-octyl-furan (4179-38-8) → (+/-)-LTB3 (88020-87-5,88099-35-8,96283-44-2,110771-27-2,127776-70-9,130194-11-5,130194-12-6,135637-50-2,135637-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2) iodine / 1) dirhodium tetraacetate / 1) 18 h, 2) CH₂Cl₂, RT 6 h

2: 1) aluminium hydride, 2) pyridinium dichromate

3: 1) NaH / 1) DME, 2h, RT, 2) 0.5 h

4: NaBH₄ / H₂O; ethanol / 2 h / Ambient temperature

With aluminium hydride; sodium tetrahydroborate; dipyridinium dichromate; iodine; sodium hydride; dirhodium tetraacetate; In ethanol; water;

DOI:10.1021/jo00312a031

upstream raw materials:

5,12-dioxo-6(E),8(E),10(E)-eicosatrienoic acid

methyl 5ζ,12ζ-dihydroxy-6(E),8(E),10(E)-eicosatrienoate

Nonanoyl chloride

methyl 4-(chlorocarbonyl)butyrate

Refernces

• 1、 Wenkert,Guo,Lavilla,Porter,Ramachandran,Sheu. "Polyene synthesis. Ready construction of retinol-carotene fragments, (±)-6(E)-LTB3 leukotrienes, and corticrocin". . p. 6203 - 6214. Retrieved 2007/10/02.