8-Hpete

Base Information

• Chemical Name: 8-Hpete
• CAS No.: 100896-35-3
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 100896-35-3.mol

Synonyms:8-HPETE;8-hydroperoxyeicosatetraenoic acid

Chemical Property of 8-Hpete

Chemical Property:

• Vapor Pressure: 3.35E-12mmHg at 25°C
• Boiling Point: 502.5°Cat760mmHg
• Flash Point: 169.1°C
• PSA: 66.76000
• Density: 1.013g/cm³
• LogP: 6.03400
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 408

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 8-Hpete

There total 10 articles about 8-Hpete 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: 32.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 8-R-HPETE (100896-35-3)

Guidance literature:

With oxygen; under 60 Torr; acetone powder preparation from Plexaure flexuosa;

DOI:10.1016/S0040-4039(00)86110-9

Reference yield:

hexyltriphenylphosphonium bromide (4762-26-9) → (5Z,9E,11E,14Z)-8-Hydroperoxy-icosa-5,9,11,14-tetraenoic acid (70968-80-8,77913-05-4,96349-43-8,100896-35-3,114128-54-0,120143-52-4,145843-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuOK / 1.) THF, 0 deg C, 10 min, 2.) 0 deg C, 3.75 h

2: 88percent HCO₂H / tetrahydrofuran / 20 h / 0 °C

3: tetrahydrofuran / 2 h / 0 °C

4: H₂O₂, AgOCOCF₃ / diethyl ether / 0.58 h / Ambient temperature

With formic acid; potassium tert-butylate; dihydrogen peroxide; silver trifluoroacetate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00213a011

Reference yield:

2-Bromo-3-((Z)-oct-2-enyl)-cyclopropanecarbaldehyde (74766-00-0,84518-39-8) → (5Z,9E,11E,14Z)-8-Hydroperoxy-icosa-5,9,11,14-tetraenoic acid (70968-80-8,77913-05-4,96349-43-8,100896-35-3,114128-54-0,120143-52-4,145843-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / 0 °C

2: H₂O₂, AgOCOCF₃ / diethyl ether / 0.58 h / Ambient temperature

With dihydrogen peroxide; silver trifluoroacetate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00213a011

upstream raw materials:

all cis 5,8,11,14-eicosatetraenoic acid

(5Z,8Z)-9-[2-Bromo-3-((Z)-oct-2-enyl)-cyclopropyl]-nona-5,8-dienoic acid

hexyltriphenylphosphonium bromide

2-Bromo-3-((Z)-oct-2-enyl)-cyclopropanecarbaldehyde

Downstream raw materials:

prostaglandin A₂