8S-Hete

Base Information

• Chemical Name: 8S-Hete
• CAS No.: 98462-03-4
• Molecular Formula: C20H32 O3
• Molecular Weight: 320.472
• European Community (EC) Number: 633-689-7
• DSSTox Substance ID: DTXSID101033819
• Nikkaji Number: J855.517F
• Wikidata: Q27074042
• Pharos Ligand ID: 8SLDHQLZ5YBJ
• Metabolomics Workbench ID: 2632
• Mol file: 98462-03-4.mol

Synonyms:8-HETE;8-hydroxyeicosatetraenoic acid;8-hydroxyeicosatetraenoic acid, (E,Z,Z,Z)-(+-)-isomer;8-hydroxyeicosatetraenoic acid, (E,Z,Z,Z)-isomer

Chemical Property of 8S-Hete

Chemical Property:

• Vapor Pressure: 7.45E-11mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 471.1°Cat760mmHg
• Flash Point: 252.8°C
• PSA: 57.53000
• Density: 0.984g/cm³
• LogP: 5.18750
• Storage Temp.: −20°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 392

Purity/Quality:

≥98% ^*data from raw suppliers

8(S)-HETE ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC(CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O
• Uses: 8(S)-HETE is a fatty acid metabolite and potential PKC and PPARα activator.

Technology Process of 8S-Hete

There total 4 articles about 8S-Hete 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:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3) + (R)-12-HETE (82337-46-0) + 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4) + (8R)-hydroxyeicosatetraenoic acid (105500-09-2,79495-84-4) + (R)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (73347-43-0,73804-65-6) + icomucret (54845-95-3,73945-47-8,83603-31-0) + 15(R)-HETE (73945-47-8,83603-31-0) + (S)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (54886-50-9,73804-65-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 8R-lipoxygenase A₅₈₉M mutant; sodium chloride; calcium chloride; In ethanol; at 20 ℃; pH=8; Enzymatic reaction;

With triphenylphosphine; In methanol; at 20 ℃; for 0.5h; Reagent/catalyst; Kinetics;

DOI:10.1074/jbc.M114.599662

Reference yield:

methyl 8(S)-hydroxy-5(Z),9(E),11(Z),14(Z)-eicosatetraenoate (105499-95-4) → 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1016/S0040-4039(00)85392-7

Reference yield:

(5Z,9E)-(S)-8-Hydroxy-11-oxo-undeca-5,9-dienoic acid methyl ester (110822-75-8) → 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h

2: NaOH / methanol; H₂O

With sodium hydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water;

DOI:10.1016/S0040-4039(00)85392-7

upstream raw materials:

methyl 8(S)-hydroxy-5(Z),9(E),11(Z),14(Z)-eicosatetraenoate

(5Z,9E)-(S)-8-Hydroxy-11-oxo-undeca-5,9-dienoic acid methyl ester

(Z)-7-[(2S,3R)-3-(2-Oxo-ethyl)-oxiranyl]-hept-5-enoic acid methyl ester

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