15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet raenoic aci

Base Information

• Chemical Name: 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet raenoic aci
• CAS No.: 70946-44-0
• Molecular Formula: C₂₁H₃₄O₃
• Molecular Weight: 334.499
• DSSTox Substance ID: DTXSID401169849
• ChEMBL ID: CHEMBL3349313
• Mol file: 70946-44-0.mol

Synonyms:15-HETE methyl ester;15-hydroxy-5,8,11,13 eicosatetraenoic acid methyl ester

Chemical Property of 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet raenoic aci

Chemical Property:

• Vapor Pressure: 6.75E-10mmHg at 25°C
• Boiling Point: 447.7°C at 760 mmHg
• Flash Point: 169.9°C
• PSA: 46.53000
• Density: 0.952g/cm³
• LogP: 5.27590
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 405

Purity/Quality:

97% ^*data from raw suppliers

15(S)-HETE methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCC=CCCCC(=O)OC)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)OC)O
• Description: 15(S)-HETE methyl ester is a synthetic derivative of 15(S)-HETE , a major arachidonic acid metabolite from the 15-lipoxygenase pathway. Methyl esters of lipids are commonly used in formulations of nutritional supplements.

Technology Process of 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet raenoic aci

There total 14 articles about 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-*eicosatet raenoic aci 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: 91.0%

(5Z,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid methyl ester (97643-28-2) → (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester (70946-44-0)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 25 ℃;

DOI:10.1039/c39850001580

Reference yield: 8.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + icomucret (54845-95-3,73945-47-8,83603-31-0) → methyl (5Z,8Z,13E)-11,12-trans-epoxy-15-hydroxy-5,8,13-eicosatrienoate + (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester (70946-44-0) + (2E,4S)-4-hydroxy-2-nonenal (119008-09-2)

Guidance literature:

icomucret; With ammonium iron (II) sulfate; ethylenediaminetetraacetic acid; dihydrogen peroxide; phosphate buffer; In chloroform; for 1h; pH=7.4;

diazomethane; In diethyl ether; ethyl acetate; for 0.25h;

DOI:10.1016/j.chemphyslip.2006.02.015

Reference yield:

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (70981-96-3) → (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester (70946-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: PPh₃ / diethyl ether / 0 °C

2: diethyl ether

With triphenylphosphine; In diethyl ether;

DOI:10.1021/jo960239r

upstream raw materials:

diazomethane

icomucret

(5Z,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid methyl ester

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid

Downstream raw materials:

15(S)-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoyl-N-(2-hydroxyethyl)amine

(7E,9E,11Z,13E)-(5R,6R,15R)-5,6,15-Trihydroxy-icosa-7,9,11,13-tetraenoic acid methyl ester

lipoxin A4

6S-Lipoxin A₄

Refernces

• 1、 Manini,Briganti,Fabbri,Picardo,Napolitano,d'Ischia. "Free radical oxidation of 15-(S)-hydroxyeicosatetraenoic acid with the Fenton reagent: characterization of an epoxy-alcohol and cytotoxic 4-hydroxy-2E-nonenal from the heptatrienyl radical pathway". . p. 14 - 22. Retrieved 2007/10/03.
• 2、 Martini, Dominique,Buono, Gerard,Lacazio, Gilles. "Regiocontrol of soybean lipoxygenase oxygenation. Application to the chemoenzymatic synthesis of methyl 15(S)-HETE and Methyl 5(S),15(S)-diHETE". . p. 9062 - 9064. Retrieved 2007/10/03.