5(S),6(R),15(S)-TRIHETE METHYL ESTER

Base Information

• Chemical Name: 5(S),6(R),15(S)-TRIHETE METHYL ESTER
• CAS No.: 97643-35-1
• Molecular Formula: C21H34 O5
• Molecular Weight: 366.498
• Hs Code.: 2918199090
• Mol file: 97643-35-1.mol

Synonyms:7,9,11,13-Eicosatetraenoicacid, 5,6,15-trihydroxy-, methyl ester, (5R,6S,7E,9E,11Z,13E,15R)- (9CI);7,9,11,13-Eicosatetraenoic acid, 5,6,15-trihydroxy-, methyl ester,[5S-(5R*,6S*,7E,9E,11Z,13E,15R*)]-; (6R)-Lipoxin A methyl ester

Chemical Property of 5(S),6(R),15(S)-TRIHETE METHYL ESTER

Chemical Property:

• Boiling Point: 540.2±50.0 °C(Predicted)
• PKA: 13.38±0.20(Predicted)
• Flash Point: 10℃ (tag closed test)
• PSA: 86.99000
• Density: 1.056±0.06 g/cm3(Predicted)
• LogP: 3.21750

Purity/Quality:

99% ^*data from raw suppliers

Lipoxin A4 methyl ester ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Lipoxin A4 methyl ester (LXA4 methyl ester) is a more lipid soluble, prodrug formulation of the transcellular metabolite LXA4. LXA4 is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of 15-HETE or 15-HpETE with human leukocytes. LXA4 is equipotent to leukotriene B4 (LTB4) in inducing superoxide generation in human neutrophils at 0.1 μM. LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis effects, natural killer cell inhibition, and monocyte migration and adhesion.

Technology Process of 5(S),6(R),15(S)-TRIHETE METHYL ESTER

There total 23 articles about 5(S),6(R),15(S)-TRIHETE METHYL ESTER 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: 90.0%

(7E,9E,11Z,13E)-(5R,6R,15R)-15-(tert-Butyl-dimethyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-icosa-7,9,11,13-tetraenoic acid methyl ester (97579-45-8,97603-05-9,97643-32-8,97643-33-9) → (7E,9E,11Z,13E)-(5R,6R,15R)-5,6,15-Trihydroxy-icosa-7,9,11,13-tetraenoic acid methyl ester (97579-46-9,97643-34-0,97643-35-1,97643-36-2,99095-27-9,99095-35-9,121786-18-3,121786-19-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1016/S0040-4039(01)80797-8

Reference yield: 82.0%

(7E,9E,11Z,13E)-(5S,6R,15S)-15-(tert-Butyl-dimethyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-icosa-7,9,11,13-tetraenoic acid methyl ester (97579-45-8,97603-05-9,97643-32-8,97643-33-9) → lipoxin A methyl ester (97643-35-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1016/S0040-4039(01)80684-5

Reference yield:

lipoxin A4 (89663-86-5,171030-11-8) → lipoxin A methyl ester (97643-35-1)

Guidance literature:

With diazomethane;

DOI:10.1016/S0040-4039(01)81500-8

upstream raw materials:

(7E,9E,11Z,13E)-(5S,6R,15S)-15-(tert-Butyl-dimethyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-icosa-7,9,11,13-tetraenoic acid methyl ester

lipoxin A₄

4-{(4S,5R)-5-[(1E,3E,5Z,7E)-(S)-9-(tert-Butyl-dimethyl-silanyloxy)-tetradeca-1,3,5,7-tetraenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester

Downstream raw materials:

lipoxin A₄

6S-Lipoxin A₄

lipoxin A4

Refernces

• 1、 Corey, E. J.,Su, Wei-guo,Cleaver, Martin B.. "A SIMPLE AND EFFICIENT SYNTHESIS OF (7E,9E,11Z,13E)-(5S,6R,15S)-TRIHYDROXYEICOSATETRAENOIC ACID (6R-LIPOXIN A)". . p. 4181 - 4184. Retrieved 2007/10/02.
• 2、 Adams, Julian,Fitzsimmons, Brian. J.,Rokach, Joshua. "SYNTHESIS OF LIPOXINS: TOTAL SYNTHESIS OF CONJUGATED TRIHYDROXY EICOSATETRAENOIC ACIDS". . p. 4713 - 4716. Retrieved 2007/10/02.