(8S,15S)-DIHETE

Base Information

• Chemical Name: (8S,15S)-DIHETE
• CAS No.: 80234-65-7
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 80234-65-7.mol

Synonyms:;(8S,15S)-dihydroxy-(5Z,9E,11Z,13E)-*eicosatetraen;(8S,15S)-DIHYDROXY-(5Z,9E,11Z,13E)-EICOS ATETRAENOI;8(S),15(S)-DIHYDROXYEICOSA-5Z,9E,11Z,13E-TETRAENOIC ACID;(8S,15S)-DIHYDROXY-(5Z,9E,11Z,13E)-EICOSATETRAENOIC ACID;

Chemical Property of (8S,15S)-DIHETE

Chemical Property:

• PSA: 77.76000
• LogP: 4.15830
• Storage Temp.: −20°C

Purity/Quality:

99% ^*data from raw suppliers

8(S),15(S)-DiHETE(Z,E,Z,E) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: 8(S),15(S)-DiHETE is formed when 15(S)-HETE is subjected to further oxidation by 15-LO. It causes eosinophil chemotaxis with an ED50 value of 1.5 μM but is not chemotactic for neutrophils. 8(S),15(S)-DiHETE antagonizes the hyperalgesic activity of 8(R),15(S)-DiHETE and LTB4 in the rat hind paw pain model.
• Uses: 8(S),15(S)-DiHETE (Z, E, Z, E) is a novel dioxygenation product of arachidonic acid.

Technology Process of (8S,15S)-DIHETE

There total 38 articles about (8S,15S)-DIHETE 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: 95.0%

(5Z,9E,11Z,13E)-(8S,15S)-8,15-Dihydroxy-icosa-5,9,11,13-tetraenoic acid methyl ester (76964-62-0) → 8(S),15(S) dihydroxy 5Z,9E,11Z,13E eicosatetraenoic acid (80234-65-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1021/ja00331a058

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → 8(R),15(S) dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (77667-08-4,80234-64-6,80234-65-7,80234-66-8,80234-67-9,93292-73-0,104125-26-0,104125-27-1,118758-87-5,125589-73-3,133577-77-2,133577-78-3,133577-79-4,133577-80-7)

Guidance literature:

Multi-step reaction with 12 steps

1: lithium hexamethyldisilazide (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide

4: aq. acid

5: lead tetraacetate / CH₂Cl₂ / -78 °C

7: 2.) sodium borohydride/ceric chloride / 2.) isopropanol

8: 1) DIPHOS, carbon tetrabromide / 2) triphenylphosphine

9: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

11: tetrabutylammonium fluoride

12: aq. potassium carbonate

With lead(IV) acetate; sodium tetrahydroborate; ceric chloride; carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

(4-carboxybutylene)triphenylphosphorane (39968-97-3) → 8(R),15(S) dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (77667-08-4,80234-64-6,80234-65-7,80234-66-8,80234-67-9,93292-73-0,104125-26-0,104125-27-1,118758-87-5,125589-73-3,133577-77-2,133577-78-3,133577-79-4,133577-80-7)

Guidance literature:

Multi-step reaction with 11 steps

3: aq. acid

4: lead tetraacetate / CH₂Cl₂ / -78 °C

6: 2.) sodium borohydride/ceric chloride / 2.) isopropanol

7: 1) DIPHOS, carbon tetrabromide / 2) triphenylphosphine

8: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

10: tetrabutylammonium fluoride

11: aq. potassium carbonate

With lead(IV) acetate; sodium tetrahydroborate; ceric chloride; carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

upstream raw materials:

(5Z,9E,11E,13Z)-(8R,15S)-8,15-Dihydroxy-icosa-5,9,11,13-tetraenoic acid methyl ester

tert-Butyl-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexyloxy]-diphenyl-silane

(4-carboxybutyl)triphenylphosphonium bromide

(S)-2-(tert-butyldiphenylsilyloxy)heptanal

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.