81517-87-5

Basic information

• Product Name: 5-hydroxyeicosatetraenoic acid lactone
• Synonyms: 5-hydroxyeicosatetraenoic acid lactone;6-[(1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraenyl]oxan-2-one
• CAS NO: 81517-87-5
• Molecular Formula: C20H30O2
• Molecular Weight: 302.45
• Mol File: 81517-87-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 445.7°C at 760 mmHg
• Flash Point: 188.6°C
• Appearance: /
• Density: 0.979g/cm³
• Vapor Pressure: 3.87E-08mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 5-hydroxyeicosatetraenoic acid lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxyeicosatetraenoic acid lactone(81517-87-5)
• EPA Substance Registry System: 5-hydroxyeicosatetraenoic acid lactone(81517-87-5)

Safety Data

• Hazardous Substances Data: 81517-87-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(21)22-19/h6-7,9-10,12-14,16,19H,2-5,8,11,15,17-18H2,1H3/b7-6-,10-9-,13-12-,16-14+

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 73279-36-4 (S)-6-((3Z,6Z,9Z)-(S)-1-Iodo-pentadeca-3,6,9-trienyl)-tetrahydro-pyran-2-one 
• 742103-77-1 6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one 

Downstream Products

• 126432-17-5 5-oxo-ETE 
• 70968-99-9 (=/-)-5-hydroxy-6-trans-8,11,14,-cis-eicosatetraenoic acid methyl ester 
• 71030-39-2 (+/-)-5-HETE 
• 78037-98-6 S-(+)-5-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid methyl ester 
• 78037-99-7 (5S)-(6E,8Z,11Z,14Z)-5-hydroxy-eicosa-6,8,11,14-tetraenoic acid, methyl ester 

Relevant articles and documents

Reactivity of Tricarbonyl(pentadienyl)iron(1+) Cations: Enantioselective Synthesis of 5-HETE Methyl Ester

The syntheses of racemic 5-HETE methyl ester (1) and of 5-HETE lactone (5-HL) were accomplished in 11 steps from tricarbonyliron(1+)hexafluorophosphate (2).A second synthesis of 1 from 2 in five steps was also achieved.Star

METHOD OF SYNTHESIZING A 5-OXO-CONJUGATED FATTY ACID

There is provided a novel chemical synthetic method for the preparation of a 5-oxo-ETE and related compounds. The method is based on a short and efficient synthesis of 5-oxo-ETE from commercially available Arachidonic acid. The method is based on the surprising discovery that a 5-oxo-conjugated fatty acid may be efficiently converted into the corresponding 5-oxo-conjugated fatty acid by reaction with the Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one)in the presence of pyridine or a substituted pyridine.

Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group

Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.