845673-68-9

Basic information

• Product Name: 5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone
• CAS NO: 845673-68-9
• Molecular Weight: 344.494
• Mol File: 845673-68-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone(845673-68-9)
• EPA Substance Registry System: 5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone(845673-68-9)

Safety Data

• Hazardous Substances Data: 845673-68-9(Hazardous Substances Data)

Upstream product

• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 6217-54-5 docosahexaenoic acid 
• 78144-19-1 5-[(3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone 

Relevant articles and documents

Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents

To discover novel peroxisome proliferator-activated receptor γ (PPARγ) agonists that could be used as antidiabetic agents, we designed docosahexaenoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPARγ. These compounds were synthesized via iodolactone as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPARγ transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPARγ transcriptional activity, was separated as an optically pure form.

Syntheses of some polyunsaturated sulfur- and oxygen-containing fatty acids related to eicosapentaenoic and docosahexaenoic acids.

With the aim of enhancing selectively the beneficial biological effects of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) a number of polyunsaturated fatty acids containing sulfur or oxygen atoms in the chain has been synthesized starting from EPA and DHA, respectively. Oxidative degradation of these acids led to the corresponding aldehydes all-(Z)-3,6,9,12-pentadecatetraenal and all-(Z)-3,6,9,12,15-octadecapentaenal. Reactions with DBU converted these aldehydes quantitatively into the conjugated isomers (2E,6Z,9Z,12Z)-pentadecatetraenal and (2E,6Z,9Z,12Z,15Z)-octadecapentaenal, respectively. The four aldehydes were transformed by a sequence of reactions comprising reduction to the alcohols, halogenation and substitution with mercapto esters into the corresponding sulfur containing polyunsaturated fatty acid esters. The oxygen containing esters were prepared from the respective alcohol by boron trifluoride catalysed reaction with ethyl diazoacetate.