111956-12-8

Basic information

• Product Name: (13R)-13-hydroxy-12-oxooctadeca-9(Z),15(Z)-dienoate
• CAS NO: 111956-12-8
• Molecular Weight: 310.434
• Mol File: 111956-12-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (13R)-13-hydroxy-12-oxooctadeca-9(Z),15(Z)-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: (13R)-13-hydroxy-12-oxooctadeca-9(Z),15(Z)-dienoate(111956-12-8)
• EPA Substance Registry System: (13R)-13-hydroxy-12-oxooctadeca-9(Z),15(Z)-dienoate(111956-12-8)

Safety Data

• Hazardous Substances Data: 111956-12-8(Hazardous Substances Data)

Upstream product

• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 

Relevant articles and documents

Synthesis of -Linoleic acid and its Use to Confirm the Pathway to 12-Oxophytodienoic acid (12-oxoPDA) in Plants: A Conspectus of the Epoxycarbonium Ion Derived Family of Metabolites from Linoleic and Linolenic Acid Hydroperoxides

Using acetylene methodology, a synthesis of -octadeca-9(Z),12(Z),15(Z)-trienoic acid is described.The isotopically marked acid is used to distinguish decisively between two possible pathways for the formation of 12-oxophtytodienoic acid (12-oxoPDA) by flax enzyme preparation in plants: (a) a route via antarafacial ring closure of a zwitterion derived from an allene epoxide (no loss of 14,14-2H2) and (b) a pathway resembling the accepted mammalian prostaglandin biosynthesis (loss of one 14-2H).Pathways to metabolic products formed in Nature from linoleic and linolenic acid are summarised in Scheme 3.The entry species is considered to be the epoxy-carbonium ion.Loss of a proton leads to an allene-epoxide from which are formed the α-ketol, the γ-ketol and 12-oxoPDA.A second group of products (colneleic and colnelenic acid, a hemiacetal, its corresponding aldehydes and an epoxy alcohol) are not formed via the allene-epoxide.The epoxy-carbonium ion can be trapped as an epoxy alcohol or rearranged via a vinyl-oxonium ion with capture by water to form a hemiacetal.Alternatively, loss of a proton from the epoxy-carbonium ion or vinyl-oxonium ion leads to colneleic and colnelenic acid.