Linolenate
It is composed of 18 carbon atoms, a carboxylic acid function, and two unsaturations (double bonds). The compound is a colorless liquid.
Several stereoisomers of octadecadienoic acid are distinguished, but only the 9-cis, 12-cis octadecadienoic acid corresponds to linoleic acid. Its biochemical designation is 18:2(n-6), with the enumeration of double bonds occurring in reverse order to the chemical nomenclature. Its melting point is -9 °C.
| MBS6086686 | Glycidyl Linolenate-d5 |
| MBS393460 | Palmityl Linolenate |
| MBS393461 | Stearyl Linolenate |
| MBS393696 | Cholesteryl Linolenate |
Synonyms :
- all cis-Delta-9,12,15-octadecatrienoate
Config Rule :
% linolenate
config(linolenate,[
chain([
carboxyl(1),
num(methandiyl,7),
car(9,hyd)~~,
car(10,hyd),
methandiyl,
car(12,hyd)~~,
car(13,hyd),
methandiyl,
car(15,hyd)~~,
car(16,hyd),
methandiyl,
methyl]),
cis(car(8),car(11),bond(car(9),car(10))),
cis(car(11),car(14),bond(car(12),car(13))),
cis(car(14),car(17),bond(car(15),car(16)))]).
Smiles String :
[C@2H2]([C](=[O])[O-])[C@2H2][C@2H2][C@2H2][C@2H2][C@2H2][C@2H2]\[CH]=[CH]/[C@2_ H2]\[CH]=[CH]/[C@2H2]\[CH]=[CH]/[C@2H2][CH3] linolenate
Fischer Diagram :
Terminal :
% linolenate
c(1,12,(0,nonchiral))-[o(1,nil)?,c(2,right)~,o(2,nil)?],
c(2,12,(0,nonchiral))-[c(1,left)~,c(3,right)~,h(2,up)~,h(1,down)~],
c(3,12,(0,nonchiral))-[c(2,left)~,c(4,right)~,h(4,up)~,h(3,down)~],
c(4,12,(0,nonchiral))-[c(3,left)~,c(5,right)~,h(6,up)~,h(5,down)~],
c(5,12,(0,nonchiral))-[c(4,left)~,c(6,right)~,h(8,up)~,h(7,down)~],
c(6,12,(0,nonchiral))-[c(5,left)~,c(7,right)~,h(10,up)~,h(9,down)~],
c(7,12,(0,nonchiral))-[c(6,left)~,c(8,right)~,h(12,up)~,h(11,down)~],
c(8,12,(0,nonchiral))-[c(7,left)~,h(13,right)~,h(14,up)~,c(9,(down,isomeric(down)))~],
c(9,12,(0,nonchiral))-[h(15,(nil,isomeric(down)))~,c(8,(up,isomeric(up)))~,c(10,cis)~~],
c(10,12,(0,nonchiral))-[c(11,(right,isomeric(up)))~,h(16,(nil,isomeric(down)))~,c(9,cis)~~],
c(11,12,(0,nonchiral))-[c(10,(left,isomeric(down)))~,c(12,(right,isomeric(down)))~,h(18,up)~,h(17,down)~],
c(12,12,(0,nonchiral))-[c(11,(left,isomeric(up)))~,h(19,(nil,isomeric(down)))~,c(13,cis)~~],
c(13,12,(0,nonchiral))-[c(14,(right,isomeric(up)))~,h(20,(nil,isomeric(down)))~,c(12,cis)~~],
c(14,12,(0,nonchiral))-[c(13,(left,isomeric(down)))~,c(15,(right,isomeric(down)))~,h(22,up)~,h(21,down)~],
c(15,12,(0,nonchiral))-[c(14,(left,isomeric(up)))~,h(23,(nil,isomeric(down)))~,c(16,cis)~~],
c(16,12,(0,nonchiral))-[c(17,(right,isomeric(up)))~,h(24,(nil,isomeric(down)))~,c(15,cis)~~],
c(17,12,(0,nonchiral))-[c(16,(left,isomeric(down)))~,c(18,right)~,h(26,up)~,h(25,down)~],
c(18,12,(0,nonchiral))-[c(17,left)~,h(27,right)~,h(29,up)~,h(28,down)~],
h(1,1,(0,nonchiral))-[c(2,up)~],
h(2,1,(0,nonchiral))-[c(2,down)~],
h(3,1,(0,nonchiral))-[c(3,up)~],
h(4,1,(0,nonchiral))-[c(3,down)~],
h(5,1,(0,nonchiral))-[c(4,up)~],
h(6,1,(0,nonchiral))-[c(4,down)~],
h(7,1,(0,nonchiral))-[c(5,up)~],
h(8,1,(0,nonchiral))-[c(5,down)~],
h(9,1,(0,nonchiral))-[c(6,up)~],
h(10,1,(0,nonchiral))-[c(6,down)~],
h(11,1,(0,nonchiral))-[c(7,up)~],
h(12,1,(0,nonchiral))-[c(7,down)~],
h(13,1,(0,nonchiral))-[c(8,left)~],
h(14,1,(0,nonchiral))-[c(8,down)~],
h(15,1,(0,nonchiral))-[c(9,(nil,isomeric(up)))~],
h(16,1,(0,nonchiral))-[c(10,(nil,isomeric(up)))~],
h(17,1,(0,nonchiral))-[c(11,up)~],
h(18,1,(0,nonchiral))-[c(11,down)~],
h(19,1,(0,nonchiral))-[c(12,(nil,isomeric(up)))~],
h(20,1,(0,nonchiral))-[c(13,(nil,isomeric(up)))~],
h(21,1,(0,nonchiral))-[c(14,up)~],
h(22,1,(0,nonchiral))-[c(14,down)~],
h(23,1,(0,nonchiral))-[c(15,(nil,isomeric(up)))~],
h(24,1,(0,nonchiral))-[c(16,(nil,isomeric(up)))~],
h(25,1,(0,nonchiral))-[c(17,up)~],
h(26,1,(0,nonchiral))-[c(17,down)~],
h(27,1,(0,nonchiral))-[c(18,left)~],
h(28,1,(0,nonchiral))-[c(18,up)~],
h(29,1,(0,nonchiral))-[c(18,down)~],
o(1,16,(-5.0E-01,nonchiral))-[c(1,nil)?],
o(2,16,(-5.0E-01,nonchiral))-[c(1,nil)?]
The Terminals for all the Config Rules are in Prolog Definite Clause Grammar (DCG) form.They can be checked in the Manual here.
The compound's PDB file can be seen here.
Doug Markham of the Institute for Cancer Research, Fox Chase Cancer Center,Philadelphia, PA, has contributed the following structure for linolenate. He computed this structure in sdf format using MacroModel, a molecular mechanics program. We have used Babel to convert the .sdf format to PDB format. You'll find it interesting to compare these structures to those computed using CONCORD.
Many thanks Doug!