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Author: Subject: linoleic acid and alpha linoleic acid
Snakeplisken
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[*] posted on 30-8-2008 at 12:24
linoleic acid and alpha linoleic acid


Hello everyone , i'm new here i hope we'll be good friends , i have a question about linoleic acid and alpha linoleic acid : do you know any link who talk about the chemical synthesis of these two acids ? or do you know yourself how to obtain synthetic linoleic and alpha linoleic acid ? very detailed please , thanks a lot for your patience ..
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Arrhenius
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[*] posted on 30-8-2008 at 12:32


Commercial reference material of these two octadecanoids is obtained by isolation from plant oils. Given that they are both highly abundant in several oils, I don't see that synthesis is a viable route to obtaining them. For one, the two unsaturations are cis, complicating the synthesis.

There is one company I used to purchase oxylipins and various fatty acid derivatives from.. the name has slipped my mind.. I'll take a look.

[Edited on 30-8-2008 by Arrhenius]
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Arrhenius
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[*] posted on 30-8-2008 at 12:35


Cayman Chemical:

Linoleic Acid
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Ritter
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[*] posted on 30-8-2008 at 12:41


Quote:
Originally posted by Snakeplisken
Hello everyone , i'm new here i hope we'll be good friends , i have a question about linoleic acid and alpha linoleic acid : do you know any link who talk about the chemical synthesis of these two acids ? or do you know yourself how to obtain synthetic linoleic and alpha linoleic acid ? very detailed please , thanks a lot for your patience ..


Since you have a computer connected to the Internet, a good place to start answering questions such as this is to use Google to find a basic review page such as the Wiki article on lineolic acid (which also contains a link to alpha-linolenic acid. See http://en.wikipedia.org/wiki/Linoleic_acid.

Both compounds could be made synthetically but are derived from natural products called oils.




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Snakeplisken
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[*] posted on 30-8-2008 at 12:50


Hello Arrhenius and Ritter thanks a lot for your help , yes that's true Arrhenius , it's certain that the chemical synthesis is not a viable route to obtain them , in fact i'm very curious because it look very difficult to obtain them chemically . Like you said Ritter the web is very helpfull , but they talk only about isolation from oils there is no trace of chemical synthesis of these two acids on the net :D
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stoichiometric_steve
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[*] posted on 30-8-2008 at 12:56


Tomorrow, someone will turn up and ask for a total synthesis of Amylopectine.



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Snakeplisken
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[*] posted on 30-8-2008 at 13:02


and i'll be very happy to help him if i can stoichiometric_steve like everyone , we help each other that's why this forum is very interressant
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Ritter
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[*] posted on 30-8-2008 at 15:06


Quote:
Originally posted by Snakeplisken
Hello Arrhenius and Ritter thanks a lot for your help , yes that's true Arrhenius , it's certain that the chemical synthesis is not a viable route to obtain them , in fact i'm very curious because it look very difficult to obtain them chemically . Like you said Ritter the web is very helpfull , but they talk only about isolation from oils there is no trace of chemical synthesis of these two acids on the net :D


Believe me, you don't wsant to get into the multi-step detail involved in the synthesis of this type of lipid. Typically you have the formation of terminal alkynes, then Grignard reactions, then catalytic hydrogenations over Lindlar catalyst to get the cis-isomer alkenes. The only way to get to certain pheromones but not the way to get to these naturally-occurring fatty acids.




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Snakeplisken
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[*] posted on 30-8-2008 at 23:03


ok thanks Ritter but remember that vitamin B12 for example was extremely difficult to obtain too ( 70 steps ! ) and woodward finally obtained it by chemical synthesis , everything is possible nothing is impossible ;)
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[*] posted on 31-8-2008 at 05:17


Quote:
Originally posted by Snakeplisken
ok thanks Ritter but remember that vitamin B12 for example was extremely difficult to obtain too ( 70 steps ! ) and woodward finally obtained it by chemical synthesis , everything is possible nothing is impossible ;)


Yes, but remember that Woodward was only trying to prove the structure, not develop a viable commercial synthesis.

I've toured a B12 plan & its all done by fermentation, not synthesis. There is one synthetic additive: 5,6-dimethylbenzimidazole.

[Edited on 31-8-2008 by Ritter]




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Snakeplisken
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[*] posted on 31-8-2008 at 07:02


Finally found something and it's only the beginning :D : Franz sondheimer obtained linoleic acid by partial hydrogenation of the diacetylenic acid !! now i must found more i hope i hope ;)
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