[jefferson987]

Ok this might be a stupid question, but Im going to ask anyway. Im looking to synthesize isotretinoin from retinol by oxidizing the hydroxy group at the end of the molecule into a carboxilic acid. For this I will use KMnO4, NaOH, and H2O at 25C.  My biggest problem is obtaining the retinol, you cant really buy the stuff and I know cod liver oil has a very high concentration of it so I figured it would be a good source. I guess I just need to figure out how to isolate the retinol from the other retinoids in the mixture, that could be really difficult.... anyone have any suggestions? Or would I be able to perform the reaction on the crude cod liver oil and have only the isotretinoin precipitate out?

[ardbeg]

you have to be careful with that oxidant because retinol has alkene groups in it.

[ardbeg]

btw - why do you want to make it?

[jefferson987]

Im doing a biological experiment with its effects on the telomerase enzyme. How would this oxidation affect the alkene groups?

[jefferson987]

Perhaps using Jones reagent will help with the unsaturated bonds? I need to figure out where I can buy chromic acid....

[Yggdrasil]

It looks like sigma aldrich sells both retinol (R7632) and isotretinoin (13-cis-retinoic acid, R3255).

[jefferson987]

Yes they do, but seeing as I'm doing this research independently I wont be able to purchase it.