Sciencemadness Discussion Board

Synthesis of alpha-Naphthoflavone (Bodybuilding Supp)

daviddale62 - 29-7-2012 at 01:46

Hello everyone first post!

So... alpha-Naphthoflavone is a aromatase inhibitor. Aromatase is an enzyme which converts testosterone into estradiol. When inhibited, aromatase is unable to do this, thus less estrogen is created within the body (and testosterone increases). This is desirable for anyone wanting to build muscles (a bodybuilder) as the hormone testosterone promotes muscle growth/hypertrophy.

alpha-naphthoflavone is termed a synthetic flavone and I have not heard of any natural occurrences in plants that could be extracted. The wikipedia entry for it states that it can be prepared from 2-naphthol and cinnamaldehyde. Could anyone suggest a route of synthesis (even low yeilding)?

I have access to glassware, reflux/distillation equipment.

Thank in advance


bbartlog - 29-7-2012 at 05:25

The abstract for the reference that Wikipedia shows does not suggest that the preparation they use would be feasible for an amateur. Alkyllithium reagents, periodinane, pyrrolidone hydrotribromide... rather forbidding, at least to my eyes. Now maybe they did it that way for reasons of their own and a more OTC method exists along similar lines, but a quick search doesn't turn up anything.

kristofvagyok - 29-7-2012 at 09:35

Quote: Originally posted by daviddale62  
I have access to glassware, reflux/distillation equipment.

Thank in advance


Orgo chemistry does not starts like "I have a distillation setup, so I must start something with it".

The mentioned compound does not require any distillation setups, I would suggest a syntehesis from 2 naphthaldehyde and acetophenone to form a chalcone, then cyclize it somehow... -there are several synthesis methods.

But making something and eat it what is made from potentially carcinogenic compounds is not a good idea, especially if a wikipedia article suggests it what could be edited by anyone.

And a last sentence: "alpha-Naphthoflavone has been shown to cause abnormal testicular development in young chickens"
-are you a chicken? Would you risk to reproduce this experiment on youself or on someone else?!