TLC-ism

Published on 24/05/2007

When I launched Laboratoire Organique I said I aimed to display organic synthesis in a rather stylish way, although I admitted I had no idea on how to fulfill such an ambitious purpose.

I wasn't helped by those who actually chose our experiment: unlike ψ*ψ, we weren't given the opportunity to work with outrageously glossy materials or, since this was meant to serve as an introduction or an outlook on organic chemistry lab work, none of our syntheses was either complicated or new.

Nevertheless, I think sometimes I managed to garnish my posts with some good stuff: old-fashioned pictures of plants embellish a couple of extractions of natural product; unprecedented in the blogosphere, world-famous actress Monica Bellucci has been seen filling a separatory funnel while I was pimping amino acids (please, don't make confusion: I reject any allegation of me trying to pimp any Monica-Belluci-look-alike girl); a rather psychedelic Georg Wittig dropped in one of my first posts, to salute the beginning of our lab course.

Now, theoretically, the brightest pictures could (and should) have been the TLCs. However, we didn't have the equipment you need to properly keep a (full-colour) record of your layers. And, above all, once we were told it was sufficient to photocopy the layers (wrapped in cellophane), I stopped worrying.

For the second special episode of Laboratoire Organique, however, I'd like to present (before you see it at the Biennale or at the Moma), the latest artistic trend: TLCism.

Here I propose, once again, all the TLCs I've posted and some new ones you haven't seen (do you remember the many coming soon's?). I'd like to know your favourite one (although I am looking forward to reading your comments on my previous post more than on this).

We begin with 9-styrylanthracene: mobile phase is n-hexane.ethyl acetate (5:1); UV light at 254 nm.

9-styrylanthracene

Nifedipine: n-hexane.ethyl acetate (1.5:1); UV light at 254 nm.

Nifedipine

Nicotine: dichloromethane:methanol:ammonia (60:10:1); UV light at 254 nm.

Nicotine

S-Methyl-3-Hydroxybutanoate: dichloromethane:methanol (98:2); revelation: potassium permanganate at basic pH.

S-Methyl-3-Hydroxybutanoate

p-Nitroacetanilide: toluene:ethyl acetate (4:1); UV light at 254 nm...

p-Nitroacetanilide

...and after Flash Chromatography, using the same mobile phase (please, notice the nasty traces of reagent, acetanilide, above the highlighted product).

Flash Chromatography of p-Nitroacetanilide

Xanthines: dichloromethane:methanol (9:1); UV light at 254 nm.

Xanthines

Chamomile (essential oils): toluene:ethyl acetate (93:7); sulphuric acid (5% in ethanol) and vanillin (1% in ethanol) in the stove.

Terpenes

Chamomile (flavonoids): ethyl acetate:acetic acid:water (100:22:27); Natural Probe (1% in ethanol) and PEG.

Flavonoids

Tacrine hydrochloride: dichloromethane:methanol:ammonia (9:1:0.1); UV light at 254 nm.

Tacrine

So, after this summary of part of the experiments there is time only for one, last thing...


Comments

  1. 24/05/2007 | 17:54

    Hmmm...not sure I'm thrilled by looking at TLC plates. I mean, don't get me wrong, they're very useful and all...but after doing like 30 of them today, I just don't see the fun.

  2. 23/03/2008 | 03:17

    hi!!! nice blog, Your test with chamomile (flavonoids): ethyl acetate:acetic acid:water (100:22:27), might help in my thesis... I was just researching on the polyphenol content of Dolichos lablab and my tlc solvent system were almost the same. Anyways, I really like your blog, it kinda make pharmchem easier.;)

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