URGENT: NutraSweet(tm) Destroys Usenet!!!!

[Joseph Bret Wood]

In article <3vmvck$fb3 at lys.vnet.net>, AL BELL <allbell at lys.vnet.net> wrote:
>Aspartame:
>
>One possibility is that old aspartame breaks down into some not-so-great 
>substance. My recollection is that aspartame that's heated for too long 
>at too high a temperature has an effect similar to that of alcohol.

Not that I'm saying anything pro or con about this debate, but the reaction
you're refering to is taught to all first year organic chemists.  It's called
hydrolysis of an ester.  Aspartame is an ester (compound [1]).  When reacted
with water in a basic or acidic solution (soda pop is acidic), it undergoes
the following reaction, giving aspartic acid and methanol as products.
Personally, I doubt that one or two cans of diet soda could harm you from the
methanol, because methanol has been a contaminant in moonshine for centuries,
yet it only causes serious side effects if the batch is particularly bad,
and/or a very large quantity is consumed.  And nutrasweet is so potent, one
can of diet coke only requires a VERY small amount of aspartame.  

                            +                    +OH2                     OH 
H3C-O-C=O             H3C-O-C-OH                  |    (3 stp)            |
      |   + H+OH2 ==>       |    + :OH2 ==> H3C-O-C-OH ======> H3C-OH  +  C=O
      R                     R                     |                       |
                                                  R              [2]      R
   [1]                
                                                                         [3]

[1] -- Aspartame              This reaction apparently requires heating in the
[2] -- Methanol               case of aspartame.  For some other hydrolysis
[3] -- Aspartic Acid          reactions, it will happen at room temperature.


-Bret Wood
-bretwood at cs.uoregon.edu