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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: lissydoll206 on June 30, 2005, 07:35:36 PM

Title: Aspartame naming
Post by: lissydoll206 on June 30, 2005, 07:35:36 PM

Hi...

  I am trying to figure out how the compound aspartame is named.  It's IUPAC name that I found is:

  I was trying to number it in a sort to try to understand where each of the groups are, but the way that it is numbered in the formula does not make sense to me.  I underlined in green the amino groups but I still can't figure out how it's numbered.
  Can someone help me figure it out?  Thanks!


3-amino-4-(1-methoxycarbonyl-2-phenyl-ethyl)amino-4-oxo-butanoic acid

Title: Re:Aspartame naming
Post by: Winga on July 01, 2005, 05:51:25 AM

By ChemDraw,

Title: Re:Aspartame naming
Post by: movies on July 01, 2005, 11:43:38 AM

Do you need help tracing what parts of the systematic name refer to what parts of the molecule, or is it just how to come up with the systematic name?

Title: Re:Aspartame naming
Post by: Dude on July 01, 2005, 12:40:51 PM

First, the word aspartame is likely just a trade name and has nothing to do with function or structure.
Everything in the IUPAC name is based off of the four carbons at the top of the picture.
1.  There is a carboxylate group (anion)- follow the four carbons and that is the base name (butanoic acid - or technically butanoate)
2.  You noted the 3-amino group
3.  Everything else is at the 4 position as a side group.

Title: Re:Aspartame naming
Post by: movies on July 01, 2005, 03:50:19 PM

Quote from: Dude on July 01, 2005, 12:40:51 PM

First, the word aspartame is likely just a trade name and has nothing to do with function or structure.

I think that this particular trade name does actually relate to the two amino acids in the structure: aspartic acid and phenylalanine methyl ester.

There is an interesting story that goes along with the discovery of this sweetener.  The chemist who made this compound in an unrelated pursuit neglected to wash his hands before eating his lunch.  He noticed that his sandwich was incredibly sweet for some reason, and came to the conclusion that is must have been this material that he had just produced in the lab.  It's certainly proven to be an effective sweetener (I think it's around 60 times sweeter than sucrose) and it's relatively safe since it's just a dipeptide.  It is problematic for the small percentage of the population that can't digest phenyalanine, however.