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Author Topic: Does artificial sweeteners are really that bad?  (Read 4728 times)

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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« on: August 24, 2004, 02:48:33 PM »
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bloodline wrote:
I've been looking into Splenda, or rather Sucralose. It's very intresting, it is simply a chlorinated (a few OH groups are replaced with Chlorine) sucrose (common table sugar) molecule.


Hmm. I did wonder what the forumation was.

One assumes that the chlorinated molecule still keys into the sweet  taste receptors but doesn't quite fit the active sites on those enzymes that are there to break it down and oxidise it for ATP generation, hence no calories.

However, (and this mostly depends which -OH groups have been substituted) is it metabolised by any other processes in the body, I wonder? I can't imagine a build up of chlorinated polysaccherides that aren't (as) easily processed normal ones.

I don't to sound alarmist and I'm sure the studies have been done but chlorinated organics are generally quite hazardous in the long term. It only takes some process to release chlorocarbon radicals in the body for some real potential damage (many insecticides rely on this effect) to occur.
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #1 on: August 24, 2004, 04:34:37 PM »
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KennyR wrote:

Nope, Splenda/Surcralose goes straight through the body. Those big chlorine groups make it as unreactive as hell (stearic hindrance), although it still has the hydroxyl kick it needs to make it taste sweet.


Same basic overall shape and dipole presumably helps fool the taste receptors. The chlorine, however, shouldn't tightly bond to the active sites in enzymes that would metabolise (IIRC hydrogen bonding plays an important role in  the keying of sugars to the appropriate enzymes) it.

Few questions (not knowing the overall structure of it)

Does sucralose hydrolyse into chlorinated glucose in the same way as ordinary sucrose?

Do (if they occur) the chlorinated glucose molecules still exist as open chain form in solution?

If this occurs, it isn't impossible that they can be incorporated into polysaccherides (linking glucose units together isn't the same as breaking them down for energy production and hence may not be affected by the chloro substitution as readily), even if they can't be metabolised as a fuel source. That would imply long term storage of these molecules in the liver etc. that could prove dangerous in the (very) long term.

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When we studied sweeteners at uni and how they work, sucralose hadn't been approved yet. That's not because it's nasty, but because the FDA are understandably anal about what goes into food.


One should hope so too. That said, they already allow a great deal of crap into food that is known (despite being passed at the time) to have adverse effects, especially in the levels that are permitted.

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You're quite right to be wary of chlorine radicals. I really don't like the idea of filling myself full of organochlorides. Tests on sucralose said in theory it could be changed to chlorofructose in the body or in the sewers later by bacteria, quite a nasty chemical. I wouldn't opt for Splenda. The environment has enough alien chlorine based horrors floating around.


Quite.
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #2 on: August 24, 2004, 05:00:02 PM »
(blows some cobwebs of crusty chemical knowledge)

Hmm, if they only exist in the open chain form, I wonder what the crystal form is like? Also, IIRC, sucrose is a 1,6' condensate of a pair of glucose rings. Only after hydrolysis does it break down into individual glucose rings that can open into chains.

As an open chain is a very high entropy system (so many conformations are possible with a similar energy), I can't imagine it would crystalise too readily so maybe it does exist in ring confromation?

Glucose tends to prefer its ring format in the crystal - an ordered shape with directional hydrogen bonding to reinforce the overall structure.

All intersting stuff, but I wouldn't want to eat it :-D

Hint to sweet toothed people: Just dont eat as much high sugar food if you are worried about weight / teeth!
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #3 on: August 24, 2004, 05:02:36 PM »
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KennyR wrote:

Sweet taste receptors aren't all that sophisticated. All you basically need is an active hydroxyl group to trigger the sweet taste. Anything that looks like sugar, will taste like sugar.


Quite odd that water itself is taseless, eh ? :-D
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #4 on: August 24, 2004, 07:11:57 PM »
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KennyR wrote:
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Quite odd that water itself is taseless, eh ? :-D


Not really Karlos, you know that water dissociates into polar hydronium and hydroxide ions, don't you? :)


Of course (I was also joking), but the dissociation constant for water is pretty damn small. The vast majority of any quantity of water consists of HOH at any given instant. Of course, in the next instant it isn't neccessarily the same set of molecules you just looked at, thanks the chain propagation mechanism that allows the ultra high mobility of hydronium ions ;-)

Water. Funkier than most people realise...
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #5 on: August 24, 2004, 07:32:07 PM »
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KennyR wrote:





Dug around my old notes. Sterically, -Cl isn't as big as -OH as the latter occupies a larger volume (think of the overall space occupuied by that group rotating though every degree of freedom it has). However looks like that's not the main issue here. The -Cl in this molecule are strategically placed where most metabolic agents try to bond with. You can't shove your phoshphate linkage onto the CH2-Cl unit like you should be able to with the original CH2-OH, so there isn't anything for the activating enzymes to get hold of.

Structurally however, there is nothing immediately obvious (to my eye) that prevents that molecule dissosiating into a seperate chlorinated glucose / fructose pair - the centeral linkage is not protected by anything close enough to block dissosiation by acid catalysed hydrolysis.
Again it would seem to come down to the fact that the dissociated molecules still have their most biologically important -OH linkage replaced with -Cl. The glucose unit (left) cannot be added to an existing chain of glucose units  but it could conciveably start a new one. Hence, I'm not totally convinced the body couldn't store this material (although metabolising it is impossible without linking phosphate).
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #6 on: August 24, 2004, 08:23:13 PM »
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KennyR wrote:

If that inertness isn't caused by stearic hindrance then I'm lost for an explanation. Organic chemistry was never my prime forte.


As I say, I'm pretty sure that, metabolically at least, the terminal Cl groups defeat any attempt at activation by phosphorylation, thus denying one's metabolism to get a handle on the thing. Just as well really ;-)
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #7 on: August 24, 2004, 11:17:31 PM »
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odin wrote:
But the *main* problem with all the artificial sweeteners I've tasted is that they all taste like dogpoo which has been left rotting under a infrared light for half a year.


Man, I'm all for creative culinary flair, but you really need to watch what you go around experimenting with :lol:
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Offline Karlos

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Re: Does artificial sweeteners are really that bad?
« Reply #8 on: August 25, 2004, 02:54:20 PM »
@bloodline

Try TV as an alternative :lol:

Unfortunately it has lasting side effects...
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