Let's play biochemical detective

[Theliterateper]

Formose is a solution made by heating formaldehyde with calcium hydroxide. It's a complex mixture of sugars with various configurations and chain branching, plus minor amounts of alcohols, acids, and other miscellaneous compounds. It's deadly to animals at 20%+ of the diet, with 25%+ killing all of them, and causes them to lose weight and have moderate to severe diarrhea. Other anomalies observed include shrunken livers and spleens and swollen kidneys and adrenal glands. At 10% and lower it actually causes higher weight gain than pure glucose solution, yet they still have mild diarrhea. Purified formose solution enables longer survival than crude formose. Now, let's speculate on formose's toxicity's mechanism(s), as well as to why it causes higher weight gain at lower amounts.

I just realized this is the wrong place. Please move this thread to Speculations.

Edited Tuesday at 08:47 AM by Theliterateper

[exchemist]

3 hours ago, Theliterateper said:

Formose is a solution made by heating formaldehyde with calcium hydroxide. It's a complex mixture of sugars with various configurations and chain branching, plus minor amounts of alcohols, acids, and other miscellaneous compounds. It's deadly to animals at 20%+ of the diet, with 25%+ killing all of them, and causes them to lose weight and have moderate to severe diarrhea. Other anomalies observed include shrunken livers and spleens and swollen kidneys and adrenal glands. At 10% and lower it actually causes higher weight gain than pure glucose solution, yet they still have mild diarrhea. Purified formose solution enables longer survival than crude formose. Now, let's speculate on formose's toxicity's mechanism(s), as well as to why it causes higher weight gain at lower amounts.

I just realized this is the wrong place. Please move this thread to Speculations.

Can you provide a typical analysis of the mixture? And can you summarise what you have read in the literature about formose? 

That would save a lot of reinventing the wheel. 

Edited Tuesday at 12:08 PM by exchemist

[KJW]

https://en.wikipedia.org/wiki/Formose_reaction

 

[Theliterateper]

9 hours ago, exchemist said:

Can you provide a typical analysis of the mixture? And can you summarise what you have read in the literature about formose? 

That would save a lot of reinventing the wheel. 

It's hard to provide a concrete composition, given that it depends on temperature and pH. Other factors, especially the presence of other inorganic compounds, can also strongly affect composition.

 

This paper shows analysis of one formose mixture: https://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202316621

[exchemist]

1 hour ago, Theliterateper said:

It's hard to provide a concrete composition, given that it depends on temperature and pH. Other factors, especially the presence of other inorganic compounds, can also strongly affect composition.

 

This paper shows analysis of one formose mixture: https://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202316621

Hmm, I see what you mean. 

I see that L-glucose is a laxative: https://en.wikipedia.org/wiki/L-Glucose

Presumably this reaction produces racemic mixtures of sugars. Can that account for the diarrhoea, do you think?  

[CharonY]

!

Moderator Note

While the OP is an invitation to some level of speculation, all are based on mainstream chemistry and there is literature that one can use as foundation. As long as the scope does not change it should be perfectly fine to stay here.

 

[studiot]

I am unclear exactly what the question is here.

However try comparing with other similar compounds, that are better known because they are not so harmful.

Quote

https://www.ncbi.nlm.nih.gov/books/NBK536930/

Lactulose, or 1,4-β-galactoside-fructose, is a non-absorbable synthetic disaccharide made of galactose and fructose.[7] The human small intestinal mucosa does not have the enzymes to split lactulose, so lactulose reaches the large bowel unchanged. Lactulose is metabolized in the colon by colonic bacteria to monosaccharides and then to volatile fatty acids, hydrogen, and methane. Lactulose reduces intestinal ammonia production and absorption in 3 ways.

Key thoughts

synthetic  (poly) saccharide

Non-absorbable

interacts with colonic bacteria

 

[Theliterateper]

1 hour ago, exchemist said:

Hmm, I see what you mean. 

I see that L-glucose is a laxative: https://en.wikipedia.org/wiki/L-Glucose

Presumably this reaction produces racemic mixtures of sugars. Can that account for the diarrhoea, do you think?  

That and the branched-chain sugars (which would presumably be included in that statement as well), plus polyols and aldonate salts.

 

Now, the rest of the symptoms/anomalies...

Edited Wednesday at 12:11 AM by Theliterateper

[TheVat]

For some reason, experiments where animals are given poison and then their reactions monitored is one of my least favorite types of scientific research.  It is worth noting that new alternative forms of testing are emerging, some with less ethical baggage.

https://www.niehs.nih.gov/health/topics/science/sya-iccvam

BTW isn't ethylene glycol one of the rxn products?  This could be a major player in the toxicity, and its effects are well known.  One metabolic byproduct of ingested ethylene glycol is oxalic acid, which can be a kidney killer.  

Edited Wednesday at 02:46 AM by TheVat

[Theliterateper]

27 minutes ago, TheVat said:

For some reason, experiments where animals are given poison and then their reactions monitored is one of my least favorite types of scientific research.  It is worth noting that new alternative forms of testing are emerging, some with less ethical baggage.

https://www.niehs.nih.gov/health/topics/science/sya-iccvam

BTW isn't ethylene glycol one of the rxn products?  This could be a major player in the toxicity, and its effects are well known.  One metabolic byproduct of ingested ethylene glycol is oxalic acid, which can be a kidney killer.  

So are glycolaldehyde (from where it comes) and glycolate (the other glycolaldehyde derivative created by Cannizzaro reactions), which are also toxic as they undergo the same metabolism as ethylene glycol.

 

Now, two down, three to go.

Edited Wednesday at 03:05 AM by Theliterateper

[exchemist]

4 hours ago, Theliterateper said:

So are glycolaldehyde (from where it comes) and glycolate (the other glycolaldehyde derivative created by Cannizzaro reactions), which are also toxic as they undergo the same metabolism as ethylene glycol.

 

Now, two down, three to go.

If you already have the answers to this, I’m out.

[Theliterateper]

40 minutes ago, exchemist said:

If you already have the answers to this, I’m out.

Truthfully, I do not know what causes the adrenal gland abnormalities, nor the extra weight gain at lower concentrations.

Edited Wednesday at 08:02 AM by Theliterateper

[exchemist]

2 hours ago, Theliterateper said:

Truthfully, I do not know what causes the adrenal gland abnormalities, nor the extra weight gain at lower concentrations.

I'm no biologist but it occurred to me there may be a threshold of toxicity below which the liver and other organs can manage to convert and excrete the toxic species, leaving a weight gain due to those sugars that can be metabolised successfully. 

[Theliterateper]

51 minutes ago, exchemist said:

I'm no biologist but it occurred to me there may be a threshold of toxicity below which the liver and other organs can manage to convert and excrete the toxic species, leaving a weight gain due to those sugars that can be metabolised successfully. 

That could be part of it, but the fact that pure glucose diets result in lower weights suggests additional mechanisms at work. I just don't know what these are.

Edited Wednesday at 10:59 AM by Theliterateper