[Doc.AElstein]

Green Coffee Extract Chlorogenic acid Nutritional Info.

Hi,
  I am coming across this “Chlorogenic acid” just now as the “important stuff” in Green Coffee Extracts.
  Being not a Chemist, as always I am trying to get a simple explanation of this “stuff”. The usual Searches in Internet are not getting me what I want. I want/ need some simple explanation I can understand of what “things” it might be grouped near in a very broad sense ( I do appreciate it may fall into many groups.)

And importantly I need some idea how it might be “Burnt” in the human body, that is to say, can I calculate somehow the Kcal per 100g from this “stuff” or alternatively the Kcal per 100g for the Green Coffee Extract that it is usually “in”.
 I am looking at about 2:1 for “Green Coffee Extract”: Chlorogenic acid in Products i am considering.
 I am guessing that Chlorogenic acid is the important thing for me to consider, and that whatever else ( the other 50%) is not important to consider? 
 
 Maybe the “Green Coffee Extract” to have general info on would help me more : I already have a “place” where I List Green Coffee Extract, and I do not want to “offend” some of you Chemi experts with my attempts to simplify more complicate Chemical Things and concepts, compounds, which necessarily make some of my “Listing” attempts irritating. !!     

  So any ideas of Kcal form  Green Coffee Extract ( or if you choose Chlorogenic acid ) and any general ideas of what things it might be considered “near to” in type.

  I hope my attempts at oversimplifying do not offend, apologies if they do. I am needing to be very ambitious in very quickly understanding as much as possible in a very vast technical area. I am very grateful for any help from you experts in “translating” your vast knowledge into simple things that i can understand and need, that is to say the  “Something” here:

  Kcal per 100g   =  “Something” x ( Green Coffee Extract per 100g )

Alan
 

[Arkcon]

I did a little Googling, and a little Wikipedia ... urm ... Ing and I have some ideas.  I'd share the sources with you, but I'm using my phone at work.  Briefly, your molecule of interest is an ester, that is an organic acid and an organic alcohol condensed together.  I want to call this molecule a hydrocarbon, but that's not technically correct, because there are other atoms present.  However, this compound isn't a nutrient, any more than caffeine or aspirin are.  These are drugs, and the pharmakogenics (spelling that wrong) of at less caffeine are well described.  The human liver turns it into something else, which is so weird that the kidneys excrete it.  It may cause a number if interesting things along the trip, but I don't expect significant (or any) caloric intake from this and other drugs.  We're not "made up of" these sorts of things.  So what would our body use them for?

[Doc.AElstein]

Hi Arkcon,
   Thanks for all that.

   Your use of the words “organic acid and an organic alcohol” sets off in my naive Laymen’s mind the desire to start using a multiplication factor somewhere between 7.1 and 3, but you are saying, I think,  in this particular case it will “pass through” then I can maybe ignore it’s  Kcal. ??
 
   This whole “Green Coffee” thing comes up a lot if one gets into Diet aids, food supplements etc. Claims that i saw up until now where of the benefits of the increased Polyphenols, EGCG’s. For some time my Wife has therefore taken the Green Coffee instead of the normal Coffee. ( As it does not taste very nice, I sometimes have a naive feeling it could be healthier.. Lol !  ). I was able to get from the manufacturers good nutritional  value for that, and it was very negligible. As is also the case with Green Tea ( drink ) , which is  similarly prophesised as beneficial in Dieting.

   However, the Green Tee Extract I am using is not so insignificant in the Kcal which I have been able to get some details on. Hence I am keen now  to check up on the Green Coffee Extract. I have not been able to find any clear Kcal, etc. Nutritional value on that yet, hence my question here.

  I have had in the past many Green Tee Supplements and think I am getting fairly happy with the Nutritional Values I have which are based partly on what I have from manufacturers and partly what I am able to include, or rather add, for the things like capsules that sometimes may not be included in values manufacturers give. ..my other Thread a few down from this one in this Sub Forum is getting that fairly well covered, i think. 

  Green Coffee Extract is a bit new to me. It appears just now in a Product combined with the Choline and Chrom Picolinate which I also asked about in this Forum recently.

_....

.  So what would our body use them for?

I am not sure if you are asking me a question there? If so... - At the moment I am just  trying ( struggling )  to keep the best “control” and record of what my Wife is consuming, along with carefully monitoring the resultant body  weight.
We still take guidance from Dieticians, and Supplement Experts, and follow sometimes their suggestions. This “Green Coffee Complex” was the latest!!- I take most of the claims slightly with a bit of salt, but here i think the idea is that on a diet the combination of things  in this  “Green Coffee Complex” will support and encourage a good energy burning metabolism both generally, and in the case of reduced  total intake in the case of a diet , - that is to say it fills in or takes over from other processes that might be reduced due to the reduced consumption. .
 
Briefly, 3 things one seems to come across...
_1)  Generally Green Tee, and Caffeine are described  as “Energizers” generally. I expect this new “Green Coffee Complex” could be similarly characterised. But the Chlorogenic acid is new to me.. so i could have this wrong..
_ 2)   This contrasts with so called “Fat Burners” which are claimed to actually stimulate fat loss. Typically they include things like L-Carnitine.
_3)   A third broad grouping “Ergonomics” are more exotic things and sometimes partly Proteins usually used in the area of bodybuilding, but sometimes also recommended in a Diet to offset the Muscle degradation that unfortunately the human body seems to reduce first in a diet before using up the Fat Reserve.

_....

    The combination of my Wife’s World record ability to live off a small Kcal intake which rewrites all the Nutritional “Burning” Value Theory, along with the increase in Kcal based on my ”investigations” of what manufacturers “leave out” occasionally, does make this info about the minor extra Kcal contribution very helpful to me

Thanks once again

Alan

[Intanjir]

Nutrition marketers can and will create and abuse categories in spectacular fashion. BTW, I think you meant ergogenic instead of ergonomic.

I highly recommend examine.com as a no nonsense starting point with these over-marketed substances.

I see no reason to suppose that chlorogenic acid would be a source of significant calories.

[Doc.AElstein]

Hi Intanjir,
   Thanks for your reply .

.
I see no reason to suppose that chlorogenic acid would be a source of significant calories.

Unfortunately in my unusual case it is helpful to minimise as many uncertainties as possible. On the one hand Arkcon mentioned organic acid and an organic alcohol which leads me to a  7.1 x or 3 x , contribution.  On the other hand he suggested the Human body would do nothing with them so a null contribution as you suggested with Choline
http://www.chemicalforums.com/index.php?topic=85419.msg309423#msg309423
and Corribus suggested with Cellulose
http://www.chemicalforums.com/index.php?topic=83937.msg304274#msg304274
So I am still not sure what to do here – whether to ignore it in terms of
Kcal = 0 x Chlorogenic acid
Or Instead
Kcal = (7.1 to  3 ) x Chlorogenic acid
Or
Kcal = Something x Green Coffee Extract
_..

... I think you meant ergogenic instead of ergonomic..

Thanks, I am not sure how that wrong word crept in. I have corrected appropriately my Files.
_...

...
I highly recommend examine.com as a no nonsense starting point with these over-marketed substances...

Thanks for that. I see at first glance no Nutritional value info there. But it does seem a good source for general info. I just tried searching for the sort of things i have been looking at, and they seem to have some info on all of them. So that is a useful link I was not aware of, Thanks

Alan

[Intanjir]

The body can utilize only a small handful of chemical moieties for energy. There are countless organic acids and alcohols that we cannot utilize for significant energy.
Since we consume so little of it, there is no obvious evolutionary pressure which would have enabled the development and maintenance of a trait to turn this into ATP.
It does not structurally resemble the chemicals we are known to turn into significant amounts of ATP.

Arkcon suggested that this is processed by the liver so that it can be removed by the kidney.
This suggests that the body attaches a highly hydrophilic glucuronic acid moiety to it in order to make the substance as a whole more water soluble so that the kidneys can filter it from the blood.
Each glucuronic acid is made from a glucose so by attaching it for excretion the body is giving up (a small amount) of energy.

[Doc.AElstein]

Hi  Intanjir

The body can utilize only a small handful of chemical moieties for energy. .

Thank you for all that. There is a an enormous amount of knowledge behind all that you have said there, and never the less you have “translated it” all in a way I think I can understand. I am very grateful.
_..

..
Each glucuronic acid is made from a glucose so by attaching it for excretion the body is giving up (a small amount) of energy.

So, just for completenes, would a good "guess" or estimate be that for my 
Kcal = "Something" x Chlorogenic acid
the " Something" could be
a bit of 3 ( 3 for organic acid )
or
a bit of 4.1 ( 4.1 for the "stolen" bit of glucose )

If so, Could you make for me an estimate of this figure, ( 1, 2, 3 etc). I expect it is a question of how much glucuronic acid or glucose is required per Chlorogenic acid.
I do appreciate working out that would be a worthy Homework for a Freshman. I would attempt if I were one! Unfortunately I have no Chemistry background ( and as I think Groucho Marx said , or similar “ There is never a Freshman around when you need one” .. Lol      Lol  )
I only need an approximate figure, if you have the time

Thanks again
Alan Elston

[Intanjir]

There is no reason to use the "organic acid" calorie value as we do not think this chemical is utilizable for energy.
Many if not most of the utilizable "organic acids" are intermediates of the citric acid cycle and this chemical does not even resemble these.
For the most part we cannot utilize organic acids as energy sources. They were not often common enough in food for us to evolve such a capability.
Those we can utilize tend to be utilizable because they happen to be an derivative chemical that we create as we utilize the energy bearing substances that are actually common in food.

A good example illustrating this is tartaric acid. This strongly resembles citric acid cycle intermediates and certainly has plenty of potential energy which could be utilized if only we had the machinery. However, we just don't have this machinery. Whereas many bacteria are chemical generalists with the ability to utilize an impressive repertoire of chemicals, mammals are adapted for a relatively small set of nutrients.

Now we do have fairly general systems for processing strange chemicals in order to detoxify them. The processing of alcohols, ketones and aldehydes by the liver will often yield ATP, but (with the exception of ethanol) the amount is almost always small enough to ignore. Also, as already mentioned, the liver will improve the kidney's ability to filter a substance by increasing the blood solubility of that substance via glucuronidation. This costs calories but in order to estimate how many you would need to estimate the fraction of the substance that was glucuronidated. Then it would be reasonable to roughly estimate this contribution as -1 x proportion glucuronidated x calories from one mole of glucose x moles of chlorogenic acid. You wouldn't directly use 4.1 as that is the calories from one gram of glucose.

However, capturing this level of detail is extremely tedious and almost painful. The expected contribution is so low compared to the general precision level of calorie estimate calculations that it is just a waste of time. We are talking about paying attention to something on the order of 1 calorie when your final estimate is going to be some number ± 100 calories or so.
I suppose it is useful as a purely pedogogical exercise, but including every such thing in any final analysis disproportionately complicates your model without providing you tangible benefit.

[Doc.AElstein]

Hi  Intanjir
Thank you once again. I have reviewed once what you have written, and will sleep on it and certainly read through again. I am learning a lot here. Thanks.

Some initial comments and feedback:

.. it would be reasonable to roughly estimate this contribution as -1 x proportion glucuronidated x calories from one mole of glucose x moles of chlorogenic acid....

  This is extremely interesting. Since this morning ( yesterday now! )  I was thinking of writing a follow up here and suggesting as .

. for the "stolen" bit of glucose ).

. – As it was stolen I was thinking may be it takes away what would have been used for energy, leading to a negative contribution ( and BTW, this could possibly be one “excuse” from the manufactures / suppliers of such products to market them as aiding in weight reduction )... I was too embarrassed that I might be talking in my ignorance total rubbish with that so I did not Post. .. And I re - read this a few times, 

.
Each glucuronic acid is made from a glucose so by attaching it for excretion the body is giving up (a small amount) of energy.

... and was not sure in “giving up” meant burning in the process, or as I think it is now clear to me, “giving” up is “losing” That is clear to me now. Thank you.

Further, This I think

....You wouldn't directly use 4.1 as that is the calories from one gram of glucose..

Is also somewhere along the lines of my

..a bit of 3 ( 3 for organic acid )
or
a bit of 4.1 ( 4.1 for the "stolen" bit of glucose )
.

So again it is helpful for you to confirm it with some technical detail but in a “language” that I can understand.

_..
I do agree with you that in this case, even in my extreme requirement,  I am really looking at a very insignificant number.

I do however find it interesting as a academic exercise, and should I get the time sometime in the future I will do that and feed back here. I did do similar for very simple things like the Na in NaCl based on the relative Moles etc.
I am just needing to move on a bit now and not get too bogged down at these points.. ***
For now I will take i think a  x -1 ( or x  -.7 or x – 1.3 )  contribution just to “remind me” of what I have learnt in this Thread.
– I have developed a Program which does all the calculations so it is just a case of whether I leave a variable set “Empty” or include the –ve  figure in it. My program goes very quickly  through and calculates the Kcal contributing from every “Thing” that I have an entry for
_...

. capturing this level of detail is extremely tedious and almost painful. .
I suppose it is useful as a purely pedogogical exercise, but including every such thing in any final analysis disproportionately complicates your model without providing you tangible benefit.

Yes I feel the pain sometimes.. Lol.    I wonder sometimes if I am a bit of a masochist.  Lol
I realise I am being a bit pedantic with all this. However every little bit helps to reduce the final sum of uncertainties and total error.
Your help has been extremely useful. It is a shame I cannot help so much in this Forum in return. ( I have a few thousand Posts in other open Forums  ( Excel Forums ) where  I mostly help. Unfortunately chemistry is way outside my Knowledge area. )

Thank you once again.
I am very grateful. I often get bogged down and stuck  at these points. ***
Your help is helping me to move back on with my project.
Alan
Doc.AElstein


_....
P.s. A last thought for me to sleep on...
I am wondering now if this

.
Many if not most of the utilizable "organic acids" are intermediates of the citric acid cycle and this chemical does not even resemble these.
For the most part we cannot utilize organic acids as energy sources. .
A good example illustrating this is tartaric acid. This strongly resembles citric acid cycle intermediates and certainly has plenty of potential energy which could be utilized if only we had the machinery. However, we just don't have this machinery. ..

Means that I am in error here
http://www.chemicalforums.com/index.php?topic=83937.msg304488#msg304488
http://www.chemicalforums.com/index.php?topic=83937.msg304276#msg304276
with my (3 x  27.44)  = 3 x Tartrate ?
At that time I saw conflicting suppliers total Kcal calculations suggesting that  some did and some did not include this contribution ??
http://www.chemicalforums.com/index.php?topic=83937.msg304322#msg304322
http://www.hansa-xsport.de/shop/HansaXsport/L-Carnitin-und-Sonstige/L-Carnitin-Pur-100::42.html

I expect in my ignorance I am reading these two things wrongly. Apologise for that I am a bit confused; they appear to be in conflict.

There is no reason to use the "organic acid" calorie value as we do not think this chemical is utilizable for energy...
Those we can utilize tend to be utilizable because they happen to be an derivative chemical that we create as we utilize the energy bearing substances that are actually common in food.
A good example illustrating this is tartaric acid. This strongly resembles citric acid cycle intermediates and certainly has plenty of potential energy which could be utilized if only we had the machinery. However, we just don't have this machinery. .

. I don't really know how many kcalories are in a gram of tartarate but using the generic value of 3 for organic acids seems fine. .

.
Tartaric acid has caloric value. Perhaps around 3kcal/g.
...

I Guess this remains a Grey Area where in this case we are not sure If the body “burns” them. Hence the Suppliers of such supplements can use this uncertainty to their advantage !!  lol.   

[Intanjir]

Oh! In the January thread I had never before considered the caloric value of tartaric and I apparently (wrongly) assumed it was one we could utilize no doubt due to its structural similarity to citric acid cycle intermediates. I then completely forgot about this. When the question came up again in the April thread I determined that it had negligible calories based on information from the HMDB entry. So, this is clearly a learning experience for me as well.

This certainly looks like one of those small organic acids that the body will use for energy, having nothing but hydroxyls and carboxyls. However this does not seem to be the case. It appears to be predominately metabolized by intestinal microbes, and what does get absorbed is probably mostly excreted intact in the urine. I would say this has negligible calories.
I base this off of the entry in the Human Metabolome Database which may be a useful resource for you:
http://www.hmdb.ca/metabolites/HMDB00956

When I said you wouldn't directly use 4.1, I meant that you needed to calculate the kcalories per mole of glucose and that you might use 4.1 in this side calculation. I wasn't referring to the organic acid contribution since I think that that would be best estimated as 0.

It would be darkly hilarious for a supplement marketer to claim that a substance would help you lose weight because the liver sacrifices energy in order to detoxify it via glucuronidation. Never mind that the ~1g of a pill would only amount to a kcalorie loss in the single digits.

Hmm a tangent question: If someone was given a large amount of a benign substance that was predominately glucuronidated would they readily become dangerously hypoglycemic or would the liver downregulate glucuronidation to avoid this?

[Doc.AElstein]

Hi  Intanjir
Thanks for coming back to clear that up.

Hmm. Looks like I need to go back and reconsider that (3 x  27.44) contribution from the L-Charitin Supplement. Clearly at least one manufacture was considering it, another not.
I am getting the strong feeling to set it to (0 x  27.44) , or maybe some “guess" in between!!   etc.
I guess I should take some consolation that despite my very limited knowledge in this area that some of the People responsible for marketing these things are not much further.
( Could also be that they have not for some reason had the benefit as I have of someone like you to give your thinking on this one ! )
_..

..
Hmm a tangent question: If someone was given a large amount of a benign substance that was predominately glucuronidated would they readily become dangerously hypoglycemic or would the liver down regulate glucuronidation to avoid this?

Sounds an interesting and possibly important question. Beyond my abilities to comment.
But I was wondering how someone , as my Wife, who has to take in so little to have any chance to lose weight, would respond to something that tries to “steal” Glucose, when she has very little there?
Maybe that is due to my naivety very stupid.
Or it gives the manufactures another abstract idea to market their product. – The product will encourage the body to change fat into carbohydrate ?? . Of course we all know the opposite of the body changing Carbohydrate  ( especially the Sugars) into Fat reserve is commonly thought to be one of the most common causes of overweight.

...
It would be darkly hilarious for a supplement marketer to claim that a substance would help you lose weight because the liver sacrifices energy in order to detoxify it via glucuronidation. Never mind that the ~1g of a pill would only amount to a kcalorie loss in the single digits..

Possibly the manufacturers answer to that might be that it “starts some process of, which then continues.” Often in a Diet getting the Body to start using its fat reserve can be a stumbling point.
_...

More “Food” ( or micro Nutrition ideas, Lol ) for thought

Thanks again
Alan and Petra Elston