Separating PUFA From Coconut Oil

yerrag

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Fully saturated fats cannot be trans-fats. This only occurs when they are not fully hydrogenated. A fatty-acid still needs at least one double bond (C=C) to have a cis or a trans orientation.

It is possible to produce fully saturated fats from canola oil, but this is not generally done. The partial hydrogenation of canola oil is certain to produce unnatural trans fats.

I think partial hydrogenation is more common because of the demonization of saturated fats and because they want margarine to closely approximate the consistency of butter. A stiffer fully-hydrogenated margarine might confuse consumers (they are confused already if they buy margarine in the first place!).
That really explains it much more succinctly Travis. Thanks a lot.

It makes a lot of sense. I recall talking with a friend whose family owns the Spring brand of refined coconut oil and hydrogenated coconut oil. She calls the hydrogenated coconut oil "lard," and that means the product is solid even in our hot local climate, as that is how lard is.

I should make a point of remembering that full hydrogenation takes away the trans-fattiness of an unsaturated fat undergoing hydrogenation.
 

yerrag

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Travis

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Nutritiondata.com only lists three vitamins in coconut oil besides the coconut triglycerols: Vitamin K, Vitamin E, and phytosterols. These are fat-soluble and exist in trace amounts (ppb). All three have double bonds and would be hydrogenated along with the tryglycerols. The phytosterols would be turned into phytostanols, which also exist naturally in foods, and Vitamin K would likely be rendered inoperable and potentially toxic.

Nutritiondata.com also has an entry for hydrogenated coconut oil that lists .6% trans-fat and .3% mono-unsaturated fat. Certain brands may vary according to the production process.

I would be happy to consume separated coconut oil, but hydrogenated coconut oil is beginning to sound worse and worse the more I think about it. You trade 1.8% PUFA for .6% trans-monoenoic fatty-acids and parts per billion amounts of Nickel and Iron.
 
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yerrag

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I must have missed something. What is separated coconut oil?

I'm content with taking vco as a supplement. Since Ray Peat isn't that much concerned about the slight amount PUFA in it, I would just stick with using virgin coconut oil. Since virgin coconut oil can come from either fresh mature coconut meat or from copra, which can be rancid, knowing by smell and taste what good virgin coconut oil helps, as you can't really trust the label at times. Good virgin coconut oil is pleasant to swallow, having a delicate taste of coconut. Some people don't like the flavor, and some people, like me, just don't like taking any oil directly from a teaspoon. But if you do some comparison tasting, the inferior virgin coconut oil tastes slightly rancid. But good vco can also taste rancid, after it's been in storage for an extended amount of time, usually exceeding a year. I think it's because of the PUFA content, however slight it still will affect the flavor.

I used to just go straight to the coconut meat, have it grated, and then blend it with fruit shakes. It tastes really good, puts some texture into the shake, especially the crunchiness. But since learning that fiber produces endotoxins, I've refrained from doing so because coconut meat is rich in both soluble and insoluble fiber.

The jury's out on whether coconut meat is the kind of fiber that would produce endotoxins though, as in another thread a post or two speaks well of their experience in eating coconut meat. Sorry for this aside.
 

Travis

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Separated coconut is simply coconut oil with the unsaturated fats separated. This is the thread title. There is an easy way to do this, but it involves ~$200 worth of materials. Check out this page on silver-ion chromatography from the Lipid Library.

This has become a standard procedure for lipid separation, and the elution orders are noted here. The saturated triglycerols will elute faster than the unsaturated triglycerols because the double-bonds complex with silver which slows their migration through the column.

Here is elution time vs concentration (and composition). The saturated fats clear the tube in under under ten minutes, while an all tri-unsaturated triglycerol takes 50 minutes.
chromatography.png


It is certainly doable if you are committed enough. 18'' liquid chromatography column here for $60, and some material to pack it with here for ~$80. This is sulfonated polystyrene cation exchange resin at ~50 mesh, and you would also need to buy silver nitrate. Here is a patent from 1982:
Partial argentation resin chromatography for separation of polyunsaturated fatty esters
Mixtures containing polyunsaturated fatty esters are fractionated by partial argentation resin chromatography, in which the mixture is eluted through a column packed with a partially silvered sulfonic acid ion exchange resin.
Simple enough description for the invention.
Moreover, catalytic hydrogenation as practiced in the production of much of our edible oils creates a complex array of positional and geometric isomers, thereby further increasing the difficulty of fractionation.
Exactly. He is on our side. Hydrogentaion is the devil.
Later, Emken et al. [JAOCS 41: 388-390 (1964)] used a silver-saturated macroreticular cation exchange resin and a single-solvent eluant to obtain relatively pure fractions of both saturated and cis and trans monounsaturated compounds from an esterified and slightly modified olive oil.... Similarly, Emken et al. [JAOCS 55(7): 561-563 (1978)] teaches that with a high surface area resin, mixtures containing saturates, as well as mono-, di-, and triunsaturates, can be readily resolved,
...can be readily resolved. He also talks about the mesh size.
The resins for use herein are sulfonated, crosslinked, polystyrene resins, otherwise known as sulfonic acid macroreticular cation exchange resins....The wet particle size of these resins are preferably in the range of about 40-400 mesh....40-60 mesh resin permits more rapid elution and is effective for mixtures of fairly dissimilar esters
And now he talks about how to 'silver' the resin.
The partially argentated resins of this invention are most readily prepared by a batch process in which the predetermined equivalents of silver ion are added to an aqueous slurry of the resin and stirring is continued until equilibrium. Silver nitrate is the preferred ion source and the Ag+ incorporation is described by the equation: RSO3 H+AgNO3 ⃡RSO3 Ag+HNO3,
This process might also require a liter or two of ethanol (everclear) to help elute the coconut oil.

If someone were to actually this; they would earn about 1,000 RPP (Ray Peat Points) for their commitment to avoiding PUFA and judicious use of technology.
 
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X3CyO

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Okay, so normal coconut oils saturated fat allows unsaturated fats to coexist without turning rancid.

Now heres another question then;
If you fry foods that contain unsaturated fats in coconut oil, would the coconut oil dilute the polyunsaturates enough to prevent damage to the body?
 

Travis

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Okay, so normal coconut oils saturated fat allows unsaturated fats to coexist without turning rancid.

Now heres another question then;
If you fry foods that contain unsaturated fats in coconut oil, would the coconut oil dilute the polyunsaturates enough to prevent damage to the body?
Good question. If you deep-fry something in coconut oil, it would be protected from atmospheric oxygen. If you deep-fry something in CANOLA oil, then there could be active lipid radicals and lipid peroxides in the CANOLA oil that could react with PUFAs in the food.

But even deep-frying something in coconut oil might create high enough temperatures to oxidize the PUFAs in the food anyway by using oxygen found in the food itself (from water?).

But even in this were the case, you would have much less PUFA in the final product using coconut oil that deep-frying something in CANOLA oil.

You could make the case that the ratio of SF/PUFA is important. In that case, the extra saturated fat consumed in coconut oil might competitively inhibit cellular membrane uptake of PUFA.

From a practical standpoint, cooking with coconut oil would be the best no matter what way you look at it. But I don't think that deep-frying anything, even in coconut oil, is going to make the food healthier.
 

yerrag

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Adding to what Travis says, using refined coconut oil would be better than using virgin coconut oil to deep-fry, as there is much less PUFA in the refined coconut oil.
 

Wagner83

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Yes I have not seen anyone do any research on this, overall it's probably more a question of balance and pros and cons of each food rather than finding the perfect foods .
I ate a lot of coconut oil yesterday and felt anxious/pretty low which I have not in a while. Half of coconut oil is lauric acid, who knows if it may be relevant to the point of feeling a difference in well being.
 

yerrag

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I ate a lot of coconut oil yesterday and felt anxious/pretty low which I have not in a while. Half of coconut oil is lauric acid, who knows if it may be relevant to the point of feeling a difference in well being.
I suppose it's because the medium chain fatty acids of coconut oil, such as lauric acid, go directly into the bloodstream. Because of the quantity you had, the fatty acid was instead used by your body, leaving glucose unused in your bloodstream. Your blood sugar went up, and the insulin response to it caused the blood sugar to go down. With your blood sugar lowered, you felt the way you did. Just a guess. I've had that happen to me before, but I couldn't figure out why. Now that you asked, and knowing about Peat's ideas, I can take a stab at it.
 

Agent207

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I suppose it's because the medium chain fatty acids of coconut oil, such as lauric acid, go directly into the bloodstream..

Lauric acid doesnt do that, just the C10 and shorter chain fatty acids. Lauric is C12 but people use to confuse this because is called a mct when it really is not, in regard to metabolism.
 

yerrag

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Okay. So it's only short chain fatty acids that will go past the liver and into the bloodstream? But how do you classify lauric acid if it isn't a short chain fatty acid, nor a medium chain fatty acid? Please clarify.
 

Travis

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I think he means that it is a medium chain fatty-acid from a molecular standpoint, but from a biological standpoint, it it metabolized more like a long-chain fatty acid.

I apologize if I have misinterpreted Agent207.

Dr. Dayrit disagrees however:
Coconut oil is rapidly metabolized because it is easily absorbed and lauric acid is easily transported. Detailed studies have shown that the majority of ingested lauric acid is transported directly to the liver where it is directly converted to energy and other metabolites rather than being stored as fat.
The Properties of Lauric Acid and Their Significance in Coconut Oil
Journal of the American Oil Chemists' Society
 

yerrag

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I think he means that it is a medium chain fatty-acid from a molecular standpoint, but from a biological standpoint, it it metabolized more like a long-chain fatty acid.

I apologize if I have misinterpreted Agent207.

Dr. Dayrit disagrees however:
The Properties of Lauric Acid and Their Significance in Coconut Oil
Journal of the American Oil Chemists' Society
Nice one Travis.

From the article: "The presence of ketone bodies in the blood stream induces an increase in insulin secretion and hypoglycaemia. Feeding an oral load of MCT (C6–C12) to rats, Bach and co-workers [30] observed a decrease in plasma levels of lactate, pyruvate and glucose together with a slight increase in plasma insulin levels. "

Why does the presence of ketones bodies induce an increase in insulin secretion and hypoglycemia?
 

yerrag

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Lauric acid doesnt do that, just the C10 and shorter chain fatty acids. Lauric is C12 but people use to confuse this because is called a mct when it really is not, in regard to metabolism.
Taken from the link above by Travis:

"Overall, studies have shown that lauric acid has properties similar to capric acid (C10) and distinctly different from palmitic acid (C16). Further, the metabolic properties of triglycerides that contain C6–C12 are distinctly different than triglycerides with fatty acids C14 and longer. "
 

Travis

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@yerrag
I suppose it's because the medium chain fatty acids of coconut oil, such as lauric acid, go directly into the bloodstream.
In a way. Medium chain triglycerides are rapidly oxidated into acetyl-CoA, which is a transport molecule for ketones. They call these ketone bodies and can be used for energy. This is all explained in the article I found called The Properties of Lauric Acid and Their Significance in Coconut Oil. You went on to say:
Because of the quantity you had, the fatty acid was instead used by your body, leaving glucose unused in your bloodstream. Your blood sugar went up, and the insulin response to it caused the blood sugar to go down. With your blood sugar lowered, you felt the way you did. Just a guess. I've had that happen to me before, but I couldn't figure out why. Now that you asked, and knowing about Peat's ideas, I can take a stab at it.
The authors seem to agree with you. Here is what they say in the paper:
The presence of ketone bodies in the blood stream induces an increase in insulin secretion and hypoglycaemia. Feeding an oral load of MCT (C6–C12) to rats, Bach and co-workers [30] observed a decrease in plasma levels of lactate, pyruvate and glucose together with a slight increase in plasma insulin levels. LCT (≥C14) had no effect on these plasma levels which suggests that LCT are not able to generate ketone bodies efficiently.
These authors place Lauric (C₁₂) acid in the category of MCTs. Myristic (C₁₄) acid and longer they consider LCTs. Before 1982, everyone considered MCTs as only Capric (C₁₀) and Caprylic (C₈) acids. Bach and Babayan reviewed the metabolism of Lauric acid in 1982 and decided it fit better in with the MCTs than the LCT. You also said in a later post.
Okay. So it's only short chain fatty acids that will go past the liver and into the bloodstream?
It is actually the longer fatty acids that bypass the liver. Here is a quote:
Under conditions where only one fatty acid is administered, they determined that 72 % of lauric acid, 58 % of myristic acid, 41 % of palmitic acid, and 28 % of stearic acid bypassed the lymphatic pathway. That is, LCFA have a greater tendency to enter the lymphatic pathway than lauric acid. This experiment also showed that lauric acid may also enter the lymphatic pathway in the absence of longer chain fatty acids.
I looked up the lymphatic pathway. My understanding is that MCTs are quickly oxidized in the liver to form an Acetyl-CoA-ketone adduct, where the ketone comes from the fatty acid. This happens fast, and happens fastest in the order of decreasing chain length. The longer saturated fatty acids diffuse through the intestinal lymph directly into the blood and attach themselves the chylomicrons in the order of increasing length (according to rats anyhow). Lauric acid, being longer than the others MCTs, will do this a bit more readily than the other MCTs, but it can also go through the liver.
The main biological reason why he puts Lauric (C₁₂) acid in the MCT category is probably because it doesn't need active carnitine transport to diffuse. Here it is in their own words:
...a lengthening of the carbon chain by two carbons slows down the rate of diffusion by about 100 times [27]. Consistent with this, Lauric acid has been shown to diffuse freely across the mitochondrial membrane, while longer chain fatty acids require carnitine [28]. Thus, Lauric acid can be rapidly transported into the mitochondria via physical diffusion or with assistance from carnitine.
 
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yerrag

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It is actually the longer fatty acids that bypass the liver.
I stand corrected. The MCT's get processed by the liver and produces ketone bodies right? The ketone bodies go into the bloodstream and are absorbed by extrahepatic tissues and converted into Acetyl-CoA, and used in the production of energy.

The authors seem to agree with you. Here is what they say in the paper: The presence of ketone bodies in the blood stream induces an increase in insulin secretion and hypoglycaemia. Feeding an oral load of MCT (C6–C12) to rats, Bach and co-workers [30] observed a decrease in plasma levels of lactate, pyruvate and glucose together with a slight increase in plasma insulin levels. LCT (≥C14) had no effect on these plasma levels which suggests that LCT are not able to generate ketone bodies efficiently.
I'm thinking that since taking coconut oil would induce insulin secretion, one should probably not take coconut oil by itself, especially in a large quantity, without accompanying it with some carbohydrates.

@Wagner83, did you have some carbs along with the coconut oil you took?
 

Wagner83

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Yep always quite a lot of carbs, potatoes, fruits etc.. It may have been a sheer coincidence, I'll just experiment more.
 

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