Stearic acid and Magnesium Stearate update

How much stearic acid is in chocolate? 

We were looking at a chocolate bar yesterday. Dark chocolate is supposed to be a health food. 

As we happened to be nutritionists, the topic of the chocolate bar's stearic acid content came up, which is a controversial fatty acid. So I did a little calculating...

The bar in question is a 72% Dark Chocolate from Belgium, with the fat coming almost exclusively from cocoa butter (except a tiny bit of lecithin; but typically under half a percent is used in chocolate manufacturing, according to Chocolate University Online). The bar weighs 1.65 oz (47 grams), contains 280 calories, and is labeled as being one serving.  

The product label says that the bar supplies 19 grams of fat, including 12 grams of saturated fat. Since about one-third of cocoa butter’s fat - and over half of its saturated fat - is known to be stearic acid, a one-bar serving of this chocolate conservatively can be assumed to contain at least 6 grams of stearic acid, which is equivalent to 6,000 milligrams (mg.). 

How does that compare to the amount of stearates commonly found in tablets and capsules?

That amount in the single small chocolate bar is equivalent to more than 1,000 tablets or capsules worth of stearate content, assuming the highest likely amount of stearic acid or magnesium stearate was used in those pills. Five milligrams is the highest I've seen on supplement Master Formulas, but many products use less or none. (Assuming 5 mg. per pill x 1,000 pills = 5,000 mg. of stearates per bottle).

So if someone had a jumbo, family-sized bottle of a thousand pills, each containing a few milligrams of stearic acid or magnesium stearate that's primarily stearic acid, that whole bottle would contain less stearic acid than a single serving 47 gram dark chocolate bar. 

Doesn't that put stearic acid consumption into perspective? Each pill contains less than 1% of what you'd get in a serving of chocolate. 

How much stearic acid is found in other common foods?

Butter contains about 12% stearic acid, by weight, as do the average beef, pork, or lamb product. Healthy olive and coconut oils contain between 2-3% stearic acid. Salmon oil naturally contains about 4% stearic acid. 

More fun facts:

• Milligrams (mg.) are thousands of a gram; micrograms (mcg.) are millionths of a gram.
• Stearic acid tends to be converted into oleic acid in the liver.
• Stearic acid is abundant in the food supply as a natural component of the fat in those foods; milk and meat fats are the primary sources. 

How much magnesium is in magnesium stearate?

The molecular weight of stearic acid (Octadecanoic acid) is 284.484 grams/mol. There are 2 stearic acid molecules in one molecule of magnesium stearate, which has a molecular weight of 591.257 grams/mol. The molecular weight of magnesium is about 24.305 grams/mol. So the amount of magnesium in a 5 mg portion of magnesium stearate is about 200 micrograms (not milligrams); about half of one one-thousandth (half of 1/1,000 or 0.0005 or 0.050%) of the 400 milligram RDA. That's also 1/20th of a percent of the RDA. 

So the amount of magesium in a pill containing magnesium stearate is negligible; it would be insignificant unless another magnesium source is added. Magnesium stearate is a form of chelated magnesium that contains only about 4% elemental magnesium by weight and about 96% stearic acid.

REFERENCES:

• Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D. A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr. 2001 Feb;55(2):88-96. PubMed PMID: 11305631.
• https://pubchem.ncbi.nlm.nih.gov/compound/5281
• https://pubchem.ncbi.nlm.nih.gov/compound/magnesium_stearate
• https://pubchem.ncbi.nlm.nih.gov/compound/5462224
• http://www.chocolateuniversityonline.com/lecithin-in-chocolate/ 
• https://www.scientificamerican.com/article/why-is-dark-chocolate-good-for-you-thank-your-microbes/
• http://www.cnn.com/2017/10/06/health/dark-chocolate-healthy-food-drayer/index.html
• https://www.nowfoods.com/now/nowledge/stearic-acid-and-magnesium-stearate
• https://epi.grants.cancer.gov/diet/foodsources/sat_fat/sa.html
• http://honestnutrition.blogspot.com/2008/04/myths-about-stearate-risks.html 
• http://spo.nmfs.noaa.gov/Circulars/CIRC276.pdf

Fish Oils: ethyl ester or triglyceride or...?

Most fish oils today are molecularly distilled, changing them from their natural triglyceride forms to ethyl ester (esterified) forms.

Anything stronger than a natural strength fish oil (up to about 30% EPA+DHA combined) is typically concentrated by molecular (vacuum) distillation to allow vaporizing at low temperatures, in the process converting to the ethyl ester form. This allows separation of the fatty acid constituents in order to add back some of the desired omega-3 fatty acids in order to concentrate them up to 60% or higher levels of the oil. This is accomplished by removing undesired fractions that were separated by the distillation, such as cholesterol, triglycerides, and various other fatty acids.

Because of the warming oceans, the naturally occurring amount of omega-3 fatty acids in most fish have declined from historically about 30% to somewhat less. Due to this change, most fish oil supplements containing 180 mg. of EPA and 120 mg. of DHA (300 mg. combined in a 1,000 mg. fish oil capsule) now need to spike the potencies by adding additional EPA and DHA fractionated from the original oils by molecular distillation. It is now unusual to find even a low strength fish oil capsule that is not at least partially molecularly distilled into ethyl ester forms. 

Some of these distilled oils are then partially reconverted to a triglyceride form in a process called reconversion that involves adding back 20% or more triglycerides to the esterified fatty acids to try to reattach the triglycerides to the fatty acids with enzymes. This imperfectly produces a highly processed combination of both triglyceride and mono-and-diglyceride forms of omega-3 with many of the original oil’s natural constituents deliberately removed (cholesterol, omega-6, omega-9, stearates, et al). This newly engineered combination is called a reconverted triglyceride form (rTG) containing typically at least 60% triglyceride form fatty acids that’s distinct from the original triglyceride (TG) form, but is as far from the original triglyceride form as can be produced by intentional chemical manipulation. Numerous brands offer this rTG form and inaccurately call it a natural triglyceride form, when it is in fact far removed from that oil.

This is done because of a prevailing and largely disproven belief that the natural triglyceride form is best. That's certainly untrue for cardiology and the form has recently been shown to be largely irrelevant to absorption and efficacy in general. 

Is Carrageenan Safe or Dangerous?

Undenatured carrageenan is a natural stabilizer, binding agent, and emulsifier used in products such as toothpaste in place of SLS and other truly undesirable ingredients commonly used in mass market products. It is also used in some vegan-friendly softgel capsule material as an alternative to animal-derived gelatin.

There is an Internet myth that carrageenan is unsafe; due primarily to confusion with a so-called “denatured carrageenan” polymer that is actually poligeenan, a heavily processed low molecular weight seaweed derivative currently used only as an x-ray imaging component. Poligeenan, previously used in pharmaceuticals, is quite different from the undenatured high molecular weight material that we use. Due to the safety concerns over poligeenan, regulations routinely require the carrageenan added to foods to have high molecular weight to ensure its integrity. But there are no unresolved safety concerns with undenatured carrageenan. 

Carrageenan has been thoroughly vetted by national and international public health authorities over a number of decades, even recently in response to the ongoing blogger-driven controversies, so there is no remaining basis of concern. Even its use in infant formulas was recently reconfirmed to be safe, and it’s helpful in distributing the nutrients more evenly to avoid the settling out that could otherwise cause uneven nutrient intake when a bottle is only partially consumed. 

After repeated investigations, the evidence for carrageenan safety is stronger than ever. Carrageenan is extremely safe and present in a number of healthy seaweeds; only the denatured form of carrageenan - a drug - is toxic. 

References:        

·        Public health and carrageenan regulation: a review and analysis. Borowitzka et al. (eds.), Nineteenth International Seaweed Symposium. DOI: 10.1007/978-1-4020-9619-8_8. Developments in Applied Phycology.

·         http://www.ncbi.nlm.nih.gov/pubmed/24467586

·         http://www.foodproductdesign.com/blogs/formulating-foods/2014/07/fao-who-carrageenan-safe-in-infant-formula.aspx

·         http://www.ncbi.nlm.nih.gov/pubmed/12389870

·         http://www.foodinsight.org/blogs/why-you-should-care-about-carrageenan

Is Sorbitol Natural?

Sorbitol is a "sugar alcohol" that occurs naturally in various fruits (apples, peaches, nectarines, plums, grapes, cherries, apricots, pears, rose hips, berries, dates, coconut) at levels of 1% or more. Wasabi can contain up to 11%, and common dried fruits (prunes, pears) almost the same level. Of course, beer would be expected to have small amounts, as well. 

Sorbitol can be commericially produced from glucose. Non-GMO sources are available. 

In higher doses (30-50 grams) sorbitol can be laxative, but it is a useful non-cariogenic sweetener that doesn't promote dental caries (cavities).