Fat Soluble Vitamin E

Posted on June 9, 2019 by Cat

By Cat, June 2007; Updated June 2019

There are two main types in the fat-soluble vitamin E family: tocopherols and tocotrienols, each of which is divided into four sub-types: alpha, beta, gamma and delta, for a total of 8 sub-types in the family. All have some vitamin E activity; each has its own individual function. According to one manufacturer, only the natural D-alpha tocopherol is maintained in human blood circulation, and is the most potent (link lost).  However, the other forms are believed to increase the vitamin E activity of D-alpha tocopherol; and they all have anti-oxidant power as free-radical scavengers. (8, 9)

Each sub-type can be esterified, either synthetically or in the body. Esterification of vitamin E involves adding a fatty acid to the alcohol group off the main ring; the most common is D-alpha tocopherol acetate (has acetic acid added), which is used in skin creams because it has a longer shelf-life than D-alpha tocopherol. (8, 9, 25)

NOTE:  Consult with your health practitioner before taking any supplements.   Overuse of supplements, just as overuse of drugs, can lead to other health problems, and some supplements can interact negatively with other supplements or drugs.

Remember that the best way to get your vitamins, minerals and other nutrients is from fresh whole foods.

See Vitamins: Intro for

  • Introduction: Vitamins
  • Vitamin Supplementation vs Whole Foods

Functions of Vitamin E

“The main function of vitamin E [primarily D-alpha tocopherol] is to maintain the integrity of the body’s intracellular membrane by protecting its physical stability and providing a defense line against tissue damage caused by oxidation. The intracellular membranes encapsulate the organelles (such as mitochondria, the cell’s nucleus, endoplasmic reticulum, and more) within the cells (18), protecting the movement of neurotransmitters, hormones, etc between the cellular fluid and the organelles.

All isomeric forms of vitamin E are antioxidants that prevent free radical damage in biological membranes.” (12A) The antioxidant ability is common to all the tocopherols and tocotrienols.

Among its many functions are (14, 19):

  • supports the immune system, which fights attacks from viruses and bacteria;
  • aids in red blood cell production and helps your body use vitamin K);
  • regulates muscle growth, nerve repair, fertility;
  • controls how red blood cells get recycled;
  • governs cell membrane health; and
  • important for gene expression.

Is Vitamin E harmful?

In early January of 2005, headlines reading “Vitamin E May Kill You” or similar phrases were broadcast across the world, shocking and scaring people out of taking vitamin E. What is the evidence behind these headlines? The following is from Dr Ron’s article (11).

The information in question comes from research reported at the American Heart Association’s Scientific Sessions, and released on the web site of the journal Annals of Internal Medicine. The researchers concluded that daily Vitamin E doses of 400 international units (IU) or more can increase the risk of death and should be avoided.

This conclusion was based on a meta-analysis of 19 Vitamin E studies that looked at 136,000 patients with heart disease, cancer or Alzheimer’s disease. “It was clear that as the Vitamin E dose increased, so does the all-cause mortality,” stated Johns Hopkins University researcher and associate professor of medicine Edgar R. Miller, MD, PhD.

But was this broad statement justified?

Dr Ron concludes it was not justified; read his article (11) for more.

Potential side effects of Vitamin E, especially from supplements when taken in excess 

This list is from Organic Facts (19):

  • Heart attack
  • Bleeding disorders
  • Prostate and neck cancer
  • Stroke
  • Nausea
  • Diarrhea
  • Weakness
  • Headache
  • Blurred vision

Dietary Sources

Seeds, nuts and grains are the richest natural sources of vitamin E.  (The germ is the plant embryo, and is rich in polyunsaturated oils which require the antioxidant protection of vitamin E to keep them viable).  Without the antioxidant, the oils would be easily oxidized, rendering them of little use to the germinating plant, as well as to the creature who consumes the germ.  For example, whole wheat flour contains wheat germ, and thus also vitamin E.  However, exposure of the ground flour to air overwhelms the available vitamin E and readily oxidizes the fragile oils in the wheat germ.  It also oxidizes the vitamin E (that’s precisely how vitamin E performs as an antioxidant), rendering it inactive.

Sprouted sunflower seeds are one of my favorite seeds that provide vitamin E. I add them to my morning smoothie, and also eat them as a snack.

Nut butters are another great source, preferably made from sprouted nuts.

Seed oils: safflower, sunflower, cottonseed, soy, canola, and corn oils. In these oils, roughly 50% of the vitamin E is in the d-alpha tocopherol form. (12B, 19) Cat’s note: It is important to note that most brands of these are rancid! They are pressed from the seeds at high pressure, which causes oxidation of the oils, also known as rancidity. They are then treated with deodorants to mask the damage done to the oils.  Also, as of the June 2019 update of this posting, soy, canola and corn oils are GMO unless labeled as Organic. If you want to use these seed oils, look for “Organic cold-pressed.”

Olive oil is also a good source of vitamin E, but many brands are not what they claim. I highly recommend only buying those from a named orchard, or labelled as “Organic.” See my article Olive Oil: The Real Deal, or Adulterated/Fake.

Fruits: Avocados are the richest fruit source of vitamin E, followed by the kiwi, nectarines, grapes, and then peaches. Avocados are also the best fruit source of lutein, the compound that protects against cataract formation and macular degeneration. Tomatoes and kiwi are other fruits high in vitamin E. (19)

Veggies: Green leafy veggies, sweet potatoes and yams (19)

Meats: fish such as trout and salmon, and grass-fed meats. (19)

Supplements

Most multi-vitamin and singular vitamin-E supplements contain either natural D-alpha-tocopherol or synthetic Dl-alpha-tocopherol, but don’t include the other members of the family. Also the usual source is from soy oil, but best to avoid that unless non-GMO.

You can also find supplements that contain the full spectrum of tocopherols, but lack any tocotrienols. The argument is that they contribute little to benefit your health, but that is not true. While they don’t have full vitamin E activity, they “exhibit antioxidant protection, especially against lipid peroxidation, therefore rendering powerful support for cardiovascular health.” (16)

According to Dr. Bruce West of Health Alert, Cataplex E2 (from Standard Process) is the best supplemental form of the full-spectrum vitamin E, as it also contains the needed cofactors.  It is best to avoid most commercially available synthetic tocopherols made from tar or  corn oil

Tocotrienol dietary supplements are usually D-tocotrienol extracts from palm or annatto oils. (10A)

Cat’s supplement: I had been taking Now Foods’Advanced Gamma-E Complex (iHerb code NOW-00811), which provides the necessary full range of vitamin E protection because it has a more natural balance of Tocopherols plus a full complement of Tocotrienols. Unfortunately, it contains soy, so I’m switching to “MRM Complete E” (iHerb code MRM-81007) which is non-GMO, and also contains CoQ10, Alpha Lipoic (ALA) and Vitamin C in addition to the full spectrum of tocopherols and tocotrienols.

Natural vs Synthetic Vitamin E

As mentioned above, the vitamin E family contains 4 forms of tocopherol (alpha, beta, gamma and delta tocopherol) and 4 forms of tocotrienol (alpha, beta, gamma and delta tocotrienol). These all differ by the length and placement of hydrocarbon chains attached to the chromanol ring (the 6-point ring at the left-end of the molecule in the sketches below).

  • 1 of the points of the chromanol ring always has an alcohol group (OH) attached (hence the “ol” in chromanol);
  • 3 of the 6 points can have either a hydrogen or a hydrocarbon chain attached; the position(s) of these determine which form (alpha, beta, gamma or delta) is meant. See Wikipedia (10A) for sketches these 4 different structures; the attached hydrogen or hydrocarbon chains are represented by R1, R2 and R3 in the sketches.
  • The remaining 2 adjacent points are also part of a ketone ring (of 5 carbons and one oxygen) attached.

In their natural (D) form, they all have activity; synthetic versions contain 50% of the natural (D) form, and 50% of the un-natural (L) form which has much less activity.

What are “D” and “L” forms?

These forms are known as “isometric types,” an organic chemistry term that refers to 2 or more molecules of the same molecular makeup (same number of carbons, hydrogens, oxygens, etc.) but different structure, either spatial (3-D arrangement of atoms) or structural (order of atoms).

Chemically, vitamin E has two stereo-isomers that are mirror images of each other, called “D” and “L” to distinguish them. Here’s an analogy:

Identical twin men, but each have only 1 arm; the D-twin has only a right arm, and the L-twin has only the left arm. When they face each other they are like mirror images. But in reality, the difference in placement of the arm can affect how they behave and the benefits they provide.

Natural Vitamin E (D-Alpha-Tocopherol)

Natural vitamin E is always “D” type, as D-alpha-tocopherol. The enzyme that makes natural vitamin E always makes the same spacial configuration (using the above example, is always the right-handed man).

Alpha-tocopherol was the first form identified as vitamin E (see image, below).

Synthetic Vitamin E (Dl-Alpha-Tocopherol)

Synthetic vitamin E has two isometric types: D-alpha-tocopherol (D-type) and Dl-alpha-tocopherol (L-type), which are mirror images of each other, and hence are not identical, and have different effects in the body. In fact, the L-form (Dl-alpha-tocopherol) can inhibit some of the good effects of natural vitamin E. (D-alpha tocopherol).

Synthetic vitamin E can be esterified to form eight isomers, but only one of these is identical to natural vitamin E (D-alpha-tocopherol). Essterification means adding a fatty acid to the molecule at  The remaining seven isomers have limited bioactivity in your body and have about half the function of natural vitamin E. See Wikipedia (10A) molecular diagrams.

Tocopherol and Tocotrienol

(images, below, from Wikimedia Commons (10C and10D))

General chemical structure of tocopherols

General chemical structure of tocotrienols.

Both have the chromanol ring structure, with an isoprenoid side chain; the difference is that tocopherol’s side chain is ‘saturated’ (no double bonds), while tocotrienol’s side chain is ‘unsaturated’ with 3 double bonds. (10A)

Cat’s note: R1, R2 and R3 in the diagrams refer to hydrocarbon chains of unspecified lengths.

See Benefits of Tocopherols, and Benefits of Tocotrienols, below.

Benefits of Tocopherols 

As mentioned above, D-alpha tocopherol is the most active, but the other tocopherols also have some activity. The following is from (19, 20) unless noted otherwise.

Tocopherols (in general) are amazing protectors throughout the body, including:

  • protecting from heart disease by limiting oxidation of LDL cholesterol;
  • protecting from disease and oxidative damage caused by free radicals;
  • protecting the skin from the signs of aging, such as wrinkles;
  • preventing brain and nerve cell damage by fighting off free radicals;

They also are beneficial to the body by:

  • improving immunity and metabolism. They stop the development of carcinogenic nitrosamines in our body. This helps in the improvement of our metabolic process.
  • reducing acne, blemishes, and other skin related issues;
  • repairing scalp damage and encourage healthy hair growth;
  • delaying growth of cataracts;
  • slowing the functional decline in Alzheimer’s and dementia patients;
  • fighting fatty liver disease;
  • helping protect the breasts and testes;
  • promoting muscle strength and development;
  • balancing hormones (symptoms of imbalance include: weight gain, PMS, anxiety, weight gain, allergies fatigue and infections of the urinary tract);
  • reducing fatigue and enhancing your level of physical endurance by promoting better blood circulation and strengthening the capillary walls which nourishes the cells.

Benefits of D-gamma tocopherol

The following is from SFGate: Healthy Eating (21) and Life Extension (22) unless noted otherwise.

This is the most common form of tocopherol in the American diet, primarily due to its high levels in corn and soy oils that are used exclusively in processed foods.

Clinical and scientific studies show that (see reference 21 for specifics):

  • Gamma tocopherol lacks one of the electron-donating methyl groups on its chromanol ring, and thus is a somewhat less potent antioxidant than alpha tocopherol. However, gamma tocopherol is better able to trap nitrogen-based free radicals such as peroxynitrite and nitrogen dioxide which damage cells and promote chronic inflammation. (21, 22)
  • It is has more powerful anti-inflammatory properties than the alpha form, especially inhibiting the formation of pro-inflammatory biochemicals called cytokines. (21)
  • It is also more effective than D-alpha form at limiting oxidation of LDL cholesterol, and thus reducing the risk of heart disease. (21)
  • There is an association of low vitamin E status with increased cancer risk. Now cancer-preventative ability has been associated with D-alpha tocopherol; this ability seems to be unique to D-gamma tocopherol. In fact, high doses of D-alpha-tocopherol decrease blood and tissue levels of D-gamma-tocopherol, and thus decrease the reduction in cancer risk. On the other hand, increasing D-gamma tocopherol increases the reduction in cancer risk. (21)

One should not conclude that D-alpha tocopherol is harmful and should be replaced with D-gamma tocopherol because both have benefits. The important thing is to maintain a healthy balance of all tocopherols and tocotrienols (22).

See also:

  • Life Extension: What Makes Gamma Tocopherol Superior to Alpha Tocopherol, pages 1 and 2 (22A, 22B)
  • Healthy Eating: Health benefits of gamma tocopherol (23)
  • NaturalPedia: Gamma-tocopherol Sources and Health Risks (24)

Benefits of Tocotrienols

Tocotrienols provide the following benefits not necessarily provided by d-alpha tocopherol. (17, unless noted otherwise). See also Tocotrienol (dot) org (15A, 15B) for more.

Reduces risk of Alzheimer’s Disease

Five European studies (published between 2010 and 2019), provide conclusive evidence  that low plasma tocotrienols and tocopherols (full spectrum vitamin E) are strongly linked to higher incidence of Alzheimer’s Disease and MCI. They also found that tocotrienols are more potent than tocopherols in preventing Alzheimer’s Disease (15B) – all the more reason to take a supplement that contains all the natural tocopherols and tocotrienols.

Reversal of Arteriosclerosis

Palm tocotrienol complex has been shown in double-blind placebo controlled human study conducted at the Kenneth Jordan Heart Foundation (US) to have the ability to reverse arteriosclerosis. Palm tocotrienol complex has the ability to reverse arterial blockage of the carotid artery and hence, reduce the risk of stroke and arteriosclerosis. The regular tocopherol does not.

Reduction of Serum Total Cholesterols and LDL-Cholesterols

Palm tocotrienol complex was proven in human and animal studies to have the ability to reduce the production of serum total cholesterols. They were reported to inhibit the enzyme HMG-CoA Reductase in the liver that is responsible for the production of cholesterols. The tocopherol has no effect on serum cholesterol.

Superior Antioxidant

Palm tocotrienol complex is a much more potent antioxidant than tocopherol. It has been shown by published research paper that alpha-tocotrienol is 40 – 60 times more potent than alpha-tocopherol in the prevention of lipid peroxidation.

All forms of vitamin E are primarily free-radical scavengers.

Anti-Cancer and Anti-Tumor Properties, especially Breast Cancer

Palm tocotrienol complex, especially delta and gamma-tocotrienol, have been shown to inhibit certain type of cancers especially human breast cancer cells. Palm tocotrienol complex has been shown by six independent research centers in the world to have the ability to inhibit both the estrogen positive and estrogen negative breast cancer cells. In those studies, alpha tocopherol has no effect at all on human breast cancer cells.

Neuron-protection: Protection on Stroke Induced Neuron-degeneration

Tocotrienol has been reported to cross the blood-brain barrier. Alpha-tocotrienol was reported in the Journal of Biological Chemistry to be much more potent than the regular alpha-tocopherol in protecting the brain cells / neurons from glutamate-induced toxicity. For full protection, nanomolar level of tocotrienol was required whereas the regular tocopherol requires micromolar level – tocotrienol is 1000-times more potent.

Fluidity properties of tocotrienols

Tocotrienols, with their unsaturated side chain, allow them to pass through the membrane bi-layer (mainly made up of unsaturated fatty acid) in a more efficient manner and faster rate compared to the all-saturated tocopherols.

Anti-Aging: First Line Protection of the Skin

Diet-derived or topically applied tocotrienols preferentially accumulate at the strata corneum of the skin. Being a more potent antioxidant, it is the skin’s first line of defense against free radicals generated by exposure to environment agents such as sun-rays (UV), ozone, chemicals, etc.

References

References 1 – 6 are common to all my vitamin pages; those specific with vitamins E and K begin with number 7.

  1. well.blogs.nytimes.com/2008/02/06/despite-risks-vitamins-popular-with-cancer-patients/
  2. (6) dailyyonder.com/four-food-groups/2010/03/04/2623
  3. ncbi abstracts (3B – 3G originally cited in Supplements for Insulin Resistance, as numbers 21A – 21F)
    1. (new) ncbi.nlm.nih.gov/pubmed/23183291
    2. (21A in Supplements for IR) ncbi.nlm.nih.gov/pubmed/7622343
    3. (21B) ncbi.nlm.nih.gov/pubmed/6278902
    4. (21C) ncbi.nlm.nih.gov/pubmed/22986984
    5. (21D) ncbi.nlm.nih.gov/pubmed/9169302
    6. (21E) ncbi.nlm.nih.gov/pubmed/3017301
    7. (21F) ncbi.nlm.nih.gov/pubmed/8131066
    8. (9A) ncbi.nlm.nih.gov/pubmed/19091068 for Nutrition Journal, December 17, 2008 on PubMed
  4. Selene River Press, by and about Dr Royal Lee, regarding Dr W. A. Price’s XFactor:
    1. Dr Royal Lee’s original article on Dr Weston A. Price’s XFactor: seleneriverpress.com/historical/dr-royal-lee-on-the-x-factor-of-dr-weston-a-price/; or see the original article: 6sd6hj41ya-flywheel.netdna-ssl.com/images/pdfs/40_weston_price_vitamin_f.pdf (I’ve also saved it as a pdf: CATSFORK > PDF FILES / Price-VitaminF-XFactor_Dr RoyalLee.pdf)
    2. Butter, Vitamin E, and the X-Factor (historical archive of Dr Lee’s article) (seleneriverpress.com/historical/butter-vitamin-e-and-the-x-factor-of-weston-a-price/)
    3. Lectures of Dr. Royal Lee, Vitamin News (seleneriverpress.com/shop/lectures-of-dr-royal-lee-volume-i-pdf-ebook/
    4. Vitamin News, a collection of all the biannual issues in one book: (seleneriverpress.com/shop/vitamin-news/
    5. SRP Historical Archives:  seleneriverpress.com/srp-historical-archives/
  5. Articles on The X-Factor of Dr. Weston A. Price:
    1. (5) realmilk.com/health/x-factor-vitamin-k2/
    2. (6) blog.radiantlifecatalog.com/bid/59999/The-Mystery-of-X-Factor-Butter-Oil-and-Vitamin-K2-Solved
  6. More articles by Dr. Royal Lee: soilandhealth.org/wp-content/uploads/02/0203CAT/royal.lee.lets.live.articles.htm
  7. Mercola: differences from vitamin b list begins here
    1. (A7) articles.mercola.com/sites/articles/archive/2008/12/23/important-cod-liver-oil-update.aspx
    2. (D1) articles.mercola.com/sites/articles/archive/2008/12/27/important-vitamin-d-update.aspx
    3. (D2) articles.mercola.com/sites/articles/archive/2011/12/14/study-shows-vitamin-d-cuts-flu-by-nearly-50.aspx?e_cid=20111209_DNL_artTest_C5
    4. (D6) articles.mercola.com/sites/articles/archive/2011/12/19/why-are-cancer-cases-rising-by-nearly-50-in-the-next-20-years.aspx
    5. (D7) articles.mercola.com/sites/articles/archive/2009/12/01/Important-New-Vitamin-D-Research-Papers.aspx
    6. (D8) articles.mercola.com/sites/articles/archive/2011/11/13/vitamin-d-for-depression.aspx
    7. (D10) articles.mercola.com/sites/articles/archive/2008/11/18/do-flu-shots-work-ask-a-vaccine-manufacturer.aspx
    8. (D15) articles.mercola.com/sites/articles/archive/2008/02/12/why-vitamin-d-supplements-are-not-the-same-as-sunlight.aspx
    9. (new) products.mercola.com/vitamin-d-supplement/
    10. (new) .mercola.com/article/vitamin-d-resources.htm
  8. Livestrong: livestrong.com/article/485077-is-d-alpha-tocopheryl-acetate-a-natural-form-of-vitamin-e/
  9. Dr. Alan Christianson: drchristianson.com/vitamin-e-the-right-amounts-for-your-optimal-health
  10. Wikipedia:
    1. vitamin E: en.wikipedia.org/wiki/Vitamin_E
    2. tocopheryl acetate: en.wikipedia.org/wiki/Tocopheryl_acetate
    3. commons.wikimedia.org/wiki/File:RRR_alpha-tocopherol.png
    4. commons.wikimedia.org/wiki/File:Tocotrienols.svg
  11. Dr Ron’s: drrons.com/can-vitamin-e-kill-you-or-is-the-media-blowing-hot-air.aspx
  12. Vitamins and Health Supplements Guide:
    1. vitamins-supplements.org
    2. vitamins-supplements.org/vitamin-E.php < link is no longer valid
  13. Healthlink Medical College of Wisconsin (originally cited for functions of vitamin E, but link is no longer valid: healthlink.mcw.edu/article/983211401.html
  14. nlm.nih.gov/medlineplus/ency/article/002406.htm
  15. Tocotrienol.org
    1. tocotrienol.org/en/
    2. tocotrienol.org/en/alzheimers-disease-correlated-with-lower-level-total-tocotrienols-tocopherols/
  16. iherb.com/pr/MRM-Complete-E-60-Softgels/10997
  17. From Carotech email re: Tocomin (mixed tocotrienols); email has been lost
  18. reference.md/files/D007/mD007425.html on intracellular membranes
  19. organicfacts.net/vitamin-e-tocopherol.html
  20. healthyfocus.org/benefits-tocopherol/
  21. SFGate: Health Eating
    1. healthyeating.sfgate.com/health-benefits-gammatocopherol-7045.html
  22. Life Extension:
    1. lifeextension.com/magazine/2002/10/report_gamma/page-01
    2. lifeextension.com/Magazine/2006/4/report_gamma/Page-02
  23. healthyeating.sfgate.com/health-benefits-gammatocopherol-7045.html
  24. naturalpedia.com/gamma-tocopherol-sources-health-risks.html (24B)
  25. healthline.com/health/tocopheryl-acetate

The following reference lists are from my original article (on my old iWeb site) but have been incorporated into the list above, or deleted if they no longer exist.

  • References for Vitamin E info (original):
  1. http://www.vitamins-supplements.org/vitamin-E.php

Sources from Vitamins-Intro page:

  1. http://well.blogs.nytimes.com/2008/02/06/despite-risks-vitamins-popular-with-cancer-patients/index.html?hp
  2. http://www.ppnf.org/catalog/ppnf/Articles/XFactor.htm
  3. http://www.vitamins-supplements.org/vitamin-E.php
  4. http://www.ppnf.org/catalog/ppnf/Articles/XFactor.htm
  5. http://www.vitaminuk.com/pages/articles/codliveroil.htm
  6. http://www.dailyyonder.com/four-food-groups/2010/03/04/2623

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