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EC / List no.: 604-195-9
CAS no.: 1406-66-2
Mol. formula: C112H192O8
Tocopherols (/toʊˈkɒfəˌrɒl/; TCP) are a class of organic chemical compounds (more precisely, various methylated phenols), many of which have vitamin E activity.
Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was named tocopherol, from Greek τόκος tókos 'birth' and φέρειν phérein 'to bear or carry', that is 'to carry a pregnancy', with the ending -ol signifying its status as a chemical alcohol.
Tocopherol is the main source found in supplements and in the European diet, where the main dietary sources are olive and sunflower oils, while γ-tocopherol is the most common form in the American diet due to a higher intake of soybean and corn oil.
Tocotrienols, which are related compounds, also have vitamin E activity. All of these various derivatives with vitamin activity may correctly be referred to as "vitamin E". Tocopherols and tocotrienolsForms
Tocopherol exists in eight different forms, four tocopherols and four tocotrienols.
All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain that allows for penetration into biological membranes.
Both the tocopherols and tocotrienols occur in α (alpha), β (beta), γ (gamma), and δ (delta) forms, determined by the number and position of methyl groups on the chromanol ring. are fat-soluble antioxidants but also seem to have many other functions in the body.
The tocotrienols have the same methyl structure at the ring and the same Greek letter-methyl-notation, but differ from the analogous tocopherols by the presence of three double bonds in the hydrophobic side chain.
The unsaturation of the tails gives tocotrienols only a single stereoisomeric carbon (and thus two possible isomers per structural formula, one of which occurs naturally), whereas tocopherols have three centers (and eight possible stereoisomers per structural formula, again, only one of which occurs naturally).
Each form has a different biological activity.
In general, the unnatural l-isomers of tocotrienols lack almost all vitamin activity, and half of the possible 8 isomers of the tocopherols (those with 2S chirality at the ring-tail junction) also lack vitamin activity.
Of the stereoisomers that retain activity, increasing methylation, especially full methylation to the alpha-form, increases vitamin activity.
In tocopherols, this is due to the preference of the tocopherol binding protein for the α-tocopherol form of the vitamin.
As a food additive, tocopherol is labeled with these E numbers: E306 (tocopherol), E307 (α-tocopherol), E308 (γ-tocopherol), and E309 (δ-tocopherol).
All of these are approved in the US, EU, and Australia and New Zealand for use as antioxidants.
Function and dietary recommendations
Mechanism of action
Tocopherols are radical scavengers, delivering an H atom to quench free radicals.
At 323 kJ/mol, the O-H bond in tocopherols is approximately 10% weaker than in most other phenols.
This weak bond allows the vitamin to donate a hydrogen atom to the peroxyl radical and other free radicals, minimizing their damaging effect.
The thus generated tocopheryl radical is relatively unreactive, but reverts to tocopherol by a redox reaction with a hydrogen donor such as vitamin C.
As they are fat-soluble, tocopherols are incorporated into cell membranes, which are protected from oxidative damage.
Dietary considerations
The U.S. Recommended Dietary Allowance (RDA) for adults is 15 mg/day.
The RDA is based on the α-tocopherol form because it is the most active form as originally tested. Tocopherol supplements are absorbed best when taken with meals.
The U.S. Institute of Medicine has set an upper tolerable intake level (UL) for vitamin E at 1,000 mg (1,500 IU) per day.
The European Food Safety Authority sets UL at 300 mg α-tocopherol equivalents /day.
Tocopherol equivalents
For dietary purposes, vitamin E activity of vitamin E isomers is expressed as α-tocopherol equivalents (a-TEs).
One a-TE is defined by the biological activity of 1 mg (natural) d-α-tocopherol in the resorption-gestation test.
According to listings by FAO and others β-tocopherol should be multiplied by 0.5, γ-tocopherol by 0.1, and α-tocotrienol by 0.3.
The IU is converted to aTE by multiplying it with 0.67.
These factors do not correlate with the antioxidant activity of Tocopherol isomers, where tocotrienols show even much higher activity in vivo.
The U.S. Department of Agriculture (USDA), Agricultural Research Services, maintains a food composition database. The last major revision was Release 28, September 2015.
In general, food sources with the highest concentrations of Tocopherol are vegetable oils, followed by nuts and seeds.
Adjusting for typical portion sizes, however, for many people in the United States the most important sources of Tocopherol include fortified breakfast cereals.
Deficiency
Main article: Tocopherol deficiency
Tocopherol deficiency is rare, and in almost all instances caused by an underlying disease rather than a diet low in vitamin E.
Tocopherol deficiency causes neurological problems due to poor nerve conduction.
These include neuromuscular problems such as spinocerebellar ataxia and myopathies.
Deficiency also may cause anemia, due to oxidative damage to red blood cells.
Supplements
Commercial Tocopherolsupplements may be classified into several distinct categories:
Fully synthetic vitamin E, "dl-α-tocopherol", the most inexpensive, most commonly sold supplement form usually as the acetate ester
Semi-synthetic "natural source" Tocopherol esters, the "natural source" forms used in tablets and multiple vitamins; these are highly fractionated d-α-tocopherol or its esters, often made by synthetic methylation of gamma and beta d,d,d tocopherol vitamers extracted from plant oils.
Less fractionated "natural mixed tocopherols" and high d-γ-tocopherol fraction supplements
Synthetic all-racemic
Synthetic Tocopherol derived from petroleum products is manufactured as all-racemic α-tocopheryl acetate with a mixture of eight stereoisomers. In this mixture, one α-tocopherol molecule in eight molecules are in the form of RRR-α-tocopherol (12.5% of the total).
The 8-isomer all-rac Tocopherol is always marked on labels simply as dl-tocopherol or dl-tocopheryl acetate, even though it is (if fully written out) dl,dl,dl-tocopherol.
The present largest manufacturers of this type are DSM and BASF.
Natural α-tocopherol is the RRR-α (or ddd-α) form.
The synthetic dl,dl,dl-α ("dl-α") form is not so active as the natural ddd-α ("d-α") tocopherol form.
This is mainly due to reduced vitamin activity of the four possible stereoisomers that are represented by the l or S enantiomer at the first stereocenter (an S or l configuration between the chromanol ring and the tail, i.e., the SRR, SRS, SSR, and SSS stereoisomers).
The three unnatural "2R" stereoisomers with natural R configuration at this 2' stereocenter, but S at one of the other centers in the tail (i.e., RSR, RRS, RSS), appear to retain substantial RRR vitamin activity, because they are recognized by the alpha-tocopherol transport protein, and thus maintained in the plasma, where the other four stereoisomers (SRR, SRS, SSR, and SSS) are not.
Thus, the synthetic all-rac-α-tocopherol, in theory, would have approximately half the vitamin activity of RRR-α-tocopherol in humans.
Experimentally, the ratio of activities of the 8 stereoisomer racemic mixture to the natural vitamin, is 1 to 1.36 in the rat pregnancy model (suggesting a measured activity ratio of 1/1.36 = 74% of natural, for the 8-isomer racemic mix).
Although it is clear that mixtures of stereoisomers are not so active as the natural RRR-α-tocopherol form, in the ratios discussed above, specific information on any side effects of the seven synthetic Tocopherol stereoisomers is not readily available.
Esters
Manufacturers also commonly convert the phenol form of the vitamins (with a free hydroxyl group) to esters, using acetic or succinic acid. These tocopheryl esters are more stable and are easy to use in vitamin supplements.
α-Tocopheryl esters are de-esterified in the gut and then absorbed as the free tocopherol.
Tocopheryl nicotinate, tocopheryl linolate, and tocopheryl palmitate esters are also used in cosmetics and some pharmaceuticals.
Mixed tocopherols
"Mixed tocopherols" in the USA contain at least 20% w/w other natural R, R,R- tocopherols, i.e. R, R,R-α-tocopherol content plus at least 25% R, R,R-β-, R, R,R-γ-, R, R,R-δ-tocopherols.
Some brands may contain 200% w/w or more of the other tocopherols and measurable tocotrienols.
Some mixed tocopherols with higher γ-tocopherol content are marketed as "High Gamma-Tocopherol".
The label should report each component in milligrams, except R, R,R-α-tocopherol may still be reported in IU.
Mixed tocopherols also may be found in other nutritional supplements.
Uses:
Tocopherols are a class or organic molecules.
Many exhibit the activity of Tocopherol.
They are commonly found in Olive and sunflower oils.
General Description
Pale yellow, viscous liquid.
Air & Water Reactions
Insoluble in water.
Tocopherol exists in four different forms designated as α, β, δ, and γ.
They present strong antioxidant activities, and it is determined as the major form of vitamin E.
Tocopherol, as a group, is composed of soluble phenolic compounds that consist of a chromanol ring and a 16-carbon phytyl chain.
The classification of the tocopherol molecules is designated depending on the number and position of the methyl substituent in the chromanol ring.
The different types of tocopherol can be presented trimethylated, dimethylated or methylated in the positions 5-, 7- and 8-.
When the carbons at position 5- and 7- are not methylated, they can function as electrophilic centers that can trap reactive oxygen and nitrogen species.
Tocopherols can be found in the diet as part of vegetable oil such as corn, soybean, sesame, and cottonseed.
Tocopherol is currently under the list of substances generally recognized as safe (GRAS) in the FDA for the use of human consumption.
Tocopherol can be used as a dietary supplement for patients with a deficit of vitamin E; this is mainly prescribed in the alpha form.
Tocopherol deficiency is rare, and it is primarily found in premature babies of very low birth weight, patients with fat malabsorption or patients with abetalipoproteinemia.
Tocopherol, due to its antioxidant properties, is studied for its use in prevention or treatment in different complex diseases such as cancer, atherosclerosis, cardiovascular diseases, and age-related macular degeneration.
It's an old-school antioxidant that occurs naturally in the skin. You can also find it in foods like spinach, nuts, seeds, and sunflower oil.
Tocopherol benefits for skin
Like fellow antioxidants vitamin C and ferulic acid, tocopherol acts like a shield that protects your skin and bod from free radical damage, says Mraz-Robinson.
Remember: Free radicals are rogue molecules that have been damaged by toxins like UVA/UVB rays or pollution. Their favorite hobbies include breaking down your skin's collagen and causing skin cancer, hyperpigmentation, and other signs of aging.
Regularly using antioxidants like tocopherol can help counteract the damage done by free radicals, and prevent it from happening in the future.
Tocopherol's wrinkle-fighting powers make it a common ingredient in anti-aging products like Roc Multi Correxion 5 In 1 Anti-Aging Chest, Neck & Face Cream.
It's also really good at battling dryness (which is why argan oil is such a great hydrator—it's naturally high in Tocopherol).
How do you use tocopherol?
Tocopherol works best when left on the skin, so look for it in day and night moisturizers (like Charlotte Tilbury Magic Cream Treat and Transform Moisturizer).
Tocopherol also works well when paired with other antioxidants, like vitamin C, for a free-radical fighting boost.
Tocopherol, however, is not for everyone. Tocopherol can be irritating, and some people are allergic to it (although a 20-year study found them to be extremely rare).
If you have sensitive skin or a skin condition like rosacea, you're also probably better off skipping tocopherol, says Mraz-Robinson.
She also says that people with acne should skip Tocopherol, since it's known to make acne flare.
However, a small 2016 study found that adding tocopherol to an acne-fighting skin care routine actually helped reduce angry flareups, so there's definitely lots of room for debate here.
But if you're worried about it making your skin react, try using a different antioxidant (like a vitamin C serum) instead for the same skin-protecting benefits.
Absorbs UV rays and helps prevent UV-induced free radical damage to skin
Acts as an anti-inflammatory agent in skin
Helps moisturize
Helps reduce pollution-related free radical damage
Why we use it: Tocopherol’s antioxidant properties not only help protect your skin, but also help protect products by acting as a preservative and preventing natural oils like coconut and jojoba from going rancid.
It’s a naturally effective multi-tasker, so it’s easy to see why we wanted to include it in body care products such as Lip Balm, Sunscreen Stick, Healing Balm, Hand Sanitizer Gel, Diaper Rash Cream, Organic Shave Oil, Organic Belly Balm, and Organic Breathe Easy Rub.
Tocopherol is a fat-soluble vitamin composed of compounds called tocopherols and tocotrienols.
This supplement contains the full spectrum of Tocopherol as it occurs in nature, i.e. all four tocopherols and all four tocotrienols (alpha, beta, delta, gamma).
Most Tocopherol supplements only contain alpha-tocopherol.
Tocopherol contributes to the protection of cells from oxidative stress, this means it is an antioxidant.
Tocopherols are another group of chemicals that make up the vitamin E family.
Both tocotrienols and tocopherols comes in four forms: alpha, beta, delta, and gamma.
The term "tocopherol" encompasses various vitamin E derivatives.
Tocopherol contains powerful antioxidants and protects cells and is, available in greater or lesser quantities in vegetable oils.
Tocopherolis thus the best plant-specific protection against oxidation.
Additionally, tocopherol binds moisture in the outer layer of the skin.
Tocopherolaffects cell renewal and has anti-inflammatory properties and reduces skin damage caused by UV radiation.
The skin texture is also much smoother.
Tocopherol is non-irritating and is very well tolerated.
Tocotrienols are a group of chemicals that are part of the vitamin E family.
Most vitamin E supplements are higher in tocopherols than tocotrienols.
Tocotrienols may help fight free radical damage to the gastrointestinal system.
Natural vitamin E includes four tocopherols, called alpha, beta, gamma and delta tocopherol respectively. The form used in the human body is alpha tocopherol, and this form is necessary to treat vitamin E deficiency.
Only this form is bound by the liver transport protein called alpha-tocopherol transport protein, which carries it to the site where it is incorporated into lipoproteins and carried to other parts of the body.
Chemistry of tocopherols
Tocopherols are made up of a chromanol ring and a 15-carbon saturated isoprenoid tail.
Natural and synthetic alpha tocopherol are different in their composition.
The natural form is made up of a molecule with methyl (-CH3) groups at the 2, 4’ and 8’ positions on the chromanol ring.
The synthetic form is made up of eight stereoisomers, all with identical antioxidant activity in vitro.
However, only four of them have the methyl ring at position 2, meaning that chemically synthesized alpha-tocopherol has 50% the biological activity of the natural form.
Alpha-tocopherol esters in supplements are chiefly succinate and acetate, and these are converted to alpha-tocopherol in the intestine before absorption.
Sources of tocopherols
Tocopherols are found in almost all plant seeds, the best sources of alpha-tocopherol include plant seeds such as almonds, sunflower seeds and hazelnuts.
Olive and canola oil are also good sources, as are tomato, avocado and spinach.
Tocopherols are the primary form of vitamin E in the leaves of all plants, and the seeds of dicots.
Gamma-tocopherol is the most common isomer of tocopherol found in the American diet, but its absorption and use appear to be significantly less, and its active excretion and metabolism higher, than for alpha-tocopherol.
About Tocopherol
Helpful information
Tocopherol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Tocopherol is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
Tocopherol is used in the following products: cosmetics and personal care products.
Other release to the environment of Tocopherol is likely to occur from: indoor use as processing aid.
Article service life
ECHA has no public registered data on the routes by which Tocopherol is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
Tocopherol is used in the following products: cosmetics and personal care products.
Tocopherol is used in the following areas: health services.
Other release to the environment of Tocopherol is likely to occur from: indoor use as processing aid.
Formulation or re-packing
Tocopherol is used in the following products: cosmetics and personal care products and pH regulators and water treatment products.
Release to the environment of Tocopherol can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites
Tocopherol is used in the following products: cosmetics and personal care products.
Tocopherol is used in the following areas: health services.
Release to the environment of Tocopherol can occur from industrial use: in processing aids at industrial sites, of substances in closed systems with minimal release, in the production of articles and as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of Tocopherol can occur from industrial use: manufacturing of the substance.
A collective name for a group of closely related lipids that contain substitutions on the 2H-1-benzopyran-6-ol nucleus and a long hydrocarbon chain of isoprenoid units.
They are antioxidants by virtue of the phenolic hydrogen.
Tocopherols react with the most reactive form of oxygen and protect unsaturated fatty acids from oxidation.
A Tocopheroltest measures the amount of Tocopherolin your blood.
Tocopherol (also known as tocopherol or alpha-tocopherol) is a nutrient that is important for many body processes.
Tocopherol helps your nerves and muscles work well, prevents blood clots, and boosts the immune system.
Tocopherol is a type of antioxidant, a substance that protects cells from damage.
Most people get the right amount of Tocopherolfrom their diet. Tocopherol is found naturally in many foods, including green, leafy vegetables, nuts, seeds, and vegetable oils. If you have too little or too much Tocopherolin your body, it can cause serious health problems.
Other names: tocopherol test, alpha-tocopherol test, Tocopherol, serum
What it is: Tocopherol is a form of Tocopherol typically derived from vegetable oils.
Our tocopherol is from sunflower seed oil from Spain and non-GMO soy beans.
What it does: Tocopherol is known as an antioxidant superhero that provides awesome protection for your skin when included in body care products.
(This shouldn’t be terribly surprising, since tocopherols make up 96% of your skin’s natural antioxidant defense system!)
both tocotrienols and tocopherols may be referred to as vitamin E.
Tocopherol is an antioxidant, which means that it helps to neutralize free radicals.
Free radicals are chemicals linked to a host of health issues, including skin aging, cancer, and numerous diseases.
Free radicals can also cause chronic inflammation.
The primary reason tocotrienols may be beneficial is because of their antioxidant properties. Cereal grains tend to be rich in tocotrienols.
Good sources include:
rice bran
oats
barley
rye
crude palm oil
IUPAC NAMES:
2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-o
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-o
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Mixed tocopherol
Mixed Tocopherols
TOCOPHEROL
Tocopherol
tocopherol
Tocopherol
Tocopherols
SYNONYMS:
VeOil30%,50%,70%ByGc
2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol
Controx VP
Covi-Ox T 30P
Covi-Ox T 50
Covi-Ox T 70
Dry E-Mix 20
E 306
E-Mix 40A
E-Mix 60
E-Mix 80
E-Mix P 20
E-Oil 600
E-Oil 700
E-Oil 705
E-Oil 800
Golden Tocopherol 70
Irganox E 217DF
Rikki N 70
Tenox GT
Tocopherols
TOCOPHEROLMIX
(TOCOPHEROL) 99% USP GRADE
D02332
Tocopherol (jp15)
Tocopherols excipient
Tocopherols excipient (nf)
Tocopherols (Technical Grade)
Tocopherol mixed, Low-alpha type, FCC, FG
Tocopherols
7616-22-0
(+/-)-gamma-Tocophero
Rac-gamma-tocopherol
UNII-ECY0XG64DO
7,8-Dimethyltocol
DL-gamma-tocopherol
E-MIX 80
ECY0XG64DO
Methyltocols
73980-80-0
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-
1406-66-2
2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
o-Xylotocopherol
.gamma.-Tocopherol7,8-Dimethyltocolo-xylotocopherol
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
CCRIS 3610
CCRIS 4506
.gamma.-Tokoferol
Tocopherol [JAN]
EINECS 231-523-4
D-.gamma.-Tocopherol
2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol
gamma-Tocopherol, DL-
SCHEMBL39640
6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-
CHEMBL420898
DTXSID5044075
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol
18-EP2270000A1
18-EP2270101A1
18-EP2272822A1
18-EP2305825A1
18-EP2308857A1
FT-0624546
FT-0626624
FT-0756458
EC 604-195-9
Q27277111
UNII-R0ZB2556P8 component QUEDXNHFTDJVIY-UHFFFAOYSA-N
2,7,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol #
2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol
