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CAS NUMBER: 10191-41-0
EC NUMBER: 233-466-0
MOLECULAR FORMULA: C29H50O2
MOLECULAR WEIGHT: 430.71
Dl-alpha-Tocopherol is a synthetic form of vitamin E, a fat-soluble vitamin with potent antioxidant properties.
Considered essential for the stabilization of biological membranes (especially those with high amounts of polyunsaturated fatty acids), d-alpha-Tocopherol is a potent peroxyl radical scavenger and inhibits noncompetitively cyclooxygenase activity in many tissues, resulting in a decrease in prostaglandin production.
Dl-alpha-Tocopherol also inhibits angiogenesis and tumor dormancy through suppressing vascular endothelial growth factor (VEGF) gene transcription.
Dl-alpha-Tocopherol is miscible with chloroform, ethanol, ether, acetone, and vegetable oils.
Dl-alpha-Tocopherol is practically insoluble in water. (±)-α-Tocopherol is unstable under alkaline conditions.
Dl-alpha-Tocopherol has been used for preparing mycobacterial emulsions.
Dl-alpha-Tocopherol has also been used to study its immunomodulatory effect on influenza virus.
Dl-alpha-Tocopherols comprise of a series (α, β, γ and δ) of chiral compounds that differ by the methylation degree of the phenol moiety of the chromanol ring.
Dl-alpha-Tocopherols function as lipid soluble antioxidants and protect cell membranes from oxidative damage. α-tocopherols are favorably absorbed by humans and their nicotinate salts can function as vitamin E supplements. Studies have also reported that vitamin E can prevent cell damage caused by pharmacologically induced epilepsy in rats.
Dl-alpha-Tocopherols 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 that is 'to carry a pregnancy', with the ending -ol signifying its status as a chemical alcohol.
Dl-alpha-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.
Dl-alpha-Tocopherols, 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".
Dl-alpha-Tocopherols and tocotrienols are fat-soluble antioxidants but also seem to have many other functions in the body.
Dl-alpha-Tocopherol is the form of vitamin E that is preferentially absorbed and accumulated in humans.
The measurement of Dl-alpha-Tocopherol was based on fertility enhancement by the prevention of miscarriages in pregnant rats relative to α-tocopherol.
Although the mono-methylated form Dl-alpha-Tocopherol is the most prevalent form of vitamin E in oils, there is evidence that rats can methylate this form to the preferred α-tocopherol, since several generations of rats retained α-tocopherol tissue levels, even when those generations were fed only γ-tocopherol through their lives.
There are three stereocenters in α-tocopherol, so this is a chiral molecule.
The eight stereoisomers of Dl-alpha-Tocopherol differ in the arrangement of groups around these stereocenters.
In the image of RRR-α-tocopherol below, all three stereocenters are in the R form.
However, if the middle of the three stereocenters were changed, this would become the structure of RSR-α-tocopherol.
These stereoisomers also may be named in an alternative older nomenclature, where the stereocenters are either in the d or l form.
Dl-alpha-Tocopherol, bonds around the stereocenters are shown as dashed lines (pointing down) or wedges (pointing up).
Dl-alpha-Tocopherol is defined as ⅔ milligrams of RRR-α-tocopherol (formerly named d-α-tocopherol or sometimes ddd-α-tocopherol).
Dl-alpha-Tocopherol is also defined as 1 milligram of an equal mix of the eight stereoisomers, which is a racemic mixture called all-rac-α-tocopheryl acetate.
This mix of stereoisomers is often called dl-α-tocopheryl acetate, even though it is more precisely dl,dl,dl-α-tocopheryl acetate).
Dl-alpha-Tocopherol of this racemic mixture is not now considered equivalent to 1 IU of natural (RRR) α-tocopherol, and the Institute of Medicine and the USDA now convert IU's of the racemic mixture to milligrams of equivalent RRR using 1 IU racemic mixture = 0.45 "milligrams α-tocopherol".
Dl-alpha-Tocopherols, although less commonly known, also belong to the vitamin E family.
Dl-alpha-Tocopherols have four natural 2' d-isomers (they have a stereoisomeric carbon only at the 2' ring-tail position).
The four Dl-alpha-Tocopherols (in order of decreasing methylation: d-α-, d-β-, d-γ-, and d-δ-tocotrienol) have structures corresponding to the four tocopherols, except with an unsaturated bond in each of the three isoprene units that form the hydrocarbon tail, whereas tocopherols have a saturated phytyl tail (the phytyl tail of tocopherols gives the possibility for 2 more stereoisomeric sites in these molecules that tocotrienols do not have).
Dl-alpha-Tocopherol has been subject to fewer clinical studies and seen less research as compared to tocopherol.
However, there is growing interest in the health effects of these compounds.
Dl-alpha-Tocopherols are radical scavengers, delivering an H atom to quench free radicals.
At 323 kJ/mol, the O-H bond in Dl-alpha-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.
Dl alpha tocopherol is a synthetic form of vitamin E and is used for its antioxidant properties.
Dl-alpha-Tocopherol is found in many personal care products such as skin creams and lotions to promote skin healing and reduce scarring after injuries such as burns.
Dl-alpha-Tocopherol is not clear if individuals allergic to dl alpha tocopherol will cross react with related derivatives.
Dl-alpha-Tocopherol is a specific form of vitamin E that’s often found in skin care products and dietary supplements.
Dl-alpha-Tocopherol’s also known as tocopheryl acetate, tocopherol acetate, or vitamin E acetate.
Dl-alpha-Tocopherol is known for its antioxidant properties.
Antioxidants help to protect your body from damaging compounds called free radicals.
Normally, free radicals form when your body converts food into energy.
However, free radicals can also come from UV light, cigarette smoke, and air pollution.
In nature, Dl-alpha-Tocopherol comes in the form of tocopheryl or tocotrienol.
Dl-alpha-Tocopherols have four forms, known as alpha, beta, gamma, and delta.
Dl-alpha-Tocopherol is the most active form of vitamin E in humans.
D-alpha-tocopherol is the most bioavailable form of alpha-tocopherol, meaning it's the type that is preferred for use by your body and is better absorbed and utilized than other forms.
Dl-alpha-tocopherol is a synthetic form of alpha-tocopherol.
This synthetic form of Dl-alpha-Tocopherol is less bioavailable than the d-alpha-tocopherol and is only half as potent, notes the Oregon State University Linus Pauling Institute.
This form of Dl-alpha-Tocopherol is frequently found in nutritional supplements and fortified foods.
DL-alpha-Tocopherol is sensitive to oxidizing agents, turning dark when exposed to air and light.
DL-alpha-Tocopherol is used mainly a an antioxidant in preparations containing fat (ointments, creams, and oils).
Dl-alpha-Tocopherol acetate is more stable and therefore preferred as an active ingredient.
DL-alpha-Tocopherol is used as an antioxidant to increase the stability of fats (oils, margarine, baking and frying fats, fish oil), fatty products (readymade desserts containing cream, soup powders, cocoa, dietetic and frozen products, potato crisps, essences, and chewing gum), and to protect vitamin A and carotene in oils and other food products.
Regular quantities are between 200 and 500 mg/kg of fat and up to 1,000 mg/kg is used in essences and chewing gum.
By adding tocopherol, the shelf life of meat products sensitive to oxidation (particularly pork and turkey) can be improved.
Dl-alpha-Tocopherol is more stable and therefore preferred for the fortification of food products with vitamin E.
Dl-alpha-Tocopherol is used as an antioxidant and active ingredient in cosmetic preparations containing fat, e.g., creams, ointments, emulsions, body and face oils, and decorative cosmetics, such as lipstick, etc.
USES:
-Oils & Fats
-Confectionery & Bakery
-Snacks & Cereals
-Cocoa & Chocolate
-Spices & Condiments
-Sauces & Dressings
-Meat Products
-Baby Food
-Soft Capsules
-Dietetic Products
-Nutraceutical Formulations
-Food Supplements
BENEFITS:
-Higher bioavailability than Synthetic Vitamin E
-Protects cell membranes and strengthens the immune system
-Reduces the risk of certain diseases
-Possibility of declaring “Source of Vitamin E” in packaging
-Fights oxidative stress by blocking free radicals
-Increases skin hydration and prevents appearance of wrinkles
-It has anti-inflammatory and healing properties
-Acts as natural barrier against UV rays and toxins
-Promotes hair growth and improves hair’s appearance
-Protects the animal during the gestation period
-Prevents the loss of nutritional value of fatty acids
PROPERTIES:
-biological source: synthetic
-assay: ≥96% (HPLC)
-form: liquid
-technique(s): HPLC: suitable
-color: faint brown to brown
-density: 0.950 g/mL at 20 °C (lit.)
-storage temp.: 2-8°C
-SMILES string: CC(C)CCCC(C)CCCC(C)CCCC1(C)CCc2c(C)c(O)c(C)c(C)c2O1
-InChI: 1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3
TECHNICAL INFORMATION:
-Solubility: Soluble in vegetable oils, alcohol, ether, acetone, fats, and chloroform. Insoluble in water.
-Storage: Store at 4° C
-Melting Point: 2.5-3.5° C
-Boiling Point: 200-220° C at 0.1 mmHg
-Density: 0.95 g/mL at 20° C
-Refractive Index: n20D 1.50-1.51
-pK Values: pKa: 11.40
SYNONYM:
alpha-tochopherol
Tocopheroxy radical
Ephanyl
all-rac-alpha-Tocopherol
UNII-7QWA1RIO01
2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
TOCOPHEROL
7QWA1RIO01
CHEMBL49563
113085-06-6
.alpha.-Tocopherol
2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-
d-.alpha.-Tocopherol
6-Chromanol, 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol
