α-Tocopherol is the most commonly available and widely known member of the vitamin E family. Vitamin E is a group of eight fat-soluble compounds that include four tocopherols and four tocotrienols.
"Alpha-tocopherol" essentially refers to the primary form of Vitamin E that is an alcohol and is important for reproduction among other functions.
Vitamin E is a group of eight fat-soluble compounds that include four tocopherols and four tocotrienols. Alpha-tocopherol is the most commonly available and widely known member of the Vitamin E family.
Tocopherol consists of α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol and is a lipophilic molecule, synthesized by photosynthetic organisms via enzymes.
The name describes the structure of the molecule:
- Alpha is the first letter of the Greek alphabet and is often used in scientific terminology to denote the first or primary item in a series. In the case of alpha-tocopherol, it refers to the most biologically active form of Vitamin E.
- Tocopherol comes from the Greek words "tocos" meaning childbirth, and "pherein" meaning to bring forth or bear. The term was coined because Vitamin E was initially recognized for its importance in successful reproduction in rats. The "ol" at the end signifies that it is an alcohol.
Vitamin E can be synthesized in the laboratory but is usually extracted from natural sources. The synthesis of Vitamin E is a complex process that involves multiple steps and reactions. Here's a simplified version of the process:
- Isophytol, a derivative of mevalonic acid, is used as the starting material.
- Isophytol is converted into 2,3-dimethyl-5-phytyl-1,4-benzoquinone through a series of reactions.
- This compound is then converted into alpha-tocopherol, the most common form of Vitamin E, through a series of reactions involving reduction and methylation.
Industrially it occurs as a fine, white powder or transparent yellow liquid.
The term α-tocopherol does not refer to a single substance, but to eight different isomers that perform the same function. Vitamin E is the most important fat-soluble antioxidant.
Vitamin E occurs naturally in cereals, in oils and, in particular in:
What it is used for and where
Medical
Tocopherol can increase the antioxidant effect of cells producing an anti-ageing effect by improving lipid metabolism, it is a key antioxidant and can be created by synthesis.
Its antioxidant action has effects on the brain (1), when, in the cardiovascular system, there are problems of diabetes caused by LDL cholesterol (2) and in liver diseases (3)
In the medical field it is an adjuvant to treat vascular diseases, as prevention for cellular diseases and for a correct functioning of the immune system.
No positive action, however, was found towards prostate cancer, as demonstrated by this study of very long duration on many samples (4).
Cosmetics
In recent years, tocopherol has often been used in cosmetic products such as detergents, shampoos and creams for its antioxidant, nutrient properties and as a skin conditioning agent.
Let us look in detail at its cosmetic properties.
- Antioxidant agent. Ingredient that counteracts oxidative stress and prevents cell damage. Free radicals, pathological inflammatory processes, reactive nitrogen species and reactive oxygen species are responsible for the ageing process and many diseases caused by oxidation.
- Fragrance. It plays a very important role in the formulation of cosmetic products as it allows perfume to be enhanced, masked or added to the final product, improving its commercial viability. The consumer always expects to find a pleasant scent in a cosmetic product.
- Skin conditioning agent - Miscellaneous. This ingredient has the task of modifying the condition of the skin when it is damaged or dry by reducing its flakiness and restoring its elasticity.
- Skin conditioning agent - Occlusive. This ingredient has the task of modifying the condition of the skin when it is damaged or dry by reducing flaking and restoring elasticity. It has a strong lipophilic character and is identified as an occlusive ingredient; it is generally composed of oily and fatty materials that remain on the skin surface and reduce trans epidermal water loss.
For more information:
"Vitamin E Tocopherol studies"
Optimal typical characteristics of the commercial product Tocopherol powder
| Appearance | Powder fine white |
| Boiling Point | 485.9±0.0 °C at 760 mmHg |
| Melting Point | 2.5-3.5ºC |
| Flash Point | 210.2±24.4 °C |
| Density | 0.9±0.1 g/cm3 |
| PSA | 29.46000 |
| Assay | ≥99.5% |
| Index of Refraction | 1.495 |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| LogP | 11.90 |
| Loss on drying | NMT 0.2% |
| Heavy Metal (Pb) | NMT 0.5 mg/kg |
| Ash | NMT 0.01% |
| As | NMT 2.0 mg/kg |
- Molecular Formula: C29H50O2
- Molecular Weight: 430.717 g/mol
- Exact Mass 430.381073
- CAS: 59-02-9 1406-18-4 2074-53-5 10191-41-0
- EC Number: 218-197-9 233-466-0 200-412-2 215-798-8 606-803-8
- UNII: N9PR3490H9
- DSSTox Substance ID:
- MDL number
- PubChem Substance ID
- 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/t21-,22-,29-/m1/s1
- InChl Key GVJHHUAWPYXKBD-IEOSBIPESA-N
- SMILES CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
- IUPAC (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
- ChEBI
- PubChem Substance ID 329751332
- MDL number MFCD00006848
- Beilstein Registry Number 94012
Synonyms:
- alpha-Tocopherol
- a-Tocopherol
- D-alpha-Tocopherol
- (2R,4'R,8'R)-alpha-Tocopherol
- 59-02-9
- dl-a-Tocopherol
- 5,7,8-Trimethyltocol
- (+)-alpha-Tocopherol
- (R,R,R)-alpha-Tocopherol
- DL-ALPHA-TOCOPHEROL
- Vitamin Ea
- Mixed tocopherols
- D-alpha tocopherol
- Syntopherol
- Denamone
- Viteolin
- Esorb
- Tocopherol (R,S)
- 2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol
- Aquasol E
- 10191-41-0
- (+)-|A-Tocopherol
- Tocopherol alpha
- a-Vitamin E
- (2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL
- 2074-53-5
- Profecundin
- Waynecomycin
- Vitamin E alpha
- Vitaplex E
- N9PR3490H9
- Vita E
- EINECS 215-798-8
- Lan-E
- Med-E
- (R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
- Antisterility vitamin
- alpha-Tocopherol acid
- Tenox GT 1
- Endo E
- Eprolin S
- Viterra E
- CHEBI:18145
- E Prolin
- Spavit E
- 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
- Almefrol
- Emipherol
- Epsilan
- Etamican
- Tokopharm
- Vascuals
- Viprimol
- Vitayonon
- Etavit
- Ilitia
- Verrol
- Evion
- alpha-Tokoferol
- (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
- 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
- BPBio1_000362
- alpha-Vitamin E
References________________________________________________________________________
(1) Sakr HF, Abbas AM, El Samanoudy AZ. Effect of vitamin E on cerebral cortical oxidative stress and brain-derived neurotrophic factor gene expression induced by hypoxia and exercise in rats. J Physiol Pharmacol. 2015 Apr;66(2):191-202.
(2) Shirpoor A, Norouzi L, Nemati S, Khadem Ansari MH. Protective effect of vitamin E against diabetes-induced oxidized LDL and aorta cell wall proliferation in rat. Iran Biomed J. 2015;19(2):117-23. doi: 10.6091/ibj.1449.2015.
(3) Miyanishi K, Hoki T, Tanaka S, Kato J. Prevention of hepatocellular carcinoma: Focusing on antioxidant therapy. World J Hepatol. 2015 Mar 27;7(3):593-9. doi: 10.4254/wjh.v7.i3.593.
(4) Ramamoorthy V, Rubens M, Saxena A, Shehadeh N. Selenium and vitamin E for prostate cancer--justifications for the SELECT study. Asian Pac J Cancer Prev. 2015;16(7):2619-27. doi: 10.7314/apjcp.2015.16.7.2619.
α-tocopherol 
