Tocopherol
[CAS# 1406-18-4]

Identification

• Classification: Food additive >> Nutrition supplements >> Vitamins
• Name: Tocopherol
• Synonyms: g-Tokoferol; Vitamin E; 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol
• Molecular Formula: C₂₉H₅₀O₂
• Molecular Weight: 430.71
• CAS Registry Number: 1406-18-4 (1406-66-2)
• EC Number: 215-798-8
• SMILES: CC1=C(C=C2CCC(OC2=C1C)(C)CCCC(C)CCCC(C)CCCC(C)C)O

Properties

• Density: 0.930 g/mL (25 °C)
• Boiling point: >200 °C
• Flash point: 392.0 °C (closed cup)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P333+P313-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Gamma-tocopherol is a form of vitamin E that has become an important nutrient of both health and industrial importance since its discovery. Gamma-tocopherol was first isolated and identified as a unique form of vitamin E in the early 20th century. Vitamin E itself was discovered as early as 1922 by Herbert Evans and Katherine Bishop while studying dietary factors necessary for reproduction in rats. The tocopherol family includes several forms (alpha, beta, gamma, and delta), each characterized by variations in their molecular structure, particularly the position and number of methyl groups on the chromanol ring.

Gamma-tocopherol is known for its powerful antioxidant properties and is essential for neutralizing free radicals that can damage cells and lead to a variety of chronic diseases, including cardiovascular disease and cancer. Unlike its more common counterpart, alpha-tocopherol, gamma-tocopherol has a higher ability to capture reactive nitrogen species, which are also associated with inflammation and oxidative stress.

Research highlights the role of gamma-tocopherol in supporting cardiovascular health by reducing inflammation and improving endothelial function. Its ability to modulate immune responses and enhance cell signaling pathways highlights its potential therapeutic applications beyond just antioxidant protection. Additionally, studies suggest that gamma-tocopherol may play a role in reducing the risk of certain cancers, such as prostate cancer, through mechanisms that modulate cell growth and apoptosis.

In addition to its biological effects, gamma-tocopherol has applications in various industrial fields. Its antioxidant properties make it an important ingredient in cosmetics and personal care products, helping to protect formulations from oxidative degradation and extend shelf life. In the food industry, gamma-tocopherol is a natural preservative that enhances the stability of oils and fats in processed foods while improving their nutritional value.

References

1994. Effects of n−3 and n−6 fatty acids on the activities and expression of hepatic antioxidant enzymes in autoimmune‐prone NZB×NZW F1 mice. Lipids. Jaya T. Venkatraman, Bysani Chandrasekar, Jong Dai Kim, Gabriel Fernandes.
DOI: 10.1007/bf02536628

1991. Supraphysiological dosages of vitamins and their implications in man. Cellular and Molecular Life Sciences. P. Walter.
DOI: 10.1007/bf01945422

1994. An improved spectrophotometric triiodide assay for lipid hydroperoxides. Lipids. Robert A. Darrow, Daniel T. Organisciak.
DOI: 10.1007/bf02536632