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Gamma-tocopherol is a tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8.
Gamma-tocopherol is found particularly in maize (corn) oil and soya bean (soybean) oils.
Gamma-tocopherol has a role as a plant metabolite, a food antioxidant and an algal metabolite.
CAS Number: 54-28-4
Molecular Formula: C28H48O2
Molecular Weight: 416.68
EINECS Number: 200-201-5
Synonyms: gamma-Tocopherol, 54-28-4, (+)-gamma-Tocopherol, 7,8-Dimethyltocol, o-Xylotocopherol, Gamma tocopherol, (R,R,R)-gamma-Tocopherol, DTXSID9049031, J213.540J, 8EF1Z1238F, DTXCID0028957, CHEBI:18185, (2R)-3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol, (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol, 3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, RRR-gamma-Tocopherol, (2R)-3,4-DIHYDRO-2,7,8-TRIMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-OL, 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-, 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-, DTXSID5044075, (2R)-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol, RefChem:639607, DTXCID3024075, 200-201-5, 231-523-4, 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol, ECY0XG64DO, D-gamma-Tocopherol, MFCD00066529, .gamma.-Tocopherol, (R)-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol, Rrr-.gamma.-tocopherol, (r,r,r)-.gamma.-tocopherol, (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol, NCGC00185764-01, (2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol, 2,7,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol, C28H48O2, D-?-Tocopherol, gamma-Tocopherol, d-, 7,8-Dimethyltocolo-xylotocopherol, (2r)-2,7,8-trimethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]chroman-6-ol, UNII-8EF1Z1238F, -Tocopherol, tocopherol gamma, Vitamin E gamma, gamma -Tocopherol, ??-Tocopherol, EINECS 200-201-5, (+)-.gamma.-Tocopherol, |A-Tocopherol (Standard), SCHEMBL120346, orb1299061, CHEMBL2151591, D--Tocopherol;(+)--Tocopherol, HY-N7148R, .GAMMA.-TOCOPHEROL [MI], MSK1515, GAMMA-TOCOPHEROL [WHO-DD], (+)-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol, HY-N7148, Tox21_113559, 7,8-Dimethyltocol; o-Xylotocopherol, LMPR02020065, AKOS040759356, DB15394, EBC-615837, CAS-54-28-4, NCGC00185764-03, BS-48945, DA-68971, FT179997, (+)-gamma-Tocopherol, >=96% (HPLC), (+)-gamma-Tocopherol, analytical standard, CS-0103047, NS00074161, C02483, F75916, 054T284, Q155753, RRR-.ALPHA.-TOCOPHEROL IMPURITY C [EP IMPURITY], DL-alpha-Tocopherol succinate calcium;-Tocopherol succinate calcium, |A-Tocopherol; (+)-|A-Tocopherol; (R,R,R)-|A-Tocopherol; 7,8-Dimethyltocol, (2R(2R*(4R*,8R*)))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-,[2R-[2R*(4R*,8R*)]]-2H-1-Benzopyran-6-ol;3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-o;(R,R,R)-γ-Tocopherol;[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol;GAMMA-TOCOPHEROL, 25MG, NEAT;VITAMIN E(GAMMA)(REAGENT / STANDARD GRADE);D-GAMMA-TOCOPHEROL;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4R,8R)-4,8,12-trimethyltridecyl-, (2R)-
Gamma-tocopherol is a vitamin E and a tocopherol.
Gamma-tocopherol is a naturally occurring form of vitamin E, belonging to the tocopherol family of lipid-soluble antioxidants.
It is one of four major tocopherols (α, β, γ, and δ), which differ in the number and position of methyl groups on the chromanol ring.
Gamma-tocopherol has the molecular formula C₂₈H₄₈O₂.
Gamma-tocopherol is widely present in plant-derived oils and foods.
It is the predominant form of vitamin E in many diets, especially in soybean oil, corn oil, sesame oil, walnuts, and pecans.
Unlike alpha-tocopherol, it is less concentrated in human tissues but still biologically significant.
Physically, gamma-tocopherol is a colorless to pale yellow, oily liquid at room temperature.
It is insoluble in water but readily soluble in fats, oils, and organic solvents.
Its lipophilic nature allows it to integrate into cell membranes.
Chemically, gamma-tocopherol acts as a powerful antioxidant.
It scavenges free radicals and protects lipids from oxidative damage.
Notably, it is especially effective at trapping reactive nitrogen species, a property that distinguishes it from alpha-tocopherol.
Biologically, gamma-tocopherol contributes to cellular protection and inflammatory regulation.
It plays a role in maintaining membrane integrity and modulating oxidative stress responses.
Research suggests it may have complementary functions to alpha-tocopherol rather than serving the same role.
Gamma-tocopherol is considered a bioactive micronutrient rather than just a passive antioxidant.
Its metabolism and biological effects differ from other vitamin E forms.
This has led to increased interest in its specific health relevance.
Gamma-tocopherol is an important dietary antioxidant and vitamin E isoform.
Its unique chemical reactivity and dietary prevalence give it distinct nutritional and biochemical importance.
Gamma-tocopherol is a tocopherol and one of the chemical compounds that comprise vitamin E. As a food additive, it has E number E308.
Gamma-tocopherol is increasingly studied as part of the broader vitamin E complex, rather than as an isolated nutrient.
Research has shown that diets rich in mixed tocopherols more closely resemble natural intake patterns.
This has shifted focus away from single-isomer supplementation toward balanced vitamin E profiles.
In biochemical systems, gamma-tocopherol localizes within lipid bilayers and lipoproteins.
Its position within membranes allows it to intercept lipid radicals early in oxidative chain reactions.
This membrane-level protection is critical for preserving cell structure and function.
Gamma-tocopherol also influences cell signaling pathways related to oxidative stress and inflammation.
It can modulate enzyme activity and gene expression associated with antioxidant defense.
These regulatory effects extend beyond simple radical scavenging.
In nutritional science, gamma-tocopherol is considered an indicator of dietary oil composition.
Higher plasma levels are often linked to consumption of soybean, corn, and seed oils.
This makes it useful as a biomarker in dietary intake studies.
From a formulation standpoint, gamma-tocopherol is valued for its chemical stability relative to some other antioxidants.
Gamma-tocopherol performs well under moderate heat and storage conditions when protected from oxygen and light.
This supports its inclusion in oil-based systems.
Molecular formula: C28H48O2
Molecular weight: 430.71 g/mol
Boiling point: 200 °C (0.1 mmHg)
Alpha rotation: +30° (C=2.0 in isooctane, 25 °C)
Density: 0.9882 g/cm3 (estimate)
Refractive index: n20/D 1.505
Flash point: 9 °C
Storage temperature: −20 °C
Solubility: Sparingly soluble in chloroform; slightly soluble in ethanol; sparingly soluble in methanol
Form: Viscous liquid
Color: Clear light brown
pKa: 11.05 ± 0.40 (predicted)
Merck index: 13,9573
BRN: 93072
Stability: Light sensitive
Cosmetics ingredients functions: Antioxidant; fragrance; skin conditioning (miscellaneous); skin conditioning (occlusive)
InChI: 1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
InChIKey: QUEDXNHFTDJVIY-DQCZWYHMSA-N
SMILES: CC(C)CCCC@@H
CCCC@@H
CCC[C@]1(C)CCc2cc(O)c(C)c(C)c2O1
LogP: 11.440 (estimated)
Gamma-tocopherol form of vitamin E has long been valued as a potent antioxidant, its little-known cousin, gamma tocopherol, may be equally important in promoting health and protecting against disease. Found in nuts, seeds, and vegetable oils, gamma tocopherol accounts for about 70% of the vitamin E in the North American diet.
Gamma-tocopherol differs structurally from alpha-tocopherol by having fewer methyl groups on the chromanol ring.
This structural difference significantly influences its chemical reactivity and biological behavior.
As a result, gamma-tocopherol interacts with reactive species in ways that alpha-tocopherol cannot.
One of the distinctive features of gamma-tocopherol is its ability to neutralize reactive nitrogen species such as peroxynitrite.
These species are involved in inflammatory and nitrosative stress pathways.
This property gives gamma-tocopherol a unique role in controlling oxidative and inflammatory damage.
In the body, gamma-tocopherol is metabolized differently from alpha-tocopherol.
Gamma-tocopherol is more rapidly broken down and excreted, primarily as water-soluble metabolites.
This explains why blood and tissue levels are typically lower despite higher dietary intake.
Gamma-tocopherol is often found together with other tocopherols and tocotrienols in natural oils.
These compounds can act synergistically, providing broader antioxidant protection than any single form alone.
This synergy is an important concept in nutrition and formulation science.
In lipid systems, gamma-tocopherol is particularly effective at protecting polyunsaturated fatty acids from oxidation.
It helps prevent rancidity and degradation in oils and fat-rich products.
This makes it valuable in food preservation and stability studies.
Gamma-tocopherol has attracted attention in inflammation and cardiometabolic research.
Some studies suggest associations with reduced inflammatory markers and oxidative stress.
These effects are thought to be linked to its nitrogen-reactive scavenging capacity.
In contrast to alpha-tocopherol, gamma-tocopherol is not the primary form retained by the liver.
The body preferentially maintains alpha-tocopherol through specific transport proteins.
This selective retention highlights the complementary rather than dominant role of gamma-tocopherol.
Overall, gamma-tocopherol is recognized as a functionally distinct vitamin E isoform.
Its value lies in its unique antioxidant chemistry rather than sheer concentration in tissues.
This distinction has shifted scientific interest toward mixed tocopherol sources rather than single-isomer supplementation.
Gamma-tocopherol is also studied for its role in oxidative balance during chronic exposure to environmental stressors.
It may help counteract damage from pollution-related nitrogen oxides.
This area of research is particularly relevant to inflammation-related conditions.
In comparison to tocotrienols, gamma-tocopherol has a saturated side chain, which affects membrane mobility.
This structural feature influences how it distributes within lipid environments.
Such differences help explain functional diversity within the vitamin E family.
Overall, gamma-tocopherol is recognized as a complementary antioxidant, not a replacement for alpha-tocopherol.
Gamma-tocopherols value lies in addressing oxidative and nitrosative stress pathways that other vitamin E forms handle less efficiently.
This complementary role underpins its growing importance in nutrition, food science, and biomedical research.
Uses:
One of the naturally occurring forms of Vitamin E. Most abundant Tocopherol in soybean and corn oils.
This Certified Spiking Solution is suitable for use as a starting material in the preparation of linearity standards, calibrators, and controls in a variety of testing applications from diagnostic testing of Vitamin E deficiency by LC-MS/MS or HPLC to quality control testing of tocopherol-based dietary supplements or pharmaceutical preparations.
Gamma-tocopherol is widely used in food and nutrition applications as a natural antioxidant.
It helps protect oils, fats, and fat-containing foods from oxidative degradation.
This improves shelf life and preserves nutritional quality.
In dietary supplements, gamma-tocopherol is included as part of mixed tocopherol formulations.
These supplements aim to provide a more complete vitamin E profile than alpha-tocopherol alone.
Its inclusion reflects its complementary biological activity.
Gamma-tocopherol is used in food science and stability studies.
It serves as a model compound for studying lipid oxidation and antioxidant mechanisms.
Researchers use it to evaluate protection of polyunsaturated fatty acids.
In cosmetics and personal care products, gamma-tocopherol is used as an antioxidant ingredient.
It helps protect formulations from oxidation and supports skin-conditioning claims.
Applications include creams, lotions, oils, and serums.
In pharmaceutical and biomedical research, gamma-tocopherol is studied for its role in inflammation and oxidative stress modulation.
It is used in experimental models investigating cardiovascular, metabolic, and inflammatory processes.
These uses are primarily research-focused rather than therapeutic.
Gamma-tocopherol is applied in nutraceutical formulation development.
It is used to design products targeting oxidative and nitrosative stress.
Its distinct reactivity guides formulation strategies.
In analytical and nutritional research, gamma-tocopherol is used as a reference compound.
It supports studies on vitamin E metabolism, bioavailability, and dietary intake assessment.
This helps differentiate the biological roles of vitamin E isoforms.
Gamma-tocopherol is used where natural antioxidant activity, lipid protection, and complementary vitamin E functionality are desired.
Gamma-tocopherol is used in edible oil fortification and blending.
It is added to vegetable oils to enhance oxidative stability while maintaining a natural antioxidant profile.
This is especially relevant for oils rich in polyunsaturated fatty acids.
In functional food development, gamma-tocopherol is incorporated to support antioxidant-related health positioning.
It is used in nutrition bars, spreads, and fortified foods.
Gamma-tocopherols presence complements other bioactive lipids and polyphenols.
Gamma-tocopherol is applied in anti-inflammatory research formulations.
It is included in experimental diets and model systems studying inflammatory and nitrosative stress pathways.
This supports mechanistic studies distinct from alpha-tocopherol.
In skin-care and dermocosmetic research, gamma-tocopherol is explored for protection against environmental stressors.
It is studied for mitigating oxidative damage induced by pollution and UV-related nitrogen species.
These applications focus on prevention rather than direct treatment.
Gamma-tocopherol is used in lipid-based drug delivery research.
Its antioxidant properties help stabilize lipid carriers and emulsions.
This supports improved shelf life and performance of lipid formulations.
In animal nutrition, gamma-tocopherol is investigated as a dietary antioxidant.
It helps protect feed lipids from oxidation and supports overall oxidative balance.
These uses are mainly experimental and formulation-driven.
Gamma-tocopherol is included in comparative vitamin E studies.
It is used to differentiate biological and metabolic effects among tocopherol isoforms.
This supports nutrition science, toxicology, and metabolism research.
Gamma-tocopherol is selected in applications that require natural lipid protection, complementary antioxidant action, and physiological relevance.
Its uses span food technology, cosmetics, nutrition, and biomedical research.
Safety Profile:
Gamma-tocopherol is generally considered to have low hazard potential and is regarded as safe when used at typical dietary, cosmetic, or formulation levels.
Gamma-tocopherol is a naturally occurring form of vitamin E present in common foods and edible oils.
No significant acute toxicity is expected from normal exposure.
Skin contact with gamma-tocopherol is usually well tolerated.
In rare cases, prolonged or repeated exposure to concentrated material may cause mild skin irritation.
Standard hygiene practices are sufficient during handling.
Eye contact may cause temporary irritation if the oily liquid comes into direct contact with the eyes.
Symptoms can include mild redness or discomfort.
Rinsing with plenty of water is generally adequate.
Inhalation risk is very low due to its low volatility.
However, inhalation of aerosols or mists during industrial processing may cause slight respiratory discomfort.
Adequate ventilation is recommended in manufacturing environments.
Ingestion of excessive amounts may lead to gastrointestinal discomfort, such as nausea or diarrhea.
Very high intakes of vitamin E compounds over long periods may interfere with blood clotting in susceptible individuals.
Such effects are associated with chronic overconsumption rather than normal dietary exposure.
