Compound
γ-tocopherol
A natural tocopherol with less antioxidant activity than alpha-tocopherol. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in beta-tocopherol, it also has three methyl groups on the 6-chromanol nucleus but at different sites.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C28H48O2
- Mass
- 416.69 g/mol
- Charge
- 0
- InChIKey
- QUEDXNHFTDJVIY-DQCZWYHMSA-N
- SMILES
- Cc1c(O)cc2c(c1C)O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
4 entities
4 entities reached.
0 reported hops4 assembled from the scaffold
What the reference databases state
Chemical structure
- 13-hydroxy-gamma-tocopherol has the functional parent γ-tocopherolCompoundChEBI CHEBI:84963Inferred only
Statements
13 statements
13 statements · 2 reference databases · Subject: γ-tocopherol · Sources: Human-GEM, Rhea
- 13-hydroxy-gamma-tocopherol is converted to γ-tocopherolCompoundRhea RHEA:45112Inferred only
- γ-tocopherol is converted to 13-hydroxy-gamma-tocopherolCompoundRhea RHEA:45112Inferred only
- γ-tocopherol is metabolised by CYP4F11ProteinHuman-GEM MAR06464Inferred only
- γ-tocopherol is metabolised by CYP4F11ProteinHuman-GEM MAR06465Inferred only
- γ-tocopherol is metabolised by CYP4F2ProteinRhea RHEA:45112Inferred only
- γ-tocopherol is metabolised by CYP4F2ProteinHuman-GEM MAR06464Inferred only
- γ-tocopherol is metabolised by CYP4F2ProteinHuman-GEM MAR06465Inferred only
- γ-tocopherol is metabolised by CYP4F22ProteinHuman-GEM MAR06464Inferred only
- γ-tocopherol is metabolised by CYP4F22ProteinHuman-GEM MAR06465Inferred only
- γ-tocopherol is metabolised by CYP4F3ProteinHuman-GEM MAR06465Inferred only
- γ-tocopherol is metabolised by CYP4F3ProteinHuman-GEM MAR06464Inferred only
- γ-tocopherol is metabolised by CYP4F8ProteinHuman-GEM MAR06464Inferred only
Show the remaining 1
- γ-tocopherol is metabolised by CYP4F8ProteinHuman-GEM MAR06465Inferred only
Reactions
10 reactions
MAM01936c+protonγ-tocopherol
Reaction pageReversibleUnbalancedGO:0005829
Human-GEM MAR06456CC BY 4.0Reference data
MAM01117c+waterγ-tocopherol+proton+peroxynitrite
Reaction pageReversibleBalancedGO:0005829
Human-GEM MAR06460CC BY 4.0Reference data
Reaction pageReversibleBalancedGO:0005829, GO:0005615
Human-GEM MAR06462CC BY 4.0Reference data
Reaction pageReversibleBalancedGO:0005829, GO:0005783
Human-GEM MAR06463CC BY 4.0Reference data
γ-tocopherol+proton+NADPH(4-)+dioxygenMAM00360c+water+NADP(3-)
Catalysed by CYP4F11 or CYP4F22 or CYP4F2 or CYP4F8 or CYP4F3
Reaction pageLeft to rightBalancedEC 1.14.14.94GO:0005829
Human-GEM MAR06464CC BY 4.0Reference data
γ-tocopherol+proton+NADPH(4-)+dioxygenMAM00360r+water+NADP(3-)
Catalysed by CYP4F11 or CYP4F22 or CYP4F2 or CYP4F8 or CYP4F3
Reaction pageLeft to rightBalancedEC 1.14.14.94GO:0005783
Human-GEM MAR06465CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR09153CC BY 4.0Reference data
γ-tocopherol+S-adenosyl-L-methionineCHEBI:18145+S-adenosyl-L-homocysteine+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:24012CC BY 4.0Reference data
γ-tocopherolCHEBI:75921
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:37983CC BY 4.0Reference data
γ-tocopherol+NADPH(4-)+dioxygen+hydron13-hydroxy-gamma-tocopherol+NADP(3-)+water
Catalysed by CYP4F2
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:45112CC BY 4.0Reference data
On the label
Labelled products
8 products
Source: NIH DSLD · Ingredient: γ-tocopherol · 8 products · Declared amount per serving: 10–100 mg (8 products)
8 labels state an amount0 do not
- CarlsonNutra-Support Prostate50 mgper 2 Softgel(s)DSLD:216239
- Douglas LaboratoriesAqua-E Water-Soluble Vitamin E Tocopherols + Tocotrienols60 mgper 5 mLDSLD:10485
- Douglas LaboratoriesAqua-E Water-Soluble Vitamin E Tocopherols + Tocotrienols60 mgper 5 mLDSLD:10486
- Jarrow FormulasAntioxidant Optimizer100 mgper 1 Tablet(s)DSLD:29117
- Jarrow FormulasCarotenAll10 mgper 1 Softgel(s)DSLD:307570
- MetagenicsFem EssentialsMixed Tocopherols · Gamma Tocopherol (Form: as mixed tocopherols)67 mgper 6 Tablet(s)DSLD:26931
- MetagenicsMultigenics without IronMixed Tocopherols · Gamma Tocopherol (Form: as mixed tocopherols)67 mgper 6 Tablet(s)DSLD:27570
- Vital NutrientsProstate Health TxVitamin E83 mgper 3 Vegetarian Capsule(s)DSLD:223300
Label record: NIH Office of Dietary Supplements · CC0
Other names
16 names
Resolves to: γ-tocopherol
- Also called
- (+)-gamma-tocopherol(+)-γ-tocopherol(2R,4'R,8'R)-gamma-tocopherol(2R,4'R,8'R)-γ-tocopherol(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol(2R)-3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol(R,R,R)-gamma-tocopherol(R,R,R)-γ-tocopherol7,8-dimethyltocolD-gamma-tocopherolD-γ-tocopherolE308gamma-TocopherolRRR-gamma-tocopherolRRR-γ-tocopherol
- Systematic name
- (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol