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Vitamin E

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Description
A generic descriptor for all tocopherols and tocotrienols that exhibit alpha-tocopherol activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of isoprenoids. (In Vitro) :α-Vitamin E ((+) -α-Tocopherol) is a peroxyl radical scavenger. The importance of this function is to maintain the integrity of long-chain polyunsaturated fatty acids in the membranes of cells and thus maintain their bioactivity.α-Vitamin E ((+) -α-Tocopherol) has been described to inhibit PKC in various cell types with consequent inhibition of platelet aggregation, endothelial cell nitric oxide production and superoxide production in neutrophils and macrophages. α-Vitamin E ((+) -α-Tocopherol) exposure induced the activation of both the MAP kinase and PI3 kinase (PI3K) pathways, suggesting that it is the oxidative stress that up-regulates kinase pathways and the antioxidant action of α-tocopherol protects the cell membrane fatty acids.α-Vitamin E ((+) -α-Tocopherol) has proposed benefits for influenza virus A infection, as well as possible activity against hepatitis B and C. α-Vitamin E shows proviral effects, particularly in HEK293T/17 cells. (In Vivo) :α-Vitamin E ((+) -α-Tocopherol) prevents the increase in the pro-inflammatory cytokines IL-1, IL-6, and IFN-γ mRNA and protein compared with the ischemic-reperfused myocardium from untreated pigs and compared to the non-injured area.α-Vitamin E (D-α-Tocopherol; intraperitoneal injection or oral administration) treatment induces an amelioration of diabetic nephropathy in mice through the activation of diacylglycerol kinase α (DGKα) and the prevention of podocyte loss.
CAS Number
59-02-9
Product Name Alternative
Alpha-Tocopherol | D-alpha tocopherol | Mixed tocopherols
Purity
>98% (HPLC)
Solubility
DMSO: 10 mM
Smiles
OC1=C (C) C (CC[C@] (CCC[C@H] (C) CCC[C@H] (C) CCCC (C) C) (C) O2) =C2C (C) =C1C
Molecular Formula
C29H50O2
Molecular Weight
430.71
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(R) -2,5,7,8-tetramethyl-2- ((4R,8R) -4,8,12-trimethyltridecyl) chroman-6-ol

Chemical Information

alpha-Tocopherol

(R,R,R)-alpha-tocopherol is an alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils. It has a role as an antioxidant, an antiviral agent, a micronutrient, an EC 2.7.11.13 (protein kinase C) inhibitor, an anticoagulant, a nutraceutical, an immunomodulator, an antiatherogenic agent, a plant metabolite and an algal metabolite. It is an enantiomer of a (S,S,S)-alpha-tocopherol.

CAS Number59-02-9
PubChem CID14985
IUPAC Name(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
Molecular FormulaC29H50O2
Molecular Weight430.7
XLogP10.7
Topological Polar Surface Area29.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count12
Heavy Atom Count31
Formal Charge0
Complexity503
SMILES
CC1=C(C2=C(CC[C@@](O2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(=C1O)C)C
InChI
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
InChIKey
GVJHHUAWPYXKBD-IEOSBIPESA-N
Chemical Structure
2D Structure
2D structure of alpha-Tocopherol
CAS: 59-02-9
CID: 14985
Formula: C29H50O2
MW: 430.7
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight430.7
XLogP310.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count12
Exact Mass430.381080833
Monoisotopic Mass430.381080833
Topological Polar Surface Area29.5 Ų
Heavy Atom Count31
Formal Charge0
Complexity503
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes