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T3634 Sigma-Aldrich

(+)-α-Tocopherol

from vegetable oil, Type V, ~1000 IU/g

Synonym: 2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol, 5,7,8-Trimethyltocol, D-α-Tocopherol, Vitamin E

  • CAS Number 59-02-9

  • Empirical Formula (Hill Notation) C29H50O2

  • Molecular Weight 430.71

  •  Beilstein/REAXYS Number 4712525

  •  EC Number 200-412-2

  •  MDL number MFCD00072045

  •  eCl@ss 34058016

  •  PubChem Substance ID 24900154

  •  NACRES NA.79

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Properties

Related Categories Allium cepa (Onion), Allium sativum (Garlic), Aloe Vera, Antioxidant and Free Radical Scavengers, Antioxidants and Cytoprotectants,
Quality Level   200
biological source   vegetable oil
type   Type V
form   viscous liquid
specific activity   ~1000 IU/g
color   clear yellow to red
refractive index   n20/D 1.505 (lit.)
bp   200-220 °C/0.1 mmHg (lit.)
density   0.95 g/mL at 25 °C (lit.)
storage temp.   −20°C
SMILES string   CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)c(C)c(C)c2O1
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
InChI key   GVJHHUAWPYXKBD-IEOSBIPESA-N

Description

General description

α-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase. It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.

Application

(+)-α-Tocopherol has been used:
• as a food supplement for juvenile cobia fish
• to evaluate its protective effect on bisphenol A induced oxidative stress in rats
• to test its chemopreventive efficacy in estrogen-mediated mammary cancer rats

Packaging

10, 100 g in ampule

Biochem/physiol Actions

Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.

α-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803. Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.

Packaging

Packaged under argon in a sealed ampule.

Other Notes

Mixed constitutional (α, β, γ, δ) isomers.

Quality

Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g

Caution

Subject to air oxidation.

Physical properties

This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
DJ2900000
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
110 °C - closed cup
Protocols & Articles

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.1 During the oxi...
Biofiles Volume 2 Article 2
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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