Merck
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T3634

Sigma-Aldrich

(+)-α-Tocopherol

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

Synonym(s):
2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol, Vitamin E, 5,7,8-Trimethyltocol, D-α-Tocopherol
Empirical Formula (Hill Notation):
C29H50O2
CAS Number:
Molecular Weight:
430.71
Beilstein:
4712525
EC Number:
MDL number:
eCl@ss:
34058016
PubChem Substance ID:
NACRES:
NA.79

Quality Level

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

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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
Packaged under argon in a sealed ampule.

Biochem/physiol Actions

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.
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.

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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