T3634

(+)-α-Tocopherol

Name: (+)-α-Tocopherol
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₅₀O₂

CAS Number:

59-02-9

Molecular Weight:

430.71

NACRES:

NA.79

PubChem Substance ID:

24900154

eCl@ss:

34058016

UNSPSC Code:

12352205

EC Number:

200-412-2

MDL number:

MFCD00072045

Beilstein/REAXYS Number:

4712525

Product Name

(+)-α-Tocopherol, from vegetable oil, Type V, ~1000 IU/g

InChI key

GVJHHUAWPYXKBD-IEOSBIPESA-N

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

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

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

Quality Level

200

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Related Categories

Biochemicals

Cell Culture Supplements & Reagents

Vitamins

Analysis Note

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

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

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.

Disclaimer

Subject to air oxidation.

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.

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.

Other Notes

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

Packaging

Packaged under argon in a sealed ampule.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Dietary alanyl-glutamine and vitamin E supplements could considerably promote the expression of GPx and PPARalpha genes, antioxidation, feed utilization, growth, and improve composition of juvenile cobia

Ding Z, et al.

Aquaculture (Amsterdam, Netherlands), 470(6), 95-102 (2017)

alpha-Tocopherol is essential for acquired chill-light tolerance in the cyanobacterium Synechocystis sp. strain PCC 6803

Yang Y, et al.

Journal of Bacteriology, 190(5), 1554-1560 (2008)

Influence of alpha-tocopherol and alpha-lipoic acid on bisphenol-A-induced oxidative damage in liver and ovarian tissue of rats

Avci B, et al.

Toxicology and Industrial Health, 32(8), 1381-1390 (2016)

Inhibition of lipid peroxidation during the reproductive period extends the lifespan of Caenorhabditis elegans.

Taro Sakamoto et al.

Journal of clinical biochemistry and nutrition, 66(2), 116-123 (2020-04-02)

Glutathione peroxidase 4 (GPx4) is a unique antioxidant enzyme that directly reduces the phospholipid hydroperoxides (PLOOH) generated in biomembranes using glutathione as the reductant. We have previously reported that the Caenorhabditis elegans gpx-quad mutant, which lacks all homologous genes of

The role of alpha-tocopherol in preventing disease: from epidemiology to molecular events

Azzi A, et al.

Molecular Aspects of Medicine, 24(6), 325-336 (2003)

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