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T3634

Sigma-Aldrich

(+)-α-Tocopherol

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

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

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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1 of 4

This Item
T1539258024V-020
vibrant-m

T3634

(+)-α-Tocopherol

vibrant-m

T1539

(+)-α-Tocopherol

vibrant-m

258024

α-Tocopherol

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−70°C

bp

200-220 °C/0.1 mmHg (lit.)

bp

200-220 °C/0.1 mmHg (lit.)

bp

-

bp

-

refractive index

n20/D 1.505 (lit.)

refractive index

n20/D 1.505 (lit.)

refractive index

-

refractive index

-

form

viscous liquid

form

liquid (≥0.88M based on potency, density and molecular wt.)

form

liquid

form

liquid

density

0.95 g/mL at 25 °C (lit.)

density

0.95 g/mL at 25 °C (lit.)

density

0.950 g/mL at 20 °C (lit.)

density

0.950 g/mL at 20 °C (lit.)

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

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.

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.

Storage Class

10 - Combustible liquids

wgk_germany

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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α-Tocopherol British Pharmacopoeia (BP) Reference Standard

BP882

α-Tocopherol

Alpha Tocopherol Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1031

Alpha Tocopherol

α-Tocopherol European Pharmacopoeia (EP) Reference Standard

T1550000

α-Tocopherol

Vitamin E water-miscible 1 ml = 500 mg DL-a-tocopherol acetate for oral use, EMPROVE® ESSENTIAL, USP

SAFC

5.00862

Vitamin E

Alpha Tocopherol United States Pharmacopeia (USP) Reference Standard

USP

1667600

Alpha Tocopherol

δ-Tocopherol analytical standard

Supelco

47784

δ-Tocopherol

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
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)
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)
Differential gene regulation and tumor-inhibitory activities of alpha-, delta-, and gamma-tocopherols in estrogen-mediated mammary carcinogenesis
Gupta S, et al.
Cancer Prevention Research (Philadelphia, Pa.), 10(12), 694-703 (2017)
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)

Articles

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.

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