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Merck

T3634

Sigma-Aldrich

(+)-α-Tocopherol

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

Sinónimos:

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

Fórmula empírica (notación de Hill):
C29H50O2
Número de CAS:
Peso molecular:
430.71
Beilstein:
4712525
Número CE:
Número MDL:
Código UNSPSC:
12352205
eCl@ss:
34058016
ID de la sustancia en PubChem:
NACRES:
NA.79

origen biológico

vegetable oil

Nivel de calidad

tpo

Type V

Formulario

viscous liquid

actividad específica

~1000 IU/g

color

clear yellow to red

índice de refracción

n20/D 1.505 (lit.)

bp

200-220 °C/0.1 mmHg (lit.)

densidad

0.95 g/mL at 25 °C (lit.)

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

GVJHHUAWPYXKBD-IEOSBIPESA-N

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Descripción general

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.

Aplicación

(+)-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

Acciones bioquímicas o fisiológicas

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.

Envase

Packaged under argon in a sealed ampule.

Otras notas

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

Calidad

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

Precaución

Subject to air oxidation.

Propiedades físicas

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.

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

230.0 °F - closed cup

Punto de inflamabilidad (°C)

110 °C - closed cup

Equipo de protección personal

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


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Visite la Librería de documentos

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)
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)
Blood alpha-tocopherol, gamma-tocopherol levels and risk of prostate cancer: a meta-analysis of prospective studies
Cui R, et al.
Testing, 9(3), e93044-e93044 (2014)
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)

Artículos

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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