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Merck

T3634

(+)-α-Tocopherol

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

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C29H50O2
Numéro CAS:
59-02-9
Poids moléculaire :
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

Principaux documents

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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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Catégories apparentées

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.

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.

Analysis Note

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

Other Notes

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

Disclaimer

Subject to air oxidation.

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
MKCZ4203
MKCX3878
MKCS2816
MKCM9275
MKCQ0940

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Consulter la Bibliothèque de documents

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)
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
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)
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