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Merck
CN

T3634

(+)-α-Tocopherol

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

Key Documents

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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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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.

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

Analysis Note

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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4203
MKCX3878
MKCS2816
MKCM9275
MKCQ0940

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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)
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)
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)
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)
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Articles

Dietary Antioxidants

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.

膳食抗氧化剂

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子（如铁、铜和镉）引起的氧化损伤。

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