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Sigma-Aldrich

α-Tocopherol

≥95.5%

Synonym(s):

(±)-α-Tocopherol, DL-all-rac-α-Tocopherol, Vitamin E

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About This Item

Empirical Formula (Hill Notation):
C29H50O2
CAS Number:
Molecular Weight:
430.71
Beilstein/REAXYS Number:
94012
EC Number:
MDL number:
UNSPSC Code:
12352205
eCl@ss:
34058016
PubChem Substance ID:
NACRES:
NA.28

biological source

synthetic

Quality Level

assay

≥95.5%

form

liquid

technique(s)

HPLC: suitable

color

faint brown to brown
yellow to very dark yellow

density

0.950 g/mL at 20 °C (lit.)

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

CC(C)CCCC(C)CCCC(C)CCCC1(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

InChI key

GVJHHUAWPYXKBD-UHFFFAOYSA-N

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General description

α-Tocopherol is the active form of vitamin E. It functions as an hydroperoxyl radical scavenger and protects the organism from oxidative damage. α-Tocopherol plays a crucial role in cell signalling and regulating immune responses. α-Tocopherol deficiency is associated with abetalipoproteinemia, cystic fibrosis and celiac disease. It has antiproliferative effects. It inhibits arsenite-induced damage of human fibroblasts.

Application

α-Tocopherol has been used:
  • as a standard to determine its concentration by reverse-phase high-performance liquid chromatography
  • to study its rescue effects on chlorine dioxide (ClO2) cytotoxicity
  • to assess its protective effects on acetaminophen (APAP)-mediated liver damage

Biochem/physiol Actions

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.

Related product

Product No.
Description
Pricing

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nutritional deficiencies and syndromes associated with alcoholism
Textbook of Clinical Neurology (Third Edition), 897-917 (2007)
Effect of vitamin E on oxidative stress level in blood, synovial fluid, and synovial tissue in severe knee osteoarthritis: a randomized controlled study
Tantavisut S, et al.
BMC Musculoskelet. Disord., 18(1), 281-281 (2017)
Early Diagnosis and Treatment of Cancer Series: Prostate Cancer E-Book: Expert Consult - Online and Print, 897-917 (2015)
Oxidative stress induced by chlorine dioxide as an insecticidal factor to the Indian meal moth, Plodia interpunctella
Kumar S, et al
Pesticide Biochemistry and Physiology, 124, 48-59 (2015)
Glycosphingolipids Prevent APAP and HMG-CoA Reductase Inhibitors-mediated Liver Damage: A Novel Method for ?Safer Drug? Formulation that Prevents Drug-induced Liver Injury
Mizrahi M, et al.
Journal of clinical and translational hepatology, 6(2), 1-8 (2018)

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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