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T3251

(±)-α-Tocopherol

Name: (±)-α-Tocopherol
Brand: SIGMA

synthetic, ≥96% (HPLC)

Synonym(s):

DL-all-rac-α-Tocopherol, Vitamin E

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₅₀O₂

CAS Number:

10191-41-0

Molecular Weight:

430.71

Beilstein/REAXYS Number:

94012

EC Number:

233-466-0

MDL number:

MFCD00006848

UNSPSC Code:

12352205

eCl@ss:

34058016

PubChem Substance ID:

24900118

NACRES:

NA.77

biological source

synthetic

Quality Level

200

assay

≥96% (HPLC)

form

liquid

technique(s)

HPLC: suitable

color

faint brown to brown
yellow to very dark yellow

solubility

H₂O: insoluble
acetone: miscible
chloroform: miscible
ethanol: miscible
vegetable oils: miscible

density

0.950 g/mL at 20 °C (lit.)

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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Related Categories

Vitamins

Application

(±)-α-Tocopherol has been used for preparing mycobacterial emulsions. It has also been used to study its immunomodulatory effect on influenza virus.

Biochem/physiol Actions

Tocopherols (vitamin E) comprise of a series (α, β, γ and δ) of chiral compounds that differ by the methylation degree of the phenol moiety of the chromanol ring. They function as lipid soluble antioxidants and protect cell membranes from oxidative damage. α-tocopherols are favorably absorbed by humans and their nicotinate salts can function as vitamin E supplements. Studies have also reported that vitamin E can prevent cell damage caused by pharmacologically induced epilepsy in rats.

Preparation Note

(±)-α-Tocopherol is miscible with chloroform, ethanol, ether, acetone, and vegetable oils. However, it is practically insoluble in water. (±)-α-Tocopherol is unstable under alkaline conditions.

pictograms

GHS07

signalword

Warning

hcodes

H317

pcodes

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

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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T1550000

α-Tocopherol

Sigma-Aldrich

T1539

(+)-α-Tocopherol

Sigma-Aldrich

T3001

(+)-α-Tocopherol acetate

USP

1667600

Alpha Tocopherol

SAFC

5.00862

Vitamin E

Supelco

47785

(+)-γ-Tocopherol

Supelco

V-020

(±)−α−Tocopherol (Vitamin E) solution

The marine n-3 PUFA DHA evokes cytoprotection against oxidative stress and protein misfolding by inducing autophagy and NFE2L2 in human retinal pigment epithelial cells.

Ida Johansson et al.

Autophagy, 11(9), 1636-1651 (2015-08-04)

Accumulation and aggregation of misfolded proteins is a hallmark of several diseases collectively known as proteinopathies. Autophagy has a cytoprotective role in diseases associated with protein aggregates. Age-related macular degeneration (AMD) is the most common neurodegenerative eye disease that evokes

Vitamin E prevents apoptosis in cortical neurons during hypoxia and oxygen reperfusion.

M Tagami et al.

Laboratory investigation; a journal of technical methods and pathology, 78(11), 1415-1429 (1998-12-05)

Cerebral ischemia followed by oxygen reperfusion induces apoptosis in hippocampal neurons in stroke-prone spontaneously hypertensive rats (SHRSP) but not in Wistar Kyoto rats (WKY). The overproduction of oxygen-free radicals that occurs in the tissues of SHRSP is implicated in reoxygenation

Release of mitochondrial Opa1 following oxidative stress in HT22 cells.

Thomas H Sanderson et al.

Molecular and cellular neurosciences, 64, 116-122 (2015-01-13)

Cellular mechanisms involved in multiple neurodegenerative diseases converge on mitochondria to induce overproduction of reactive oxygen species, damage to mitochondria, and subsequent cytochrome c release. Little is currently known regarding the contribution mitochondrial dynamics play in cytochrome c release following

Dietary supplementation with vitamin E and C attenuates dexamethasone-induced glucose intolerance in rats.

Deon B Williams et al.

American journal of physiology. Regulatory, integrative and comparative physiology, 302(1), R49-R58 (2011-10-28)

Glucocorticoid excess induces marked insulin resistance and glucose intolerance. A recent study has shown that antioxidants prevent dexamethasone (DEX)-induced insulin resistance in cultured adipocytes. The purpose of this investigation was to examine the effects of dietary vitamin E and C

Molecular features of the cytotoxicity of an NHE inhibitor: Evidence of mitochondrial alterations, ROS overproduction and DNA damage.

Francesca Aredia et al.

BMC cancer, 16(1), 851-851 (2016-11-07)

NH exchangers (NHEs) play a crucial role in regulating intra/extracellular pH, which is altered in cancer cells, and are therefore suitable targets to alter cancer cell metabolism in order to inhibit cell survival and proliferation. Among NHE inhibitors, amiloride family

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