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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

NACRES:

NA.77

PubChem Substance ID:

24900118

eCl@ss:

34058016

UNSPSC Code:

12352205

EC Number:

233-466-0

MDL number:

MFCD00006848

Beilstein/REAXYS Number:

94012

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Properties

biological source

synthetic

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

Description

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.

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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

WGK 1

ppe

Eyeshields, Gloves

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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

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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

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Global Trade Item Number

SKU	GTIN
T3251-100G	04061835549979
T3251-25G	04061835522613
T3251-500G	04061837343940
T3251-5G	04061835514281