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T3251

Sigma-Aldrich

(±)-α-Tocopherol

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:
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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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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), 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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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
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
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
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
Farhan Basit et al.
Cell death & disease, 8(3), e2716-e2716 (2017-03-31)
Inhibition of complex I (CI) of the mitochondrial respiratory chain by BAY 87-2243 ('BAY') triggers death of BRAFV600E melanoma cell lines and inhibits in vivo tumor growth. Here we studied the mechanism by which this inhibition induces melanoma cell death.
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