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Merck

T3251

(±)-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
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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InChI key

GVJHHUAWPYXKBD-UHFFFAOYSA-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

SMILES string

CC(C)CCCC(C)CCCC(C)CCCC1(C)CCc2c(C)c(O)c(C)c(C)c2O1

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

Quality Level

200

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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

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk

WGK 1

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7274
MKCQ7144
MKCQ4711
MKCQ0574
MKCN9253

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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
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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