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T0452

Sigma-Aldrich

D-α-Tocotrienol

from rice, ≥75% (GC)

Synonym(s):

3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol

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About This Item

Empirical Formula (Hill Notation):
C29H44O2
CAS Number:
1721-51-3
Molecular Weight:
424.66
UNSPSC Code:
12352205
NACRES:
NA.79

biological source

rice

Quality Level

200

assay

≥75% (GC)

form

liquid

color

colorless to brown

mp

30-31 °C

storage temp.

−20°C

SMILES string

O1[C@@](CCc2c1c(c(c(c2C)O)C)C)(CC\C=C(\CC\C=C(\CCC=C(C)C)/C)/C)C

InChI

1S/C29H44O2/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/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

InChI key

RZFHLOLGZPDCHJ-XZXLULOTSA-N

Related Categories

General description

Tocotrienols belong to the vitamin E family and have an unsaturated isoprenoid side chain. The various isoforms of tocotrienols differ in their methyl substitution in the chromanol head. α-Tocotrienol present in crude palm oil is regarded as a natural supplement.

Biochem/physiol Actions

α-Tocotrienol is an effective free radical scavengerand elicits protective functionality during oxidative stress in microsomes. It is a strong antioxidant, which reduces inflammation and is used in cancer treatment. α-tocotrienol supplementation may reduce cholesterol levels in hypercholesterolemia. α-tocotrienol is neuroprotective as it blocks glutamate-induced cell death in neuronal cells.
α-Tocotrienol may be used along with other isoforms to differentiate tocotrienol activities.
Tocotrienols are widely utilized for their strong antioxidant properties. The various isoforms of tocotrienols differ in their methyl substitution in the chromanol head. α-tocotrienol demonstrates neuroprotective properties by blocking glutamate-induced cell death in neuronal cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ6492
SLCD9270
SLBV4744
SLBH2309V
SLBG8379

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Hyunil Ha et al.
Biochemical and biophysical research communications, 406(4), 546-551 (2011-03-01)
Vitamin E, an essential nutrient with powerful antioxidant activity, is the mixture of two classes of compounds, tocopherols (TPs) and tocotrienols (TTs). Although TTs exhibit better bone protective activity than α-TP, the underlying mechanism is poorly understood. In this study
Han-A Park et al.
Stroke, 42(8), 2308-2314 (2011-07-02)
α-Tocotrienol (TCT) represents the most potent neuroprotective form of natural vitamin E that is Generally Recognized As Safe certified by the U.S. Food and Drug Administration. This work addresses a novel molecular mechanism by which α-TCT may be protective against
Tocotrienol is a cardioprotective agent against ageing-associated cardiovascular disease and its associated morbidities
Ramanathan N, et al.
Nutrition & Metabolism, 15(1), 6-6 (2018)
Savita Khanna et al.
Journal of neurochemistry, 98(5), 1474-1486 (2006-08-23)
The natural vitamin E tocotrienols possess properties not shared by tocopherols. Nanomolar alpha-tocotrienol, not alpha-tocopherol, is potently neuroprotective. On a concentration basis, this finding represents the most potent of all biological functions exhibited by any natural vitamin E molecule. We
Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling
Packer L, et al.
The Journal of Nutrition, 131(2), 369S-373S (2001)
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