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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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling
Packer L, et al.
The Journal of Nutrition, 131(2), 369S-373S (2001)
Vladimir Gogvadze et al.
International journal of cancer, 127(8), 1823-1832 (2010-01-28)
Release of mitochondrial proteins such as cytochrome c, AIF, Smac/Diablo etc., plays a crucial role in apoptosis induction. A redox-silent analog of vitamin E, alpha-tocopheryl succinate (alpha-TOS), was shown to stimulate cytochrome c release via production of reactive oxygen species
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)
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
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
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