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Key Documents

T0577

Sigma-Aldrich

D-δ-Tocotrienol

from rice, ≥65% (GC)

Synonym(s):

(R-(E,E))-3,4-Dihydro-2,8-dimethyl-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):
C27H40O2
CAS Number:
25612-59-3
Molecular Weight:
396.61
UNSPSC Code:
12352205
NACRES:
NA.79

biological source

rice

Quality Level

100

form

liquid

concentration

≥65% (GC)

color

yellow to orange

storage temp.

−20°C

SMILES string

O1[C@@](CCc2c1c(cc(c2)O)C)(CC\C=C(\CC\C=C(\CCC=C(C)C)/C)/C)C

InChI

1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1

InChI key

ODADKLYLWWCHNB-LDYBVBFYSA-N

General description

D-δ-Tocotrienol is a bioavailable isomer of vitamin E and has farnesyl side chain. Palm oil is rich in δ-Tocotrienol.

Biochem/physiol Actions

D-δ-Tocotrienol suppresses ras sarcoma (Ras) protein levels. It elicits anti-proliferative functionality in melanoma cells by halting cell cycle and favoring apoptosis. δ-Tocotrienol is cytotoxic to human lung adenocarcinoma and glioblastoma cancer cells. δ-Tocotrienol possesses anti-inflammatory, antidiabetic and neuroprotective functionality. It is an effective hypocholesterolemic agent and an inhibitor of lipid peroxidation.
Tocotrienols are widely utilized for their strong antioxidant properties. The various isoforms of tocotrienols differ in their methyl substitution in the chromanol head. δ-tocotrienol, effectively blocks cleavage of SREBPs, ultimately decreasing the amount of cholesterol synthesized in the liver.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8293
MKCW7636
MKCV9363
MKCP0148
MKCL4007

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Cytotoxicity and apoptotic activities of alpha-, gamma-and delta-tocotrienol isomers on human cancer cells
Lim SW, et al.
BMC Complementary and Alternative Medicine, 14(1), 469-469 (2014)
The Impact of delta-Tocotrienol and Geranylgeraniol on Cell Cycle Progression and Apoptosis in Human and Murine Melanoma Cells
Fernandes NV, et al.
Faseb Journal (2010)
Jing-Shu Zhang et al.
Toxicology, 285(1-2), 8-17 (2011-04-02)
Tocotrienol is considered a beneficial effect agent on inhibition of tumor development. In this study, we focused on the effects of δ-tocotrienol and its possible mechanism on induction of death in human colon cancer SW620 cells. δ-Tocotrienol inhibited proliferation of
Pharmacological potential of tocotrienols: a review
Ahsan H, et al.
Nutrition & Metabolism, 11(1), 52-52 (2014)
Kazim Husain et al.
Molecular cancer therapeutics, 10(12), 2363-2372 (2011-10-06)
The NF-κB transcription factor functions as a crucial regulator of cell survival and chemoresistance in pancreatic cancer. Recent studies suggest that tocotrienols, which are the unsaturated forms of vitamin E, are a promising class of anticancer compounds that inhibit the
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