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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

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 Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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A review of characterization of tocotrienols from plant oils and foods
Ahsan H, et al.
Journal of Chemical Biology, 8(2), 45-59 (2015)
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)
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
Jinghai Chen et al.
Circulation, 123(6), 584-593 (2011-02-02)
Omega-3 polyunsaturated fatty acids (eicosapentaenoic acid and docosahexaenoic acid) from fish oil ameliorate cardiovascular diseases. However, little is known about the effects of ω-3 polyunsaturated fatty acids on cardiac fibrosis, a major cause of diastolic dysfunction and heart failure. The
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