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Merck
CN

T0577

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

Key Documents

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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

biological source

rice

form

liquid

concentration

≥65% (GC)

color

yellow to orange

storage temp.

−20°C

Quality Level

100

Related Categories

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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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)
A review of characterization of tocotrienols from plant oils and foods
Ahsan H, et al.
Journal of Chemical Biology, 8(2), 45-59 (2015)
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)
Xiangming Ji et al.
Anticancer research, 32(7), 2647-2655 (2012-07-04)
Non-small cell lung cancer (NSCLC), accounting for 80% of lung cancers, is the leading cause of all cancer deaths. Previously, we demonstrated that delta-tocotrienol inhibits NSCLC cell proliferation, invasion and induces apoptosis by down-regulation of the Notch-1 signaling pathway. The
Pharmacological potential of tocotrienols: a review
Ahsan H, et al.
Nutrition & Metabolism, 11(1), 52-52 (2014)
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