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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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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)
Merriline M Satyamitra et al.
Radiation research, 175(6), 736-745 (2011-03-26)
δ-Tocotrienol (DT3), a vitamin E isoform, is associated with strong antioxidant and immunomodulatory properties. We confirmed the potent antioxidant activity in membrane systems and showed that DT3 is an effective radiation protector and mitigator. DT3 (4 μM, P < 0.001)
Asaf A Qureshi et al.
Lipids in health and disease, 10, 239-239 (2011-12-22)
Changes in immune function believed to contribute to a variety of age-related diseases have been associated with increased production of nitric oxide (NO). We have recently reported that proteasome inhibitors (dexamethasone, mevinolin, quercetin, δ-tocotrienol, and riboflavin) can inhibit lipopolysaccharide (LPS)-induced
Mudit Mudit et al.
Natural product communications, 5(10), 1623-1626 (2010-12-03)
4-Hydroxyphenylmethylene hydantoin (PMH, 1), isolated from the Red Sea sponge Hemimycale arabica, and delta-tocotrienol (3), isolated from the tocotrienol-rich fraction of palm oil, are important antimetastatic and antiproliferative natural products that proved effective against metastatic prostate and breast cancers, respectively.
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