.DELTA.-TOCOTRIENOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H40O2
Molecular Weight	396.6053
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1

InChI

InChIKey=ODADKLYLWWCHNB-LDYBVBFYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://nutritionandmetabolism.biomedcentral.com/articles/10.1186/1743-7075-11-52
Curator's Comment: description was created based on several sources, including http://www.fda.gov/downloads/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/ucm359902.pdf

Delta-tocotrienol is a member of vitamin E family. Tocotrienols are natural compounds found in a number of vegetable oils, wheat germ, barley, and certain types of nuts and grains. Tocotrienol-rich products such as DeltaGold® are gerally recognized as safe and are commecrially available as a dietary supplements. Tocotrienols possess powerful neuroprotective, antioxidant, anti-cancer and cholesterol lowering properties. The mechanism involved in anti-cancer activity of tocotrienols are still unclear, and include activation of caspases, downregulation of Bcl-2 and cyclin D, inhibition of angiogenesis, inhibition of cell proliferation though cell cycle arrest, downregulation of Raf/Erk pathway.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://clinicaltrials.gov/ct2/show/NCT02634606	Preventing	Natural Metabolite	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://clinicaltrials.gov/ct2/show/NCT01571921	Primary	Natural Metabolite	Unknown Approved Use Unknown
Pancreatic cancer 97 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26844278	Primary	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
miR-429 mediates δ-tocotrienol-induced apoptosis in triple-negative breast cancer cells by targeting XIAP.	2015	26629059
A Phase I Safety, Pharmacokinetic, and Pharmacodynamic Presurgical Trial of Vitamin E δ-tocotrienol in Patients with Pancreatic Ductal Neoplasia.	2015 Dec	26844278

Patents

Sample Use Guides

In Vivo Use Guide

Tocotrienols are natural compounds found in a number of vegetable oils, wheat germ, barley, and certain types of nuts and grains. As a dietary supplement, delta-tocotrienol is available as oral capsules, each containing 50 mg of DeltaGold Tocotrienols, featuring delta-tocotrienol (90%) and gamma-tocotrienol (10%).

Route of Administration: Oral

In Vitro Use Guide

Cell viability was determined at 24 hours by a MTT assay. Cells (5×103 cells per well) were grown overnight in 96-well plates. Fresh medium (200 μL) with different doses of δ-tocotrienol or ethanol was added and incubated at 37°C at 5% CO2 for 24 hours. After 24 hours of incubation, MDA-MB-231 and MDA-MB-468 cells were incubated for an additional 4 hours with 20 μL MTT (5 mg/mL). The supernatant was then removed, and 150 μL DMSO was added. The absorbance at 490 nm was measured with a microplate reader. MDA-MB-231 and MDA-MB-468 cells, also known as human triple negative breast cancer cells, were treated in the presence of various concentrations (0-100 μM) of δ-tocotrienol for 24 hours.

Name

Type

Language

.DELTA.-TOCOTRIENOL

Common Name

English

DELTA-TOCOTRIENOL

Common Name

English

(R)-.DELTA.-TOCOTRIENOL

Common Name

English

Delta Tocotrienol [WHO-DD]

Common Name

English

8-METHYLTOCOTRIENOL

Common Name

English

D-DELTA-TOCOTRIENOL

Common Name

English

J17.358D

Code

English

2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,8-DIMETHYL-2-((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIENYL)-, (2R)-

Systematic Name

English

2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,8-DIMETHYL-2-((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIEN-1-YL)-, (2R)-

Systematic Name

English

2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,8-DIMETHYL-2-(4,8,12-TRIMETHYL-3,7,11-TRIDECATRIENYL)-, (R-(E,E))-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68318