Tocotrienol

Base Information

• Chemical Name: Tocotrienol
• CAS No.: 6829-55-6
• Deprecated CAS: 9074-33-3
• Molecular Formula: C26H38O2
• Molecular Weight: 382.57900
• UNII: 0867I0N41V
• DSSTox Substance ID: DTXSID601336446
• Nikkaji Number: J578.410G
• Wikidata: Q27236375
• NCI Thesaurus Code: C68318
• Metabolomics Workbench ID: 47322
• ChEMBL ID: CHEMBL120643
• Mol file: 6829-55-6.mol

Synonyms:Tocotrienol;Tocotrienols

Chemical Property of Tocotrienol

Chemical Property:

• PSA: 29.46000
• LogP: 7.67530
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 382.287180451
• Heavy Atom Count: 28
• Complexity: 567

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC1(CCC2=C(O1)C=CC(=C2)O)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CCC1(CCC2=C(O1)C=CC(=C2)O)C)/C)/C)C
• Recent ClinicalTrials: Tocotrienol Against the Progression of End Stage Liver Disease
• Recent EU Clinical Trials: Tocotrienol and Bevacizumab in metastatic colorectal cancer. A randomized phase II marker trial
• Recent NIPH Clinical Trials: The verification study of improvements in cognitive functions: A randomized double-blind placebo-controlled trial
• General Description: Tocotrienols, including α-, γ-, and δ-forms, are natural farnesylated benzopyran compounds with notable hypocholesterolemic properties. They function by posttranscriptionally suppressing HMG-CoA reductase, a critical enzyme in cholesterol biosynthesis, with γ-tocotrienol demonstrating significantly higher inhibitory activity than α-tocotrienol. Both synthetic and natural tocotrienols exhibit comparable efficacy in cholesterol-lowering effects, particularly when lacking the 5-methyl substitution, as seen in γ- and δ-tocotrienols. These findings highlight their potential as therapeutic agents for managing hypercholesterolemia.

Refernces

Hypocholesterolemic Activity of Synthetic and Natural Tocotrienols

10.1021/jm00098a002

The study investigates the hypocholesterolemic activity of synthetic and natural tocotrienols, which are farnesylated benzopyran natural products that exhibit cholesterol-lowering effects both in vitro and in vivo. The research explores the mechanism of their hypolipidemic action, which involves posttranscriptional suppression of HMG-CoA reductase, a key enzyme in cholesterol biosynthesis. The study presents an efficient synthetic route to tocotrienols and their isolation from palm oil distillate. It was found that γ-tocotrienol has a 30-fold greater activity toward cholesterol biosynthesis inhibition compared to α-tocotrienol in HepG2 cells in vitro. The synthetic (racemic) and natural (chiral) tocotrienols exhibit nearly identical cholesterol biosynthesis inhibition and HMG-CoA reductase suppression properties. The study also examines the role of various tocotrienols, including α-, γ-, and δ-tocotrienols, in inhibiting cholesterol synthesis. The findings suggest that tocotrienols lacking the 5-methyl substitution, such as γ- and δ-tocotrienols, possess significantly greater cholesterol synthesis suppressive activity compared to α-tocotrienol.