alpha-tocotrienol
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)
 
Notes:
Occurs in wheat, barley, rye and palm oil. Alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions.; Compared to tocopherols, alpha- Tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentration help to prevent stroke-related neurodegeneration. (PMID: 16771695 ). alpha- Tocotrienol is found to have vitamine E activity.
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    • BOC Sciences
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      Product(s):
      58864-81-6 alpha-Tocotrienol
      à-Tocotrienol is a form of vitamin E, a class of eight fat-soluble compounds. It was shown to induce apoptosis and inhibit prol
       
       
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CAS Number: 58864-81-6Picture of molecule3D/inchi
FDA UNII: B6LXL1832Y
Nikkaji Web: J1.455.578A
Beilstein Number: 5484296
MDL: MFCD11045308
XlogP3-AA: 9.30 (est)
Molecular Weight: 424.66808000
Formula: C29 H44 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 541.70 °C. @ 760.00 mm Hg (est)
Flash Point: 432.00 °F. TCC ( 222.30 °C. ) (est)
logP (o/w): 10.760 (est)
Soluble in:
 water, 5.375e-007 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
alpha-Tocotrienol
Odor: characteristic
Use: à-Tocotrienol is a form of vitamin E, a class of eight fat-soluble compounds. It was shown to induce apoptosis and inhibit prol
Santa Cruz Biotechnology
For experimental / research use only.
a-Tocotrienol >98%
Sigma-Aldrich
For experimental / research use only.
alpha-Tocotrienol
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for alpha-tocotrienol usage levels up to:
 not for fragrance use.
 
Recommendation for alpha-tocotrienol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5282347
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
Chemidplus: 0058864816
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References:
 (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5282347
Pubchem (sid): 135268652
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C14153
HMDB (The Human Metabolome Database): HMDB06327
FooDB: FDB002434
FDA Listing of Food Additive Status: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 barley
Search Trop  Picture
 palm oil
Search  PMC Picture
 rye seed
Search Trop  Picture
 wheat
Search Trop  Picture
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Synonyms:
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-, (2R)-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)
3,4-dihydro-2,5,7,8-tetramethyl-2R-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl)]-2H-1-benzopyran-6-ol
(2R)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-ol
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-6-chromanol
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]chroman-6-ol
(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
(2R,3'E,7'E)-a-tocotrienol
(R)-a-tocotrienol
(R)-alpha-tocotrienol
a-tocotrienol
D-a-tocotrienol
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Articles:
PubMed: Tocotrienol Rich Palm Oil Extract Is More Effective Than Pure Tocotrienols at Improving Endothelium-Dependent Relaxation in the Presence of Oxidative Stress.
PubMed: Muscadine grape seed oil as a novel source of tocotrienols to reduce adipogenesis and adipocyte inflammation.
PubMed: A tocotrienol-enriched formulation protects against radiation-induced changes in cardiac mitochondria without modifying late cardiac function or structure.
PubMed: A tocotrienol series with an oxidative terminal prenyl unit from Garcinia amplexicaulis.
PubMed: Effects of late administration of pentoxifylline and tocotrienols in an image-guided rat model of localized heart irradiation.
PubMed: α-Tocopherol does not accelerate depletion of γ-tocopherol and tocotrienol or excretion of their metabolites in rats.
PubMed: Tocotrienols promote apoptosis in human breast cancer cells by inducing poly(ADP-ribose) polymerase cleavage and inhibiting nuclear factor kappa-B activity.
PubMed: Tissue distribution of vitamin E metabolites in rats after oral administration of tocopherol or tocotrienol.
PubMed: Tissue distribution of α- and γ-tocotrienol and γ-tocopherol in rats and interference with their accumulation by α-tocopherol.
PubMed: A Regenerative Antioxidant Protocol of Vitamin E and α-Lipoic Acid Ameliorates Cardiovascular and Metabolic Changes in Fructose-Fed Rats.
PubMed: A tocotrienol-rich fraction from grape seeds inhibits oxidative stress induced by tert-butyl hydroperoxide in HepG2 cells.
PubMed: Tocotrienol suppresses adipocyte differentiation and Akt phosphorylation in 3T3-L1 preadipocytes.
PubMed: GAPDH as housekeeping gene for human skin fibroblast senescent model.
PubMed: Daily supplementation of tocotrienol-rich fraction or alpha-tocopherol did not induce immunomodulatory changes in healthy human volunteers.
PubMed: Tocotrienols induce apoptosis and autophagy in rat pancreatic stellate cells through the mitochondrial death pathway.
PubMed: Cytochrome P450-dependent metabolism of vitamin E isoforms is a critical determinant of their tissue concentrations in rats.
PubMed: Triton WR1339, an inhibitor of lipoprotein lipase, decreases vitamin E concentration in some tissues of rats by inhibiting its transport to liver.
PubMed: Postprandial metabolic fate of tocotrienol-rich vitamin E differs significantly from that of alpha-tocopherol.
PubMed: The effects of a tocotrienol-rich fraction on experimentally induced atherosclerosis in the aorta of rabbits.
PubMed: Tocotrienol-rich fraction from palm oil and gene expression in human breast cancer cells.
PubMed: Alpha-tocotrienol provides the most potent neuroprotection among vitamin E analogs on cultured striatal neurons.
PubMed: Dietary alpha-tocopherol decreases alpha-tocotrienol but not gamma-tocotrienol concentration in rats.
PubMed: Comparative effects of a tocotrienol-rich fraction and tocopherol in aspirin-induced gastric lesions in rats.
PubMed: Tocotrienol levels in various tissues of Sprague-Dawley rats after intragastric administration of tocotrienols.
PubMed: Effect of sesaminol on plasma and tissue alpha-tocopherol and alpha-tocotrienol concentrations in rats fed a vitamin E concentrate rich in tocotrienols.
PubMed: Effect of either gamma-tocotrienol or a tocotrienol mixture on the plasma lipid profile in hamsters.
PubMed: Dose-dependent suppression of serum cholesterol by tocotrienol-rich fraction (TRF25) of rice bran in hypercholesterolemic humans.
PubMed: Oral toxicity of a tocotrienol preparation in rats.
PubMed: The combined effects of novel tocotrienols and lovastatin on lipid metabolism in chickens.
PubMed: Novel tocotrienols of rice bran suppress cholesterogenesis in hereditary hypercholesterolemic swine.
PubMed: Palm vitamin E and the healing of ethanol-induced gastric lesions.
PubMed: Diet-derived and topically applied tocotrienols accumulate in skin and protect the tissue against ultraviolet light-induced oxidative stress.
PubMed: Lipidaemic effects of tocotrienols, tocopherols and squalene: studies in the hamster.
PubMed: Comparative antioxidant activity of tocotrienols and other natural lipid-soluble antioxidants in a homogeneous system, and in rat and human lipoproteins.
PubMed: Effects of alpha-tocopherol and tocotrienols on blood pressure and linoleic acid metabolism in the spontaneously hypertensive rat (SHR).
PubMed: Cereal grains, alpha tocotrienol and cholesterol metabolism in the rat.
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