tocotrienol
2H-1-benzopyran-6-ol, 3,4-dihydro-2-methyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-
Identification
| Name | tocotrienol |
| IUPAC | 2-methyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol |
| CAS Number | 6829-55-6 |
| FDA UNII | 0867I0N41V |
| Molecular Formula | C26 H38 O2 |
| Molecular Weight | 382.58726000 |
| Nikkaji Number | J578.410G |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | GRN 307 |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 507.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 410.00 °F. TCC ( 209.90 °C. ) (est) |
| logP (o/w) | 9.380 (est) |
| Soluble in | water, 2.475e-005 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | oral care agents |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | antioxidants |
| Recommendation for tocotrienol usage levels up to | not for fragrance use. |
| Recommendation for tocotrienol flavor usage levels up to | not for flavor use. |
American International Chemical, Inc.
Consistent sources
North American supplier for globally sourced ingredients.
Potential Uses
Natural Occurrence
Synonyms
2H-1-
benzopyran-6-ol, 3,4-dihydro-2-methyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-
2-
methyl-2-(4,8,12-trimethyl-trideca-3,7,11-trienyl)-chroman-6-ol
2-
methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-ol
2-
methyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-6-chromanol
2-
methyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
2-
methyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
tocotrienols
PubMed:
Anti-invasive Activity against Cancer Cells of Phytochemicals in Red Jasmine Rice (Oryza sativa L.).
PubMed:
Tocopherol and tocotrienol contents of different varieties of rice in Malaysia.
PubMed:
Activation of autophagy and AMPK by gamma-tocotrienol suppresses the adipogenesis in human adipose derived stem cells.
PubMed:
Chamaerops humilis L. var. argentea André date palm seed oil: a potential dietetic plant product.
PubMed:
The concentrations of tocols and γ-oryzanol compounds in rice bran oil obtained by fractional extraction with supercritical carbon dioxide.
PubMed:
Vitamin E tocotrienol supplementation improves lipid profiles in chronic hemodialysis patients.
PubMed:
Comparison of dietary tocotrienols from barley and palm oils in hen's egg yolk: transfer efficiency, influence of emulsification, and effect on egg cholesterol.
PubMed:
Tocol composition and supercritical carbon dioxide extraction of lipids from barley pearling flour.
PubMed:
Bioactive lipids, radical scavenging potential, and antimicrobial properties of cold pressed clove (Syzygium aromaticum) oil.
PubMed:
Tocotrienol (unsaturated vitamin E) suppresses degranulation of mast cells and reduces allergic dermatitis in mice.
PubMed:
Gamma tocotrienol, a potent radioprotector, preferentially upregulates expression of anti-apoptotic genes to promote intestinal cell survival.
PubMed:
Rice bran extract protects from mitochondrial dysfunction in guinea pig brains.
PubMed:
γ-Tocotrienol induced cell cycle arrest and apoptosis via activating the Bax-mediated mitochondrial and AMPK signaling pathways in 3T3-L1 adipocytes.
PubMed:
Rice varietal differences in bioactive bran components for inhibition of colorectal cancer cell growth.
PubMed:
High expression of tocochromanol biosynthesis genes increases the vitamin E level in a new line of giant embryo rice.
PubMed:
γ-Tocotrienol attenuates triglyceride through effect on lipogenic gene expressions in mouse hepatocellular carcinoma Hepa 1-6.
PubMed:
Studies targeting α-glucosidase inhibition, antiangiogenic effects, and lipid modification regulation: background, evaluation, and challenges in the development of food ingredients for therapeutic purposes.
PubMed:
Combination of saponification and dispersive liquid-liquid microextraction for the determination of tocopherols and tocotrienols in cereals by reversed-phase high-performance liquid chromatography.
PubMed:
Evaluation of γ-oryzanol content and composition from the grains of pigmented rice-germplasms by LC-DAD-ESI/MS.
PubMed:
Investigation of tocotrienol biosynthesis in rice (Oryza sativa L.).
PubMed:
Comparative effects of tocotrienol-rich fraction, α-tocopherol and α-tocopheryl acetate on inflammatory mediators and nuclear factor kappa B expression in mouse peritoneal macrophages.
PubMed:
Involvement of de novo ceramide synthesis in gamma-tocopherol and gamma-tocotrienol-induced apoptosis in human breast cancer cells.
PubMed:
Use of recovered frying oils in chicken and rabbit feeds: effect on the fatty acid and tocol composition and on the oxidation levels of meat, liver and plasma.
PubMed:
Effects of sodium alginate bead encapsulation on the storage stability of durum wheat (Triticum durum Desf.) bran oil extracted by supercritical CO2.
PubMed:
Physiological effects and tissue distribution from large doses of tocotrienol in rats.
PubMed:
Increased α-tocotrienol content in seeds of transgenic rice overexpressing Arabidopsis γ-tocopherol methyltransferase.
PubMed:
Delta-tocotrienol augments cisplatin-induced suppression of non-small cell lung cancer cells via inhibition of the Notch-1 pathway.
PubMed:
Identification of α-tocotrienolquinone epoxides and development of an efficient molecular distillation procedure for quantitation of α-tocotrienol oxidation products in food matrices by high-performance liquid chromatography with diode array and fluorescence detection.
PubMed:
Distinct roles of different forms of vitamin E in DHA-induced apoptosis in triple-negative breast cancer cells.
PubMed:
Effect of fermentation time and vegetable concentrate addition on quality parameters of organic Botifarra Catalana, a cured-cooked sausage.
PubMed:
Response of urinary biomarkers of systemic oxidation to oral iron supplementation in healthy men.
PubMed:
Chemical characterization of chestnut cultivars from three consecutive years: chemometrics and contribution for authentication.
PubMed:
Development of a method for oral administration of hydrophobic substances to Caenorhabditis elegans: pro-longevity effects of oral supplementation with lipid-soluble antioxidants.
PubMed:
Delta-tocotrienol suppresses Notch-1 pathway by upregulating miR-34a in nonsmall cell lung cancer cells.
PubMed:
Effect of EPI-743 on the clinical course of the mitochondrial disease Leber hereditary optic neuropathy.
PubMed:
Tocotrienol attenuates triglyceride accumulation in HepG2 cells and F344 rats.
PubMed:
Optimization and validation of the reversed-phase high-performance liquid chromatography with fluorescence detection method for the separation of tocopherol and tocotrienol isomers in cereals, employing a novel sorbent material.
PubMed:
Tocopherols in rose hips (Rosa spp.) during ripening.
PubMed:
Determination of tocopherol and tocotrienol content of Greek barley varieties under conventional and organic cultivation techniques using validated reverse phase high-performance liquid chromatography method.
PubMed:
Separation of α-tocotrienol oxidation products and eight tocochromanols by HPLC with DAD and fluorescence detection and identification of unknown peaks by DAD, PBI-EIMS, FTIR, and NMR.
PubMed:
Assessment of the oxidative stability of conventional and high-oleic sunflower oil by means of solid-phase microextraction-gas chromatography.
PubMed:
γ-Tocotrienol inhibits cell viability through suppression of β-catenin/Tcf signaling in human colon carcinoma HT-29 cells.
PubMed:
Induction of expression and functional activity of P-glycoprotein efflux transporter by bioactive plant natural products.
PubMed:
The 21st century form of vitamin E--tocotrienol.
PubMed:
Natural vitamin E α-tocotrienol protects against ischemic stroke by induction of multidrug resistance-associated protein 1.
PubMed:
Inhibition of cell growth and induction of apoptosis in non-small cell lung cancer cells by delta-tocotrienol is associated with notch-1 down-regulation.
PubMed:
Mevalonate depletion mediates the suppressive impact of geranylgeraniol on murine B16 melanoma cells.
PubMed:
A Regenerative Antioxidant Protocol of Vitamin E and α-Lipoic Acid Ameliorates Cardiovascular and Metabolic Changes in Fructose-Fed Rats.
PubMed:
γ-Tocotrienol inhibits angiogenesis of human umbilical vein endothelial cell induced by cancer cell.
PubMed:
Intake of antioxidants and risk of type 2 diabetes in a cohort of male smokers.
PubMed:
d-δ-Tocotrienol-mediated cell cycle arrest and apoptosis in human melanoma cells.
PubMed:
Antioxidant activity and inhibition of lipid peroxidation in germinating seeds of transgenic soybean expressing OsHGGT.
PubMed:
Nutritional value of the Chilean seaweeds Cryptonemia obovata and Rhodymenia corallina.
PubMed:
Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:
A tocotrienol-rich fraction from grape seeds inhibits oxidative stress induced by tert-butyl hydroperoxide in HepG2 cells.
PubMed:
gamma-Tocotrienol reduces squalene hydroperoxide-induced inflammatory responses in HaCaT keratinocytes.
PubMed:
alpha-Tocopherol attenuates the cytotoxic effect of delta-tocotrienol in human colorectal adenocarcinoma cells.
PubMed:
Suppression of gamma-tocotrienol on UVB induced inflammation in HaCaT keratinocytes and HR-1 hairless mice via inflammatory mediators multiple signaling.
PubMed:
Analysis of multiple metabolites of tocopherols and tocotrienols in mice and humans.
PubMed:
Tocotrienol distribution in foods: estimation of daily tocotrienol intake of Japanese population.
PubMed:
Effect of polyoxyethylene sorbitan esters and sodium caseinate on physicochemical properties of palm-based functional lipid nanodispersions.
PubMed:
Vitamin E tocotrienols improve insulin sensitivity through activating peroxisome proliferator-activated receptors.
PubMed:
delta-Tocotrienol suppresses VEGF induced angiogenesis whereas alpha-tocopherol does not.
PubMed:
Influence of genetic and environmental factors on selected nutritional traits of Triticum monococcum.
PubMed:
A novel mechanism of natural vitamin E tocotrienol activity: involvement of ERbeta signal transduction.
PubMed:
Vitamin E profile as a reliable authenticity discrimination factor between chestnut (Castanea sativa Mill.) cultivars.
PubMed:
Cross-fertilization for enhancing tocotrienol biosynthesis in rice plants and QTL analysis of their F2 progenies.
PubMed:
CoulArray electrochemical evaluation of tocopherol and tocotrienol isomers in barley, oat and spelt grains.
PubMed:
d-δ-Tocotrienol-mediated suppression of the proliferation of human PANC-1, MIA PaCa-2, and BxPC-3 pancreatic carcinoma cells.
PubMed:
Simultaneous extraction of tocotrienols and tocopherols from cereals using pressurized liquid extraction prior to LC determination.
PubMed:
Inhibitory effects of gamma-tocotrienol on invasion and metastasis of human gastric adenocarcinoma SGC-7901 cells.
PubMed:
Inhibition of proliferation and induction of apoptosis by gamma-tocotrienol in human colon carcinoma HT-29 cells.
PubMed:
Antiangiogenic and anticancer potential of unsaturated vitamin E (tocotrienol).
PubMed:
Tocotrienol content in hen eggs: its fortification by supplementing the feed with rice bran scum oil.
PubMed:
Tocotrienol inhibits secretion of angiogenic factors from human colorectal adenocarcinoma cells by suppressing hypoxia-inducible factor-1alpha.
PubMed:
Tocopherols and tocotrienols in wheat genotypes in the HEALTHGRAIN Diversity Screen.
PubMed:
Specific accumulation of gamma- and delta-tocotrienols in tumor and their antitumor effect in vivo.
PubMed:
Effect of astaxanthin in combination with alpha-tocopherol or ascorbic acid against oxidative damage in diabetic ODS rats.
PubMed:
Induction of characteristic hepatocyte proliferative lesion with dietary exposure of Wistar Hannover rats to tocotrienol for 1 year.
PubMed:
Tocopherols and tocotrienols in sea buckthorn (Hippophae rhamnoides L.) berries during ripening.
PubMed:
Tumor anti-angiogenic effect and mechanism of action of delta-tocotrienol.
PubMed:
Anti-angiogenic function of tocotrienol.
PubMed:
Dietary tocotrienol reduces UVB-induced skin damage and sesamin enhances tocotrienol effects in hairless mice.
PubMed:
Tocotrienol-rich fraction of palm oil exhibits anti-inflammatory property by suppressing the expression of inflammatory mediators in human monocytic cells.
PubMed:
Effect of apoE genotype and vitamin E on biomarkers of oxidative stress in cultured neuronal cells and the brain of targeted replacement mice.
PubMed:
Gamma-tocotrienol-induced apoptosis in human gastric cancer SGC-7901 cells is associated with a suppression in mitogen-activated protein kinase signalling.
PubMed:
Influence of growth temperature on the amounts of tocopherols, tocotrienols, and gamma-oryzanol in brown rice.
PubMed:
Comprehensive analysis of vitamin E constituents in human plasma by liquid chromatography-mass spectrometry.
PubMed:
Quantification of vitamin E and gamma-oryzanol components in rice germ and bran.
PubMed:
In vivo angiogenesis is suppressed by unsaturated vitamin E, tocotrienol.
PubMed:
Intestinal epithelial cells absorb gamma-tocotrienol faster than alpha-tocopherol.
PubMed:
Distribution of tocotrienols in rats fed a rice bran tocotrienol concentrate.
PubMed:
Tocopherol and tocotrienol levels of foods consumed in Hawaii.
PubMed:
Antioxidant contents and antioxidative properties of traditional rye breads.
PubMed:
Quantitation of tocotrienol and tocopherol in various rice brans.
PubMed:
Reinvestigation of the effect of heat pretreatment of corn fiber and corn germ on the levels of extractable tocopherols and tocotrienols.
PubMed:
Postprandial metabolic fate of tocotrienol-rich vitamin E differs significantly from that of alpha-tocopherol.
PubMed:
Quantitation of fatty acids, sterols, and tocopherols in turpentine (Pistacia terebinthus Chia) growing wild in Turkey.
PubMed:
Does gamma-tocopherol play a role in the primary prevention of heart disease and cancer? A review.
PubMed:
Down-regulation of telomerase activity in DLD-1 human colorectal adenocarcinoma cells by tocotrienol.
PubMed:
Postprandial levels of the natural vitamin E tocotrienol in human circulation.
PubMed:
Molecular mechanism of antioxidant synergism of tocotrienols and carotenoids in palm oil.
PubMed:
Quantification of tocopherols and tocotrienols in portuguese olive oils using HPLC with three different detection systems.
PubMed:
Dietary supplements and related products: a brief summary.
PubMed:
Tocopherol and tocotrienol content of hazelnut cultivars grown in portugal.
PubMed:
Inhibitory effect of tocotrienol on eukaryotic DNA polymerase lambda and angiogenesis.
PubMed:
Vitamin E composition of walnuts (Juglans regia L.): a 3-year comparative study of different cultivars.
PubMed:
Hypolipidemic and antioxidant properties of tocotrienol rich fraction isolated from rice bran oil in experimentally induced hyperlipidemic rats.
PubMed:
Antiangiogenic potency of vitamin E.
PubMed:
Yield and composition of grape seed oils extracted by supercritical carbon dioxide and petroleum ether: varietal effects.
PubMed:
DNA chip analysis of comprehensive food function: inhibition of angiogenesis and telomerase activity with unsaturated vitamin E, tocotrienol.
PubMed:
Rice bran extract prevents the elevation of plasma peroxylipid in KKAy diabetic mice.
PubMed:
Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention.
PubMed:
Effects of tocopherols and tocotrienols on body composition and bone calcium content in adrenalectomized rats replaced with dexamethasone.
PubMed:
Anti-angiogenic potential of tocotrienol in vitro.
PubMed:
Simultaneous determination of vitamin E homologs in chicken meat by liquid chromatography with fluorescence detection.
PubMed:
Dietary antioxidant intake and risk of type 2 diabetes.
PubMed:
Palm fruit chemistry and nutrition.
PubMed:
Anti-angiogenic activity of tocotrienol.
PubMed:
Normal phase high-performance liquid chromatography method for the determination of tocopherols and tocotrienols in cereals.
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:
Synergistic antioxidative properties of phenolics from natural origin toward low-density lipoproteins depend on the oxidation system.
PubMed:
Tocotrienols inhibit human glutathione S-transferase P1-1.
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:
Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.).
PubMed:
Dietary sesame seeds elevate alpha- and gamma-tocotrienol concentrations in skin and adipose tissue of rats fed the tocotrienol-rich fraction extracted from palm oil.
PubMed:
Relationship between fatty acid profile and vitamin E content in maize hybrids (Zea mays L.).
PubMed:
Oral toxicity of a tocotrienol preparation in rats.
PubMed:
Antioxidant activity of tocopherols, tocotrienols, and gamma-oryzanol components from rice bran against cholesterol oxidation accelerated by 2,2'-azobis(2-methylpropionamidine) dihydrochloride.
PubMed:
Tocotrienols inhibit growth of ZR-75-1 breast cancer cells.
PubMed:
Vitamin E and factors affecting atherosclerosis in rabbits fed a cholesterol-rich diet.
PubMed:
Vitamin E and beta-carotene affect natural killer cell function.
PubMed:
Determination of RS,E/Z-tocotrienols by HPLC.
PubMed:
Removal of fat from cow's milk decreases the vitamin E contents of the resulting dairy products.
PubMed:
Pharmacokinetics and bioavailability of alpha-, gamma- and delta-tocotrienols under different food status.
PubMed:
Isolation and identification of novel tocotrienols from rice bran with hypocholesterolemic, antioxidant, and antitumor properties.
PubMed:
Selective uptake of dietary tocotrienols into rat skin.
PubMed:
Liquid chromatographic determination of tocopherols and tocotrienols in vegetable oils, formulated preparations, and biscuits.
PubMed:
Changes in tocopherol and plastochromanol-8 contents in seeds and oil of oilseed rape (Brassica napus L.) during storage as influenced by temperature and air oxygen.
PubMed:
Novel HPLC analysis of tocopherols, tocotrienols, and cholesterol in tissue.
PubMed:
Palm vitamin E and the healing of ethanol-induced gastric lesions.
PubMed:
Effect of dietary antioxidants on serum lipid contents and immunoglobulin productivity of lymphocytes in Sprague-Dawley rats.
PubMed:
A rapid method for the determination of vitamin E forms in tissues and diet by high-performance liquid chromatography using a normal-phase diol column.
PubMed:
Liquid chromatographic determination of tocopherols and tocotrienols in margarine, infant foods, and vegetables.
PubMed:
Response of hypercholesterolemic subjects to administration of tocotrienols.
PubMed:
Carotenoids, retinoids, tocopherols and tocotrienols in the diet; the Finnish Mobile Clinic Health Examination Survey.
PubMed:
Influence of oxidized deep-frying fat and iron on the formation of food mutagens in a model system.
PubMed:
Long-term tocotrienol supplementation and glutathione-dependent enzymes during hepatocarcinogenesis in the rat.
PubMed:
Long-term administration of tocotrienols and tumor-marker enzyme activities during hepatocarcinogenesis in rats.
PubMed:
Effect of palm oil on lipid and lipoprotein metabolism and eicosanoid production in rats.
PubMed:
The tocopherol, tocotrienol, and vitamin E content of the average Finnish diet.
PubMed:
Serum alpha-tocopherol levels after high-dose enteral vitamin E administration in patients with acute respiratory failure.
PubMed:
Effects of Low-Temperature Acclimation and Oxygen Stress on Tocopheron Production in Euglena gracilis Z.
PubMed:
Specific determination of alpha-tocopherol in food and feed by fluorometry. Part 1. Manual method.
PubMed:
High-performance liquid chromatographic determination of tocopherols and tocotrienols and its application to diets and plasma of Finnish men. I. Analytical method.