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2H-1-benzopyran-6-ol, 3,4-dihydro-2-methyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-

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CAS Number: 6829-55-6Picture of molecule3D/inchi
Other(deleted CASRN):9074-33-3
FDA UNII: 0867I0N41V
Nikkaji Web:J578.410G
XlogP3-AA:8.20 (est)
Molecular Weight:382.58726000
Formula:C26 H38 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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 FDA/DG SANTE Petitions, Reviews, Notices:
GRN 307 Palm oil-derived tocols with tocotrienols and a-tocopherol as the principal components View - notice PDF
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)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: oral care agents
skin conditioning
uv absorbers
American International Chemical, LLC.
Tocotrienols (Natural e3®)
Safety Information:
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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
Recommendation for tocotrienol usage levels up to:
 not for fragrance use.
Recommendation for tocotrienol flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9929901
National Institute of Allergy and Infectious Diseases:Data
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9929901
Pubchem (sid):135258138
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
HMDB (The Human Metabolome Database):Search
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 found in nature
2H-1-benzopyran-6-ol, 3,4-dihydro-2-methyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-


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.
natural analogs of tocopherols exhibiting antioxidant activity. these tocol derivatives and isomers contain a benzopyran ring and an unsaturated isoprenoid side chain.
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