EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)

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CAS Number: 25612-59-3Picture of molecule3D/inchi
Nikkaji Web:J17.358D
Beilstein Number:5449575
XlogP3-AA:8.60 (est)
Molecular Weight:396.61420000
Formula:C27 H40 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 517.30 °C. @ 760.00 mm Hg (est)
Flash Point: 415.00 °F. TCC ( 212.80 °C. ) (est)
logP (o/w): 9.840 (est)
Soluble in:
 water, 6.914e-006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
tocotrienol, delta >98%
Santa Cruz Biotechnology
For experimental / research use only.
delta-Tocotrienol >98%
For experimental / research use only.
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:
natural substances and extractives
Recommendation for delta-tocotrienol usage levels up to:
 not for fragrance use.
Recommendation for delta-tocotrienol flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5282350
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5282350
Pubchem (sid):135115273
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
KEGG (GenomeNet):C14156
HMDB (The Human Metabolome Database):HMDB30008
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
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2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, (R-(E,E))-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-
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)-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)


PubMed:Anti-inflammatory γ- and δ-tocotrienols improve cardiovascular, liver and metabolic function in diet-induced obese rats.
PubMed:Tocotrienol-Rich Fraction from Rice Bran Demonstrates Potent Radiation Protection Activity.
PubMed:Physicochemical and functional properties of yeast fermented brown rice flour.
PubMed:A new formulation of Gamma Delta Tocotrienol has superior bioavailability compared to existing Tocotrienol-Rich Fraction in healthy human subjects.
PubMed:Dietary Tocotrienol/γ-Cyclodextrin Complex Increases Mitochondrial Membrane Potential and ATP Concentrations in the Brains of Aged Mice.
PubMed:Tocopherols and tocotrienols in serum and liver of dairy cows receiving conjugated linoleic acids or a control fat supplement during early lactation.
PubMed:EGR-1/Bax pathway plays a role in vitamin E δ-tocotrienol-induced apoptosis in pancreatic cancer cells.
PubMed:δ-Tocotrienol treatment is more effective against hypoxic tumor cells than normoxic cells: potential implications for cancer therapy.
PubMed:δ-tocotrienol induces human bladder cancer cell growth arrest, apoptosis and chemosensitization through inhibition of STAT3 pathway.
PubMed:Delta-tocotrienol suppresses radiation-induced microRNA-30 and protects mice and human CD34+ cells from radiation injury.
PubMed:New bioactive chromanes from Litchi chinensis.
PubMed:α-Tocopherol suppresses antiangiogenic effect of δ-tocotrienol in human umbilical vein endothelial cells.
PubMed:Antioxidant activities of tocopherols/tocotrienols and lipophilic antioxidant capacity of wheat, vegetable oils, milk and milk cream by using photochemiluminescence.
PubMed:The use of delta-tocotrienol and lovastatin for anti-osteoporotic therapy.
PubMed:Cytotoxicity and apoptotic activities of alpha-, gamma- and delta-tocotrienol isomers on human cancer cells.
PubMed:Tocochromanols and carotenoids in sorghum (Sorghum bicolor L.): diversity and stability to the heat treatment.
PubMed:Acute toxicity of subcutaneously administered vitamin E isomers delta- and gamma-tocotrienol in mice.
PubMed:Synergistic inhibition of cancer cell proliferation with a combination of δ-tocotrienol and ferulic acid.
PubMed:Delta-tocotrienol induces apoptotic cell death via depletion of intracellular squalene in ED40515 cells.
PubMed:δ-Tocotrienol oxazine derivative antagonizes mammary tumor cell compensatory response to CoCl2-induced hypoxia.
PubMed:Therapeutic efficacy of vitamin E δ-tocotrienol in collagen-induced rat model of arthritis.
PubMed:High environmental stress yields greater tocotrienol content while changing vitamin e profiles of wild emmer wheat seeds.
PubMed:Oxazine derivatives of γ- and δ-tocotrienol display enhanced anticancer activity in vivo.
PubMed:Tocopherol and tocotrienol contents of different varieties of rice in Malaysia.
PubMed:Improved antitumor activity and reduced cardiotoxicity of epirubicin using hepatocyte-targeted nanoparticles combined with tocotrienols against hepatocellular carcinoma in mice.
PubMed:Advanced glycation inhibition and protection against endothelial dysfunction induced by coumarins and procyanidins from Mammea neurophylla.
PubMed:Anti-melanogenic effects of δ-tocotrienol are associated with tyrosinase-related proteins and MAPK signaling pathway in B16 melanoma cells.
PubMed:Chamaerops humilis L. var. argentea André date palm seed oil: a potential dietetic plant product.
PubMed:Radioprotective efficacy of delta-tocotrienol, a vitamin E isoform, is mediated through granulocyte colony-stimulating factor.
PubMed:Novel liquid chromatography-mass spectrometry method shows that vitamin E deficiency depletes arachidonic and docosahexaenoic acids in zebrafish (Danio rerio) embryos.
PubMed:Concentrations of tocols and γ-oryzanol compounds in rice bran oil obtained by fractional extraction with supercritical carbon dioxide.
PubMed:Nutritional Supplement-5 with a Combination of Proteasome Inhibitors (Resveratrol, Quercetin, δ-Tocotrienol) Modulate Age-Associated Biomarkers and Cardiovascular Lipid Parameters in Human Subjects.
PubMed:Delta-tocotrienol protects mice from radiation-induced gastrointestinal injury.
PubMed:Gene delivery via the hybrid vector of recombinant adeno-associated virus and polyethylenimine.
PubMed:Bioactive lipids, radical scavenging potential, and antimicrobial properties of cold pressed clove (Syzygium aromaticum) oil.
PubMed:Increases in both acute and chronic temperature potentiate tocotrienol concentrations in wild barley at 'Evolution Canyon'.
PubMed:Vitamin E δ-tocotrienol prolongs survival in the LSL-KrasG12D/+;LSL-Trp53R172H/+;Pdx-1-Cre (KPC) transgenic mouse model of pancreatic cancer.
PubMed:Supplementation with natural forms of vitamin E augments antigen-specific TH1-type immune response to tetanus toxoid.
PubMed:High expression of tocochromanol biosynthesis genes increases the vitamin E level in a new line of giant embryo rice.
PubMed:Pure tocotrienol concentrate protected rat gastric mucosa from acute stress-induced injury by a non-antioxidant mechanism.
PubMed:Nonlinear absorption kinetics of self-emulsifying drug delivery systems (SEDDS) containing tocotrienols as lipophilic molecules: in vivo and in vitro studies.
PubMed:[Experimental study on delta-tocotrienol inhibits the Wnt pathway in the colon cancer cell SW620].
PubMed:Vitamin E δ-tocotrienol induces p27(Kip1)-dependent cell-cycle arrest in pancreatic cancer cells via an E2F-1-dependent mechanism.
PubMed:Mitochondrial-dependent anticancer activity of δ-tocotrienol and its synthetic derivatives in HER-2/neu overexpressing breast adenocarcinoma cells.
PubMed:Prolonged survival and delayed progression of pancreatic intraepithelial neoplasia in LSL-KrasG12D/+;Pdx-1-Cre mice by vitamin E δ-tocotrienol.
PubMed:Optimization of tocotrienols as antiproliferative and antimigratory leads.
PubMed:Suppression of Nitric Oxide Production and Cardiovascular Risk Factors in Healthy Seniors and Hypercholesterolemic Subjects by a Combination of Polyphenols and Vitamins.
PubMed:Effects of tocotrienol and lovastatin combination on osteoblast and osteoclast activity in estrogen-deficient osteoporosis.
PubMed:Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species.
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:Inhibition of nitric oxide and inflammatory cytokines in LPS-stimulated murine macrophages by resveratrol, a potent proteasome inhibitor.
PubMed:Mechanism of radioprotection by δ-tocotrienol: pharmacokinetics, pharmacodynamics and modulation of signalling pathways.
PubMed:δ- and γ-tocotrienols induce classical ultrastructural apoptotic changes in human T lymphoblastic leukemic cells.
PubMed:Rapid baseline-separation of all eight tocopherols and tocotrienols by reversed-phase liquid-chromatography with a solid-core pentafluorophenyl column and their sensitive quantification in plasma and liver.
PubMed:A new xanthone from the bark of Calophyllum thorelii.
PubMed:Chemical characterization of chestnut cultivars from three consecutive years: chemometrics and contribution for authentication.
PubMed:Plasma vitamin E and coenzyme Q10 are not associated with a lower risk of acute myocardial infarction in Singapore Chinese adults.
PubMed:Delta-tocotrienol suppresses Notch-1 pathway by upregulating miR-34a in nonsmall cell lung cancer cells.
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:Inhibition of nitric oxide in LPS-stimulated macrophages of young and senescent mice by δ-tocotrienol and quercetin.
PubMed:Induction of DNA damage and caspase-independent programmed cell death by vitamin E.
PubMed:Suppression of nitric oxide induction and pro-inflammatory cytokines by novel proteasome inhibitors in various experimental models.
PubMed:Vitamin E δ-tocotrienol augments the antitumor activity of gemcitabine and suppresses constitutive NF-κB activation in pancreatic cancer.
PubMed:Inhibitory effects of palm α-, γ- and δ-tocotrienol on lipopolysaccharide-induced nitric oxide production in BV2 microglia.
PubMed:Tocotrienols and cardiovascular health.
PubMed:Tocotrienols inhibit AKT and ERK activation and suppress pancreatic cancer cell proliferation by suppressing the ErbB2 pathway.
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:Palm tocotrienols decrease levels of pro-angiogenic markers in human umbilical vein endothelial cells (HUVEC) and murine mammary cancer cells.
PubMed:A paraptosis-like cell death induced by δ-tocotrienol in human colon carcinoma SW620 cells is associated with the suppression of the Wnt signaling pathway.
PubMed:Hematopoietic Recovery and Amelioration of Radiation-Induced Lethality by the Vitamin E Isoform δ-Tocotrienol.
PubMed:δ-Tocotrienol and quercetin reduce serum levels of nitric oxide and lipid parameters in female chickens.
PubMed:d-δ-Tocotrienol-mediated cell cycle arrest and apoptosis in human melanoma cells.
PubMed:Tocotrienols inhibit lipopolysaccharide-induced pro-inflammatory cytokines in macrophages of female mice.
PubMed:Synthesis of fluorescent analogues of the anticancer natural products 4-hydroxyphenylmethylene hydantoin and delta-tocotrienol.
PubMed:Cytotoxicity of δ-tocotrienols from Kielmeyera coriacea against cancer cell lines.
PubMed:Effect of δ-tocotrienol on melanin content and enzymes for melanin synthesis in mouse melanoma cells.
PubMed:Delta-tocotrienol protects mouse and human hematopoietic progenitors from gamma-irradiation through extracellular signal-regulated kinase/mammalian target of rapamycin signaling.
PubMed:Gamma delta tocotrienols reduce hepatic triglyceride synthesis and VLDL secretion.
PubMed:Proapoptotic effects of long-chain vitamin E metabolites in HepG2 cells are mediated by oxidative stress.
PubMed:alpha-Tocopherol attenuates the cytotoxic effect of delta-tocotrienol in human colorectal adenocarcinoma cells.
PubMed:19F MRI of 3D CEM cells to study the effects of tocopherols and tocotrienols.
PubMed:High plasma levels of vitamin E forms and reduced Alzheimer's disease risk in advanced age.
PubMed:Beneficial effects of vitamin E isomer supplementation on static and dynamic bone histomorphometry parameters in normal male rats.
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:Antifibrotic effects of tocotrienols on human Tenon's fibroblasts.
PubMed:Tocotrienols suppress proinflammatory markers and cyclooxygenase-2 expression in RAW264.7 macrophages.
PubMed:Suppression of tumor growth by palm tocotrienols via the attenuation of angiogenesis.
PubMed:d-δ-Tocotrienol-mediated suppression of the proliferation of human PANC-1, MIA PaCa-2, and BxPC-3 pancreatic carcinoma cells.
PubMed:Vitamin E delta-tocotrienol levels in tumor and pancreatic tissue of mice after oral administration.
PubMed:Growth inhibition of human MDA-mB-231 breast cancer cells by delta-tocotrienol is associated with loss of cyclin D1/CDK4 expression and accompanying changes in the state of phosphorylation of the retinoblastoma tumor suppressor gene product.
PubMed:Biosynthesis of the vitamin E compound delta-tocotrienol in recombinant Escherichia coli cells.
PubMed:Arterial compliance and vitamin E blood levels with a self emulsifying preparation of tocotrienol rich vitamin E.
PubMed:Inhibition of oxidative metabolism of tocopherols with omega-N-heterocyclic derivatives of vitamin E.
PubMed:Configuration of the vitamin E analogue garcinoic acid extracted from Garcinia Kola seeds.
PubMed:Tumor anti-angiogenic effect and mechanism of action of delta-tocotrienol.
PubMed:Circular dichroism of tocopherols versus tocotrienols.
PubMed:Assignment of the 1H and 13C NMR of tocotrienols.
PubMed:Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties.
PubMed:Comprehensive analysis of vitamin E constituents in human plasma by liquid chromatography-mass spectrometry.
PubMed:Tocotrienols: the emerging face of natural vitamin E.
PubMed:Tocotrienols induce apoptosis and autophagy in rat pancreatic stellate cells through the mitochondrial death pathway.
PubMed:Tocotrienols in health and disease: the other half of the natural vitamin E family.
PubMed:Tocotrienols potentiate lovastatin-mediated growth suppression in vitro and in vivo.
PubMed:Dose dependent elevation of plasma tocotrienol levels and its effect on arterial compliance, plasma total antioxidant status, and lipid profile in healthy humans supplemented with tocotrienol rich vitamin E.
PubMed:Cinnamacrins A-C, cinnafragrin D, and cytostatic metabolites with alpha-glucosidase inhibitory activity from Cinnamosma macrocarpa.
PubMed:Tocopherol and tocotrienol levels of foods consumed in Hawaii.
PubMed:Reinvestigation of the effect of heat pretreatment of corn fiber and corn germ on the levels of extractable tocopherols and tocotrienols.
PubMed:Does gamma-tocopherol play a role in the primary prevention of heart disease and cancer? A review.
PubMed:Cinnafragrins A-C, dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans, and structure revision of capsicodendrin.
PubMed:Down-regulation of telomerase activity in DLD-1 human colorectal adenocarcinoma cells by tocotrienol.
PubMed:Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense.
PubMed:Insig-dependent ubiquitination and degradation of 3-hydroxy-3-methylglutaryl coenzyme a reductase stimulated by delta- and gamma-tocotrienols.
PubMed:Comparative antioxidant activity of tocotrienols and the novel chromanyl-polyisoprenyl molecule FeAox-6 in isolated membranes and intact cells.
PubMed:Tocotrienols: Vitamin E beyond tocopherols.
PubMed:Inhibitory effect of tocotrienol on eukaryotic DNA polymerase lambda and angiogenesis.
PubMed:Tumor suppressive effects of tocotrienol in vivo and in vitro.
PubMed:Composition of fatty acids triacylglycerols and unsaponifiable matter in Calophyllum calaba L. oil from Guadeloupe.
PubMed:Application of supercritical fluid chromatography in the quantitative analysis of minor components (carotenes, vitamin E, sterols, and squalene) from palm oil.
PubMed:Tocotrienols reduce 25-hydroxycholesterol-induced monocyte-endothelial cell interaction by inhibiting the surface expression of adhesion molecules.
PubMed:Tocotrienol: the natural vitamin E to defend the nervous system?
PubMed:Separation of vitamin E (tocopherol, tocotrienol, and tocomonoenol) in palm oil.
PubMed:Vitamin E and breast cancer.
PubMed:A developmental study on the appearance of tocopherols and tocotrienols in developing palm mesocarp (Elaeis guineensis).
PubMed:Alpha-tocotrienol provides the most potent neuroprotection among vitamin E analogs on cultured striatal neurons.
PubMed:Prenylated xanthones and tocotrienols from Garcinia virgata.
PubMed:Pro-apoptotic mechanisms of action of a novel vitamin E analog (alpha-TEA) and a naturally occurring form of vitamin E (delta-tocotrienol) in MDA-MB-435 human breast cancer cells.
PubMed:Simultaneous determination of vitamin E homologs in chicken meat by liquid chromatography with fluorescence detection.
PubMed:Anti-angiogenic activity of tocotrienol.
PubMed:Inhibitory effect of delta-tocotrienol, a HMG CoA reductase inhibitor, on monocyte-endothelial cell adhesion.
PubMed:Vitamin E isoforms alpha-tocotrienol and gamma-tocopherol prevent cerebral infarction in mice.
PubMed:Cytotoxic prenylated xanthones and the unusual compounds anthraquinobenzophenones from Cratoxylum sumatranum.
PubMed:Does lack of tocopherols and tocotrienols put women at increased risk of breast cancer?
PubMed:Vitamin E inhibition of normal mammary epithelial cell growth is associated with a reduction in protein kinase C(alpha) activation.
PubMed:Determination of RS,E/Z-tocotrienols by HPLC.
PubMed:Palm tocotrienols protect ApoE +/- mice from diet-induced atheroma formation.
PubMed:Antiproliferative and apoptotic effects of tocopherols and tocotrienols on preneoplastic and neoplastic mouse mammary epithelial cells.
PubMed:Antiproliferative and apoptotic effects of tocopherols and tocotrienols on normal mouse mammary epithelial cells.
PubMed:Simple high-performance liquid chromatographic method for the determination of tocotrienols in human plasma.
PubMed:Separation and Identification of Tocotrienol Isomers by HPLC-MS and HPLC-NMR Coupling.
PubMed:Tocotrienols inhibit the growth of human breast cancer cells irrespective of estrogen receptor status.
PubMed:Inhibition of proliferation of estrogen receptor-negative MDA-MB-435 and -positive MCF-7 human breast cancer cells by palm oil tocotrienols and tamoxifen, alone and in combination.
PubMed:Dietary alpha-tocopherol attenuates the impact of gamma-tocotrienol on hepatic 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in chickens.
PubMed:Lymphatic transport of alpha-, gamma- and delta-tocotrienols and alpha-tocopherol in rats.
PubMed:Differences in the plasma transport and tissue concentrations of tocopherols and tocotrienols: observations in humans and hamsters.
PubMed:[The effect of gamma rays on vitamin E factors in solution. II. Tributyrine solutions of alpha, beta, gamma, and delta tocotrienol].
PubMed:The isolation and properties of delta-tocotrienol from Hevea latex.
Constit. of palm oil. Nutriceutical with anticancer props. and a positive influence on the blood lipid profile
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