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14101-61-2,MFCD00901547
Catalog No.:AA007LE5

14101-61-2 | γ-Tocotrienol

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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA007LE5
Chemical Name:
γ-Tocotrienol
CAS Number:
14101-61-2
Molecular Formula:
C28H42O2
Molecular Weight:
410.6319
MDL Number:
MFCD00901547
SMILES:
CC(=CCCC1(C)CCc2c(O1)c(C)c(c(c2)O)C)CCC=C(CCC=C(C)C)C
Properties
Computed Properties
 
Complexity:
625  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
9  
XLogP3:
8.9  

Literature

Title: Gamma tocotrienol, a potent radioprotector, preferentially upregulates expression of anti-apoptotic genes to promote intestinal cell survival.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20131001

Title: Modulation of microRNA 20b with resveratrol and longevinex is linked with their potent anti-angiogenic action in the ischaemic myocardium and synergestic effects of resveratrol and γ-tocotrienol.

Journal: Journal of cellular and molecular medicine 20121001

Title: A key regulator of cholesterol homoeostasis, SREBP-2, can be targeted in prostate cancer cells with natural products.

Journal: The Biochemical journal 20120901

Title: Vitamin E forms inhibit IL-13/STAT6-induced eotaxin-3 secretion by up-regulation of PAR4, an endogenous inhibitor of atypical PKC in human lung epithelial cells.

Journal: The Journal of nutritional biochemistry 20120601

Title: δ- and γ-tocotrienols induce classical ultrastructural apoptotic changes in human T lymphoblastic leukemic cells.

Journal: Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada 20120601

Title: Distinct roles of different forms of vitamin E in DHA-induced apoptosis in triple-negative breast cancer cells.

Journal: Molecular nutrition & food research 20120601

Title: First evidence that γ-tocotrienol inhibits the growth of human gastric cancer and chemosensitizes it to capecitabine in a xenograft mouse model through the modulation of NF-κB pathway.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120415

Title: Gamma-tocotrienol induces apoptosis and autophagy in prostate cancer cells by increasing intracellular dihydrosphingosine and dihydroceramide.

Journal: International journal of cancer 20120201

Title: γ-Tocotrienol protects against mitochondrial dysfunction and renal cell death.

Journal: The Journal of pharmacology and experimental therapeutics 20120201

Title: Tissue distribution of α- and γ-tocotrienol and γ-tocopherol in rats and interference with their accumulation by α-tocopherol.

Journal: Lipids 20120201

Title: Tocotrienols prevent hydrogen peroxide-induced axon and dendrite degeneration in cerebellar granule cells.

Journal: Free radical research 20120201

Title: Gamma-tocotrienol modulation of senescence-associated gene expression prevents cellular aging in human diploid fibroblasts.

Journal: Clinics (Sao Paulo, Brazil) 20120201

Title: Gamma-tocotrienol induced apoptosis is associated with unfolded protein response in human breast cancer cells.

Journal: The Journal of nutritional biochemistry 20120101

Title: Tocotrienols confer resistance to ischemia in hypercholesterolemic hearts: insight with genomics.

Journal: Molecular and cellular biochemistry 20120101

Title: Inhibition of mitochondrial cytochrome c release and suppression of caspases by gamma-tocotrienol prevent apoptosis and delay aging in stress-induced premature senescence of skin fibroblasts.

Journal: Oxidative medicine and cellular longevity 20120101

Title: γ-Tocotrienol inhibits HGF-dependent mitogenesis and Met activation in highly malignant mammary tumour cells.

Journal: Cell proliferation 20111201

Title: Induction of expression and functional activity of P-glycoprotein efflux transporter by bioactive plant natural products.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111101

Title: Tocotrienamines and tocopheramines: reactions with radicals and metal ions.

Journal: Bioorganic & medicinal chemistry 20111101

Title: Direct inhibition of osteoclast formation and activity by the vitamin E isomer gamma-tocotrienol.

Journal: International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20111101

Title: Role of immunoregulatory transcription factors in differential immunomodulatory effects of tocotrienols.

Journal: Free radical biology & medicine 20110701

Title: γ-Tocotrienol induces growth arrest through a novel pathway with TGFβ2 in prostate cancer.

Journal: Free radical biology & medicine 20110515

Title: Gamma-tocotrienol as an effective agent in targeting prostate cancer stem cell-like population.

Journal: International journal of cancer 20110501

Title: Development and validation of a reversed-phase HPLC method for the determination of γ-tocotrienol in rat and human plasma.

Journal: Biomedical chromatography : BMC 20110501

Title: γ-Tocotrienol is a novel inhibitor of constitutive and inducible STAT3 signalling pathway in human hepatocellular carcinoma: potential role as an antiproliferative, pro-apoptotic and chemosensitizing agent.

Journal: British journal of pharmacology 20110501

Title: Reduction of radiation-induced vascular nitrosative stress by the vitamin E analog γ-tocotrienol: evidence of a role for tetrahydrobiopterin.

Journal: International journal of radiation oncology, biology, physics 20110301

Title: Pentoxifylline enhances the radioprotective properties of γ-tocotrienol: differential effects on the hematopoietic, gastrointestinal and vascular systems.

Journal: Radiation research 20110301

Title: γ-Tocotrienol induces apoptosis in human T cell lymphoma through activation of both intrinsic and extrinsic pathways.

Journal: Current pharmaceutical design 20110101

Title: Tissue distribution of vitamin E metabolites in rats after oral administration of tocopherol or tocotrienol.

Journal: Journal of nutritional science and vitaminology 20110101

Title: Redox-silent tocotrienol esters as breast cancer proliferation and migration inhibitors.

Journal: Bioorganic & medicinal chemistry 20101115

Title: {Gamma}-tocotrienol inhibits pancreatic tumors and sensitizes them to gemcitabine treatment by modulating the inflammatory microenvironment.

Journal: Cancer research 20101101

Title: Gamma delta tocotrienols reduce hepatic triglyceride synthesis and VLDL secretion.

Journal: Journal of atherosclerosis and thrombosis 20101027

Title: γ-Tocotrienol but not γ-tocopherol blocks STAT3 cell signaling pathway through induction of protein-tyrosine phosphatase SHP-1 and sensitizes tumor cells to chemotherapeutic agents.

Journal: The Journal of biological chemistry 20101022

Title: Co-ordinated autophagy with resveratrol and γ-tocotrienol confers synergetic cardioprotection.

Journal: Journal of cellular and molecular medicine 20101001

Title: The tocotrienol-rich fraction from rice bran enhances cisplatin-induced cytotoxicity in human mesothelioma H28 cells.

Journal: Phytotherapy research : PTR 20100901

Title: gamma-Tocotrienol reduces squalene hydroperoxide-induced inflammatory responses in HaCaT keratinocytes.

Journal: Lipids 20100901

Title: Gamma-tocotrienol promotes TRAIL-induced apoptosis through reactive oxygen species/extracellular signal-regulated kinase/p53-mediated upregulation of death receptors.

Journal: Molecular cancer therapeutics 20100801

Title: Tocotrienol enriched palm oil prevents atherosclerosis through modulating the activities of peroxisome proliferators-activated receptors.

Journal: Atherosclerosis 20100701

Title: gamma-Tocotrienol controls proliferation, modulates expression of cell cycle regulatory proteins and up-regulates quinone reductase NQO2 in MCF-7 breast cancer cells.

Journal: Anticancer research 20100701

Title: Suppression of gamma-tocotrienol on UVB induced inflammation in HaCaT keratinocytes and HR-1 hairless mice via inflammatory mediators multiple signaling.

Journal: Journal of agricultural and food chemistry 20100609

Title: Intestinal absorption of gamma-tocotrienol is mediated by Niemann-Pick C1-like 1: in situ rat intestinal perfusion studies.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100601

Title: Gamma-tocotrienol protects hematopoietic stem and progenitor cells in mice after total-body irradiation.

Journal: Radiation research 20100601

Title: Id1, inhibitor of differentiation, is a key protein mediating anti-tumor responses of gamma-tocotrienol in breast cancer cells.

Journal: Cancer letters 20100528

Title: Synergistic anticancer effects of combined gamma-tocotrienol and celecoxib treatment are associated with suppression in Akt and NFkappaB signaling.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20100501

Title: Gamma- and delta-tocotrienols exert a more potent anticancer effect than alpha-tocopheryl succinate on breast cancer cell lines irrespective of HER-2/neu expression.

Journal: Life sciences 20100424

Title: Inhibitory effects of gamma-tocotrienol on invasion and metastasis of human gastric adenocarcinoma SGC-7901 cells.

Journal: The Journal of nutritional biochemistry 20100301

Title: Vitamin E exhibits bone anabolic actions in normal male rats.

Journal: Journal of bone and mineral metabolism 20100301

Title: Synergistic actions of atorvastatin with gamma-tocotrienol and celecoxib against human colon cancer HT29 and HCT116 cells.

Journal: International journal of cancer 20100215

Title: Anti-proliferative effects of gamma-tocotrienol on mammary tumour cells are associated with suppression of cell cycle progression.

Journal: Cell proliferation 20100201

Title: Combined gamma-tocotrienol and erlotinib/gefitinib treatment suppresses Stat and Akt signaling in murine mammary tumor cells.

Journal: Anticancer research 20100201

Title: Design and preliminary structure-activity relationship of redox-silent semisynthetic tocotrienol analogues as inhibitors for breast cancer proliferation and invasion.

Journal: Bioorganic & medicinal chemistry 20100115

Title: Enhanced antiproliferative and apoptotic response to combined treatment of gamma-tocotrienol with erlotinib or gefitinib in mammary tumor cells.

Journal: BMC cancer 20100101

Title: In vivo evidence of gamma-tocotrienol as a chemosensitizer in the treatment of hormone-refractory prostate cancer.

Journal: Pharmacology 20100101

Title: gamma-Tocotrienol modulates the paracrine secretion of VEGF induced by cobalt(II) chloride via ERK signaling pathway in gastric adenocarcinoma SGC-7901 cell line.

Journal: Toxicology 20100101

Title: Effect of experimental treatment on GAPDH mRNA expression as a housekeeping gene in human diploid fibroblasts.

Journal: BMC molecular biology 20100101

Title: gamma-Tocotrienol prevents oxidative stress-induced telomere shortening in human fibroblasts derived from different aged individuals.

Journal: Oxidative medicine and cellular longevity 20100101

Title: Intersection of the tocopherol and plastoquinol metabolic pathways at the plastoglobule.

Journal: The Biochemical journal 20091223

Title: Deleterious effects of nicotine on the ultrastructure of oocytes: role of gamma-tocotrienol.

Journal: Medical science monitor : international medical journal of experimental and clinical research 20091201

Title: Endoplasmic reticulum stress mediates gamma-tocotrienol-induced apoptosis in mammary tumor cells.

Journal: Apoptosis : an international journal on programmed cell death 20091101

Title: Suppression in mevalonate synthesis mediates antitumor effects of combined statin and gamma-tocotrienol treatment.

Journal: Lipids 20091001

Title: Specific accumulation of gamma- and delta-tocotrienols in tumor and their antitumor effect in vivo.

Journal: The Journal of nutritional biochemistry 20090801

Title: Gamma-tocotrienol, a tocol antioxidant as a potent radioprotector.

Journal: International journal of radiation biology 20090701

Title: Is vitamin E toxic to neuron cells?

Journal: Cellular and molecular neurobiology 20090601

Title: Combined treatment of gamma-tocotrienol with statins induce mammary tumor cell cycle arrest in G1.

Journal: Experimental biology and medicine (Maywood, N.J.) 20090601

Title: Inhibition of proliferation and induction of apoptosis by gamma-tocotrienol in human colon carcinoma HT-29 cells.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20090501

Title: gamma-Tocotrienol ameliorates intestinal radiation injury and reduces vascular oxidative stress after total-body irradiation by an HMG-CoA reductase-dependent mechanism.

Journal: Radiation research 20090501

Title: gamma-Tocotrienol induces mitochondria-mediated apoptosis in human gastric adenocarcinoma SGC-7901 cells.

Journal: The Journal of nutritional biochemistry 20090401

Title: Design and QSAR study of analogs of gamma-tocotrienol with enhanced antiproliferative activity against human breast cancer cells.

Journal: Journal of molecular graphics & modelling 20090401

Title: Beneficial effects of tocotrienol and tocopherol on bone histomorphometric parameters in sprague-dawley male rats after nicotine cessation.

Journal: Calcified tissue international 20090101

Title: Evidence of gamma-tocotrienol as an apoptosis-inducing, invasion-suppressing, and chemotherapy drug-sensitizing agent in human melanoma cells.

Journal: Nutrition and cancer 20090101

Title: Gamma-tocotrienol suppresses prostate cancer cell proliferation and invasion through multiple-signalling pathways.

Journal: British journal of cancer 20081202

Title: Suppression of cell proliferation and gene expression by combinatorial synergy of EGCG, resveratrol and gamma-tocotrienol in estrogen receptor-positive MCF-7 breast cancer cells.

Journal: International journal of oncology 20081001

Title: Gamma-tocotrienol-induced apoptosis in human gastric cancer SGC-7901 cells is associated with a suppression in mitogen-activated protein kinase signalling.

Journal: The British journal of nutrition 20080601

Title: Synergistic antiproliferative effects of gamma-tocotrienol and statin treatment on mammary tumor cells.

Journal: Lipids 20071201

Title: Preparation and in vivo evaluation of a water-soluble prodrug for 2R-gamma-tocotrienol and as a two-step prodrug for 2,7,8-trimethyl-2S-(beta-carboxyethyl)-6-hydroxychroman (S-gamma-CEHC) in rat.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070901

Title: A short and convenient chemical route to optically pure 2-methyl chromanmethanols. Total asymmetric synthesis of beta-, gamma-, and delta-tocotrienols.

Journal: The Journal of organic chemistry 20070831

Title: Intestinal epithelial cells absorb gamma-tocotrienol faster than alpha-tocopherol.

Journal: Lipids 20070301

Title: Distribution of tocotrienols in rats fed a rice bran tocotrienol concentrate.

Journal: Bioscience, biotechnology, and biochemistry 20070201

Title: Gamma-tocotrienol inhibits nuclear factor-kappaB signaling pathway through inhibition of receptor-interacting protein and TAK1 leading to suppression of antiapoptotic gene products and potentiation of apoptosis.

Journal: The Journal of biological chemistry 20070105

Title: In silico prediction of pregnane X receptor activators by machine learning approaches.

Journal: Molecular pharmacology 20070101

Title: [Occurrence and function of tocochromanols in plants, animals and men].

Journal: Postepy biochemii 20070101

Title: gamma-Tocotrienol inhibits ErbB3-dependent PI3K/Akt mitogenic signalling in neoplastic mammary epithelial cells.

Journal: Cell proliferation 20061201

Title: Apoptosis induction by gamma-tocotrienol in human hepatoma Hep3B cells.

Journal: The Journal of nutritional biochemistry 20061001

Title: Insig-dependent ubiquitination and degradation of 3-hydroxy-3-methylglutaryl coenzyme a reductase stimulated by delta- and gamma-tocotrienols.

Journal: The Journal of biological chemistry 20060901

Title: Comparative effects of alpha-tocopherol and gamma-tocotrienol against hydrogen peroxide induced apoptosis on primary-cultured astrocytes.

Journal: Journal of the neurological sciences 20060415

Title: Preferential radiation sensitization of prostate cancer in nude mice by nutraceutical antioxidant gamma-tocotrienol.

Journal: Life sciences 20060327

Title: Induction of drug metabolizing enzymes by vitamin E.

Journal: Journal of plant physiology 20050701

Title: Intracellular signaling mechanisms mediating the antiproliferative and apoptotic effects of gamma-tocotrienol in neoplastic mammary epithelial cells.

Journal: Journal of plant physiology 20050701

Title: Gamma-tocotrienol inhibits neoplastic mammary epithelial cell proliferation by decreasing Akt and nuclear factor kappaB activity.

Journal: Experimental biology and medicine (Maywood, N.J.) 20050401

Title: Modulation of Cyp3a11 mRNA expression by alpha-tocopherol but not gamma-tocotrienol in mice.

Journal: Free radical biology & medicine 20050215

Title: Gamma-tocotrienol metabolism and antiproliferative effect in prostate cancer cells.

Journal: Annals of the New York Academy of Sciences 20041201

Title: Tocotrienols activate the steroid and xenobiotic receptor, SXR, and selectively regulate expression of its target genes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20041001

Title: Nitric oxide synthase activity in blood vessels of spontaneously hypertensive rats: antioxidant protection by gamma-tocotrienol.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20030901

Title: Gamma-tocotrienol, a vitamin E homolog, is a natriuretic hormone precursor.

Journal: Journal of lipid research 20030801

Title: HPLC analysis of vitamin E isoforms in human epidermis: correlation with minimal erythema dose and free radical scavenging activity.

Journal: Free radical biology & medicine 20030201

Title: Influence of route of administration on the absorption and disposition of alpha-, gamma- and delta-tocotrienols in rats.

Journal: The Journal of pharmacy and pharmacology 20030101

Title: Effect of either gamma-tocotrienol or a tocotrienol mixture on the plasma lipid profile in hamsters.

Journal: Annals of nutrition & metabolism 20020101

Title: Vitamin E inhibition of normal mammary epithelial cell growth is associated with a reduction in protein kinase C(alpha) activation.

Journal: Cell proliferation 20011201

Title: Oral toxicity of a tocotrienol preparation in rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010801

Title: Pharmacokinetics and bioavailability of alpha-, gamma- and delta-tocotrienols under different food status.

Journal: The Journal of pharmacy and pharmacology 20010101

Title: Alpha- and gamma-tocotrienols are metabolized to carboxyethyl-hydroxychroman derivatives and excreted in human urine.

Journal: Lipids 20010101

Title: Apoptosis and cell-cycle arrest in human and murine tumor cells are initiated by isoprenoids.

Journal: The Journal of nutrition 19990401

Title: M A Newaz, et al. Nitric Oxide Synthase Activity in Blood Vessels of Spontaneously Hypertensive Rats: Antioxidant Protection by Gamma-Tocotrienol. J Physiol Pharmacol. 2003 Sep;54(3):319-27.

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Tags:14101-61-2 Molecular Formula|14101-61-2 MDL|14101-61-2 SMILES|14101-61-2 γ-Tocotrienol