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beta-tocopherol
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-rel-

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Name:(2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
CAS Number: 148-03-8Picture of molecule3D/inchi
Other(deleted CASRN):16662-70-7
ECHA EINECS - REACH Pre-Reg:205-708-5
FDA UNII: 8K9365K9PX
XlogP3-AA:10.30 (est)
Molecular Weight:416.68896000
Formula:C28 H48 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:nutrient supplements
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 516.00 to 517.00 °C. @ 760.00 mm Hg (est)
Flash Point: 400.00 °F. TCC ( 204.70 °C. ) (est)
logP (o/w): 10.724 (est)
Soluble in:
 alcohol
 water, 1.069e-006 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
beta-Tocopherol >96%
Odor: characteristic
Use: b-Tocopherol is a natural phenolic compound found in several plants. b-Tocopherol biologically actives less than a-Tocopherol.
Santa Cruz Biotechnology
For experimental / research use only.
rac-β-Tocopherol solution
 
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
 
Pictogram
 
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:
Category:
nutrient supplements
Recommendation for beta-tocopherol usage levels up to:
 not for fragrance use.
 
Recommendation for beta-tocopherol flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Opinion on mixed tocopherols, tocotrienol tocopherol and tocotrienols as sources for vitamin E added as a nutritional substance in food supplements[1] - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing aids and Materials in Contact with food (AFC)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):148-03-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :8989
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
Chemidplus:0000148038
 
References:
 (2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:148-03-8
Pubchem (cid):8989
Pubchem (sid):134975264
 
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):C14152
HMDB (The Human Metabolome Database):HMDB06335
FooDB:FDB012381
FDA Listing of Food Additive Status:View
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 barley
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 caraway
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 coconut
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 coffee bean
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 coriander
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 corn
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 cranberry
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 fennel
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 garlic bulb
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 grape
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 lychee
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 oat
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 onion seed oil
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 oregano leaf
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 rice
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 rosemary
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 rosemary leaf
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 sesame seed oil
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 soybean cotyledon
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 soybean embryo
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 soybean seed coat
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 walnut english walnut
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 walnut english walnut nut
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Synonyms:
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-rel-
2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-
3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
(2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
 

Articles:

PubMed:Final report on the safety assessment of Tocopherol, Tocopheryl Acetate, Tocopheryl Linoleate, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate, Tocopheryl Succinate, Dioleyl Tocopheryl Methylsilanol, Potassium Ascorbyl Tocopheryl Phosphate, and Tocophersolan.
PubMed:Nutritional value, chemical composition, antioxidant activity and enrichment of cream cheese with chestnut mushroom Agrocybe aegerita (Brig.) Sing.
PubMed:Subcritical extraction of flaxseed oil with n-propane: Composition and purity.
PubMed:Antioxidant activities of tocopherols/tocotrienols and lipophilic antioxidant capacity of wheat, vegetable oils, milk and milk cream by using photochemiluminescence.
PubMed:Influence of deficit irrigation strategies on fatty acid and tocopherol concentration of almond (Prunus dulcis).
PubMed:Tocochromanols and carotenoids in sorghum (Sorghum bicolor L.): diversity and stability to the heat treatment.
PubMed:Unique variability of tocopherol composition in various seed oils recovered from by-products of apple industry: rapid and simple determination of all four homologues (α, β, γ and δ) by RP-HPLC/FLD.
PubMed:Fatty acid composition and tocopherol profiles of safflower (Carthamus tinctorius L.) seed oils.
PubMed:Peripheral blood mononuclear cell-based metabolomic profiling of a chronic unpredictable mild stress rat model of depression.
PubMed:Olive oil pilot-production assisted by pulsed electric field: impact on extraction yield, chemical parameters and sensory properties.
PubMed:Tocopherol and tocotrienol contents of different varieties of rice in Malaysia.
PubMed:Both genetic and dietary factors underlie individual differences in DNA damage levels and DNA repair capacity.
PubMed:Total phenolic compounds and tocopherols profiles of seven olive oil varieties grown in the south-west of Spain.
PubMed:[Further chemical investigation of leaves of Aquilaria Sinensis].
PubMed:Evaluation of Antimicrobial Activity of Bauhinia purpurea Leaves Under In Vitro Conditions.
PubMed:Influence of sunflower oil qualities and antioxidants on oxidative stability on whey-based salad dressings.
PubMed:The fatty acid and tocopherol constituents of the seed oil extracted from 21 grape varieties (Vitis spp.).
PubMed:Chemical composition and molecular speciation of the triacylglycerol of the oils of Lonchocarpus sericeus and Lonchocarpus cyanescens.
PubMed:Nutritional composition of Zizyphus lotus L. seeds.
PubMed:In vitro antioxidant and antimicrobial activity cycloart-23-ene-3β,-25-diol (B2) isolated from Pongamia pinnata (L. Pierre).
PubMed:γ-Tocopherol methyltransferase from the green alga Chlamydomonas reinhardtii: functional characterization and expression analysis.
PubMed:Determination of tocopherol contents of some olive varieties harvested at different ripening periods.
PubMed:Legumes are valuable sources of tocopherols.
PubMed:Supercritical CO₂extraction of oleoresin from marigold (Tagetes erecta L.) flowers and determination of its antioxidant components with online HPLC-ABTS(·+) assay.
PubMed:Contribution of pollinator-mediated crops to nutrients in the human food supply.
PubMed:The effect of β-carotene on lumbar osteophyte formation.
PubMed:Comparative study of lipophilic and hydrophilic antioxidants from in vivo and in vitro grown Coriandrum sativum.
PubMed:Intake of antioxidants and risk of type 2 diabetes in a cohort of male smokers.
PubMed:Chromatographic techniques for the determination of alkyl-phenols, tocopherols and other minor polar compounds in raw and roasted cold pressed cashew nut oils.
PubMed:Plasma micronutrients and the acquisition and clearance of anal human papillomavirus infection: the Hawaii HPV cohort study.
PubMed:Temperature dependence of autoxidation of perilla oil and tocopherol degradation.
PubMed:Characterization of a potential nutraceutical ingredient: pomegranate (Punica granatum L.) seed oil unsaponifiable fraction.
PubMed:The comparison of black currant juice and vitamin E for the prevention of oxidative stress.
PubMed:Vitamin E and Hippophea rhamnoides L. extract reduce nicotine-induced oxidative stress in rat heart.
PubMed:High plasma levels of vitamin E forms and reduced Alzheimer's disease risk in advanced age.
PubMed:Influence of the cyanotoxin microcystin-LR on tocopherol in Alfalfa seedlings (Medicago sativa).
PubMed:Implications for degenerative disorders: antioxidative activity, total phenols, flavonoids, ascorbic acid, beta-carotene and beta-tocopherol in Aloe vera.
PubMed:alpha-Tocopherol enhances degranulation in RBL-2H3 mast cells.
PubMed:Oxidative stress and longevity in okinawa: an investigation of blood lipid peroxidation and tocopherol in okinawan centenarians.
PubMed:Compound 48/80 causes oxidative stress in the adrenal gland of rats through mast cell degranulation.
PubMed:Investigation of liquid wax components of Egyptian jojoba seeds.
PubMed:Degradation of tocopherols in rice bran oil submitted to heating at different temperatures.
PubMed:Replacement of alpha-tocopherol by beta-tocopherol enhances resistance to photooxidative stress in a xanthophyll-deficient strain of Chlamydomonas reinhardtii.
PubMed:Dietary beta-tocopherol and serum concentrations of sex hormone-binding globulin.
PubMed:Antioxidants and periodontitis in 60-70-year-old men.
PubMed:Comparison of the inhibitory effects of vitamin E analogues on melanogenesis in mouse B16 melanoma cells.
PubMed:Alpha-tocopherol: looking beyond an antioxidant.
PubMed:Dietary beta-tocopherol and linoleic acid, serum insulin, and waist circumference predict circulating sex hormone-binding globulin in premenopausal women.
PubMed:Bioaccessibility of Carotenoids and Tocopherols in Marine Microalgae, Nannochloropsis sp. and Chaetoceros sp.
PubMed:Long-chain carboxychromanols, metabolites of vitamin E, are potent inhibitors of cyclooxygenases.
PubMed:Dietary marine-derived tocopherol has a higher biological availability in mice relative to alpha-tocopherol.
PubMed:Distribution of alpha-, gamma (+beta)- and delta-tocopherol in the seminal plasma, spermatozoa and seminal vesicles of rabbit.
PubMed:Separation of alpha-, beta-, gamma-, delta-tocopherols and alpha-tocopherol acetate on a pentaerythritol diacrylate monostearate-ethylene dimethacrylate monolith by capillary electrochromatography.
PubMed:Dietary alpha-, beta-, gamma- and delta-tocopherols in lung cancer risk.
PubMed:Tocopherol metabolism, oxidation and recycling under high light stress in Arabidopsis.
PubMed:Genetic possibilities for altering sunflower oil quality to obtain novel oils.
PubMed:In vivo gamma-tocopherol supplementation decreases systemic oxidative stress and cytokine responses of human monocytes in normal and asthmatic subjects.
PubMed:Enhanced anti-proliferative effects of combinatorial treatment of delta-tocopherol and resveratrol in human HMC-1 cells.
PubMed:Brain tumor and role of beta-carotene, a-tocopherol, superoxide dismutase and glutathione peroxidase.
PubMed:Risk factors for isolated biliary atresia, National Birth Defects Prevention Study, 1997-2002.
PubMed:Antibacterial constituents from Stemona sessilifolia.
PubMed:Comprehensive analysis of vitamin E constituents in human plasma by liquid chromatography-mass spectrometry.
PubMed:[Vitamin E inhibits homocysteine-mediated smooth muscle cell proliferation].
PubMed:Antioxidative stress response of Lepidium sativum due to exposure to cyanobacterial secondary metabolites.
PubMed:A pharmacological action of vitamin E unrelated to its antioxidant capacity.
PubMed:Increased alpha-tocopherol content in soybean seed overexpressing the Perilla frutescens gamma-tocopherol methyltransferase gene.
PubMed:Ty3/gypsy-like retrotransposon knockout of a 2-methyl-6-phytyl-1,4-benzoquinone methyltransferase is non-lethal, uncovers a cryptic paralogous mutation, and produces novel tocopherol (vitamin E) profiles in sunflower.
PubMed:Significant differences in the electrochemical behavior of the alpha-, beta-, gamma-, and delta-tocopherols (vitamin E).
PubMed:Vitamin E composition of walnuts (Juglans regia L.): a 3-year comparative study of different cultivars.
PubMed:Characterization of monochloramine toxicity on PC12 cells and protective effect of tocopherol via antioxidative function.
PubMed:Almonds in the diet simultaneously improve plasma alpha-tocopherol concentrations and reduce plasma lipids.
PubMed:Vitamins C and E prevent endothelial VEGF and VEGFR-2 overexpression induced by porcine hypercholesterolemic LDL.
PubMed:The cytotoxicity of vitamin E is both vitamer- and cell-specific and involves a selectable trait.
PubMed:Antioxidant dehydrotocopherols as a new chemical character of Stemona species.
PubMed:I read recently that foods high in vitamin E may be more beneficial than supplements containing vitamin E. Please explain.
PubMed:Antioxidants, carotenoids, and risk of rectal cancer.
PubMed:Vitamins C and E downregulate vascular VEGF and VEGFR-2 expression in apolipoprotein-E-deficient mice.
PubMed:Fern constituents: dryocrassy formate, sitostanyl formate and 12alpha-hydroxyfern-9(11)-ene from Cyathea podophylla.
PubMed:Serum vitamins and the subsequent risk of bladder cancer.
PubMed:Vitamins A and E in serum in relation to weight and lung function in patients with advanced pulmonary disease.
PubMed:Vitamin E biosynthesis: biochemistry meets cell biology.
PubMed:Alpha-tocopherol induces expression of connective tissue growth factor and antagonizes tumor necrosis factor-alpha-mediated downregulation in human smooth muscle cells.
PubMed:Characterization of gamma-tocopherol methyltransferases from Capsicum annuum L and Arabidopsis thaliana.
PubMed:Alpha-tocopherol prevents apoptosis of vascular endothelial cells via a mechanism exceeding that of mere antioxidation.
PubMed:Three series of high molecular weight alkanoates found in Amazonian plants.
PubMed:Tocopherols enhance neurogenesis in dentate gyrus of adult rats.
PubMed:Isolation and characterization of homogentisate phytyltransferase genes from Synechocystis sp. PCC 6803 and Arabidopsis.
PubMed:Oxidized low density lipoprotein-induced LFA-1-dependent adhesion and transendothelial migration of monocytes via the protein kinase C pathway.
PubMed:The role of 2-methyl-6-phytylbenzoquinone methyltransferase in determining tocopherol composition in Synechocystis sp. PCC6803.
PubMed:Relationship between fatty acid profile and vitamin E content in maize hybrids (Zea mays L.).
PubMed:Effects of dietary sesame seeds on plasma tocopherol levels.
PubMed:Rapid high-performance liquid chromatographic method for the simultaneous determination of retinol, alpha-tocopherol and beta-carotene in human plasma and low-density lipoproteins.
PubMed:Differential inhibition by alpha- and beta-tocopherol of human erythroleukemia cell adhesion: role of integrins.
PubMed:Electron transport chain defect and inefficient respiration may underlie pulmonary hypertension syndrome (ascites)-associated mitochondrial dysfunction in broilers.
PubMed:Effect of vitamin E on the development of atherosclerosis.
PubMed:Analysis of olive and hazelnut oil mixtures by high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry of triacylglycerols and gas-liquid chromatography of non-saponifiable compounds (tocopherols and sterols).
PubMed:Specific cellular responses to alpha-tocopherol.
PubMed:Vitamin E: non-antioxidant roles.
PubMed:Vitamin E mediated response of smooth muscle cell to oxidant stress.
PubMed:Modulation of alpha-tropomyosin expression by alpha-tocopherol in rat vascular smooth muscle cells.
PubMed:Alpha-tocopherol decreases interleukin-1 beta release from activated human monocytes by inhibition of 5-lipoxygenase.
PubMed:Alpha-tocopherol but not beta-tocopherol inhibits thrombin-induced PKC activation and endothelin secretion in endothelial cells.
PubMed:alpha-tocopherol inhibits the respiratory burst in human monocytes. Attenuation of p47(phox) membrane translocation and phosphorylation.
PubMed:Lycopene in association with alpha-tocopherol inhibits at physiological concentrations proliferation of prostate carcinoma cells.
PubMed:alpha-Tocopherol specifically inactivates cellular protein kinase C alpha by changing its phosphorylation state.
PubMed:alpha-Tocopherol protects PC12 cells from hyperoxia-induced apoptosis.
PubMed:RRR-alpha-tocopherol regulation of gene transcription in response to the cell oxidant status.
PubMed:Molecular basis of alpha-tocopherol control of smooth muscle cell proliferation.
PubMed:Alpha-tocopherol as a modulator of smooth muscle cell proliferation.
PubMed:Relative stability of carotenoid radical cations and homologue tocopheroxyl radicals. A real time kinetic study of antioxidant hierarchy.
PubMed:The effect of alpha-tocopherol on the synthesis, phosphorylation and activity of protein kinase C in smooth muscle cells after phorbol 12-myristate 13-acetate down-regulation.
PubMed:Affinity for alpha-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs.
PubMed:High D-glucose does not affect binding of alpha-tocopherol to human erythrocytes.
PubMed:Signalling functions of alpha-tocopherol in smooth muscle cells.
PubMed:The effect of alpha-tocopherol and beta-tocopherol on proliferation, protein kinase C activity and gene expression in different cell lines.
PubMed:Certification of fat-soluble vitamins, carotenoids, and cholesterol in human serum: Standard Reference Material 968b.
PubMed:The role of hydrogen peroxide and RRR-alpha-tocopherol in smooth muscle cell proliferation.
PubMed:Tocopherols in camel's plasma and tissues.
PubMed:d-alpha-tocopherol inhibition of vascular smooth muscle cell proliferation occurs at physiological concentrations, correlates with protein kinase C inhibition, and is independent of its antioxidant properties.
PubMed:Vitamin E: a sensor and an information transducer of the cell oxidation state.
PubMed:Tocopherols and 6-hydroxy-chroman-2-carbonitrile derivatives inhibit vascular smooth muscle cell proliferation by a nonantioxidant mechanism.
PubMed:Modulation of activator protein-1 (AP-1) transcription factor and protein kinase C by hydrogen peroxide and D-alpha-tocopherol in vascular smooth muscle cells.
PubMed:d-alpha-tocopherol control of cell proliferation.
PubMed:Isolation and properties of gamma-tocopherol methyltransferase in Euglena gracilis.
PubMed:Molecular basis of alpha-tocopherol inhibition of smooth muscle cell proliferation in vitro.
PubMed:Effects of the consumption of cigarettes, alcohol and foods on serum concentrations of carotenoids, retinol and tocopherols in healthy inhabitants living in a rural area of Hokkaido.
PubMed:[Condition of cell membranes in simulated motion sickness and use of alpha-tocopherol].
PubMed:Physical and chemical scavenging of singlet molecular oxygen by tocopherols.
PubMed:Response of whole blood, erythrocyte and plasma vitamin E content to dietary vitamin E intake in the chick.
PubMed:Oral alpha-tocopherol supplements decrease plasma gamma-tocopherol levels in humans.
PubMed:Tocopherols and tocotrienols in Finnish foods: human milk and infant formulas.
PubMed:Vitamin E requirement of mink with special reference to tocopherol composition in plasma, liver, and adipose tissue.
PubMed:Biopotency of vitamin E in barley.
PubMed:High-performance liquid chromatographic determination of tocopherols and tocotrienols and its application to diets and plasma of Finnish men. II. Applications.
PubMed:High-performance liquid chromatographic determination of tocopherols and tocotrienols and its application to diets and plasma of Finnish men. I. Analytical method.
PubMed:Measurement of alpha-, beta-, and gamma tocopherol in serum by liquid chromatography.
PubMed:Biological activity of vitamin E compounds and natural materials by the resorption-gestation test, and chemical determination of the vitamin E activity in foods and feeds.
PubMed:Distribution of tocopherols in human plasma and red blood cells.
PubMed:The uptake and utilization of beta-tocopherol by higher plants and algae.
PubMed:Studies on vitamin E: The isolation of beta-tocopherol from wheat germ oil.
 
Notes:
a natural tocopherol with less antioxidant activity than alpha-tocopherol. it exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2h-1-benzopyran-6-ol nucleus. as in gamma-tocopherol, it also has three methyl groups on the 6-chromanol nucleus but at different sites. Isol. from vegetable sources, e.g. spinach chloroplasts (Spinacia oleracea), soybean oil, corn oil and wheat germ. Antioxidant. Member of Vitamin E group Beta-tocopherol is an antioxidant which is synthesized by photosynthetic organisms and play important roles in human and animal nutrition. betatocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis).The phenoxonium cation of beta-tocopherol is stable for several minutes. (PMID: 16771430); beta-Tocopherol (?-tocopherol) is a type of tocopherol with formula C28H48O2.
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