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7559-04-8 | D-ALPHA-TOCOPHERYLQUINONE
CAS No: 7559-04-8 Catalog No: AG003P8C MDL No:
Product Description
Catalog Number:
AG003P8C
Chemical Name:
D-ALPHA-TOCOPHERYLQUINONE
CAS Number:
7559-04-8
IUPAC Name:
2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
InChI:
InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
InChI Key:
LTVDFSLWFKLJDQ-IEOSBIPESA-N
EC Number:
231-450-8
UNII:
ZO763K43XR
Properties
Complexity:
697
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
446.376g/mol
Formal Charge:
0
Heavy Atom Count:
32
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
446.716g/mol
Monoisotopic Mass:
446.376g/mol
Rotatable Bond Count:
15
Topological Polar Surface Area:
54.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
8.8
Literature
| Title | Journal |
|---|---|
| New pterosin sesquiterpenes and antitubercular constituents from Pteris ensiformis. | Chemistry & biodiversity 20131001 |
| A0001 in Friedreich ataxia: biochemical characterization and effects in a clinical trial. | Movement disorders : official journal of the Movement Disorder Society 20120701 |
| Circulating antioxidant profile of pregnant women with asthma. | Clinical nutrition (Edinburgh, Scotland) 20120201 |
| Towards a modern definition of vitamin E-evidence for a quinone hypothesis. | Bioorganic & medicinal chemistry letters 20120101 |
| α-Tocopherol quinone inhibits β-amyloid aggregation and cytotoxicity, disaggregates preformed fibrils and decreases the production of reactive oxygen species, NO and inflammatory cytokines. | Neurochemistry international 20101201 |
| Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia. | Molecules (Basel, Switzerland) 20101118 |
| Cytotoxic flavonoids from the leaves of Cryptocarya chinensis. | Journal of natural products 20100924 |
| Occurrence, biosynthesis and function of isoprenoid quinones. | Biochimica et biophysica acta 20100901 |
| Modulation of the mitochondrial cytochrome bc1 complex activity by chromanols and related compounds. | Chemical research in toxicology 20100101 |
| Endogenous adenosine selectively modulates oxidant stress via the A1 receptor in ischemic hearts. | Antioxidants & redox signaling 20091101 |
| On-line liquid chromatography and circular dichroism detection of stereo-isomers of alpha-tocopherol derivatives generated by an electrochemical reaction. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20080701 |
| Gamma-tocopheryl quinone, not alpha-tocopheryl quinone, induces adaptive response through up-regulation of cellular glutathione and cysteine availability via activation of ATF4. | Free radical research 20080701 |
| [Role of alpha-tocopherol in oxidative stress of rat thymocytes induced by hydrogen peroxide and menadione]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20080101 |
| Generation of superoxide and singlet oxygen from alpha-tocopherolquinone and analogues. | Free radical research 20070601 |
| Vitamin E metabolism. | Molecular aspects of medicine 20070101 |
| Oxidant stress and damage in post-ischemic mouse hearts: effects of adenosine. | Molecular and cellular biochemistry 20060701 |
| Distribution of tocopheryl quinone in mitochondrial membranes and interference with ubiquinone-mediated electron transfer. | Biochemical pharmacology 20060528 |
| Effect of elevated temperature on development of tocopherolquinones in oils. | Journal of agricultural and food chemistry 20060322 |
| Enhanced ferredoxin-dependent cyclic electron flow around photosystem I and alpha-tocopherol quinone accumulation in water-stressed ndhB-inactivated tobacco mutants. | Planta 20051001 |
| Ebselen: a thioredoxin reductase-dependent catalyst for alpha-tocopherol quinone reduction. | Toxicology and applied pharmacology 20050901 |
| Tocopherol metabolism using thermochemolysis: chemical and biological properties of gamma-tocopherol, gamma-carboxyethyl-hydroxychroman, and their quinones. | Chemical research in toxicology 20050601 |
| [Effect of alpha-tocopherol and its derivatives on actinomycin D induced apoptosis of rat thymocytes]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20050101 |
| [Cytotoxic effect of vitamin E short-chain derivatives on rat thymocytes]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20050101 |
| Alpha-tocopherol and alpha-tocopheryl quinone levels in cervical intraepithelial neoplasia and cervical cancer. | American journal of obstetrics and gynecology 20040501 |
| Prenatal cocaine administration increases glutathione and alpha-tocopherol oxidation in fetal rat brain. | Brain research. Developmental brain research 20031230 |
| Supernatant protein factor in complex with RRR-alpha-tocopherylquinone: a link between oxidized Vitamin E and cholesterol biosynthesis. | Journal of molecular biology 20030926 |
| Electrophile tocopheryl quinones in apoptosis and mutagenesis: thermochemolysis of thiol adducts with proteins and in cells. | Lipids 20030901 |
| gamma-Tocopheryl quinone induces apoptosis in cancer cells via caspase-9 activation and cytochrome c release. | Carcinogenesis 20030301 |
| Mössbauer studies of the non-heme iron and cytochrome b559 in a Chlamydomonas reinhardtii PSI- mutant and their interactions with alpha-tocopherol quinone. | FEBS letters 20030130 |
| Abnormal incorporation and utilization of alpha-tocopherol in erythrocyte membranes of streptozotocin-induced diabetic rats. | European journal of pharmacology 20021205 |
| Determination of tocopherols, tocopherolquinones and tocopherolhydroquinones by gas chromatography-mass spectrometry and preseparation with lipophilic gel chromatography. | Journal of chromatography. A 20021108 |
| Vitamin E oxidation in human atherosclerotic lesions. | Circulation research 20020222 |
| Comparison of gas chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry methods to quantify alpha-tocopherol and alpha-tocopherolquinone levels in human plasma. | Analytical biochemistry 20020201 |
| Gamma-tocopheryl quinone stimulates apoptosis in drug-sensitive and multidrug-resistant cancer cells. | Lipids 20020201 |
| Mutagenicity of tocopheryl quinones: evolutionary advantage of selective accumulation of dietary alpha-tocopherol. | Nutrition and cancer 20020101 |
| Effects of tocopheryl quinone on the heart: model experiments with xanthine oxidase, heart mitochondria, and isolated perfused rat hearts. | Free radical biology & medicine 20010415 |
| No reduction of alpha-tocopherol quinone by glutathione in rat liver microsomes. | Biochemical pharmacology 20010315 |
| Polychlorinated biphenyl-induced effects on metabolic enzymes, AP-1 binding, vitamin E, and oxidative stress in the rat liver. | Toxicology and applied pharmacology 20010301 |
| Long-chain n-3 fatty acids specifically affect rat coagulation factors dependent on vitamin K: relation to peroxidative stress. | Arteriosclerosis, thrombosis, and vascular biology 20010301 |
| Redox changes of cytochrome b(559) in the presence of plastoquinones. | The Journal of biological chemistry 20010105 |
| [Effect of alpha-tocopherol, tocopheryl quinone and other complexes with tocopherol-binding proteins on the activity of enzymes metabolizing arachidonic acid]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20010101 |
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