alpha-Tocopherolquinone - CAS 7559-04-8
Catalog number: 7559-04-8
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C29H50O3
Molecular Weight:
446.7
COA:
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Chemical Family:
Quinones
Description:
alpha-Tocopherolquinone isolated from the herbs of Isodon adenantha. It has antioxidant effect, which can inhibit lipid peroxidation and reduce cell division in both the glioma cell clone and fetal brain cells.
Purity:
> 95%
Appearance:
Yellow oil
Synonyms:
2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-p-benzoquinon;
MSDS:
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Application:
antihypertensive; platelet aggregation inhibitor; phytotoxic;
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
Density:
0.947g/cm3
1.A function for the vitamin E metabolite alpha-tocopherol quinone as an essential enzyme cofactor for the mitochondrial fatty acid desaturases.
Infante JP FEBS Lett. 1999 Mar 5;446(1):1-5.
A critical analysis of the changes in fatty acid patterns and their metabolism elicited by vitamin E deficiency leads to the proposal that a major role of dietary RRR-alpha-tocopherol (alpha-TOC) is as an enzymatic precursor of alpha-tocopherolquinone (alpha-TQ) whose semiquinone radical functions as an essential enzyme cofactor for the fatty acid desaturases of the recently elucidated carnitine-dependent, channeled, mitochondrial desaturation-elongation pathway; a detailed mechanism for its function is proposed. Pathophysiological states produced by vitamin E deficiency and alpha-TOC transfer protein defects, such as ataxia, myopathy, retinopathy, and sterility are proposed to develop from the effects of impaired alpha-TQ-dependent desaturases and the resulting deficiency of their polyenoic fatty acid products.
2.Tocopherol metabolism, oxidation and recycling under high light stress in Arabidopsis.
Kobayashi N;DellaPenna D Plant J. 2008 Aug;55(4):607-18. doi: 10.1111/j.1365-313X.2008.03539.x. Epub 2008 Apr 30.
Tocopherols are synthesized and accumulated by all plants and many cyanobacteria. The quenching and scavenging of reactive oxygen species and lipid peroxy radicals by tocopherols can result in the formation of various tocopherol oxidation compounds. A targeted GC/MS profiling method was developed to quantify all tocopherols and pathway intermediates, and 23 potential alpha- and gamma-tocopherol oxidation products. This method was used to study the response of wild-type Arabidopsis (Col) and the tocopherol biosynthetic mutants vte1, vte2 and vte4 during 12 h low- and high-light treatments (LL and HL, 90 and 1500 mumol photon m(-2) sec(-1), respectively) and a subsequent 12 h dark recovery period. All tocopherols and pathway intermediates exhibited HL-dependent increases except 2,3-dimethyl-6-phytyl-1,4-benzoquinone (DMPBQ) in vte1 and beta-tocopherol in Col. Profiling of potential tocopherol oxidation products during HL treatment indicated the presence of only alpha-tocopherolquinol (alpha-TQH(2)) in Col and only gamma-tocopherolquinol (gamma-TQH(2)) in vte4, both of which accumulated to similar levels and with similar kinetics the two genotypes. However, during dark recovery, the level of alpha-TQH(2) in Col decreased several times faster than that of gamma-TQH(2) in vte4, suggesting the presence of biochemical processes with higher specificity for alpha-TQH(2).
3.[Age-related change in the alpha-tocopherolquinone/alpha-tocopherol ratio in the rat erythrocyte membrane].
Yanagawa K;Takeda H;Matsumiya T;Takasaki M Nihon Ronen Igakkai Zasshi. 1999 May;36(5):335-41.
alpha-Tocopherol (alpha-Toc), a lipophilic phenolic antioxidant that is localized mainly in the biomembrane, protects cells against oxidation-associated cytotoxicity by prevention of membrane lipid peroxidation, maintenance of the redox balance intracellular thiols and stabilization of the membrane structure. We investigated the age-related changes in redox dynamics of alpha-Toc in plasma and erythrocyte membrane of an elderly (66 weeks old) and young group (10 weeks old). Total, alpha-, beta + gamma-, delta-Toc and alpha-tocopherolquinone (alpha-TocQ) in plasma and erythrocyte membrane were determined by high-performance liquid chromatography (HPLC) with a series of multiple coulometric working electrodes (CWE). Rat venous blood sample was divided into plasma and erythrocyte layers by centrifugation, and then erythrocyte membrane sample was prepared according to the method of Dodge et al. under a stream of nitrogen. In plasma, total and alpha-Toc concentrations were increased, and beta + gamma-, delta-Toc and alpha-TocQ concentrations were decreased age-dependently. In the erythrocyte membrane, total, alpha-TocQ concentrations and three fractions of tocopherols decreased age-dependently.
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CAS 7559-04-8 alpha-Tocopherolquinone

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