α-Tocopherol phosphateCAS# 38976-17-9 |
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Quality Control & MSDS
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| Cas No. | 38976-17-9 | SDF | Download SDF |
| PubChem ID | 94493 | Appearance | Powder |
| Formula | C29H51O5P | M.Wt | 510.69 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | alpha-Tocopherol phosphate; TocP; vitamin E phosphate | ||
| Solubility | DMSO : ≥ 100 mg/mL (195.81 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] dihydrogen phosphate | ||
| SMILES | CC1=C2C(=C(C(=C1C)OP(=O)(O)O)C)CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C | ||
| Standard InChIKey | JUIUXBHZFNHITF-IEOSBIPESA-N | ||
| Standard InChI | InChI=1S/C29H51O5P/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(34-35(30,31)32)23(5)24(6)28(26)33-29/h20-22H,9-19H2,1-8H3,(H2,30,31,32)/t21-,22-,29-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
α-Tocopherol phosphate Dilution Calculator
α-Tocopherol phosphate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9581 mL | 9.7907 mL | 19.5814 mL | 39.1627 mL | 48.9534 mL |
| 5 mM | 0.3916 mL | 1.9581 mL | 3.9163 mL | 7.8325 mL | 9.7907 mL |
| 10 mM | 0.1958 mL | 0.9791 mL | 1.9581 mL | 3.9163 mL | 4.8953 mL |
| 50 mM | 0.0392 mL | 0.1958 mL | 0.3916 mL | 0.7833 mL | 0.9791 mL |
| 100 mM | 0.0196 mL | 0.0979 mL | 0.1958 mL | 0.3916 mL | 0.4895 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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α-Tocopherol (vitamin E phosphate) is the compound demonstrating the highest vitamin E activity, which is available both in its natural form as RRR-alpha-tocopherol isolated from plant sources.
References:
[1]. Jensen SK, et al. Alpha-tocopherol stereoisomers. Vitam Horm. 2007;76:281-308.
[2]. Manor D, et al. The alpha-tocopherol transfer protein. Vitam Horm. 2007;76:45-65.
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Effect of phosphate, ascorbic acid and alpha-tocopherol injected at one-location with tumbling on quality of roast beef.[Pubmed:21075546]
Meat Sci. 2011 Mar;87(3):223-8.
The purpose of this study was to evaluate if continuous non-vacuum or vacuum tumbling improves the quality of roast beef utilizing the one location injection. Basically, fresh roast beef treated by one location injection with tumbling had significantly different quality compared to non-tumbled ones. However, the cooked roast beef did not significantly exhibit better quality due to tumbling. There was insignificant difference of TBARS value for whole meat among treatments at day 0. The control had significantly higher TBARS value compared to roast beef with non-vacuum and vacuum tumbled samples at day 2. At 4, 7 and 14 days of refrigerated storage, the control maintained the significantly highest values when compared to the other treatments that had similar TBARS values. The addition of three antioxidants was the major contributor to lipid stability of the cooked roast beef.
Induction of VEGF expression by alpha-tocopherol and alpha-tocopheryl phosphate via PI3Kgamma/PKB and hTAP1/SEC14L2-mediated lipid exchange.[Pubmed:25290554]
J Cell Biochem. 2015 Mar;116(3):398-407.
In several studies, vitamin E has been observed to influence angiogenesis and vasculogenesis. We recently showed that the phosphorylated form of alpha-tocopherol (alphaT), alpha-tocopheryl phosphate (alphaTP), increases the expression of the vascular endothelial growth factor (VEGF). Thus, alphaTP may act as an active lipid mediator increasing VEGF expression, angiogenesis, and vasculogenesis. Here, we investigated the molecular signaling mechanisms by which alphaTP induces VEGF expression using cultured HEK293 cells as model system. alphaT and more so alphaTP increased VEGF-promoter activity in a phosphatidylinositol-3-kinase gamma (PI3Kgamma)-dependent manner. In contrast, after overexpression of PI3Kgamma and/or protein kinase B (PKB), VEGF promoter activity was inhibited by alphaT and more so by alphaTP. Inhibition by alphaT and alphaTP was dependent on the lipid kinase activity of PI3Kgamma, whereas an induction was seen with the protein kinase activity, consistent with a model in which PKB inhibition by alphaT or alphaTP occurs only when activated at the plasma membrane and possibly involves a phosphatase such as PHLPP1. PI3Kgamma-induced VEGF expression was reduced when the human tocopherol-associated protein 1 (hTAP1/SEC14L2) was overexpressed suggesting formation of an inactive PI3Kgamma/hTAP1 heterodimer, that could be reactivated by alphaT and more so by alphaTP. We suggest a novel signaling mechanism by which alphaTP stimulates PI3Kgamma activity by stimulating hTAP-mediated phosphatidylinositol exchange and presentation to the enzyme and/or dissociation of an inactive heterodimer. At cellular level, hTAP may act as sensor for intracellular lipid information (location, type, and amount of lipid) and translate it into responses of PI3K-mediated signaling and gene expression.
Modulation of gene expression by alpha-tocopherol and alpha-tocopheryl phosphate in THP-1 monocytes.[Pubmed:20923704]
Free Radic Biol Med. 2010 Dec 15;49(12):1989-2000.
The natural vitamin E analog alpha-tocopheryl phosphate (alphaTP) modulates atherosclerotic and inflammatory events more efficiently than the unphosphorylated alpha-tocopherol (alphaT). To investigate the molecular mechanisms involved, we have measured plasma levels of alphaTP and compared the cellular effects of alphaT and alphaTP in THP-1 monocytes. THP-1 cell proliferation is slightly increased by alphaT, whereas it is inhibited by alphaTP. CD36 surface expression is inhibited by alphaTP within hours without requiring transport of alphaTP into cells, suggesting that alphaTP may bind to CD36 and/or trigger its internalization. As assessed by gene expression microarrays, more genes are regulated by alphaTP than by alphaT. Among a set of confirmed genes, the expression of vascular endothelial growth factor is induced by alphaTP as a result of activating protein kinase B (PKB/Akt) and is associated with increased levels of reactive oxygen species (ROS). Increased Akt(Ser473) phosphorylation and induction of ROS by alphaTP occur in a wortmannin-sensitive manner, indicating the involvement of phosphatidylinositol kinases. The induction of Akt(Ser473) phosphorylation and ROS production by alphaTP can be attenuated by alphaT. It is concluded that alphaTP and alphaT influence cell proliferation, ROS production, and Akt(Ser473) phosphorylation in an antagonistic manner, most probably by modulating phosphatidylinositol kinases.
alpha-tocopherol and alpha-tocopheryl phosphate interact with the cannabinoid system in the rodent hippocampus.[Pubmed:21843633]
Free Radic Biol Med. 2011 Nov 1;51(9):1643-55.
alpha-Tocopherol (alpha-TOH), a dietary component of vitamin E, is well known for its antioxidant capacity. Nevertheless, recent studies have pointed out non-anti-radical properties including cellular and genomic actions. Decreased levels of alpha-tocopherol in the brain are associated with neuronal dysfunctions ranging from mood disorders to neurodegeneration. All these behavioral effects of alpha-tocopherol deficiency probably do not rely simply on its anti-radical properties, but could also be reminiscent of a not-yet characterized neuromodulatory action. We have thus measured the direct actions of alpha-tocopherol and of its natural phosphate derivative, alpha-tocopheryl phosphate (alpha-TP), on synaptic transmission in rodent hippocampus. These compounds had opposite actions on both glutamatergic and GABAergic transmission: whereas alpha-TOH potentiated these transmissions, alpha-TP inhibited them. Interestingly, these effects were both mediated by cannabinoid receptors (CB1Rs), because they were blocked by the CB1R antagonist AM251. Although alpha-tocopherol and alpha-tocopheryl phosphate did not directly bind CB1R, both alpha-TP and CB1R agonists inhibited forskolin-evoked Erk1/2 phosphorylation in a nonadditive manner. Furthermore, both alpha-tocopherol and alpha-tocopheryl phosphate attenuated depolarization-induced suppression of excitation and CB1R agonist-mediated hypothermia. Therefore, we identify alpha-tocopherol as new lipid modulator of the cannabinoid system in the rodent hippocampus, i.e., a novel "non-anti-radical" action of vitamin E, which may have some preeminent impact in neuronal disorders associated with vitamin E deficiency.
