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Alpha-Tocotrienol

CAS# 1721-51-3

Alpha-Tocotrienol

Catalog No. BCN3724----Order now to get a substantial discount!

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Quality Control of Alpha-Tocotrienol

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Chemical structure

Alpha-Tocotrienol

3D structure

Chemical Properties of Alpha-Tocotrienol

Cas No. 1721-51-3 SDF Download SDF
PubChem ID 5282347 Appearance Powder
Formula C29H44O2 M.Wt 424.7
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
SMILES CC1=C(C(=C2CCC(OC2=C1C)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C)O
Standard InChIKey RZFHLOLGZPDCHJ-XZXLULOTSA-N
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.
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.
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.

Source of Alpha-Tocotrienol

The stem bark of Garcinia virgata

Biological Activity of Alpha-Tocotrienol

Description1. Alpha-Tocotrienol can exert anti-apoptotic neuroprotective action independently of its antioxidant property. 2. Alpha-Tocotrienol inhibits osteoclastic bone resorption by suppressing RANKL expression and signaling and bone resorbing activity. 3. Alpha-Tocotrienol supplementation counteracts the lipid peroxidation but not the barrier perturbation in the stratum corneum (SC) induced by 10% benzoyl peroxide (BPO).

Alpha-Tocotrienol Dilution Calculator

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Alpha-Tocotrienol Molarity Calculator

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Preparing Stock Solutions of Alpha-Tocotrienol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3546 mL 11.773 mL 23.546 mL 47.0921 mL 58.8651 mL
5 mM 0.4709 mL 2.3546 mL 4.7092 mL 9.4184 mL 11.773 mL
10 mM 0.2355 mL 1.1773 mL 2.3546 mL 4.7092 mL 5.8865 mL
50 mM 0.0471 mL 0.2355 mL 0.4709 mL 0.9418 mL 1.1773 mL
100 mM 0.0235 mL 0.1177 mL 0.2355 mL 0.4709 mL 0.5887 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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References on Alpha-Tocotrienol

Topical alpha-tocotrienol supplementation inhibits lipid peroxidation but fails to mitigate increased transepidermal water loss after benzoyl peroxide treatment of human skin.[Pubmed:12521598]

Free Radic Biol Med. 2003 Jan 15;34(2):170-6.

Benzoyl peroxide (BPO) is a commonly used drug in the treatment of acne vulgaris, but it induces unwanted side effects related to stratum corneum (SC) function. Since it has been recently shown to oxidize SC antioxidants, it was hypothesized that antioxidant supplementation may mitigate the BPO-induced SC changes. To test this, 11 subjects were selected to be topically supplemented with Alpha-Tocotrienol (5% w/vol) for 7 d on defined regions of the upper back, while the contralateral region was used for vehicle-only controls. Starting on day 8, all test sites were also treated with BPO (10%) for 7 d; the Alpha-Tocotrienol supplementation was continued throughout the study. A single dose of BPO depleted 93.2% of the total vitamin E. While continuing the BPO exposure for 7 d further depleted vitamin E in both vehicle-only and Alpha-Tocotrienol-treated sites, significantly more vitamin E remained in the Alpha-Tocotrienol-treated areas. Seven BPO applications increased lipid peroxidation. Alpha-Tocotrienol supplementation significantly mitigated the BPO-induced lipid peroxidation. The transepidermal water loss was increased 1.9-fold by seven BPO applications, while there was no difference between Alpha-Tocotrienol treatment and controls. The data suggest that Alpha-Tocotrienol supplementation counteracts the lipid peroxidation but not the barrier perturbation in the SC induced by 10% BPO.

Alpha-tocotrienol provides the most potent neuroprotection among vitamin E analogs on cultured striatal neurons.[Pubmed:15527824]

Neuropharmacology. 2004 Nov;47(6):904-15.

Oxidative stress and apoptosis play pivotal roles in the pathogenesis of neurodegenerative diseases. We investigated the effects of vitamin E analogs on oxidative stress and apoptosis using primary neuronal cultures of rat striatum. A tocotrienol-rich fraction of edible oil derived from palm oil (Tocomin 50%), which contains alpha-tocopherol, and alpha-, gamma- and delta-tocotrienols, significantly inhibited hydrogen peroxide (H2O2)-induced neuronal death. Each of the tocotrienols, purified from Tocomin 50% by high-performance liquid chromatography, significantly attenuated H2O2-induced neurotoxicity, whereas alpha-tocopherol did not. alpha-, gamma- and delta-Tocotrienols also provided significant protection against the cytotoxicity of a superoxide donor, paraquat, and nitric oxide donors, S-nitrosocysteine and 3-morpholinosydnonimine. Moreover, tocotrienols blocked oxidative stress-mediated cell death with apoptotic DNA fragmentation caused by an inhibitor of glutathione synthesis, L-buthionine-[S,R]-sulfoximine. In addition, Alpha-Tocotrienol, but not gamma- or delta-tocotrienol, prevented oxidative stress-independent apoptotic cell death, DNA cleavage and nuclear morphological changes induced by a non-specific protein kinase inhibitor, staurosporine. These findings suggest that Alpha-Tocotrienol can exert anti-apoptotic neuroprotective action independently of its antioxidant property. Among the vitamin E analogs examined, Alpha-Tocotrienol exhibited the most potent neuroprotective actions in rat striatal cultures.

alpha-Tocotrienol inhibits osteoclastic bone resorption by suppressing RANKL expression and signaling and bone resorbing activity.[Pubmed:21352805]

Biochem Biophys Res Commun. 2011 Mar 25;406(4):546-51.

Vitamin E, an essential nutrient with powerful antioxidant activity, is the mixture of two classes of compounds, tocopherols (TPs) and tocotrienols (TTs). Although TTs exhibit better bone protective activity than alpha-TP, the underlying mechanism is poorly understood. In this study, we investigated whether alpha-TT and alpha-TP can modulate osteoclastic bone resorption. We found that alpha-TT but not alpha-TP inhibits osteoclastogenesis in coculture of osteoblasts and bone marrow cells induced by either IL-1 or combined treatment with 1alpha,25(OH)(2) vitamin D(3) and prostaglandin E(2). In accordance with this, only alpha-TT inhibited receptor activator of NF-kappaB ligand (RANKL) expression in osteoblasts. In addition, alpha-TT but not alpha-TP inhibited RANKL-induced osteoclast differentiation from precursors by suppression of c-Fos expression, possibly through inhibiting ERK and NF-kappaB activation. This anti-osteoclastogenic effect was reversed when c-Fos or an active form of NFATc1, a critical downstream of c-Fos during osteoclastogenesis, was overexpressed. Furthermore, only alpha-TT reduced bone resorbing activity of mature osteoclasts without affecting their survival. Overall, our results demonstrate that alpha-TT but not alpha-TP has anti-bone resorptive properties by inhibiting osteoclast differentiation and activation, suggesting that alpha-TT may have therapeutic value for treating and preventing bone diseases characterized by excessive bone destruction.

Increased alpha-tocotrienol content in seeds of transgenic rice overexpressing Arabidopsis gamma-tocopherol methyltransferase.[Pubmed:22763462]

Transgenic Res. 2013 Feb;22(1):89-99.

Vitamin E comprises a group of eight lipid soluble antioxidant compounds that are an essential part of the human diet. The alpha-isomers of both tocopherol and tocotrienol are generally considered to have the highest antioxidant activities. gamma-tocopherol methyltransferase (gamma-TMT) catalyzes the final step in vitamin E biosynthesis, the methylation of gamma- and delta-isomers to alpha- and beta-isomers. In present study, the Arabidopsis gamma-TMT (AtTMT) cDNA was overexpressed constitutively or in the endosperm of the elite japonica rice cultivar Wuyujing 3 (WY3) by Agrobacterium-mediated transformation. HPLC analysis showed that, in brown rice of the wild type or transgenic controls with empty vector, the alpha-/gamma-tocotrienol ratio was only 0.7, much lower than that for tocopherol (~19.0). In transgenic rice overexpressing AtTMT driven by the constitutive Ubi promoter, most of the gamma-isomers were converted to alpha-isomers, especially the gamma- and delta-tocotrienol levels were dramatically decreased. As a result, the Alpha-Tocotrienol content was greatly increased in the transgenic seeds. Similarly, over-expression of AtTMT in the endosperm also resulted in an increase in the Alpha-Tocotrienol content. The results showed that the alpha-/gamma-tocopherol ratio also increased in the transgenic seeds, but there was no significant effect on alpha-tocopherol level, which may reflect the fact that gamma-tocopherol is present in very small amounts in wild type rice seeds. AtTMT overexpression had no effect on the absolute total content of either tocopherols or tocotrienols. Taken together, these results are the first demonstration that the overexpression of a foreign gamma-TMT significantly shift the tocotrienol synthesis in rice, which is one of the world's most important food crops.

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