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β-Tocopherol (β-Tocopherol)

Cat No.:V71933 Purity: ≥98%
β-Tocopherol is an analogue of vitamin E and has anti-oxidant effect.
β-Tocopherol (β-Tocopherol)
β-Tocopherol (β-Tocopherol) Chemical Structure CAS No.: 16698-35-4
Product category: Tyrosinase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
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Product Description
β-Tocopherol is an analogue of vitamin E and has anti-oxidant effect. β-Tocopherol inhibits tyrosinase activity and melanin synthesis. β-Tocopherol also prevents the inhibition of cell growth and PKC activity caused by d-α-Tocopherol.
β-Tocopherol is a naturally occurring analog of vitamin E, belonging to the tocopherol family. It is found in various vegetable oils and is known for its potent antioxidant properties. β-Tocopherol is a key component of the cellular defense system against oxidative stress. In addition to its role as an antioxidant, it exhibits significant biological activities, including the inhibition of tyrosinase activity and melanin synthesis, making it a compound of interest in dermatological research for skin pigmentation modulation. It also plays a role in cell signaling, as it can prevent the inhibition of cell growth and protein kinase C (PKC) activity caused by d-α-tocopherol.
Biological Activity I Assay Protocols (From Reference)
Targets
β-Tocopherol targets tyrosinase, the key enzyme in melanin biosynthesis, and protein kinase C (PKC), an enzyme involved in cell signaling pathways. It inhibits tyrosinase activity, thereby reducing melanin production. β-Tocopherol also prevents the inhibition of PKC activity caused by d-α-tocopherol. Through its antioxidant properties, it scavenges free radicals and protects cells from oxidative damage.
ln Vitro
β-Tocopherol demonstrates potent in vitro antioxidant activity. It effectively inhibits tyrosinase activity and melanin synthesis. In B16 melanoma cells, β-Tocopherol (250 µg/mL, 72 hours) downregulates the expression of tyrosinase and tyrosinase-related protein-2 (TRP-2), leading to a 28% inhibition of melanin synthesis without significant cytotoxicity. It also suppresses PMA-induced human erythrocyte adhesion.
ln Vivo
In vivo activity data for β-Tocopherol are not extensively documented in available literature. As a vitamin E analog, it is expected to contribute to the overall antioxidant defense system in vivo. Its ability to inhibit melanin synthesis suggests potential efficacy in animal models of hyperpigmentation. Further in vivo studies are needed to fully characterize its efficacy and pharmacokinetic profile.
Enzyme Assay
The in vitro enzyme assay for β-Tocopherol involves measuring its inhibition of tyrosinase activity. Mushroom tyrosinase is commonly used as a model enzyme. The assay typically uses L-DOPA as a substrate, and the formation of dopachrome is monitored spectrophotometrically at 475 nm. β-Tocopherol is incubated with the enzyme and substrate at various concentrations. The IC50 value is determined by fitting the inhibition data to a dose-response curve.
Cell Assay
In vitro cellular assays for β-Tocopherol typically use B16 melanoma cells to assess its effects on melanogenesis. Cells are treated with β-Tocopherol at various concentrations for 72 hours. Melanin content is measured spectrophotometrically. Tyrosinase activity is assessed by measuring the oxidation of L-DOPA in cell lysates. The expression of melanogenesis-related proteins such as tyrosinase and TRP-2 is analyzed by Western blot.
Animal Protocol
In vivo animal experiments for β-Tocopherol are not extensively documented. As a vitamin E analog, standard in vivo studies would involve animal models of oxidative stress or hyperpigmentation. β-Tocopherol would be administered via oral or topical routes. Markers of oxidative stress, melanin content in skin, and histopathological analysis would be assessed.
ADME/Pharmacokinetics
The pharmacokinetic properties of β-Tocopherol are expected to be similar to those of other tocopherols. As a lipophilic vitamin E analog, it is absorbed via the lymphatic pathway and distributed to various tissues, particularly adipose tissue and cell membranes. Its antioxidant activity contributes to its overall pharmacological profile. Further pharmacokinetic studies are necessary to fully characterize its absorption, distribution, metabolism, and excretion.
Toxicity/Toxicokinetics
Toxicological data for β-Tocopherol are not extensively available. As a naturally occurring vitamin E analog, it is generally considered safe and well-tolerated. No significant cytotoxicity was observed in B16 cells at concentrations up to 250 µg/mL. Further toxicological studies would be required for clinical development.
References

[1]. d-alpha-tocopherol control of cell proliferation. Mol Aspects Med. 1993; 14(3): 265-71.

[2]. 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. Proc Natl Acad Sci U S A.

[3]. Comparison of the inhibitory effects of vitamin E analogues on melanogenesis in mouse B16 melanoma cells. Cytotechnology. 2009 Apr; 59(3): 183-90.

Additional Infomation
β-Tocopherol is a tocopherol in which the 5 and 8 positions of the chroman-6-ol core are replaced by methyl groups. While it is found in low amounts in many plant oils, only cottonseed oil contains significant amounts. It is both a plant metabolite and a food ingredient. It is a form of vitamin E and also a tocopherol. β-Tocopherol has been reported in perilla, soybeans, and several other organisms with relevant data. It is a natural tocopherol with lower antioxidant activity than α-Tocopherol. Its antioxidant activity is due to the phenolic hydroxyl hydrogen on its 2H-1-benzopyran-6-ol core. Similar to γ-Tocopherol, it also has three methyl groups on the 6-chromanol core, but in different positions.
β-Tocopherol is a naturally occurring vitamin E analog with antioxidant and tyrosinase-inhibitory activities. It is found in various vegetable oils and is a component of the cellular defense system against oxidative stress. β-Tocopherol is used in research on melanogenesis, oxidative stress, and cell signaling. No clinical trials or regulatory approvals have been reported for this compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H48O2
Molecular Weight
416.68
Exact Mass
416.365
CAS #
16698-35-4
PubChem CID
6857447
Appearance
Colorless to light yellow liquid
Density
0.933g/cm3
Boiling Point
516.267°C at 760 mmHg
Melting Point
< 25 °C
Flash Point
204.683°C
LogP
8.531
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
12
Heavy Atom Count
30
Complexity
475
Defined Atom Stereocenter Count
3
SMILES
O1C2C(C([H])([H])[H])=C([H])C(=C(C([H])([H])[H])C=2C([H])([H])C([H])([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])O[H]
InChi Key
WGVKWNUPNGFDFJ-DQCZWYHMSA-N
InChi Code
InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
Chemical Name
(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (239.99 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3999 mL 11.9996 mL 23.9992 mL
5 mM 0.4800 mL 2.3999 mL 4.7998 mL
10 mM 0.2400 mL 1.2000 mL 2.3999 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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