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γ-Tocopherol

Alias: γTocopherol; γ Tocopherol
Cat No.:V38644 Purity: ≥98%
γ-Tocopherol (D-γ-Tocopherol) is a potent cyclooxygenase inhibitor.
γ-Tocopherol
γ-Tocopherol Chemical Structure CAS No.: 54-28-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
γ-Tocopherol (D-γ-Tocopherol) is a potent cyclooxygenase inhibitor. γ-Tocopherol is the natural form of vitamin E found in many plant seeds, like corn oil and soybeans. γ-Tocopherol has anti~inflammatory properties and anti-cancer activity.
γ-Tocopherol (D-γ-Tocopherol, CAS 54-28-4) is a naturally occurring form of vitamin E found in many plant seeds, such as corn oil and soybeans. It is a potent cyclooxygenase (COX) inhibitor and has anti-inflammatory properties and anti-cancer activity. The compound has the ability to scavenge free radicals, protecting cell membranes from oxidative damage. It inhibits human cancer cell cycle progression and cell proliferation by down-regulation of cyclins.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of γ-Tocopherol include cyclooxygenase (COX), for which it acts as a potent inhibitor. By inhibiting COX, the compound reduces inflammation. It also targets free radicals as an antioxidant, scavenging them and protecting against oxidative damage. The compound inhibits cancer cell cycle progression and proliferation by down-regulating cyclins. These targets make it relevant for inflammation, cancer, and cardiovascular research.
ln Vitro
Although it is highly absorbed and can build up in several human tissues, gamma-tocopherol (D-γ-tocopherol) is mostly converted to 2,7,8-trimethyl-2-(β-carboxyethyl) -6-Hydroxychroman (gamma-CEHC), which is primarily eliminated by urine [1]. The incidence of prostate cancer and cardiovascular disease is inversely correlated with plasma concentrations of γ-tocopherol (D-γ-tocopherol) [1].
In vitro, γ-Tocopherol inhibits COX activity and demonstrates anti-inflammatory properties. It scavenges free radicals and protects cell membranes from oxidative damage. The compound inhibits human cancer cell cycle progression and cell proliferation by down-regulating cyclins. These in vitro activities support its use in research on inflammation, cancer, oxidative stress, and cardiovascular disease.
ln Vivo
In vivo, γ-Tocopherol is an orally bioavailable form of vitamin E with potential antioxidant, anti-inflammatory, and anti-cancer activities. It has been studied for its potential health benefits, including cardiovascular protection and cancer prevention. The compound is found in corn oil and soybean oil and is used as a dietary supplement and in nutritional research. Its in vivo effects are well-documented in vitamin E research.
Enzyme Assay
In vitro enzyme assays for γ-Tocopherol involve measuring COX-1 and COX-2 inhibition. The compound is incubated with COX enzymes at concentrations ranging from 0.1-1000 μM, and enzyme activity is measured using prostaglandin production assays. IC50 values are determined. Antioxidant activity is assessed using DPPH, ABTS, or ORAC assays. Cancer cell proliferation is assessed using cell viability assays. All assays include appropriate controls and reference compounds.
Cell Assay
In vitro cell-based assays for γ-Tocopherol are conducted using cancer cell lines for anti-cancer studies, and inflammatory cells for anti-inflammatory studies. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Cell proliferation is assessed using MTT or CellTiter-Glo assays. Cell cycle analysis is performed using propidium iodide staining. Inflammatory cytokine production is measured by ELISA. ROS levels are measured using fluorescent probes. Experiments include vehicle controls and positive controls.
Animal Protocol
In vivo animal studies with γ-Tocopherol are conducted in models of cancer, inflammation, and cardiovascular disease. The compound is administered via oral dietary supplementation at doses ranging from 10-1000 mg/kg. Tumor growth is measured in cancer models. Inflammatory markers are assessed in inflammation models. Cardiovascular parameters are measured. Each group consists of 6-10 animals with vehicle-treated controls. Data are analyzed using standard statistical methods.
ADME/Pharmacokinetics
Pharmacokinetic properties of γ-Tocopherol include its oral bioavailability and distribution to various tissues. As a lipophilic vitamin E form (MW 416.68, C28H48O2), it is absorbed with dietary fats and transported in lipoproteins. The compound is metabolized through oxidation and conjugation, with elimination via biliary and renal excretion. Its pharmacokinetics are influenced by dietary fat intake and metabolic rate.
Toxicity/Toxicokinetics
Toxicological data for γ-Tocopherol indicate that it is generally well-tolerated as a form of vitamin E. No significant toxicity has been reported at typical dietary and supplement doses. High doses may cause bleeding risk due to anticoagulant effects. Comprehensive safety data are available from vitamin E research and clinical use. As with all research chemicals, appropriate safety precautions should be taken during handling.
References

[1]. Gamma-Tocopherol, the Major Form of Vitamin E in the US Diet, Deserves More Attention. Am J Clin Nutr. 2001 Dec;74(6):714-22.

Additional Infomation
γ-Tocopherol is a tocopherol in which the 7th and 8th positions of the cromoglycan-6-ol core are replaced by methyl groups. It is primarily found in corn and soybean oil. γ-Tocopherol is a plant metabolite, a food antioxidant, and an algal metabolite. It is a form of vitamin E and a tocopherol. γ-Tocopherol is currently being studied in the clinical trial NCT00836368 (Study on the in vitro basophil response to allergen-induced allergic asthma after γ-tocopherol supplementation in patients). γ-Tocopherol has been reported in perilla, soybeans, and several other organisms with relevant data. γ-Tocopherol is a naturally occurring, fat-soluble form of vitamin E with high oral bioavailability, found in certain nuts and seeds, and possesses potential antioxidant activity. Although the exact mechanism of action of this tocopherol is not fully understood, γ-Tocopherol appears to have the ability to scavenge free radicals, thereby protecting the body from oxidative damage. It is a natural tocopherol, and its antioxidant activity is lower than that of α-Tocopherol. Its antioxidant activity is due to the phenolic hydroxyl hydrogen on its 2H-1-benzopyran-6-ol core. Similar to β-tocopherol, it also contains three methyl groups on its 6-chromanol core, but in different positions.
γ-Tocopherol is a naturally occurring form of vitamin E found in corn oil and soybeans. It is a potent COX inhibitor with anti-inflammatory and anti-cancer activities. The compound scavenges free radicals, protects against oxidative damage, and inhibits cancer cell proliferation. It is used in research on inflammation, cancer, oxidative stress, and cardiovascular disease. Available as a dietary supplement and research chemical.
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 #
54-28-4
PubChem CID
92729
Appearance
Colorless to light yellow liquid
Density
0.933g/cm3
Boiling Point
200 °C (0.1 mmHg)
Melting Point
-67.50 °C. @ 760.00 mm Hg
Flash Point
206ºC
Index of Refraction
n20/D 1.505
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
O1C2=C(C([H])([H])[H])C(C([H])([H])[H])=C(C([H])=C2C([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
QUEDXNHFTDJVIY-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)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
Chemical Name
(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
Synonyms
γTocopherol; γ Tocopherol
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) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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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)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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