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γ-Tocopherol-d4 (γ-Tocopherol d4)

Cat No.:V74834 Purity: ≥98%
γ-Tocopherol-d4 is the deuterated form of γ-Tocopherol.
γ-Tocopherol-d4 (γ-Tocopherol d4)
γ-Tocopherol-d4 (γ-Tocopherol d4) Chemical Structure CAS No.: 1329652-13-2
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
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Product Description
γ-Tocopherol-d4 is the deuterated form of γ-Tocopherol. γ-Tocopherol (D-γ-Tocopherol) is a potent cyclooxygenase inhibitor. γ-Tocopherol is the natural form of vitamin E found in many plant seeds, such as corn oil and soybeans. γ-Tocopherol has anti-inflammatory activities and anti-cancer activity.
gamma-Tocopherol-d4 is a deuterated form of gamma-tocopherol (D-gamma-tocopherol), a naturally occurring vitamin E isoform found in plant seeds such as corn and soybean oil. As a lipophilic antioxidant, this stable isotope-labeled compound is used as an internal standard for the quantification of gamma-tocopherol in biological samples via LC-MS/MS. gamma-Tocopherol exhibits anti-inflammatory properties and has demonstrated anticancer activity in research models.
Biological Activity I Assay Protocols (From Reference)
Targets
gamma-Tocopherol-d4 is a potent cyclooxygenase (COX) enzyme inhibitor, targeting both COX-1 and COX-2. By binding to these enzymes, it blocks the conversion of arachidonic acid to prostaglandins, thereby reducing inflammation. It also acts as a potent antioxidant by scavenging reactive oxygen and nitrogen species.
ln Vitro
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, gamma-tocopherol-d4 exhibits significant antioxidant activity by scavenging free radicals and reactive nitrogen species. The non-deuterated gamma-tocopherol effectively inhibits COX enzymes, with lower doses showing anti-inflammatory and anticancer effects. In vitro studies reveal that gamma-tocopherol reduces prostaglandin synthesis and suppresses inflammatory cytokine production in activated immune cells.
ln Vivo
Due to limited in vivo data for the deuterated form, gamma-tocopherol itself reduces systemic inflammation and tumor growth in animal models. It lowers levels of pro-inflammatory mediators such as prostaglandins and cytokines in models of induced inflammation. The compound also demonstrates protective effects against oxidative stress-induced tissue damage in vivo.
Enzyme Assay
Binding affinity to COX enzymes is assessed using a COX inhibition assay kit. Purified ovine or human COX-1 and COX-2 enzymes are incubated with arachidonic acid in the presence of serially diluted gamma-Tocopherol-d4 (1-100 uM). Prostaglandin production is measured by ELISA, and the IC50 is calculated from the dose-response curve.
Cell Assay
For in vitro cellular assays, murine macrophages (RAW 264.7) are stimulated with lipopolysaccharide (LPS, 1 ug/mL) in the presence of serially diluted gamma-Tocopherol-d4 (0.1-100 uM) for 24 hours. Supernatants are collected, and inflammatory cytokines (e.g., TNF-alpha, IL-6, PGE2) are quantified by ELISA. Nitric oxide (NO) production is measured using the Griess assay.
Animal Protocol
A mouse model of acute inflammation is induced by carrageenan injection into the hind paw. gamma-Tocopherol-d4 is administered orally or intraperitoneally at doses of 10-100 mg/kg, 1 hour before carrageenan challenge. Paw edema is measured using a plethysmometer at 0, 1, 2, 4, and 6 hours post-injection. The percentage inhibition of edema is calculated compared to vehicle-treated controls.
ADME/Pharmacokinetics
gamma-Tocopherol-d4 has a molecular weight of 420.70 g/mol and a formula of C28H44D4O2. It is soluble in ethanol, DMSO, and lipid-based solvents. As a small lipophilic molecule, it is absorbed through the gastrointestinal tract and distributed to lipid-rich tissues. Its deuterated form is used primarily as an analytical standard for pharmacokinetic studies.
Toxicity/Toxicokinetics
At higher doses, gamma-Tocopherol-d4 can cause toxicity and adverse effects such as liver damage and disruption of cellular functions. In animal models, very high doses of vitamin E isoforms have been associated with hemorrhagic effects and impaired blood coagulation. Research use should determine the optimal dosage to maximize benefits while minimizing potential risks.
References

[1]. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.

[2]. 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
gamma-Tocopherol-d4 is a research-grade stable isotope-labeled compound not approved for clinical use. It is intended for use as an internal standard in LC-MS/MS quantification of gamma-tocopherol in biological matrices. It is also used to study the pharmacokinetics and biodistribution of dietary vitamin E isoforms. This product is for laboratory research purposes only, not for human therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H48O2
Molecular Weight
416.679529190063
Exact Mass
420.39
CAS #
1329652-13-2
PubChem CID
71752599
Appearance
White to light yellow solid powder
LogP
10.3
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
CC1C(=C(O)C([H])=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC=12)C([H])([H])[H]
InChi Key
QUEDXNHFTDJVIY-HYPXHKDHSA-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/i5D3,19D
Chemical Name
(2R)-5-deuterio-2,8-dimethyl-7-(trideuteriomethyl)-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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (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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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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