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| Other Sizes |
| Targets |
γ-Terpinene exerts its biological effects through multiple mechanisms. As an antioxidant, it neutralizes free radicals, reducing oxidative damage. It is a potent antinociceptive agent, significantly inhibiting glutamate-induced nociception. The compound interacts with various cellular targets, including cell membrane proteins, enzymes, and other biomolecules. It can inhibit the activity of enzymes involved in essential fatty acid biosynthesis, thereby reducing inflammation. Its antibacterial activity involves increasing membrane permeability and decreasing bacterial growth.
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| ln Vitro |
In vitro, γ-Terpinene demonstrates potent antioxidant activity by scavenging free radicals including DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonate)). It reduces the growth of Trypanosoma evansi in a concentration-dependent manner. It increases membrane permeability and decreases the growth of Xanthomonas oryzae bacteria. The compound's antioxidant and antimicrobial activities have been characterized in various in vitro assays. It also shows anti-inflammatory activity by inhibiting inflammatory mediator production.
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| ln Vivo |
In male Swiss mice weighing 20-30 g, γ-TPN (12.5, 25 mg/kg; po; single dose) dramatically shortens the time the stimulated paw is licked during both test phases[1]. γ-Terpinene significantly inhibits glutamate-induced nociception in mice when administered systemically (po; 1.56, 3.125, and 6.25 mg/kg) or centrally (it or icv; 10 and 20 μg/site)[1].
In vivo, γ-Terpinene has been shown to be an orally active antioxidant and antinociceptive agent. It significantly inhibits glutamate-induced nociception. In animal models, γ-Terpinene exhibits potent antinociception activity. The compound has been studied for pain relief, with efficacy observed at doses of 6.25 mg/kg orally or 10-20 μg/site centrally. Its antioxidant properties contribute to its protective effects against oxidative stress. γ-Terpinene is also studied for its anti-inflammatory and antibacterial activities in vivo. |
| Enzyme Assay |
Non-cell-based assays for γ-Terpinene include antioxidant activity measurements using DPPH radical scavenging and ABTS assays. The compound's ability to scavenge free radicals is measured by its IC₅₀ in these assays. Antimicrobial activity is assessed by minimum inhibitory concentration (MIC) determination against bacterial and fungal strains. Enzyme inhibition assays are used to evaluate inhibition of enzymes involved in fatty acid biosynthesis or inflammatory pathways. Binding studies with membrane proteins or receptors may be performed to characterize the compound's interactions with potential targets.
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| Cell Assay |
Cellular assays for γ-Terpinene are performed using various cell lines including immune cells, cancer cells, or primary cells. Cells are treated with γ-Terpinene at various concentrations, and cellular responses are measured. Cytotoxicity is assessed by MTT assays. Anti-inflammatory activity is evaluated by measuring NO production, pro-inflammatory cytokine secretion (TNF-α, IL-1β, IL-6), and NF-κB activation in LPS-stimulated macrophages. Antioxidant activity is assessed by measuring intracellular ROS levels, glutathione levels, and antioxidant enzyme activities. Antinociceptive activity is evaluated in neuronal cell models.
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| Animal Protocol |
In vivo experiments with γ-Terpinene are conducted in rodent models. For antinociception studies, mice are treated with γ-Terpinene orally or intraperitoneally, and pain responses are measured using the formalin test, hot plate test, or tail flick test. The compound's ability to inhibit glutamate-induced nociception is evaluated. For anti-inflammatory studies, animal models of inflammation (carrageenan-induced paw edema, ear edema) are used. Antioxidant activity is assessed in models of oxidative stress by measuring oxidative markers in tissues. For antimicrobial studies, animal models of infection are used to evaluate efficacy.
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| ADME/Pharmacokinetics |
γ-Terpinene is orally active and exhibits favorable pharmacokinetic properties as a monoterpene. Following oral administration, the compound is absorbed from the gastrointestinal tract and distributed to tissues. It is metabolized primarily in the liver and excreted via urine. The compound's bioavailability, half-life, and tissue distribution have been characterized in preclinical studies. γ-Terpinene shows good oral bioavailability and brain penetration, consistent with its antinociceptive activity. However, detailed PK data are limited.
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| Toxicity/Toxicokinetics |
The toxicity of γ-Terpinene has been evaluated in preclinical studies. As a natural monoterpene found in many essential oils, γ-Terpinene is generally considered safe at low concentrations. The compound has a favorable safety profile with no significant acute toxicity at therapeutic doses. At high doses, monoterpenes can cause irritation or toxicity. Comprehensive toxicological studies including genotoxicity, organ toxicity, and developmental toxicity are limited. The compound is for research use only and is not approved as a therapeutic agent.
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| References |
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| Additional Infomation |
γ-Terpinene is one of three isomeric monoterpenes, distinguished by the positions of its two double bonds (the other two being α-terpinene and β-terpinene). In γ-terpinene, the double bonds are located at positions 1 and 4 of the menthol skeleton. It possesses antioxidant, plant metabolism, volatile oil component, and human exogenous metabolism functions. It is a monoterpene and also a cyclohexadiene. γ-Terpinene has been reported to exist in tea trees (Camellia sinensis), Artemisia thanscula, and other organisms with relevant data. Terpinene is one of three isomeric hydrocarbons, all belonging to the terpene class of compounds. γ-Terpinene is one of these three isomeric hydrocarbons. It is naturally occurring and has been isolated from various plants (Wikipedia). It is a major component of citrus fruit essential oils and possesses strong antioxidant activity. It has a lemon scent and is widely used in the food, fragrance, soap, cosmetic, pharmaceutical, tobacco, confectionery, and perfume industries (http://www.gyanflavoursexport.com). See also: cold-pressed lemon oil (partial); citrus oil (partial); coriander oil (partial).
γ-Terpinene (CAS# 99-85-4) is a monoterpene with the molecular formula C₁₀H₁₆ and a molecular weight of 136.23. It is also known as p-Mentha-1,4-diene. γ-Terpinene is an orally active antioxidant compound that can scavenge radicals directly and has potent antinociception activity. It is found in various plants including tea tree oil, lavender oil, and pine oil, and contributes to the aroma profile of foods. The compound exerts antioxidant effects by neutralizing free radicals and possesses antibacterial, anti-inflammatory, and skin-healing properties. As of current knowledge, γ-Terpinene is not approved as a therapeutic agent but is used in research for its biological activities. |
| Molecular Formula |
C10H16
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|---|---|
| Molecular Weight |
136.23
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| Exact Mass |
136.125
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| CAS # |
99-85-4
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| PubChem CID |
7461
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.8±0.1 g/cm3
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| Boiling Point |
183.0±0.0 °C at 760 mmHg
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| Melting Point |
-10 °C
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| Flash Point |
51.7±0.0 °C
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| Vapour Pressure |
1.1±0.2 mmHg at 25°C
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| Index of Refraction |
1.476
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| LogP |
4.36
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
171
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)C1=CCC(=CC1)C
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| InChi Key |
YKFLAYDHMOASIY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
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| Chemical Name |
1-methyl-4-propan-2-ylcyclohexa-1,4-diene
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| Synonyms |
γ-Terpinene
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (734.05 mM)
H2O: 100 mg/mL (734.05 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.35 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 (18.35 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (18.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10 mg/mL (73.41 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.3405 mL | 36.7026 mL | 73.4053 mL | |
| 5 mM | 1.4681 mL | 7.3405 mL | 14.6811 mL | |
| 10 mM | 0.7341 mL | 3.6703 mL | 7.3405 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.
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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05803031 | Completed | Drug: Melaleuca Alternifolia Oil Procedure: Non-surgical periodontal debridement |
Periodontal Pocket | Ain Shams University | November 1, 2022 | Not Applicable |
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