| Size | Price | |
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| Other Sizes |
| Targets |
Trypanosoma
alpha-Terpinene exhibits a multi-target mechanism of action typical of many terpenes. Its primary antimicrobial and antiparasitic effect is thought to be through disruption of the cell membrane integrity of the target organism. It interacts with the lipid bilayer, increasing membrane fluidity and permeability, leading to leakage of cellular contents and ion gradients. This is believed to be the mechanism for its trypanocidal activity against Trypanosoma evansi. Its antioxidant properties are due to its ability to scavenge free radicals and reduce oxidative stress. In cancer cells, it has been shown to induce apoptosis by activating the intrinsic (mitochondrial) pathway and modulating the NF-kappaB signaling pathway, a key regulator of cell survival and inflammation. |
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| ln Vitro |
In vitro, alpha-Terpinene has been shown to be active against Trypanosoma evansi. In culture, it inhibits the growth of the parasite with a half-maximal inhibitory concentration (IC₅0) in the range of 10-50 ug/mL. It also exhibits antifungal activity against various dermatophytes and Candida species. Against the yeast Candida albicans, the MIC is typically in the range of 0.1-1% (v/v). Its antioxidant activity is well-documented; it can scavenge DPPH radicals in a dose-dependent manner. In cancer cell lines, it has been shown to inhibit the activation of NF-kappaB, leading to decreased cell viability. For example, in human lung cancer cells, alpha-terpinene can induce G0/G1 cell cycle arrest and apoptosis.
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| ln Vivo |
In vivo, alpha-terpinene has demonstrated efficacy in a mouse model of Trypanosoma evansi infection. In this model, mice infected with T. evansi were treated with alpha-terpinene (e.g., 50-200 mg/kg/day, intraperitoneally) for 4 days. The treatment significantly reduced parasitemia and increased the survival rate of the mice compared to the untreated control group. The increased longevity observed in treated mice is attributed to the trypanocidal effect of alpha-terpinene. It has also been studied in a rat model of arthritis and has been shown to reduce paw edema, indicating anti-inflammatory effects. However, its high volatility and hydrophobicity limit its bioavailability for systemic use. The compound is often used in combination with other agents, such as DMSO, to enhance its delivery.
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| Enzyme Assay |
A non-cellular DPPH radical scavenging assay is commonly used to measure the antioxidant activity of alpha-Terpinene. A 0.1 mM solution of DPPH in methanol is prepared. alpha-Terpinene is dissolved in methanol at various concentrations (10-500 ug/mL). 100 uL of the DPPH solution is mixed with 100 uL of the alpha-Terpinene solution in a 96-well plate. The mixture is incubated in the dark at room temperature for 30 minutes. The decrease in absorbance is measured at 517 nm. The percentage of scavenging activity is calculated as [(Abs control - Abs sample) / Abs control] × 100. Butylated hydroxytoluene (BHT) or Trolox is used as a positive control. The IC₅0 (half-maximal inhibitory concentration) for DPPH scavenging is then determined.
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| Cell Assay |
A standard in vitro cell-based assay for alpha-Terpinene uses Trypanosoma evansi parasites. Parasites are grown in culture at 37degC in a suitable medium, such as Baltz medium supplemented with 15% horse serum. For the assay, 1 × 10⁶ parasites/well are seeded in a 96-well plate. alpha-Terpinene is added at concentrations ranging from 0.1-200 ug/mL, in triplicate. The plate is incubated at 37degC for 24-48 hours. Parasite motility and viability are assessed microscopically using a hemocytometer and by the MTT assay. The EC₅0 is defined as the concentration of the compound that reduces the number of motile parasites by 50% compared to the control. For cytotoxicity against mammalian cells, a mouse fibroblast cell line (e.g., L929 or NIH/3T3) is used in a parallel MTT assay to calculate the selectivity index.
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| Animal Protocol |
A typical in vivo animal study for alpha-Terpinene uses a mouse model of African trypanosomiasis (T. evansi). Six- to eight-week-old female Swiss or BALB/c mice (18-22 g) are used. Mice are infected intraperitoneally with 1 × 10⁴ T. evansi parasites. Following infection, the mice are randomly divided into groups (n=6). alpha-Terpinene is dissolved in PBS containing 5% DMSO and 5% Tween-80. It is administered intraperitoneally at doses of 50, 100, and 200 mg/kg once daily for 4 consecutive days, starting 24 hours after infection. A control group receives the vehicle only. Parasitemia is monitored daily by microscopic examination of tail blood smears. The cumulative mortality in each group is recorded for 30 days. The mean survival time for each group is calculated. At the end of the study, the level of liver enzymes (ALT, AST) in the blood is measured to assess hepatotoxicity.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of alpha-Terpinene are not well-documented. As a lipophilic, volatile monoterpene (MW 136.23, logP ~4.0), it is likely to be rapidly absorbed through most routes of administration (oral, IP, inhalation). It would distribute widely to tissues, including the brain. It is primarily metabolized in the liver by cytochrome P450 enzymes (phase I) and undergoes phase II conjugation (glucuronidation). Its metabolites are excreted in the urine. The elimination half-life is expected to be relatively short (likely 1-4 hours). Due to its volatile nature, a significant portion may be exhaled unchanged. Detailed PK parameters are not publicly available for research-grade alpha-Terpinene.
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| Toxicity/Toxicokinetics |
No comprehensive toxicity data is available for alpha-Terpinene. As a component of tea tree oil, it is known to be an irritant and can be toxic if ingested in high quantities. The oral LD₅0 in rats is reported to be >2,000 mg/kg, indicating moderate toxicity. It is a known skin sensitizer and may cause allergic reactions. In the mouse trypanosomiasis studies, alpha-Terpinene was well-tolerated at the tested doses up to 200 mg/kg IP, with no significant weight loss or overt toxicity reported. However, these studies were short-term. Standard safety precautions (gloves, lab coat, eye protection) should be used. For research use only; not for human therapeutic administration.
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| References |
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| Additional Infomation |
α-Terpinene is one of three isomers of monoterpenes, distinguished by the different positions of their two double bonds (the other two being β-terpinene and γ-terpinene). The double bonds in α-terpinene are located at positions 1 and 3 of the menthol skeleton. It is a volatile oil component and a plant metabolite. It is a monoterpene and also a cyclohexadiene. α-Terpinene has been reported to exist in tea plants (Camellia sinensis), Artemisia thancula, and other organisms with relevant data.
alpha-Terpinene is not an approved drug. It is a research chemical isolated from natural sources and is considered a lead compound for the development of new therapies for African trypanosomiasis. Its mechanism of action is thought to be primarily through disruption of the parasitic cell membrane, leading to cell lysis. It also has well-documented antioxidant and anti-inflammatory properties. The compound is of interest for treating T. evansi infection as an alternative to currently used drugs that have problems with toxicity and resistance. No clinical trials have been registered for alpha-Terpinene. For research use only; not for human therapeutic or diagnostic use. |
| Molecular Weight |
136.23
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|---|---|
| Exact Mass |
136.125
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| CAS # |
99-86-5
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| PubChem CID |
7462
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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 |
174.1±0.0 °C at 760 mmHg
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| Melting Point |
< 25 °C
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| Flash Point |
46.1±0.0 °C
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| Vapour Pressure |
1.6±0.1 mmHg at 25°C
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| Index of Refraction |
1.476
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| LogP |
4.53
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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=CC=C(C)CC1
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| InChi Key |
YHQGMYUVUMAZJR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3
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| Chemical Name |
1-methyl-4-propan-2-ylcyclohexa-1,3-diene
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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)
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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. |
| 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.
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