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| Other Sizes |
| Targets |
(1R)-alpha-Pinene modulates multiple molecular targets involved in inflammatory and oxidative stress pathways. It inhibits the activation of nuclear factor-kappa B (NF-kappaB) and mitogen-activated protein kinase (MAPK) signaling pathways, which are central to inflammatory responses. Additionally, alpha-pinene has been shown to interact with acetylcholine esterase (AChE) and gamma-aminobutyric acid (GABA) receptors, contributing to its neuroactive properties. It also influences the arachidonic acid cascade, leading to reduced synthesis of pro-inflammatory prostaglandins (e.g., PGE-1). Its antimicrobial activity is primarily attributed to disruption of bacterial cell membrane integrity and inhibition of bacterial efflux pumps.
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| ln Vitro |
In vitro, alpha-pinene demonstrates concentration-dependent growth inhibition of Bacillus cereus, Staphylococcus aureus, and other bacterial pathogens, with MIC values typically in the range of 200-1,000 ug/mL. The compound also exhibits antifungal activity against Candida albicans and other common fungi. In anti-inflammatory assays using LPS-stimulated macrophages, alpha-pinene reduces the production of pro-inflammatory cytokines (TNF-alpha, IL-1beta, IL-6) and nitric oxide (NO) in a dose-dependent manner. Neuroprotective effects have been observed in neuronal cell cultures exposed to oxidative stress, where alpha-pinene reduces reactive oxygen species (ROS) accumulation and prevents apoptosis. Furthermore, it acts as a weak acetylcholinesterase inhibitor, with IC50 values generally >500 uM.
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| ln Vivo |
In vivo animal studies have confirmed the anti-inflammatory and analgesic effects of alpha-pinene. In rodent models of acute inflammation (carrageenan-induced paw edema) and chronic inflammation (adjuvant-induced arthritis), oral administration of alpha-pinene (10-100 mg/kg) significantly reduces paw swelling and inflammatory markers. Analgesic effects have been demonstrated in acetic acid-induced writhing and hot plate tests. The compound also exhibits bronchodilator activity in asthma models, improving lung function parameters. Behavioral studies have shown anxiolytic-like effects in the elevated plus maze and light-dark box tests. Antimicrobial efficacy has been observed in mouse models of bacterial infection, with alpha-pinene treatment leading to reduced bacterial loads and improved survival.
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| Enzyme Assay |
A typical non-cellular enzyme assay for alpha-pinene involves testing its ability to inhibit acetylcholinesterase (AChE) activity using Ellman's colorimetric method. The reaction mixture contains 50 uL of AChE solution (0.2 U/mL), 50 uL of test compound (alpha-pinene at varying concentrations), and 100 uL of 5,5′-dithiobis-(2-nitrobenzoic acid) (DTNB, 0.5 mM) in 100 mM phosphate buffer (pH 8.0). After pre-incubation for 10 min, 50 uL of acetylthiocholine iodide (0.5 mM) is added to initiate the reaction. Absorbance is measured at 412 nm every 30 sec for 5 min. The percentage inhibition is calculated relative to control wells containing buffer only. IC50 values are determined by nonlinear regression using dose-response curves.
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| Cell Assay |
In vitro cellular assays for alpha-pinene are typically conducted using macrophage cell lines (RAW 264.7) or neuronal cell lines (SH-SY5Y). Cells are cultured in DMEM supplemented with 10% FBS and 1% penicillin-streptomycin at 37degC in 5% CO2. Cells are seeded in 96-well plates at 1 × 10⁵ cells/well and allowed to adhere overnight. For anti-inflammatory studies, cells are pre-treated with alpha-pinene (1-500 uM) for 1 h, then stimulated with 1 ug/mL LPS for 24 h. Culture supernatants are collected for cytokine measurement by ELISA (TNF-alpha, IL-1beta, IL-6). Cell viability is assessed using MTT assay (0.5 mg/mL, 4 h) to exclude compound cytotoxicity. For neuroprotection studies, cells are exposed to oxidative stress induced by H2O2 (100-300 uM) in the presence or absence of alpha-pinene, and ROS production is measured using DCFH-DA fluorescent probe.
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| Animal Protocol |
In vivo animal studies for alpha-pinene commonly use adult male Swiss albino mice or Wistar rats (6-8 weeks old, 20-30 g). For anti-inflammatory assays, carrageenan (1% in saline, 50 uL) is injected into the subplantar region of the right hind paw 1 h after oral administration of alpha-pinene (10, 50, 100 mg/kg). Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 h post-injection. Percent inhibition is calculated relative to vehicle-treated controls. For antimicrobial efficacy studies, mice are infected intraperitoneally with bacterial suspension (e.g., Staphylococcus aureus, 1 × 10⁶ CFU/mouse). alpha-Pinene is administered intraperitoneally at 10-100 mg/kg daily. Survival rate and bacterial load in organs are assessed. All procedures require institutional animal ethics approval.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of alpha-pinene are characterized by rapid absorption following oral administration with low bioavailability due to extensive first-pass metabolism. Following inhalation, bioavailability is significantly higher (~60%) due to direct entry into the systemic circulation via pulmonary absorption. alpha-Pinene is highly lipophilic (log P ~4.4), leading to extensive tissue distribution and ability to cross the blood-brain barrier. Metabolism occurs primarily via CYP450-mediated oxidation, including hydroxylation at methyl side-chains and allylic oxidation of the cyclohexenyl backbone, yielding carboxylic acid metabolites. The elimination half-life in humans is approximately 2-4 hours. Peak breath concentrations are observed 30 min after ingestion.
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| Toxicity/Toxicokinetics |
Toxicological data indicate that alpha-pinene exhibits low acute toxicity, with oral LD50 values in rats ranging from approximately 3,700-5,000 mg/kg. The compound is not considered mutagenic in standard Ames tests. Skin contact may cause mild irritation in sensitive individuals, and inhalation of high concentrations can cause respiratory irritation and central nervous system depression. Subchronic toxicity studies in rats at doses up to 100 mg/kg/day revealed no significant adverse effects on major organ systems. alpha-Pinene is generally recognized as safe (GRAS) for use as a food additive and flavoring agent by regulatory agencies when used within approved limits. No significant reproductive or developmental toxicity has been reported. For research use only.
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| References | |
| Additional Infomation |
(+)-α-pinene is the (+)-enantiomer of α-pinene. It is a metabolite found in both plants and humans. It is the enantiomer of (-)-α-pinene. (+)-α-pinene has been reported to exist in Artemisia xerophytica, Salvia officinalis, and other organisms with relevant data.
(1R)-alpha-Pinene is not approved as a pharmaceutical drug for human use but is widely employed in essential oils, aromatherapy, cosmetics, and as a natural flavoring agent in the food industry. Its pharmacological mechanisms involve multi-target modulation of inflammatory (NF-kappaB, COX-2) and neuroactive pathways (GABA, AChE). Preclinical studies have shown potential for treating respiratory conditions (bronchitis, asthma), inflammatory diseases, and anxiety-related disorders. Limited clinical studies have evaluated its effects on pulmonary function in humans. No Phase III clinical trials have been registered for alpha-pinene as a drug. The compound serves as a valuable natural product lead for drug discovery and as a reference standard in analytical chemistry. For research use only; not for therapeutic administration in humans. |
| Molecular Formula |
C10H16
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|---|---|
| Molecular Weight |
136.2340
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| Exact Mass |
136.125
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| CAS # |
7785-70-8
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| PubChem CID |
82227
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
157.9±7.0 °C at 760 mmHg
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| Melting Point |
-62 °C
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| Flash Point |
32.2±0.0 °C
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| Vapour Pressure |
3.5±0.1 mmHg at 25°C
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| Index of Refraction |
1.479
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| LogP |
4.37
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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 |
0
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| Heavy Atom Count |
10
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| Complexity |
186
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C(C([H])([H])[H])=C([H])C([H])([H])[C@]1([H])C2([H])[H]
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| InChi Key |
GRWFGVWFFZKLTI-RKDXNWHRSA-N
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| InChi Code |
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1
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| Chemical Name |
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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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