α-Pinene

• CAS: 80-56-8
• Catalog Number: ACM80568
• Category: Main Products
• Molecular Weight: 136.23
• Molecular Formula: C10H16
• Synonyms: 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Boiling Point: 155 - 156 °C (lit.)
• Density: 0.858 g/mL at 25 °C (lit.)
• Appearance: Liquid

Case Study

α-Pinene as a Potent Anti-Inflammatory Agent in Alleviating Nociceptive Responses

Rahimi K, et al. Brain Research Bulletin, 2023, 203, 110774.

α-Pinene's ability to reduce pro-inflammatory cytokines and oxidative stress markers suggests it holds promise as a therapeutic agent for managing inflammation and pain.
Methodology: Mice were administered α-pinene (1, 5, or 10 mg/kg) for 7 days prior to a formalin injection to induce nociceptive pain. Nociceptive behavior was observed, and biochemical analyses were performed to measure levels of TNF-α, IL-1β, COX-1, and oxidative stress markers, such as SOD, GSH, CAT, and MDA, in the spinal cord and skin tissue.
Results: The results showed that α-pinene, particularly at doses of 5 and 10 mg/kg, significantly reduced nociceptive behaviors. Additionally, α-pinene decreased the levels of pro-inflammatory cytokines TNF-α and IL-1β in the spinal cord and hind paw skin. The expression of COX-1 protein in the spinal cord was also reduced. At the formalin injection site, α-pinene pretreatment alleviated oxidative stress by increasing antioxidant levels (SOD, GSH, CAT) and decreasing oxidant markers (MDA).

Neuroprotective Role of α-pinene in Ketamine-Induced Schizophrenia Model

Moghaddam AH, et al. IBRO Neuroscience Reports, 2024, 16, 182-189.

α-pinene has emerged as a promising neuroprotective agent in schizophrenia (SCZ) models. In a recent study, the neurobehavioral and biochemical effects of α-pinene were explored in male mice with ketamine-induced SCZ. This model mimics the oxidative stress, cognitive deficits, and mood disturbances commonly associated with the disorder. Mice were divided into six groups, receiving either vehicle, control, positive control, ketamine, or α-pinene at 50 mg/kg or 100 mg/kg.
Administration of α-pinene significantly improved cognitive impairments and reduced anxiety-like and depressive behaviors. On a biochemical level, α-pinene treatment elevated brain glutathione (GSH), total antioxidant capacity (TAC), dopamine levels, and enzymatic activities of catalase (CAT) and superoxide dismutase (SOD). Concurrently, it lowered malondialdehyde (MDA) levels, a marker of oxidative damage.
These findings suggest that α-pinene mitigates the neurobehavioral and oxidative damage induced by ketamine, supporting its potential as a therapeutic agent in SCZ. Its dual antioxidative and anxiolytic effects underline its promise in treating disorders characterized by oxidative stress and neurodegeneration. Thus, α-pinene may offer a novel approach to addressing cognitive and emotional deficits in SCZ.

Catalytic Alkylation of α-pinene with Isobut-5 for High-Energy Biofuel Production

Jiao Z, et al. Energy Advances, 2024, 3(7), 1571-1580.

The alkylation of α-pinene with isobutene/iso-butane (Isobut-5) under acidic catalysis has demonstrated significant potential for the production of bio-based, high-energy density fuels. This study investigates the catalytic performance of various zeolite molecular sieves, including Hβ, HY, HZSM-5, HZSM-35, and HSAPO-11, in facilitating the alkylation reaction between α-pinene and Isobut-5. The reaction yields valuable C14 and C20 hydrocarbon fractions with excellent fuel properties after hydrogenation.
The reaction was conducted using a high-pressure reactor with a mixture of α-pinene, pinane, and the catalyst, under a nitrogen atmosphere to remove oxygen. Isobut-5 was injected into the reactor, and the system was stirred at 420 rpm for 5 hours. The products were analyzed to determine the efficacy of the catalysts.
Among the tested zeolites, Hβ-25n showed superior performance due to its optimal micro- and mesoporous structure and acidity, which facilitated the adsorption of α-pinene and promoted efficient alkylation. Its short pore channels also improved the diffusion of both reactants and alkylation products. Regeneration studies revealed that calcination at 600°C effectively removed coke deposits, restoring catalytic activity and preventing side reactions.

Development of High-Energy-Density Biofuels from α-Pinene and Lignin-Based Phenols via Alkylation and Hydrodeoxygenation

Wang Y, et al. Fuel, 2024, 374, 132513.

Conversion of natural monoterpene α-pinene from conifer oil into high energy density fuel (HEDF) has attracted increasing attention in sustainable biofuel development.
α-pinene was subjected to alkylation reaction with lignin-based phenols. The reaction was carried out in a three-necked flask equipped with a reflux condenser and a magnetic stirring device. In a typical operation, 60 mmol of lignin-based phenols were first heated to 160°C and stirred uniformly. Subsequently, 0.5 g of phosphotungstic acid (HPW) was added, and 60 mmol of α-pinene was added dropwise. The reaction mixture was kept at a constant temperature for 4 h, then cooled to room temperature and the catalyst was separated by centrifugation. The obtained alkylation product was named ALMs-1. The unreacted feedstock and light components were removed by vacuum distillation, and the upgraded product (named ALMs-2) was subsequently subjected to hydrodeoxygenation (HDO). The HDO reaction was carried out in an autoclave (HT-100FJ-C) with 20 g of ALMs-2 as the reactant, 20 mL of cyclohexane (or water for phenol) as the solvent, and 0.4 g of Pd/C and 2.0 g of HPW as the catalyst. The reaction conditions were 4 MPa H2, 200 °C, and 48 h. The organic phase product obtained after the HDO reaction was named HDOALMs-2. Subsequently, cyclohexane and heavy components were removed by vacuum distillation, and saturated hydrocarbon products mainly composed of monoalkylated products were finally obtained, named HDOMALPs. Vacuum distillation after the reaction produced a hydrocarbon fraction rich in saturated monoalkylated products, showing good fuel properties. These products are particularly promising as HEDF because of their high energy content and compatibility with existing fuel infrastructure.

Custom Reviews

August 18, 2023

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Important organic synthetic materials
α-Pinene can synthesize a series of perfume products, such as camphor and borneol.

Custom Q&A

What is the Molecular formula of α-Pinene?

C10H16

What is the Molecular weight of α-Pinene?

136.23

What is the EC number of α-Pinene?

201-291-9

What is the InChIKey of α-Pinene?

GRWFGVWFFZKLTI-UHFFFAOYSA-N

What is the SMILES of α-Pinene?

CC1=CCC2CC1C2(C)C

What is the Form of α-Pinene?

Liquid

What is the Industrial application of α-Pinene?

α-Pinene has various industrial applications. It is used as a fragrance ingredient in perfumes, soaps, and other cosmetic products. It is also utilized as a flavoring agent in foods and beverages. In addition, α-pinene is employed as a precursor for the synthesis of other chemicals, including synthetic fragrances and flavors.

What is the Solubility of α-Pinene?

α-Pinene is not very soluble in water but is highly soluble in organic solvents like ethanol, diethyl ether, and chloroform.

What is the Biological activity of α-Pinene?

α-Pinene exhibits certain biological activities. It has been found to have antimicrobial, anti-inflammatory, and insecticidal properties. Additionally, α-pinene is known for its potential respiratory benefits and has been utilized in traditional medicine for its expectorant and bronchodilatory effects.

What is the Density of α-Pinene?

0.858 g/mL at 25℃