alpha-Pinene
[CAS# 80-56-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Olefins (cyclic and non-cyclic)
• Name: alpha-Pinene
• Synonyms: 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; 2-Pinene; Pin-2(3)-ene
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• CAS Registry Number: 80-56-8 (2437-95-8)
• EC Number: 201-291-9
• SMILES: CC1=CCC2CC1C2(C)C

Properties

• Density: 0.858
• Melting point: -55 °C
• Boiling point: 154-157 °C
• Refractive index: 1.465-1.467
• Flash point: 38 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315
• Safety Statements: P264-P280-P302+P352-P321-P332+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Aspiration hazard	Asp. Tox.	1	H304
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	2	H330
Flammable liquids	Flam. Liq.	1	H224
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2B	H320

• Transport Information: UN 2368

Discovery and Applications

Alpha-pinene is a naturally occurring monoterpene that has attracted the attention of scientists and industry for its unique pine aroma and multiple uses since its discovery. Alpha-pinene was first isolated and identified from pine resin in the 19th century and is responsible for the characteristic smell of pine forests. It is one of the most common terpenes in nature and is found in the essential oils of conifers such as pine, fir and cedar. Its discovery marked the early recognition of terpenoid chemistry and its potential applications in perfumery and other fields.

Chemically, alpha-pinene belongs to the family of bicyclic monoterpenes, specifically a bicyclic hydrocarbon with two isomeric forms: alpha-pinene and beta-pinene. Alpha-pinene is characterized by its unique fresh, woody and resinous aroma, reminiscent of pine needles and forest air. This aromatic profile makes it a highly regarded ingredient in perfumery, used as a base note in masculine and outdoor-themed fragrances, adding depth and authenticity.

In perfumery, alpha-pinene enhances fragrance compositions by imparting a natural, outdoorsy scent, evoking feelings of freshness and vitality. It blends harmoniously with other aromatic compounds, contributing to the creation of fine fragrances and consumer products such as air fresheners, soaps and detergents. α-pinene’s ability to evoke memories of nature has made it a popular choice for products designed to recreate the sensory experience of the outdoors.

In addition to its aromatic properties, α-pinene has significant medicinal properties that have attracted attention in pharmacological research. It is an important ingredient in traditional and modern medicines due to its anti-inflammatory, bronchodilator and antimicrobial effects. α-pinene is actively studied for its potential in treating respiratory diseases and enhancing cognitive function through aromatherapy, highlighting its role in promoting health and well-being.

The versatility of α-pinene extends to industrial applications, where it is a precursor for a variety of chemicals and renewable materials. Through catalytic processes, α-pinene can be converted into compounds such as camphene and synthetic fragrances. In addition, α-pinene derivatives are used in the production of resins, adhesives and bio-based polymers, contributing to the development of sustainable materials with less environmental impact.

Challenges to commercializing α-pinene include optimizing extraction methods, ensuring a stable supply chain, and exploring environmentally friendly synthetic pathways to sustainably meet global demand. Ongoing research focuses on improving production efficiency and expanding the application of α-pinene in biotechnology and renewable energy, with the potential to make progress in biofuels and green chemistry.

References

2024. Enhanced Synergistic Antioxidant and Antibacterial Effects of Stable Nanoemulsions Prepared from Blends of Thyme, Black Pepper, Cinnamon, and Garlic Essential Oils. BioNanoScience, 14(4).
DOI: 10.1007/s12668-024-01718-0

2009. Chemical composition and mechanisms underlying the spasmolytic and bronchodilatory properties of the essential oil of Nepeta cataria L. Journal of Ethnopharmacology, 121(3).
DOI: 10.1016/j.jep.2008.11.004

2005. Ozonolysis of alpha-pinene and beta-pinene: kinetics and mechanism. The Journal of Chemical Physics, 122(11).
DOI: 10.1063/1.1862616