alpha-Phellandrene
[CAS# 99-83-2]

Identification

• Classification: Flavors and spices
• Name: alpha-Phellandrene
• Synonyms: 2-methyl-5-propan-2-ylcyclohexa-1,3-diene
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• CAS Registry Number: 99-83-2
• EC Number: 202-792-5
• SMILES: CC1=CCC(C=C1)C(C)C

Properties

• Density: 0.8±0.1 g/cm³, Calc.^*, 0.835 g/mL (Expl.)
• Index of Refraction: 1.469, Calc.^*, 1.471-1.477 Expl.)
• Boiling Point: 171.5 ºC (760 mmHg), Calc.^*, 175 ºC (Expl.)
• Flash Point: 43.7±13.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs Software.

Safety Data

• Hazard Symbols: GHS02;GHS08 Danger
• Hazard Statements: H226-H314
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Aspiration hazard	Asp. Tox.	1	H304
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Respiratory sensitization	Resp. Sens.	1	H334
Skin sensitization	Skin Sens.	1B	H317

Discovory and Applicatios

Alpha-Phellandrene is a naturally occurring monoterpene hydrocarbon found in the essential oils of various plants, including species of the genera Eucalyptus, Citrus, and Anethum. It is characterized by a distinctive, citrusy, and slightly peppery aroma and exists as two geometric isomers, α- and β-phellandrene. The α-isomer, commonly referred to as alpha-Phellandrene, has been identified in a range of botanical sources and has been the subject of extensive research regarding its chemical properties and applications.

The discovery of alpha-Phellandrene can be traced back to the early studies of essential oils, where researchers first isolated and characterized the compound from plant extracts. Advances in chromatographic and spectroscopic techniques allowed for a more detailed understanding of its structure and behavior. Analytical studies have confirmed its presence in the volatile oils of several aromatic plants, contributing to their fragrance and functional properties.

Alpha-Phellandrene has been extensively utilized in the fragrance and flavor industries. Its distinct aroma makes it a valuable component in the formulation of perfumes, soaps, and other scented personal care products. The compound is also used as a flavoring agent in food products, particularly in applications requiring citrus or herbal notes. The volatility and pleasant scent of alpha-Phellandrene contribute to its role in enhancing aromatic profiles in consumer products.

The compound has also been investigated for its role in natural insect-repellent formulations. Studies have documented its presence in plant-derived insect deterrents, where it functions as a bioactive component. This has led to its incorporation into eco-friendly pest control solutions, particularly in formulations derived from essential oils.

In industrial applications, alpha-Phellandrene has been examined as a potential bio-based solvent due to its chemical properties. Its solubility and reactivity have been explored in formulations requiring plant-derived solvents, including applications in cleaning products and coatings. The interest in renewable and biodegradable solvents has contributed to research into the efficacy of monoterpenes like alpha-Phellandrene in these fields.

The compound is also used as an intermediate in chemical synthesis, serving as a starting material for the production of various derivatives. Its reactivity with oxygen and other chemical species has been studied to develop functionalized compounds for industrial and pharmaceutical applications. The transformation of alpha-Phellandrene into other terpene-based compounds has been a subject of synthetic organic chemistry research.

Standardization and quality control measures have been established to ensure the consistent composition of alpha-Phellandrene in commercial applications. Essential oil extraction techniques and analytical methods, such as gas chromatography-mass spectrometry (GC-MS), are widely used to verify purity and concentration levels. Regulatory bodies have set guidelines for its use in consumer products to ensure safety and compliance with industry standards.

The well-documented discovery and application of alpha-Phellandrene have contributed to its widespread use across multiple industries. The continued study of its properties and potential new applications underscores its significance as a natural monoterpene with established functions in fragrance, flavoring, industrial processes, and chemical synthesis. Ongoing research aims to further optimize its utilization while maintaining the safety and efficacy of its applications.

References

2024. Enhancing orofacial pain relief: a-phellandrene complexed with hydroxypropyl-�-cyclodextrin mitigates orofacial nociception in rodents. Naunyn-Schmiedeberg's Archives of Pharmacology, 397(12).
DOI: 10.1007/s00210-024-03561-2

2024. Inhibitory effect of Eucalyptus globulus essential oil against Botryosphaeria dothidea and Fomitiporia mediterranea fungi causing wood diseases in viticulture. Vegetos, 37(6).
DOI: 10.1007/s42535-024-01081-1

2024. Exploring phytochemistry, antioxidant capacity, and biological potential of essential oils obtained from Euphorbiaceae species. Phytochemistry Reviews, 23(5).
DOI: 10.1007/s11101-024-10031-3