(3E)-beta-ocimene
[CAS# 13877-91-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Hydrocarbon spice >> Olefin
• Name: (3E)-beta-ocimene
• Synonyms: 3,7-Dimethyl-1,3,6-octatriene
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• CAS Registry Number: 13877-91-3
• EC Number: 237-641-2
• SMILES: CC(=CC/C=C(C)/C=C)C

Properties

• Solubility: Insoluble (2.7E^-3 g/L) (25 °C), Calc.^*
• Density: 0.776±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 73 °C^**
• Refractive index: 1.4875 (589.3 nm 20 °C)^***
• Flash point: 46.9±13.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US)

^*** Dupont, G.

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08;GHS09 Danger
• Risk Statements: H226-H304-H315-H319-H335-H400-H410-H411
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P273-P280-P301+P316-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P331-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Aspiration hazard	Asp. Tox.	1	H304
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

(3E)-β-Ocimene is a naturally occurring organic compound found in the essential oils of a variety of plants, particularly basil, lavender, and mint. Its discovery dates back to the early exploration of plant aromatics by botanists and chemists. The unique odor and biological activity of the compound has attracted the interest of the scientific community, leading to the study of its chemical composition, biosynthesis, and its ecological role in plant physiology and ecology.

(3E)-β-Ocimene has a pleasant floral aroma and is widely used in the perfume and fragrance industry. Its fresh and slightly fruity aroma makes it a key ingredient in perfumes, colognes, and scented products. The compound helps enhance the overall aroma, adding depth and complexity to various perfume formulations.

In addition to its aromatic properties, (3E)-β-Ocimene can be used as a flavor enhancer in food and beverage products. It provides a sweet, herbal flavor reminiscent of fresh herbs and flowers, making it a popular flavoring agent in confectionery, beverages, and cooking. The compound enhances the sensory appeal of foods and provides a naturally refreshing taste experience.

(3E)-β-Ocimene has therapeutic and mood-enhancing effects, leading to its application in aromatherapy. Inhaling the aroma of this compound is believed to relax, reduce stress, and uplift mood. It is often used in aromatherapy blends, diffusers, massage oils, and bath products to create a calming and rejuvenating atmosphere.

(3E)-β-Ocimene has insect repellent properties and is used in natural insect repellent formulations to repel mosquitoes, flies, and other insects, helping people avoid insect bites and outdoor discomfort. The compound's insect repellent activity makes it a top choice for botanical insect repellents and outdoor sprays.

In nature, (3E)-β-Ocimene plays a role in plant communication and ecological interactions. It is a volatile organic compound released by plants to communicate with neighboring plants, attract pollinators, and deter herbivores. The compound is released in response to herbivore feeding or environmental stress, signaling neighboring plants and activating defense mechanisms that aid plant survival and ecosystem recovery.

(3E)-β-Ocimene has potential biomedical uses, including its anti-inflammatory, antioxidant, and anticancer properties. Studies have shown that the compound may be effective in controlling inflammation, oxidative stress-related diseases, and certain types of cancer. Additional studies are ongoing to explore its pharmacological effects and potential clinical applications in human health.

References

Roman Kaiser. Meaningful Scents Around the World: Olfactory, Chemical, Biological, and Cultural ConsiderationsThis book takes the reader on a fascinating fragrant journey around the world to some of the exciting places the author has visited during his 30 years of olfactory research. Following an introductory section to the world of natural scents, including their biological meaning and history, the fragrance and flavor chemist, Roman Kaiser, who is renowned for his 'headspace' analytical technique, revisits some memorable scents.