2-Methylcyclooctanone
[CAS# 10363-27-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Alicyclic ketone
• Name: 2-Methylcyclooctanone
• Synonyms: 2-methylcyclooctan-1-one
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• CAS Registry Number: 10363-27-6
• EC Number: 652-072-3
• SMILES: CC1CCCCCCC1=O

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.440, Calc.^*
• Boiling Point: 205.3±8.0 °C (760 mmHg), Calc.^*
• Flash Point: 70.9±10.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-Methylcyclooctanone is an organic compound classified as a cyclic ketone, notable for its distinctive ring structure with an eight-carbon cycle and a methyl group attached to the second carbon. It was first identified in the mid-20th century as researchers began to explore derivatives of cyclooctanone, a compound primarily used as an intermediate in organic synthesis. Advances in analytical techniques allowed scientists to isolate and characterize 2-methylcyclooctanone, opening the door for further research into its potential uses in various fields.

The primary application of 2-methylcyclooctanone lies in the fragrance and flavor industries, where it is valued for its unique odor profile. The compound imparts a woody, musky scent, making it suitable for perfumes, colognes, and other personal care products. Its scent profile can enhance the depth and complexity of fragrance formulations, particularly in products aimed at evoking natural, earthy tones. Due to its distinctive aroma, 2-methylcyclooctanone is also used as a flavoring agent in certain food products, although this application is more limited and highly regulated.

Beyond its sensory applications, 2-methylcyclooctanone serves as an intermediate in organic synthesis, facilitating the production of various cyclic compounds. It is utilized in the synthesis of complex organic molecules, particularly in the development of pharmaceuticals and agrochemicals. Researchers have found that modifying the structure of cyclooctanone derivatives can lead to compounds with enhanced biological activity, underscoring 2-methylcyclooctanone’s utility in medicinal chemistry.

The compound’s unique ring structure has also made it a subject of academic interest in stereochemistry and reaction mechanisms. The spatial arrangement of the eight-membered ring with a substituent methyl group presents challenges and opportunities for studying ring strain and reactivity, contributing to a deeper understanding of cyclic ketone behavior in chemical reactions.

In recent years, studies have examined the potential of 2-methylcyclooctanone in material sciences, exploring its use in developing polymers and other advanced materials. While still in early stages, these studies aim to assess whether the compound’s stability and structural properties could improve certain material characteristics, such as flexibility and durability.

In conclusion, 2-methylcyclooctanone is a versatile organic compound with applications in fragrance, flavor, organic synthesis, and materials science. From its initial discovery to its diverse uses across industries, this cyclic ketone remains a valuable substance with a unique profile. Ongoing research continues to explore new applications and deepen our understanding of its chemical properties, ensuring its relevance in multiple fields.

References

2011. Synthetic Studies on Dicyclopenta[a,d]cyclooctane Terpenoids: Construction of the Core Structure of Fusicoccins and Ophiobolins on the Route Involving a Wagner-Meerwein Rearrangement. The Journal of Organic Chemistry, 76(17).
DOI: 10.1021/jo201357p