1,8-Oxido-p-menthane

1,8-Oxido-p-menthane, also known as cineole epoxide, is a bicyclic monoterpenoid ether, a volatile organic compound found in various essential oils. This compound is formed from the epoxidation of cineole (eucalyptol), a major component of eucalyptus oil and other aromatic plants. Its structure features an oxygen bridge between the C-1 and C-8 positions of the p-menthane ring system. 1,8-Oxido-p-menthane contributes to the characteristic fragrance and potential biological activities associated with these oils. Its presence often indicates a certain level of oxidation or modification of the parent cineole molecule. Its applications are primarily associated with fragrance and potential medicinal properties.

1,8-Oxido-p-menthane meaning with examples

• In a GC-MS analysis of a poorly stored eucalyptus oil, researchers identified 1,8-Oxido-p-menthane as a degradation product, suggesting that cineole had been exposed to oxygen. The presence of this epoxide could affect the therapeutic efficacy or aroma of the oil. The compound itself is not as studied, but its formation implies the importance of storing volatile oils in airtight, dark containers.
• A perfumer incorporated 1,8-Oxido-p-menthane into a fragrance formulation to add a subtle, nuanced herbal top note. Its inclusion offered a fresher, more intriguing layer to the composition. It was found to increase the complexity of the perfume, making it appealing to a wide audience. The epoxide provided a different smell than the commonly used cineole and gave the perfumer freedom for new fragrance families.
• Toxicological studies considered 1,8-Oxido-p-menthane as part of the overall safety profile of eucalyptus extracts. Because the epoxide can be formed by oxidation of the parent compound, researchers tested the resulting compound as a result of this transformation. The resulting study tested the impact of the epoxide on the skin, respiration, and consumption in the subject. It was observed to be far less impactful to toxicity in the study when compared to the parent cineole.
• Researchers investigating the enzymatic pathways in plants observed the formation of 1,8-Oxido-p-menthane during specific stages of monoterpene metabolism. Its presence served as an indicator of the oxidative processes affecting the overall production of fragrant molecules. The ability to measure levels of 1,8-Oxido-p-menthane provided another tool for understanding the biochemistry of these natural oils in the plant and their respective functions.