(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-Methanoazuleno[5,6-d]-1,3-dioxole
[CAS# 211299-54-6]

Identification

• Name: (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-Methanoazuleno[5,6-d]-1,3-dioxole
• Synonyms: Ambrocenide; (1R,8R,10S,13R)-5,5,7,9,9,13-hexamethyl-4,6-dioxatetracyclo[6.5.1.01,10.03,7]tetradecane
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.43
• CAS Registry Number: 211299-54-6
• EC Number: 427-580-1
• SMILES: C[C@@H]1CC[C@@H]2[C@@]13C[C@H](C2(C)C)C4(C(C3)OC(O4)(C)C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.518, Calc.^*
• Boiling Point: 302.0±10.0 °C (760 mmHg), Calc.^*
• Flash Point: 122.8±12.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methylene blue [5,6-d]-1,3-dioxole, also known as sclareolide, is a compound naturally found in clary sage (Salvia sclarea) and other related plants. It has attracted great attention in various industries due to its unique structural properties and wide range of applications.

The discovery of sclareolide stems from the traditional use of clary sage in perfumes and herbal medicine. For centuries, clary sage has been valued for its pleasant aroma and potential therapeutic benefits. Scientific exploration of the composition of clary sage essential oil led to the identification and isolation of sclareolide, which has a unique bicyclic structure that contributes to its stability and versatility.

One of the main applications of sclareolide is in the perfume industry. Its ability to enhance and fix odors makes it an important ingredient in perfumes, colognes, and other scented products. Sclafolide acts as a fixative, helping to stabilize volatile aroma compounds and prolong their scent on the skin. This property is particularly important for creating high-quality perfumes that retain their aroma for a long time. In addition, sclafolide is highly valued for its subtle, sweet, and woody notes that complement a variety of perfume formulations.

In addition to its role in perfumery, sclafolide can also be used in the flavoring industry. It is used as a flavoring agent in a variety of food and beverage products, imparting a pleasant and mild taste to the products. Its ability to enhance flavor profiles without masking their taste makes it suitable for use in confectionery, baked goods, and alcoholic beverages. Sclafolide's natural origin and Generally Recognized As Safe (GRAS) status further support its use in food applications.

In addition to its use in flavors and seasonings, sclafolide has also attracted attention in the pharmaceutical and biotechnology fields. Studies have shown that sclafolide exhibits potential biological activities, including anti-inflammatory, antioxidant, and anticancer properties. These activities make it a candidate for further investigation as a therapeutic agent. For example, studies have shown that sclareolide may inhibit the growth of certain cancer cells, indicating its potential as a complementary treatment in oncology.

Another notable application of sclareolide is in the cosmetics industry. Its antioxidant properties help protect the skin from damage caused by free radicals and environmental stressors. Sclareolide is incorporated into skin care products such as creams, lotions, and serums to provide anti-aging benefits, improve skin elasticity, and promote a healthy complexion. Due to its natural origin and mild effects, it is well suited for use in products designed for sensitive skin.

In addition, sclareolide has shown potential as an insect repellent and pesticide. Studies have shown that it can effectively repel certain pests and insects, making it a natural alternative to synthetic chemicals. This application is particularly important in agriculture, which requires sustainable and environmentally friendly pest management solutions.

The production of sclareolide typically involves extraction and purification from clary sage essential oil, but it can also be synthesized through biotechnological methods. Advances in microbial fermentation and synthetic biology are making the production process more efficient and sustainable, ensuring a steady supply of high-purity sclareolide for a variety of applications.

References

2024. Solar-driven photocatalytic hydrogen production thiophene-quinoxaline-based polymer dots with tunable molecular weight. *Polymer Journal*, 56(10).
DOI: 10.1038/s41428-024-00945-2

2023. Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics. *Monatshefte für Chemie - Chemical Monthly*, 154(2).
DOI: 10.1007/s00706-022-03030-7