Ketoketal
[CAS# 56309-94-5]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Alicyclic ketone
• Name: Ketoketal
• Synonyms: Dicyclohexane-4,4'dione monoethylene ketal; 1,1'-Bicyclohexane-4,4'dione monoethylene ketal; 4-(1,4-Dioxaspiro[4.5]dec-8-yl)cyclohexanone
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.33
• CAS Registry Number: 56309-94-5
• EC Number: 423-860-2
• SMILES: C1CC(=O)CCC1C2CCC3(CC2)OCCO3

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 102 °C (Expl.)
• Index of Refraction: 1.512, Calc.^*
• Boiling Point: 365.4±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 166.2±14.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H412
• Safety Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Ketoketal is a unique class of compounds characterized by the presence of both ketone and ketal functional groups. These compounds have attracted significant interest in the fields of organic chemistry, drug delivery, and biomaterials due to their versatile chemical properties. The ketoketal structure consists of a ketone group adjacent to a ketal group, forming a stable molecular arrangement that can undergo various chemical transformations. The discovery of ketoketals can be traced back to early organic chemistry research, where they were synthesized as intermediates for more complex reactions. Over time, scientists have gained deeper insights into their stability and reactivity, particularly in aqueous environments.

The initial exploration of ketoketals focused on their synthesis and use as intermediates in organic reactions. Their chemical stability and the ability to undergo selective hydrolysis under certain conditions have made them particularly interesting for applications in drug delivery. Ketoketals are capable of encapsulating therapeutic agents and releasing them in a controlled manner. This feature is particularly useful in developing sustained-release formulations for drugs, where controlled release is needed over an extended period. Ketoketals are also advantageous in drug delivery because they are stable under neutral conditions but undergo hydrolysis in the presence of acidic or basic environments, allowing for targeted release at specific sites within the body.

In addition to their applications in drug delivery, ketoketals are also used in the development of biomaterials. Their stable structure allows them to be incorporated into polymers, which can be used in a variety of biomedical applications, including tissue engineering and wound healing. The chemical stability and potential for modification make ketoketals ideal for creating materials with desirable mechanical properties. These materials can be engineered to degrade over time, releasing bioactive agents in a controlled manner, which is particularly useful for applications that require long-term functionality.

Ketoketals also play a significant role in organic synthesis, where they are employed as intermediates for creating more complex molecules. Their reactivity and stability make them valuable in the synthesis of fine chemicals and pharmaceuticals. Ketoketals have been utilized in several synthetic strategies, enabling the production of complex compounds used in various industries, including pharmaceuticals and agrochemicals.

Overall, ketoketals represent an important class of compounds with a wide range of potential applications. Their stability, reactivity, and ability to undergo controlled hydrolysis have made them valuable in the development of drug delivery systems, biomaterials, and organic synthesis. As research continues, the versatility of ketoketals will likely lead to the discovery of new applications, further enhancing their importance in chemical and biomedical research.

References

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