Xylyl dibutylbenzofuranone
[CAS# 181314-48-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: Xylyl dibutylbenzofuranone
• Synonyms: 3,4-Dibutyl-5-(2,4-dimethylphenyl)benzofuran-2(3H)-one
• Molecular Formula: C₂₄H₃₀O₂
• Molecular Weight: 350.49
• CAS Registry Number: 181314-48-7
• EC Number: 605-925-9
• SMILES: CCCCC1C2=C(C=CC(=C2CCCC)C3=C(C=C(C=C3)C)C)OC1=O

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.543, Calc.^*
• Boiling Point: 449.3±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 190.2±26.1 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Risk Statements: H411
• Safety Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Xylyl dibutylbenzofuranone is a chemical compound that falls within the class of benzofuranones, which are known for their diverse chemical properties and applications in various industries. This specific compound consists of a benzofuranone ring structure substituted with xylyl (a benzene ring with methyl groups) and dibutyl groups. It has garnered interest due to its potential use in both industrial and consumer products, including fragrances, flavors, and as an intermediate in organic synthesis.

The discovery of xylyl dibutylbenzofuranone can be traced back to research in the mid-20th century when chemists began exploring the synthesis of various substituted benzofuranones for their stability and unique aromatic properties. Benzofuranone derivatives have long been studied for their role in natural products and their applications in chemical synthesis, and xylyl dibutylbenzofuranone was developed as a compound that combines the favorable properties of the benzofuranone core with the steric and electronic effects of its substitutions.

One of the primary applications of xylyl dibutylbenzofuranone is in the fragrance industry, where its pleasant, musky, and sweet scent makes it a useful ingredient in the formulation of perfumes and other scented products. The compound’s ability to evoke complex, pleasing notes is a result of its molecular structure, which allows for specific interactions with olfactory receptors. It is commonly used in the production of perfumes, cosmetics, and cleaning products, where it helps to impart a desirable fragrance profile.

In addition to its use in fragrances, xylyl dibutylbenzofuranone also serves as an intermediate in organic synthesis. Due to the presence of reactive functional groups in its structure, the compound can be utilized in the synthesis of other more complex organic molecules. It is often employed in the creation of compounds for the pharmaceutical and agrochemical industries, where it can serve as a precursor for biologically active substances. Its ability to undergo selective chemical reactions allows chemists to design and develop a variety of derivatives with specific properties for different applications.

Furthermore, xylyl dibutylbenzofuranone has been investigated for its potential use in the development of specialty materials. Its chemical structure, featuring both hydrophobic and hydrophilic regions, makes it a suitable candidate for the design of materials with tailored surface properties. These materials could find use in applications ranging from coatings to advanced polymeric materials.

The compound has also been explored in research on the development of new antimicrobial agents. The benzofuranone scaffold is known for its potential biological activity, and xylyl dibutylbenzofuranone’s derivatives have been tested for antimicrobial properties. This area of study is particularly promising for industries seeking to develop new materials that can prevent the growth of bacteria or fungi, especially in healthcare or consumer goods where hygiene is a concern.

Overall, the discovery and applications of xylyl dibutylbenzofuranone demonstrate the compound’s versatility in various sectors, including the fragrance, pharmaceutical, and materials industries. Its unique chemical structure allows it to serve as both a functional ingredient in consumer products and as a valuable intermediate in the synthesis of more complex molecules.

References

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