Nootkatone
[CAS# 4674-50-4]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Decenone
• Name: Nootkatone
• Synonyms: (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.34
• CAS Registry Number: 4674-50-4
• EC Number: 225-124-4
• SMILES: C[C@@H]1CC(=O)C=C2[C@]1(C[C@@H](CC2)C(=C)C)C

Properties

• Melting point: 35-39 °C
• Flash point: 100 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Nootkatone, with the chemical formula C15H22O, is a natural sesquiterpene ketone known for its distinctive aroma and diverse applications. It is primarily extracted from grapefruit and certain other citrus fruits, where it contributes to their characteristic fragrance. This compound has garnered interest for its applications in fragrance, flavoring, and even in various therapeutic and pest control uses.

The discovery of nootkatone is rooted in the study of essential oils and their components. Nootkatone was first identified in grapefruit oil, where its unique odor profile distinguished it from other terpenes. The synthesis of nootkatone from natural sources involves extracting and purifying the compound from grapefruit oil or using biosynthetic methods. The compound's characteristic aroma, described as woody and citrusy, has made it a valuable ingredient in the fragrance industry.

In the fragrance and flavoring industries, nootkatone is utilized for its pleasant and distinctive scent. It is a key component in many perfumes and colognes, providing a fresh, woody, and citrus note. Additionally, nootkatone is used as a flavoring agent in food and beverages, enhancing the sensory qualities of products with its unique taste profile. Its inclusion in various consumer products highlights its importance in enhancing product appeal through aroma and flavor.

Nootkatone's applications extend beyond fragrance and flavoring to include potential therapeutic and pest control uses. Research has shown that nootkatone possesses antimicrobial properties, which have led to its exploration as a natural antimicrobial agent. This potential has applications in developing new antimicrobial products or incorporating it into existing formulations to enhance their effectiveness.

In pest control, nootkatone has been studied for its insect repellent properties. It has shown promise as a natural alternative to synthetic insect repellents, offering an effective means of deterring pests such as mosquitoes. The compound's safety profile and efficacy in repelling insects make it an attractive option for developing environmentally friendly pest control solutions.

In summary, nootkatone is a versatile sesquiterpene ketone with significant applications in fragrance, flavoring, and pest control. Its unique aromatic properties and potential therapeutic uses highlight its importance across various industries.

References

2024. Combating multidrug-resistant (MDR) Staphylococcus aureus infection using terpene and its derivative. World Journal of Microbiology and Biotechnology, 40.
DOI: 10.1007/s11274-024-04190-w

2023. Identification of volatile compounds and their bioactivities from unpolar fraction of Alpinia oxyphylla Miq. and mining key genes of nootkatone biosynthesis. Natural Product Research, 37.
DOI: 10.1080/14786419.2023.2220063

2023. Nootkatone attenuates airway inflammation in asthmatic mice through repressing ROS-induced NLRP3 inflammasome activation. Biochemistry and Cell Biology, 101.
DOI: 10.1139/bcb-2023-0009