2-Methyl-5-isopropenyl-2-cyclohexenone
[CAS# 99-49-0]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Decenone
• Name: 2-Methyl-5-isopropenyl-2-cyclohexenone
• Synonyms: Carvone; DL-Carvone; Karvon; Limonen-6-one; NSC 6275; p-Mentha-1(6),8-dien-2-one
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• CAS Registry Number: 99-49-0
• EC Number: 202-759-5
• SMILES: CC1=CCC(CC1=O)C(=C)C

Properties

• Solubility: Slightly soluble (1.2 g/L) (25 ºC), Calc.^*
• Density: 0.963 g/cm³ (15 ºC)^**
• Melting point: 230 ºC^***
• Boiling point: 232 ºC (760.0 Torr)^****
• Refractive index: 1.710^*****
• Flash point: 88.9±0.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Schmidt, Harry; Ather. Ole, Riechstoffe, Parfumer., Essenz. u. Aromen 1953, V3, P75-6.

^*** Koedam, A.; Pharmaceutisch Weekblad 1981, V116(35), P1057-63.

^**** Arizaga, Beatriz; Journal of Chemical Technology and Biotechnology 2007, V82(6), P532-538.

^***** Wilson, John B.; Journal of the Association of Official Agricultural Chemists 1930, V13, P389-97.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H317
• Precautionary Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P354+P338-P317-P321-P330-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

2-Methyl-5-isopropenyl-2-cyclohexenone is an organic compound belonging to the family of cyclohexenones, with a structure characterized by a cyclohexene ring substituted with both a methyl group and an isopropenyl group. This compound is known for its distinct chemical properties and is primarily of interest in the field of organic chemistry due to its potential applications as a synthetic intermediate.

The discovery and synthesis of 2-methyl-5-isopropenyl-2-cyclohexenone have been documented in scientific literature, where it has been shown to be synthesized via various methods, such as reactions involving conjugate additions to cyclohexenone derivatives. The compound's synthesis has been reported in several chemical journals, particularly those focused on the synthesis of organic compounds and intermediates. Its structural features, including the position of the methyl and isopropenyl substituents, contribute to its reactivity and make it useful in various synthetic processes.

In terms of applications, 2-methyl-5-isopropenyl-2-cyclohexenone has been explored in the synthesis of a range of other chemical compounds. One of its primary applications is as an intermediate in the synthesis of more complex molecules, particularly in the context of creating compounds with potential biological activity or applications in materials science. Its ability to undergo further reactions, such as cyclization or functional group transformations, makes it a useful building block in organic synthesis.

The compound has also been investigated in the context of the fragrance industry, as its structure suggests that it may contribute to the formation of certain aromatic compounds when used as a precursor. While its use in commercial fragrance products is not widespread, the potential for its application in flavor and fragrance chemistry exists due to its chemical structure, which could give rise to pleasant, volatile organic molecules when subjected to specific synthetic conditions.

Overall, 2-methyl-5-isopropenyl-2-cyclohexenone is primarily valued as a chemical intermediate in organic synthesis, with potential applications in the development of more complex compounds, especially in the fields of medicinal chemistry and materials science.

References

2024. Chemical composition diversity in wild populations of Artemisia sieberi Besser under the same climate conditions. Genetic Resources and Crop Evolution.
DOI: 10.1007/s10722-024-02234-6

2024. Limonene oxide isomerization: a broad study of acid catalyst effects. Reaction Kinetics, Mechanisms and Catalysis, 137.
DOI: 10.1007/s11144-024-02774-z

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