26127-86-6

Basic information

• Product Name: carvoxime
• Synonyms: carvoxime;(5R)-2-Methyl-5β-(1-methylethenyl)-2-cyclohexen-1-one oxime;(R)-2-Methyl-5-isopropenyl-2-cyclohexene-1-oneoxime;(R)-Carvoxime;1-Carvoxime
• CAS NO: 26127-86-6
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Mol File: 26127-86-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: carvoxime(CAS DataBase Reference)
• NIST Chemistry Reference: carvoxime(26127-86-6)
• EPA Substance Registry System: carvoxime(26127-86-6)

Safety Data

• Hazardous Substances Data: 26127-86-6(Hazardous Substances Data)

Upstream product

• 6485-40-1 (R)-Carvone 

Downstream Products

• 5524-05-0 (2R,5R)-5-isopropenyl-2-methylcyclohexanone 
• 20549-48-8 (+)-neodihydrocarveol 
• 6485-40-1 (R)-Carvone 
• 619-01-2 (1R,2R,4R)-dihydrocarveol 
• 31198-76-2 carvoxime 
• 3792-53-8 2-methyl-5-(prop-1-en-2-yl)cyclohexanone 
• 63843-08-3 8-chloro-p-menth-6-en-2-one oxime 
• 499-70-7 carvomenthone 
• 2051-53-8 5-isopropyl-2-methylphenylamine 
• 53567-64-9 carvylamine 
• 358359-87-2 (2S,4S)-p-mentha-6,8-dien-2-ylamine 
• 74837-96-0 p-menth-6-en-2-one oxime 
• 69658-72-6 p-mentha-6,8-dien-2-on-(O-acetyl oxime ) 
• 62311-60-8 N-p-mentha-6,8-dien-2-yl-benzamide 

Relevant articles and documents

Synthesis of nitrogen-containing monoterpenoids with antibacterial activity

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (?)-menthone oxime (?)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 μg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found–oxime 14 and lactams (?)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 μM, 43.0 μM and 4.6 μM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.

Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis

It was shown for the first time that dihydrocarvone can be selectively produced by gold-catalyzed one-pot transformation of carvone oxime. This reaction was carried out at 100 °C under hydrogen pressure of 9 bar over 1.9 wt.% Au/TiO2 catalyst using methanol as a solvent. Dihydrocarvone synthesis was shown to occur via carvone formation with the subsequent hydrogenation of its conjugated C=C double bond. Application of Au/TiO2 catalyst for both deoximation and selective hydrogenation of olefinic C=C functional group is reported for the first time. The combination of these steps provides optimization of the synthetic method for dihydrocarvone production from carvone oxime which is a key intermediate in carvone synthesis from limonene. Despite a lower reaction rate than in the case of carvone, a significant increase in the stereoselectivity towards trans-dihydrocarvone was observed in the case of carvone oxime hydrogenation. The ratio between trans- and cis-dihydrocarvone was close to 4.0 compared to 1.8 achieved in the case of carvone hydrogenation.

THE BIOTRANSFORMATION OF CARVOXIME AND DEHYDROCARVOXIME WITH CELL SUSPENSION CULTURES OF NICOTIANA TABACUM

In newly initiated cell suspension cultures of Nicotiana tabacum (4R)-(-)-and (4S)-(+)-carvoximes and (1S,4R)-(+)-dihydrocarvoxime were hydrolysed to the corresponding ketones and then the resultant ketones were reduced to the corresponding alcohols.Key words: Nicotiana tabacum; Solanaceae; tissue culture; biotransformation; hydrolysis; carvoxime; dihydrocavoxime.