1196-01-6

Usage

Uses

Used in Antioxidant Applications:
(-)-Verbenone is used as an antioxidant component in essential oils for studying antioxidant activity in lipid model systems. This application is significant for understanding the potential of (-)-Verbenone in preserving and extending the shelf life of various products, particularly those containing lipids.
Used in Pheromone Research:
In the field of entomology, (-)-Verbenone is used as an antiaggregation pheromone to counteract the aggregation pheromone released by the western pine beetle (WPB). This application is crucial for managing and controlling the population of these beetles, which can cause significant damage to pine forests.
Used in Chemical Synthesis:
(-)-Verbenone, being a clear light yellow to yellow liquid, can be utilized as a starting material or intermediate in the synthesis of various chemical compounds. Its unique chemical structure with both chiral centers having an S configuration makes it a valuable component in the development of new molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1

Upstream product

• 7785-26-4 (-)-α-pinene 
• 18881-04-4 (S)-cis-Verbenol 
• 80-57-9 verbenone 
• 546-67-8 lead(IV) tetraacetate 
• 924265-28-1 (1R,2R,4R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octan-5-one 
• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 177698-18-9 α-pinene 
• 18172-67-3 beta-pinene 
• 135503-45-6 (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one 
• 35408-03-8 (+)-apoverbenone 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 1028464-68-7 (Z)-verbenol 
• 149404-73-9 (1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol 

Downstream Products

• 374111-67-8 (1S,5R)-6,6-dimethyl-4-styrylbicyclo[3.1.1]hept-3-en-2-one 
• 461669-31-8 (1S,5R)-6,6-Dimethyl-4-((1E,3E)-4-phenyl-buta-1,3-dienyl)-bicyclo[3.1.1]hept-3-en-2-one 
• 149404-74-0 (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 
• 22571-78-4 (+)-cis-pinononoic acid 
• 1262444-47-2 (1S,2S,5S)-4,6,6-trimethyl-2-[2-{(S)-6-phenylpyridin-2-yl}phenyl]bicyclo-[3.1.1]hept-3-en-2-ol 
• 935670-67-0 (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 
• 99-87-6 4-methylisopropylbenzene 

Relevant academic research and scientific papers

Silica supported Ru(salophen)Cl: An efficient and robust heterogeneous catalyst for epoxidation of alkenes with sodium periodate

In the present work, heterogenization of Ru(salophen)Cl via its axial ligation to silica-bound imidazole, SiIm, is reported. The heterogeneous catalyst, [Ru(salophen)Cl-SiIm], was characterized by elemental analysis, SEM, TEM, FT-IR and diffuse reflectance UV-Vis spectroscopic techniques. The catalyst, which is not soluble in water and common organic solvents, was used for efficient epoxidation of cyclic and linear alkenes with NaIO4 under agitation with magnetic stirring. This new heterogenized catalyst is of high stability and reusability in the oxidation reactions. The effect of reaction parameters such as solvent and oxidant in the epoxidation of cis-cyclooctene were also investigated.

Enantiomer Resolution by Crystalization with Chiral Hosts: Application to Monoterpenes, Verbenone and Apoverbenone

Chiral hosts (2R,3R)-(-)-2,3-O-isopropylidene-1,1,4,4-tetrakis(2-methylphenyl)-1,2,3,4-butanetetrol (1) and (2R,3R)-(-)-2,3-O-isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol (5), enantioselectively from crystalline 1:1 inclusion complexes with (1S,5S)-(-)-verbenone (2) and (1R,5R)-(+)-apoverbenone (6), respectively, and by applying this chiral discrimination in crystallization, anantiopure verbenone and apoverbenone are obtained.

Polymer-supported diimine molybdenum carbonyl complexes as highly reusable and efficient pre-catalysts in epoxidation of alkenes

By reaction of aldehydic polystyrene and ethylene diamine, polystyrene-imine-amine reagent was produced. Reaction of this reagent with benzaldehyde and 4-nitrobenzaldehyde resulted in polystyrene-diimines (3a and 3b). These reagents were used for the immobilization of molybdenum hexacarbonyl. The functionalized polystyrene and supported-diimine molybdenum carbonyl catalysts were characterized by FT-IR spectrum and CHN analysis. The molybdenum content of catalysts was determined by neutron activation analysis. Supported-diimine molybdenum carbonyl pre-catalysts (3aM and 3bM) were used in epoxidation of cyclooctene, and the reaction parameters such as solvent and oxidant were optimized and the epoxidation of different alkenes was investigated in optimizing these conditions. The obtained results in the presence of polymer-supported diimine molybdenum carbonyl pre-catalysts (3aM and 3bM) showed that they were very active and selective in the epoxidation of a wide range of alkenes. The reusability of the supported pre-catalysts was also studied. The results showed that they were highly reusable in epoxidation of alkenes.

Allylic and benzylic oxidation using cobalt(II) alkyl phosphonate modified silica

The allylic and benzylic oxidation of a range of substrates proceeds in good yield using catalytic quantities of cobalt(II) alkyl phosphonate modified silica and tert-butyl hydroperoxide.

Aerobic oxidation of α-pinene catalyzed by carbon nanotubes

Carbon nanotubes (CNTs) and nitrogen-doped CNTs (NCNTs) as metal-free catalysts exhibited an excellent activity in the selective oxidation of α-pinene with molecular oxygen as the terminal oxidant. Two distinct pathways, i.e. epoxidation and allylic oxidation, were active in this reaction. Enhancement of epoxidation was observed over CNTs, yielding the highest epoxidation/allylic oxidation products ratio. Excellent activity was achieved over NCNTs, giving 54.5% α-pinene conversion and 272.4 mmol g-1 h-1 mass-normalized activity, which compete with that of the state-of-the-art metal catalysts. Allylic oxidation was enhanced over NCNTs, using which equimolar amounts of epoxide and allylic products were produced. Thus, N-doping boosted the overall conversion and the yields of both epoxidation and allylic oxidation products, which was supported by the results of theoretical simulation.

Transformation of α-pinene using Picea abies suspension culture

α-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not transformed further. trans-Pinocarveol, myrtenol, cis-verbenol, and α-terpineol were byproducts of intermediate abundance. When subjected to the action of the suspension culture, cis-verbenol was not only transformed to verbenone but also isomerized to trans-verbenol. The transformation of α-pinene was fast, and the products were detected within one minute. The absolute configuration of the major products corresponded to that of the starting α-pinene enantiomer.

Formation of trans-verbenol and verbenone from α-pinene catalysed by immobilised Picea abies cells

Both enantiomers and the raceinate of α-pinene were transformed by Picea abies cells immobilised on alginate. The main products were cis- and trans-verbenol, the later being further transformed to verbenone. The enantiomeric purity of each product more or less corresponded to that of the substrate. Transformation by free cells was faster than that by the immobilised cells. The ratio of products differed to some extent between the transformation by tree and immobilised cells.

THE MICROBIOLOGICAL HYDROXYLATION OF SOME PINANE MONOTERPENOIDS BY CEPHALOSPORIUM APHIDICOLA

The microbiological oxidations of some pinane alcohols at C-4 by Cephalosporium aphidicola is described. - Key words: Cephalosporium aphidicola; biotransformation; pinanes; monoterpenoids.

Chiral synthesis of maconelliol: A novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, Maconellicoccus hirsutus

The chiral synthesis of maconelliol, [2,2-dimethyl-3-(1-methylethylidene) cyclobutyl] methanol, the alcohol moiety of the major sex pheromone component isolated from the pink hibiscus mealybug, Maconellicoccus hirsutus, is described. The compound was synthesized in six steps from alpha-pinene and the key step is dehydration of 5 to 7 through the intermediate 6. The absolute configuration of the naturally occurring maconelliol was determined as R.

Synthesis of new enantiomerically pure β-amino alcohols of the pinane series

A series of new β-amino alcohols with pinane structure, (+)- and (?)-3α-amino-10β-pinan-4β-ols, 4β-amino-10β-pinan-3α-ol, and 4α-amino-10β-pinan-3α-ol have been synthesized with the goal of using them as organocatalysts in the aldol reaction of isatin with acetone.