1196-01-6

Basic information

• Product Name: (-)-VERBENONE
• Synonyms: (1S)-(-)-pin-2-en-4-one;2-Pinen-4-one, (1S,5S)-(-)-;6,6-trimethyl-(1s)-bicyclo[3.1.1]hept-3-en-2-on;Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-;Bicyclo[3.1.1]hept-3-en-2-one,4,6,6-trimethyl-,;Verbenone,(l);(1S)-(-)-VERBENONE;(1S,5S)-2-PINEN-4-ONE
• CAS NO: 1196-01-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 201-292-4
• Product Categories: Miscellaneous Natural Products;Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 1196-01-6.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 227-228 °C(lit.)
• Flash Point: 185 °F
• Appearance: Clear light yellow to yellow/Liquid
• Density: 0.975 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0773mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• BRN: 1907623
• CAS DataBase Reference: (-)-VERBENONE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-VERBENONE(1196-01-6)
• EPA Substance Registry System: (-)-VERBENONE(1196-01-6)

Safety Data

• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 1196-01-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear light yellow to yellow liquid

Uses

(-)-Verbenone is used to study antioxidant activity of essential oil components in lipid model systems.

Definition

ChEBI: A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.

General Description

(1S)-(-)-Verbenone is one of the main components of the essential oil of Suregada zanzibariensis leaves. It can be prepared by the biotransformation of (-)-α-pinene. (1S)-(-)-Verbenone acts as an antiaggregation pheromone towards the aggregation pheromone released by western pine beetle (WPB).

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

• 149404-73-9 (1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol 
• 7785-26-4 (-)-α-pinene 
• 80-56-8 Pinene 
• 924265-28-1 (1R,2R,4R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octan-5-one 
• 1820-09-3 Verbenol 
• 18881-04-4 (S)-cis-Verbenol 
• 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 
• 80-57-9 verbenone 
• 1028464-68-7 (Z)-verbenol 
• 80-56-8 rac-α-pinene 
• 473-66-5 (+/-)-[2,6,6-trimethylbicyclo[3.1.1]heptan-4-one] 
• 177698-18-9 α-pinene 

Downstream Products

• 18881-04-4 (S)-cis-Verbenol 
• 154966-65-1 (1S,5R)-4,6,6-trimethyl-3-phenylthiobicyclo<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 
• 499797-46-5 4-[2-((1S,6R)-6-Isopropyl-1-methyl-cyclohex-3-enyl)-ethyl]-4-methyl-cyclohexa-2,5-dienone 
• 499797-42-1 4-[2-((1S,2R)-4,5-Dihydroxy-2-isopropyl-1-methyl-cyclohexyl)-ethyl]-4-methyl-cyclohexa-2,5-dienone 

Relevant articles and documents

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.

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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.

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.

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.

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Development of rapid and selective epoxidation of α-pinene using single-step addition of H2O2in an organic solvent-free process

This study reports substantial improvement in the process for oxidising α-pinene, using environmentally friendly H2O2 at high atom economy (～93%) and selectivity to α-pinene oxide (100%). The epoxidation of α-pinene with H2O2 was catalysed by tungsten-based polyoxometalates without any solvent. The variables in the screening parameters were temperatures (30-70 °C), oxidant amount (100-200 mol%), acid concentrations (0.02-0.09 M) and solvent types (i.e., 1,2-dichloroethane, toluene, p-cymene and acetonitrile). Screening the process parameters revealed that almost 100% selective epoxidation of α-pinene to α-pinene oxide was possible with negligible side product formation within a short reaction time (～20 min), using process conditions of a 50 °C temperature in the absence of solvent and α-pinene/H2O2/catalyst molar ratio of 5?:?1?:?0.01. A kinetic investigation showed that the reaction was first-order for α-pinene and catalyst concentration, and a fractional order (～0.5) for H2O2 concentration. The activation energy (Ea) for the epoxidation of α-pinene was ～35 kJ mol-1. The advantages of the epoxidation reported here are that the reaction could be performed isothermally in an organic solvent-free environment to enhance the reaction rate, achieving nearly 100% selectivity to α-pinene oxide.

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant

A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).