18881-04-4

Basic information

• Product Name: (S)-CIS-VERBENOL
• Synonyms: (1S)-CIS-VERBENOL;(S)-CIS-VERBENOL;[1S-(1alpha,2beta,5alpha)]-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;(S)-CIS-VERBENOL, 95% (50+% E.E.);BICYCLO[3.3.1]HEPT-3-EN-2-OL,4,6,6-TRIMETHYL-,[1S-(1a,2b,5a)]-;(1S,1α,5α)-4,6,6-Trimethylbicyclo[3.1.1]hepta-3-ene-2β-ol;(1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2β-ol;(1α,5α)-4,6,6-Trimethylbicyclo[3.1.1]hepta-3-ene-2β-ol
• CAS NO: 18881-04-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 242-645-2
• Product Categories: Fine Intermediate
• Mol File: 18881-04-4.mol

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 214.9°Cat760mmHg
• Flash Point: 84.5°C
• Appearance: Bordeaux to dark brown-red/Powder
• Density: 1.002g/cm³
• Vapor Pressure: 0.0332mmHg at 25°C
• Refractive Index: 1.511
• PKA: 14.56±0.60(Predicted)
• BRN: 2206582
• CAS DataBase Reference: (S)-CIS-VERBENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-CIS-VERBENOL(18881-04-4)
• EPA Substance Registry System: (S)-CIS-VERBENOL(18881-04-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 18881-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pest Control Industry:
(S)-CIS-VERBENOL is used as a pheromone dispenser for attracting and trapping harmful forest, horticultural, and agricultural insects. This application helps in managing and controlling insect populations that can cause significant damage to crops and forests.
Used in Chemical Research:
(S)-CIS-VERBENOL is used as a research compound in the study of its anti-oxidative and anti-inflammatory properties. This allows scientists to explore its potential applications in various fields, such as pharmaceuticals and cosmetics, where these properties can be harnessed for beneficial effects.

InChI:InChI=1/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7?,8?,9-/m0/s1

Upstream product

• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 7722-84-1 dihydrogen peroxide 
• 67-64-1 acetone 
• 7785-26-4 (-)-α-pinene 
• 98-83-9 isopropenylbenzene 
• 19890-04-1 (-)-Essigsaeure-(trans-verbenyl)ester 
• 108394-25-8 (+)-Essigsaeure-(cis-pin-3-en-2-yl)ester 
• 546-67-8 lead(IV) tetraacetate 
• 7785-70-8 (+)-α-pinene 
• 1260669-72-4 (-)-verbenol acetate 
• 29135-40-8 (1S,4R,5S)-2-pinen-4-yl p-nitrobenzoate 
• 80-57-9 (-)-Verbenone 
• 80-57-9 verbenone 

Downstream Products

• 80-57-9 verbenone 
• 99-87-6 4-methylisopropylbenzene 
• 7316-84-9 pinan-4-ol 
• 190715-28-7 6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene 
• 16814-28-1 (+/-)-4-trans-(2-Olivetyl)-pinen 
• 1203-21-0 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-ol acetate 
• 22571-78-4 (+)-cis-pinononoic acid 
• 288848-24-8 (1S,3R)-3-acetyl-2,2-dimethylcyclobutane carboxylic acid 
• 916595-88-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Individual stereoisomers of verbenol and verbenone express bioactive features

Naturally occurring terpene core compounds have been used extensively in both pharmaceutical and cosmetic industry. However, since chirality of these compounds has profound influence on the level of their bioactivity, the aim of the present study was to a

Stereospecific synthesis of S-(?)-trans-verbenol and its antipode by inversion of sterically hindered alcohols

S-(?)-trans-Verbenol (1) and its antipode, R-(+)-trans-verbenol (1′) have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols (1 and 1′) from commercially available starting materials S-α-pinene and R-α-pinene was reported. The key steps were mainly depended on the effective SN2 stereo-inversion of the hydroxy group of sterically hindered alcohols (3 and 3′), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.

Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst

Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.

Cis-dioxidomolybdenum(VI) complexes with chiral tetradentate Schiff bases: Synthesis, spectroscopic characterization and catalytic activity in sulfoxidation and epoxidation

New chiral mononuclear cis-dioxidomolybdenum(VI) complexes, MoO2L1-MoO2L7, have been synthesized by the reaction of MoO2(acac)2 with tetradentate Schiff bases derived from various substitut

Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis

The chemoselective reduction of α,β-unsaturated ketones by use of an economic and readily available Mg catalyst has been developed. Excellent yields for a wide range of ketones have been achieved under mild reaction conditions, short times, and low catalyst loadings (0.2-0.5 mol %).

Oxy-functionalization of olefins with neat and heterogenized binuclear V(IV)O and Fe(II)complexes: Effect of steric hindrance on product selectivity and output in homogeneous and heterogeneous phase

Neat {[VO(sal2bz)]2; [Fe(sal2bz)(H2O)2]2·2H2O} and zeolite-Y immobilized {[VO(sal2bz)]2-Y; [Fe(sal2bz)(H2O)2]2-Y} binuclear complexes have been prepared and characterized by spectroscopic techniques (IR, UV–vis), elemental analyses (CHN, ICP-OES), thermal study (TGA), scanning electron micrograph (SEM), adsorption study (BET)and X-ray diffraction (XRD)patterns. Neat (homogeneous)and immobilized (heterogeneous)complexes were employed as catalysts in the oxidation of olefins, namely, cyclohexene, limonene and α-pinene in the presence of 30% hydrogen peroxide. 100% conversion of cyclohexene and α-pinene was obtained while limonene was oxidized up to 90%. Homogeneous catalysts showed highly selective result as neat [VO(sal2bz)]2 complex has provided 87% cyclohexane-1,2-diol and neat [Fe(sal2bz)(H2O)2]2·2H2O complex has provided 79% verbenone in oxidation of cyclohexene and α-pinene, respectively. We have observed that due to steric hindrance, formation of olefinic oxidation products increases on moving from α-pinene to limonene and limonene to cyclohexene. Additionally. recovered heterogeneous catalysts showed intact results up to two consecutive runs. Probable catalytic mechanism has been proposed for oxidation of cyclohexene.

Practical method for increasing optical purity of cis-verbenol

R/S mixture of monoterpene alcohol cis-verbenol can be separated in preparative scale by its conversion into phthalic mono-ester and subsequent crystallization of its diastereomeric salts with (R)-α-methylbenzylamine and (S)-α-methylbenzylamine. Finally, basic methanolysis of the resolved phthalic mono-esters results (S)-cis-verbenol and (R)-cis-verbenol in high enantiomeric and diastereomeric purity.

Green and simple preparation method for synthesizing (-)-trans-verbenol and enantiomer (+)-trans-verbenol thereof

The invention provides a green and simple preparation method for synthesizing (-)-trans-verbenol and enantiomer (+)-trans-verbenol thereof. The method is characterized by comprising the following steps: using (-)-cis-verbenol and (+)-cis-verbenol, utilizing a Mitsunobu reaction, and performing hydroxyl configuration inversion so as torespectively obtain the (-)-trans-verbenol and (+)-trans-verbenol, wherein the yield of the (-)-trans-verbenol is 81%, and the yield of the (+)-trans-verbenol is 80%. The synthetic method in the invention comprises novel, effective and environment-friendly steps and procedures. Compared with the conventional trans-verbenol synthesis method, the method disclosed by the invention avoids use of lead tetraacetate (an oxidizing agent) and benzene toxic solvents. The raw trans-verbenol can be prepared by alpha-pinene oxidation, and the (-)-trans-verbenol and (+)-trans-verbenol can be used for controlling bark beetles in China.

A Cu-Doped ZIF-8 metal organic framework as a heterogeneous solid catalyst for aerobic oxidation of benzylic hydrocarbons

Mixed-metal metal organic frameworks have received considerable attention in recent years and it has been shown that the activity of the parent metal organic framework (MOF) is often enhanced upon doping with external metal ions within the framework. In this context, Cu2+ ions with different loadings were incorporated within the ZIF-8 framework to obtain a series of Cu-doped ZIF-8 materials and their activity was examined in the aerobic oxidation of hydrocarbons. The as-synthesized Cu-doped solids were characterized by powder X-ray diffraction (XRD), ultraviolet diffuse reflectance spectroscopy (UV-DRS), scanning electron microscopy (SEM), Fourier Transform infrared (FT-IR), electron paramagnetic resonance (EPR) and inductively coupled plasma (ICP) analysis. The experimental results revealed that the activity of Cu-doped ZIF-8 is much higher than that of the parent ZIF-8 in all the tested substrates at 120 °C. Furthermore, the activity of the Cu-doped ZIF-8 with the highest Cu loading was eight fold higher than that of the parent ZIF-8 in the aerobic oxidation of cyclooctane (1) at 120 °C with more than 80% selectivity to the corresponding cyclooctanol/cyclooctanone (ol/one) mixture. Cu-doped ZIF-8 was reused two times with no significant drop in its activity under identical conditions. Furthermore, comparison of the two times reused solid with that of the fresh solid by powder XRD and SEM analysis revealed identical structural integrity and morphology, respectively during the oxidation reactions.

Cobalt-Catalyzed Hydroboration of Alkenes, Aldehydes, and Ketones

An operationally convenient and general method for hydroboration of alkenes, aldehydes, and ketones employing Co(acac)3 as a precatalyst is reported. The hydroboration of alkenes in the presence of HBpin, PPh3, and NaOtBu affords good to excellent yields with high Markovnikov selectivity with up to 97:3 branched/linear selectivity. Moreover, Co(acac)3 could be used effectively to hydroborate aldehydes and ketones in the absence of additives under mild reaction conditions. Inter- and intramolecular chemoselective reduction of the aldehyde group took place over the ketone functional group.