1820-09-3

Basic information

• Product Name: (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
• Synonyms: (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;trans-v1rbenol
• CAS NO: 1820-09-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 217-335-5
• Mol File: 1820-09-3.mol
• Article Data: 54

Chemical Properties

• Melting Point: 24°C
• Boiling Point: 234.73°C (rough estimate)
• Appearance: /
• Density: 0.9657
• Refractive Index: 1.4908 (estimate)
• PKA: 14.56±0.60(Predicted)
• CAS DataBase Reference: (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol(1820-09-3)
• EPA Substance Registry System: (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol(1820-09-3)

Safety Data

• Hazardous Substances Data: 1820-09-3(Hazardous Substances Data)

Usage

General Description

The chemical "(1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol" is a bicyclic terpene alcohol with a molecular formula C10H16O. It is a colorless liquid with a strong odor and is commonly found in many essential oils, including citronella and eucalyptus. It is used as a fragrance ingredient in perfumes and as a flavoring agent in the food and beverage industry. This chemical has also been studied for its potential therapeutic properties, including its antimicrobial, anti-inflammatory, and analgesic effects. Additionally, it has been used in traditional medicine for its insect repellent properties.

Upstream product

• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 473-06-3 chrysanthenone 
• 7785-70-8 (+)-α-pinene 
• 7722-84-1 dihydrogen peroxide 
• 67-64-1 acetone 
• 18309-32-5 Verbenone 
• 1203-21-0 trans-verbenyl acetate 
• 19890-07-4 (1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl acetate 
• 1820-09-3 Verbenol 
• 80-57-9 verbenone 
• 80-57-9 (-)-Verbenone 
• 18881-04-4 (S)-cis-Verbenol 

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 
• 38344-42-2 (R)-(-)-α-phellandren-8-ol 
• 23727-12-0 (S)-o-mentha-4,6-dien-8-ol 
• 511519-12-3 (R)-p-mentha-1⁽⁷⁾,2-dien-8-ol 
• 39776-66-4 4α-Hydroxy-10β-pinan 
• 16814-28-1 (+/-)-4-trans-(2-Olivetyl)-pinen 
• 22571-78-4 (+)-cis-pinononoic acid 
• 108448-46-0 (-)-(S)-2,2,4-trimethyl-3-cyclohexene-1-methanol 
• 1307886-98-1 (1S,2S,6R)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 
• 1361947-93-4 (1S,5R,6S)-6-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enyl nicotinate 
• 1361947-97-8 (1S,2S,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diyl dinicotinate 

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.

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.