473-67-6

Basic information

• Product Name: CIS-VERBENOL
• Synonyms: 2-Pinen-4-ol;4,6,6-trimethyl-bicyclo(3.1.1)hept-3-en-2-o;4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol;Berbenol;d-Verbenol;VERBENOL;FEMA 3594;Bicyclo[3.1.1]hept-3-en-2-ol,4,6,6-trimethyl-
• CAS NO: 473-67-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 207-470-8
• Mol File: 473-67-6.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 227.5°Cat760mmHg
• Flash Point: 85°C
• Appearance: white crystals
• Density: 0.992g/cm³
• PKA: 14.56±0.60(Predicted)
• CAS DataBase Reference: CIS-VERBENOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-VERBENOL(473-67-6)
• EPA Substance Registry System: CIS-VERBENOL(473-67-6)

Safety Data

• Hazardous Substances Data: 473-67-6(Hazardous Substances Data)

Usage

Chemical Properties

Verbenol has a fresh pine, ozone odor.

Occurrence

Reported found in spearmint oil, Scotch spearmint oil, juniper berry, juniper berry (alcoholic extract), myrtle berry, mango, angelica root oil and mastic gum fruit and leaf oil.

Preparation

Prepared from levo-α-pinene (also written (l)- or (–)-α-pinene). The corresponding dextro-isomer ((d)- or (+)-α-pinene) is not suitable.

InChI:InChI=1S/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 
• 19890-04-1 (-)-Essigsaeure-(trans-verbenyl)ester 
• 1260669-72-4 (-)-verbenol acetate 
• 18881-04-4 (S)-cis-Verbenol 
• 29135-40-8 (1S,4R,5S)-2-pinen-4-yl p-nitrobenzoate 
• 80-57-9 (-)-Verbenone 
• 7785-70-8 (+)-α-pinene 
• 98-83-9 isopropenylbenzene 
• 546-67-8 lead(IV) tetraacetate 
• 18309-32-5 Verbenone 

Downstream Products

• 109841-86-3 benzyl-((1S,4R)-pin-2-en-4-yl)-ether 
• 144732-81-0 (-)-(1S)-<(1α,2α,5α)-4,6,6-trimethylbicyclo<3.1.1>hept-3-en-2-yl> 2,6-dichlorobenzoate 
• 39776-66-4 4α-Hydroxy-10β-pinan 
• 1203-21-0 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-ol acetate 
• 22571-78-4 (+)-cis-pinononoic 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 
• 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 
• 66885-03-8 (+)-cis-verbenol epoxide 
• 18309-32-5 Verbenone 
• 924265-29-2 (+)-verbenone epoxide 
• 1309581-65-4 2-hydroxy-1-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanone 

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

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.

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.