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 rac-α-pinene 
• 7722-84-1 dihydrogen peroxide 
• 67-64-1 acetone 
• 80-56-8 Pinene 
• 7785-26-4 (-)-α-pinene 
• 18309-32-5 Verbenone 
• 7785-70-8 (+)-α-pinene 
• 1203-21-0 trans-verbenyl acetate 
• 473-06-3 chrysanthenone 
• 80-57-9 (-)-Verbenone 
• 18881-04-4 (S)-cis-Verbenol 
• 29135-40-8 (1S,4R,5S)-2-pinen-4-yl p-nitrobenzoate 
• 1260669-72-4 (-)-verbenol acetate 
• 546-67-8 lead(IV) tetraacetate 

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 
• 109841-86-3 benzyl-((1S,4R)-pin-2-en-4-yl)-ether 
• 1298063-01-0 (1S,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 
• 1307886-99-2 epoxide-(-)-trans-verbenole 
• 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 

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.

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.