469-92-1

Basic information

• Product Name: (-)-CLOVENE
• Synonyms: 3a,7-Methano-3aH-cyclopentacyclooctene, 1,4,5,6,7,8,9,9a-octahydro-1,1,7beta-trimethyl-;3a,7-Methano-3aH-cyclopentacyclooctene, 1,4,5,6,7,8,9,9a-octahydro-1,1,7-trimethyl-, [3aR-(3aalpha,7alpha,9abeta)]-;Cloven;(3aR)-1,4,5,6,7,8,9,9aα-Octahydro-3aβ,7β-methano-1,1,7-trimethyl-3aH-cyclopentacyclooctene;(3aR,9aα)-1,4,5,6,7,8,9,9a-Octahydro-1,1,7-trimethyl-3aβ,7β-methano-3aH-cyclopentacyclooctene
• CAS NO: 469-92-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 469-92-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 261.1°Cat760mmHg
• Flash Point: 109.3°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: n20/D 1.495
• Storage Temp.: 2-8°C
• BRN: 2044272
• CAS DataBase Reference: (-)-CLOVENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-CLOVENE(469-92-1)
• EPA Substance Registry System: (-)-CLOVENE(469-92-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 469-92-1(Hazardous Substances Data)

Usage

General Description

(-)-CLOVENE is a chemical compound that belongs to the class of sesquiterpenes. It is a natural organic compound found in plants suchjson as clove oil and certain species of the genus Selinum. The chemical structure of (-)-CLOVENE consists of 15 carbon atoms, 24 hydrogen atoms, and two oxygen atoms, with an isoprene unit forming the basic building block. (-)-CLOVENE is known for its spicy, woody, and floral aroma, and is often used in the fragrance and flavor industry. It also has potential medicinal properties, including antioxidant and antimicrobial effects, making it a subject of interest for pharmaceutical research and development.

InChI:InChI=1/C15H24/c1-13(2)9-5-12-6-10-14(3)7-4-8-15(12,13)11-14/h5,9,12H,4,6-8,10-11H2,1-3H3

Upstream product

• 87-44-5 β-caryophyllene 
• 87-44-5 β-caryophyllene 

Downstream Products

• 511-83-1 Clovensaeure 
• 469-91-0 Clovan 

Relevant articles and documents

Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid

The conversion of caryophyllene upon contact with Al2O3 and SiO2 impregnated with sulfuric acid was carried out, and the components of the resulting mixtures were identified. Having in hands such “standard” mixtures greatl

Rearrangement of (-)-β-caryophyllene. A product analysis and force field study

The rearrangement of (-)-β-caryophyllene (1) with sulfuric acid in ether has been reinvestigated. In the early stage, a multitude of products is formed. Of these, fourteen hydrocarbons (3, 4, 6-17) and four alcohols (5, 18-20) were obtained pure. From the very beginning, the tricycloundecenes 15-17 assumulate quickly. This indicates that a previously unknown rearrangement of 1 by protonation of the exocyclic double bond followed by transannular ring closure is a main reaction, and that the conformation βα is involved. Three hydrocarbons (3, 4, 8) and three alcohols (5, 18, 19) proved to be stable. They are the main components in the late stage. A complete rearrangement scheme followed from a force field analysis using MMP2. First, all conformations up to 4 kcal above the global minimum of each product and each carbenium ion necessary for its formation were detected automatically using the search program HUNTER. Second, the conformation favoring a specific transformation was searched for. For transannular cyclizations, the conformation with the shortest distance between the atoms to be bound and, for ring openings and 1,2-shifts, the conformation with the smallest dihedral angle between the empty p-orbital and the bond to be broken were selected. In all cases, the selection criteria proved valid: The stereochemistry of the conformations selected matched the stereochemistry of the products observed. On the basis of the results presented, a fully automated search program for favorable rearrangement paths may be developed.