5208-59-3

Basic information

• Product Name: β-bourbonene
• Synonyms: β-bourbonene;Cyclobuta1,2:3,4dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1S,3aS,3bR,6aS,6bR)-;BETA-BOURBONENE;(1S,3aS,3bR,6aS,6bR)-Decahydro-3a-methyl-6-methylene-1-isopropylcyclobuta[1,2:3,4]dicyclopentene;(1S,3bβ,6aβ,6bα)-Decahydro-3aα-methyl-6-methylene-1-isopropylcyclobuta[1,2:3,4]dicyclopentene;4(15)-Bourbonene
• CAS NO: 5208-59-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 5208-59-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 255.9°Cat760mmHg
• Flash Point: 104.9°C
• Appearance: /
• Density: 0.93g/cm³
• CAS DataBase Reference: β-bourbonene(CAS DataBase Reference)
• NIST Chemistry Reference: β-bourbonene(5208-59-3)
• EPA Substance Registry System: β-bourbonene(5208-59-3)

Safety Data

• Hazardous Substances Data: 5208-59-3(Hazardous Substances Data)

Usage

General Description

β-bourbonene, also known as bourbonene, is a natural sesquiterpene hydrocarbon found in various essential oils, including those derived from the leaves and flowers of the Laurus nobilis (bay laurel) and the bark of the Cinnamomum zeylanicum (cinnamon) trees. It is a colorless liquid with a spicy, woody, and sweet aroma. β-bourbonene is used in the fragrance industry for its pleasant scent and is also being researched for its potential pharmaceutical properties. It has been found to exhibit antibacterial activity and could have potential as an anti-inflammatory, antioxidant, and anticancer agent. Additionally, β-bourbonene may have potential as a natural pesticide due to its repelling effects on certain insects.

Upstream product

• 84077-33-8 C₁₈H₂₆O₆ 
• 84077-36-1 (-)-(1S,2R,6S,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>dec-4-en-3-one 
• 112837-18-0 (4S)-(-)-4,5-dihydroxy-3-methyl-2-butenoic acid 1,4-lactone 
• 81480-31-1 (S)-(-)-4-methyl-5-trityloxymethyl-2(5H)-furanone 
• 84077-38-3 (-)-diethyl ((1R,2R,3R,6R,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-yl)malonate 
• 84077-35-0 (-)-(1S,2R,5S,6S,7R)-10-ethylenedioxy-3,6-dimethyl-5-pivaloyloxymethyl-4-oxatricyclo<5.3.0.0^2,6>decan-3-ol 
• 84077-32-7 (-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone 
• 84077-39-4 (-)-(1R,2R,3R,6R,7R)-3-(1,3-dihydroxyprop-2-yl)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decane 
• 84077-37-2 (-)-(1S,2R,3S,6S,7R)-10-ethylenedioxy-6-methyltricyclo<5.3.0.0^2,6>decan-3-ol 
• 695-56-7 1,4-dioxaspiro[4.4]non-6-ene 
• 13844-03-6 (1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 23986-74-5 germacrene D 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 5208-58-2 α-bourbonene 

Relevant articles and documents

The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements

Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane, and bourbonane group as well as isogermacrene D were identified as main products and made available as reference compounds for structure investigations and stereochemical assignments of plant constituents. δ-Amorphene, one of the rearrangement products, was identified as a natural product for the first time. The absolute configuration of γ-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. (C) 2000 Elsevier Science Ltd.

CONFORMATIONAL CONTROL OF ENOLATE GEOMETRY: A SHORT SYNTHESIS OF GERMACRENE-D

A synthesis of (+/-)-germacrene-D is reported that employs a site- and stereoselective enolization of a conformationally biased ten-membered ring ketone.