68832-35-9

Basic information

• Product Name: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-
• Synonyms: 9-epi-β-caryophyllene;(E)-(1R,9R)-4,11,11-Trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene;(+)-9βH-caryophyllene;9-epi-(E)-caryophyllene;β-caryophyllene;9-epi-caryophyllene;9-epi-E-caryophyllene
• CAS NO: 68832-35-9
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Mol File: 68832-35-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 268.4±10.0 °C(Predicted)
• Density: 0.89±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-(68832-35-9)
• EPA Substance Registry System: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-(68832-35-9)

Safety Data

• Hazardous Substances Data: 68832-35-9(Hazardous Substances Data)

Upstream product

• 61824-50-8 (Z)-(1R,9S)-4,11,11-Trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-one 
• 372-97-4 farnesyl pyrophosphate 

Downstream Products

• 88514-14-1 (1R,6R,10S)-5,12,12-Trimethyl-9-methylene-4-oxa-tricyclo[8.2.0.0^3,5]dodecan-6-ol 
• 19431-76-6 caryophyllenol-II 
• 1139-30-6 caryophyllene epoxide 
• 57082-24-3 caryophyllene acetate 
• 469-92-1 (-)-Clovene 
• 58404-89-0 β-caryolanol 
• 1217184-42-3 (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate 
• 19431-79-9 (1S,5S,9R)-10,10-Dimethyl-2,6-dimethylene-bicyclo[7.2.0]undecan-5-ol 
• 19431-76-6 caryophyllenol-I 
• 32214-91-8 Acetic acid (Z)-(1R,5R,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-yl ester 

Relevant articles and documents

An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma

The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.