87680-39-5

Basic information

• Product Name: (3S,6R,7S)-1,10-bisaboladien-3-ol
• Synonyms: (3S,6R,7S)-1,10-bisaboladien-3-ol
• CAS NO: 87680-39-5
• Molecular Weight: 222.371
• Mol File: 87680-39-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (3S,6R,7S)-1,10-bisaboladien-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6R,7S)-1,10-bisaboladien-3-ol(87680-39-5)
• EPA Substance Registry System: (3S,6R,7S)-1,10-bisaboladien-3-ol(87680-39-5)

Safety Data

• Hazardous Substances Data: 87680-39-5(Hazardous Substances Data)

Upstream product

• 1723-80-4 4-(6-methyl-5-hepten-2-yl)-2-cyclohexen-1-one 
• 917-54-4 methyllithium 
• 344903-14-6 8-Benzenesulfonyl-8-(1,5-dimethyl-hex-4-enyl)-1,4-dioxa-spiro[4.5]dec-6-ene 
• 112837-26-0 (1R,2R,3S)-2,3-epoxy-3-methylcyclohexyl tosylate 
• 58917-27-4 (R)-sulcatol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 112837-28-2 (1S,5S,6S)-5-iodo-1-methyl-7-oxabicyclo[4.1.0]heptane 
• 112837-25-9 (1R,2R,6S)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol 
• 18890-22-7 (R)-3-methylcyclohex-2-en-1-ol 
• 140710-03-8 2-Iodo-3-methyl-2-cyclohexen-1-one 
• 1193-18-6 3-methylcyclohexen-2-one 
• 343239-55-4 4-[(1S)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 
• 75-24-1 trimethylaluminum 
• 81841-89-6 4,4-(ethylenedioxy)-1-(phenylsulfonyl)cyclohexene 

Downstream Products

• 19888-22-3 β-sesquiphellandrene 
• 38738-45-3 (-)-zingiberene 

Relevant articles and documents

Bisabolane, cyclonerane, and harziane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum cf44-2

Three undescribed bisabolane derivatives, trichaspin, trichaspsides A and B, three undescribed cyclonerane sesquiterpenes, 9-cycloneren-3,7,11-triol, 11-cycloneren-3,7,10-triol, and 7,10-epoxycycloneran-3,11,12-triol, and one undescribed harziane diterpene, 11-hydroxy-9-harzien-3-one, were obtained from the culture of Trichoderma asperellum cf44-2, an endophyte of the marine brown alga Sargassum sp. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and MS data, and their absolute configurations were established by ECD or specific optical rotation data. Trichaspin features an unprecedented ethylated bisabolane skeleton, while trichaspsides A and B represent the first aminoglycosides of bisabolane and norbisabolane sesquiterpenes, respectively. Nine of the compounds were evaluated for inhibition of five marine-derived pathogenic bacteria and toxicity to a marine zooplankton.

Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones

We recently synthesized all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol, including three stink bug pheromones, via a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones. However, yields of trans isomers were low, and scaling reactions using expensive catalysts were cumbersome. Now we describe a new synthesis of bisabolenol stink bug pheromones via (S)- and (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enones prepared by enantioselective Michael additions of methyl vinyl ketone to (S)- and (R)-citronellals and lithium hydroxide monohydrate-catalyzed stereoselective cyclizations of intermediate ketoaldehydes. Addition of methyllithium to these enones provided cis- and trans-1,10-bisaboladien-3-ols, which were separated by chromatography on silica and further converted to 10,11-epoxy-1-bisabolen-3-ols. Thus, we developed more convenient syntheses of pheromones of the rice stink bug, the harlequin bug, and brown marmorated stink bug.

COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS

A composition (useful for attracting Halyomorpha halys) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols : trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl (2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.