18679-55-5

Basic information

• Product Name: (+)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-one
• CAS NO: 18679-55-5
• Molecular Weight: 168.236
• Mol File: 18679-55-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-one(18679-55-5)
• EPA Substance Registry System: (+)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-one(18679-55-5)

Safety Data

• Hazardous Substances Data: 18679-55-5(Hazardous Substances Data)

Upstream product

• 98-55-5 terpineol 
• 54145-81-2 p-methane-α-1,2-epoxy-8-ol 
• 138-86-3 limonene. 
• 10067-30-8 8,9-diacetoxy-p-menth-1-ene 
• 56031-82-4 2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol 
• 18679-48-6 2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) 
• 470-82-6 eucalyptol 

Downstream Products

• 500698-82-8 6-amino-cyclodecanol 
• 135420-47-2 1,3,3-trimethyl-6-phenyl-2-oxa-bicyclo[2.2.2]octan-6-ol 
• 135488-37-8 5-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-one 
• 72257-53-5 (-)-α2-acetyloxy-1,8-cineole 
• 72257-53-5 (+)-α2-acetyloxy-1,8-cineole 
• 18679-48-6 (+/-)-β2-hydroxy-1,8-cineole 
• 18679-48-6 2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) 
• 72257-53-5 cis-2-acetoxy-1,8-cineole 
• 72257-53-5 (+)-β2-acetyloxy-1,8-cineole 
• 72257-53-5 (-)-β2-acetyloxy-1,8-cineole 
• 867133-54-8 6-(α-bromo-isopropyl)-3-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 58701-26-1 6-isopropyl-3-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 135420-66-5 4-[2-(1,3,3-Trimethyl-6-phenyl-2-oxa-bicyclo[2.2.2]oct-6-yloxy)-ethyl]-morpholine 
• 135420-63-2 Diisopropyl-[2-(1,3,3-trimethyl-6-phenyl-2-oxa-bicyclo[2.2.2]oct-6-yloxy)-ethyl]-amine 

Relevant articles and documents

Syntheses of chiral 1,8-cineole metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole- containing capsules

The chiral metabolites in human urine were investigated after ingestion of a 1,8-cineole (eucalyptol)-containing enterocoated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (-/+)-α2-hydroxy-1,8- cineole, (-/+)-β2-hydroxy-1,8-cineole, (-/+)-9-hydroxy-1,8-cineole, and (-/+)-2-oxo-1,8-cineole were prepared. To achievethis aim, after acetylation of the synthesized racemic 2-and 9-hydroxy-1,8-cineoles, pig liver esterase- or yeast-mediated hydrolysis provided the (-)-alcohols with their antipodal(+)-acetates with enantiomeric excess of 33-100 %. Dess-Martin periodinane oxidation of the alcohol (+)-α2-hydroxy-1,8-cineole, obtained by hydrolysis of the resolved acetate, provided the corresponding (+)-2-oxo-1,8-cineole, meanwhile the oxidation of (-)-α2-hydroxy-1,8-cineole gave (-)-2-oxo-1,8-cineole. Using these standards seven metabolites (+/-)-α2-hydroxy-1,8-cineole, (+/-)-β2-hydroxy-1,8-cineole, (+/-)-α3-hydroxycineole,(+/-)-3-oxo-1, 8-cineole, 4-hydroxy-1,8-cineole, 7-hydroxy-1,8-cineole, and (+/-)-9-hydroxy-1,8-cineole, all liberated from their glucuronides, were identified in urine by GCMS on a chiral stationary phase after consumption of 10 mg of 1,8-cineole. Metabolite screening using 2H3-1,8- cineol as the internal standard revealed (+/-)-α2-hydroxy-1,8-cineole as the predominant metabolite followed by (+/-)-9-hydroxy-1,8-cineole. Furthermore, the results showed that one enantiomer is always formed preferentially.