66965-44-4

Basic information

• Product Name: (1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one
• Synonyms: 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octan-6-one;(+/-)-2-Oxocineole;(+/-)-2-keto-1,8-cineol;1,8-Epoxy-p-menthan-2-on;1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-one;1,8-epoxy-p-menthan-2-one
• CAS NO: 66965-44-4
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• Mol File: 66965-44-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 230.6±23.0 °C(Predicted)
• Density: 1.027±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one(66965-44-4)
• EPA Substance Registry System: (1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one(66965-44-4)

Safety Data

• Hazardous Substances Data: 66965-44-4(Hazardous Substances Data)

Usage

Description

(1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one, also known as "methylionone," is a bicyclic ketone with the molecular formula C10H16O2. It features two fused rings and a carbonyl group, contributing to its distinct chemical structure.

Uses

Used in Fragrance Industry:
(1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one is used as a scent ingredient for its woody, floral, and violet-like odor profile. It is valued in perfumes and other scented products for adding a rich and long-lasting aroma.
Used in Flavoring Industry:
(1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one is also utilized as a flavoring agent in certain foods and beverages, enhancing their taste and aroma.

Upstream product

• 873990-46-6 1,3,3-trimethyl-6-oxo-2-oxa-bicyclo[2.2.2]octane-5-carboxylic acid 
• 71208-23-6 1-(2,6-dimethyl-3,4-dihydro-2H-pyran-2-yl)-ethanone 
• 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) 
• 107553-94-6 1-(2,6-Dimethyl-3,4-dihydro-2H-pyran-2-yl)-2-diazo-1-ethanone 
• 107553-95-7 (1S,2R,5S,7R)-5,7-Dimethyl-6-oxa-tricyclo[3.2.1.0^2,7]octan-8-one 
• 470-82-6 1,8-Cineole 
• 4112-22-5 chromyl acetate 

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 
• 136135-80-3 1,3,3-Trimethyl-5-[1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-meth-(Z)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one 
• 135488-37-8 5-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-one 
• 76843-95-3 (+/-)-exo-2-hydroxy-1,8-cineol phenylurethane 
• 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 

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.

FORMATION OF REACTIVE TRICYCLIC INTERMEDIATES VIA THE INTRAMOLECULAR CYCLOPROPANATION OF DIHYDROPYRANS. SYNTHESIS OF EUCALYPTOL

Tricyclic compound 3 was synthesized via a cyclopropanation reaction promoted by 2.This highly srained compound was found to undergo selective chemical transformations to give oxa-bicyclic ketones.This methodology was applied in a total synthesis of the monoterpene, eucalyptol.

Process for the preparation of 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octan-6-ones

1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octan-6-ones are prepared by first epoxidizing α-terpineol with a peracid and thereafter oxidizing the resulting product with an appropriate oxidizing agent.