72257-53-5

Basic information

• Product Name: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate
• Synonyms: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate;7-Oxabicycloheptane-3-methane-alpha,alpha,6-trimethylacetate;2-Oxabicyclo2.2.2octan-6-ol, 1,3,3-trimethyl-, acetate;Acetic acid 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl ester
• CAS NO: 72257-53-5
• Molecular Formula: C12H20O3
• Molecular Weight: 212.2854
• EINECS: 276-542-9
• Mol File: 72257-53-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 253.5°C at 760 mmHg
• Flash Point: 99.9°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.0182mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate(72257-53-5)
• EPA Substance Registry System: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate(72257-53-5)

Safety Data

• Hazardous Substances Data: 72257-53-5(Hazardous Substances Data)

Usage

Description

1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate is a complex bicyclic acetate chemical compound characterized by two fused cyclic rings and an acetate group. It features a branched structure with three methyl groups attached to carbon atoms and an oxygen atom within the bicyclic ring system.

Uses

Used in Fragrance and Flavor Industry:
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate is used as a fragrance and flavoring agent for its sweet, fruity, and floral aroma, enhancing the sensory experience of various products.
Used in Food Products:
In the food industry, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate is used as a flavoring agent to impart a pleasant taste and aroma to food products, improving their overall appeal.
Used in Perfumes and Personal Care Products:
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate is also utilized as a component in perfumes and personal care products, where it contributes to the creation of unique and desirable scents.
Used in Medicinal or Pharmaceutical Products:
Due to its unique molecular structure, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl acetate may have potential applications in medicinal or pharmaceutical products, although further research would be required to explore these possibilities.

InChI:InChI=1/C12H20O3/c1-8(13)14-10-7-9-5-6-12(10,4)15-11(9,2)3/h9-10H,5-7H2,1-4H3

Upstream product

• 98-55-5 terpineol 
• 18679-55-5 (+/-)-2-oxo-1,8-cineole 
• 75-36-5 acetyl chloride 
• 18679-48-6 (+/-)-β2-hydroxy-1,8-cineole 
• 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) 
• 38223-62-0 (1S,4R,6S)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 103665-39-0 (-)-(1R,2R,4S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane-6-ol 

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.

Enantiomeric purity and odor characteristics of 2- and 3-acetoxy-1,8- cineoles in the rhizomes of Alpinia galanga Willd.

(S)-(+)-O-methylmandelate esters of trans- and cis-1,3,3-trimethyl-2- oxabicyclo[2.2.2]octan-5- and 6-ols (2- and 3-hydroxy-1,8-cineoles) were prepared, and eight diastereomers were separated. The absolute configuration of the asymmetric carbons of the cineole moiety of each diastereomer was determined by 1H NMR data according to the Mosher theory. Each mandelate was reduced with LiAlH4 to obtain optically pure hydroxy-1,8-cineoles, this being followed by acetylation to afford optically pure acetoxy-1,8-cineoles. These acetates were subjected to chiral GC, using a cyclodextrin column, and the enantiomeric purity of trans- and cis-1,3,3-trimethyl-2- oxabicyclo[2.2.2]octan-5-and 6-yl acetates in the aroma concentrate from the rhizomes of Alpinia galanga was determined as 93.9 (5S), 19.4 (5R), 63.5 (6R), and 100 (6R) % ee, respectively. The aroma character of each enantiomer was also evaluated by GC-sniffing.