70222-88-7

Basic information

• Product Name: (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one
• Synonyms: (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one;(1R,4S)-1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-one;6-oxocineole
• CAS NO: 70222-88-7
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 274-451-9
• Mol File: 70222-88-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 230.6°C at 760 mmHg
• Flash Point: 87.1°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 0.0654mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one(70222-88-7)
• EPA Substance Registry System: (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one(70222-88-7)

Safety Data

• Hazardous Substances Data: 70222-88-7(Hazardous Substances Data)

Usage

Description

(R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one is a chemical compound characterized by its unique bicyclic structure and is identified as a ketone. It has a relatively low melting point of 81-84 degrees Celsius and a boiling point of 105-108 degrees Celsius, which makes it suitable for various industrial applications.

Uses

Used in Fragrance Industry:
(R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one is used as a key ingredient in the fragrance industry for its pleasant, fruity odor. It is particularly favored in the production of perfumes and other scented products, where it adds a sweet and floral note to the overall composition.
Used in Food Industry:
In the food industry, (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one is utilized as a flavoring agent. Its ability to impart a sweet and fruity taste makes it a popular choice for enhancing the flavor profiles of various food products.
Used in Chemical Synthesis:
(R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one also serves as a chemical intermediate in the synthesis of other compounds. Its unique structure and properties make it a valuable building block for creating a range of different chemical products.
Used in Consumer Goods Manufacturing:
Due to its versatile applications and pleasing scent, (R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one is commonly utilized in the manufacture of various consumer goods, where it contributes to the sensory experience of the products.

InChI:InChI=1/C10H16O2/c1-9(2)7-4-5-10(3,12-9)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

Upstream product

• 18679-48-6 (1R)-6β-hydroxycineole 
• 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) 

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 
• 136135-82-5 5-[1-[4-(3-Dimethylamino-propoxy)-phenyl]-meth-(Z)-ylidene]-1,3,3-trimethyl-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 
• 22420-02-6 5-benzylidene-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-one 
• 120203-86-3 1,3,3-trimethyl-5-(phenylmethylene)-2-oxabicyclo<2.2.2>octan-6-one 
• 135488-38-9 1,3,3-trimethyl-5-(4-methoxybenzylidene)-2-oxa-bicyclo [2.2.2] octan-6-one 
• 135488-39-0 5-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octan-6-one 
• 156473-18-6 1,3,3-trimethyl-5-<(4-methylthiophenyl)methylene>-2-oxabicyclo<2.2.2>octan-6-one 
• 135420-48-3 6-benzyl-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-6-ol 
• 136135-81-4 1,3,3-Trimethyl-5-[1-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-meth-(Z)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one 
• 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) 

Relevant articles and documents

Synthesis of oxygenated cineole derivatives from cineole: Utility of cytochrome P450cin as an enantioselective catalyst

The oxidation of cineole to (1R)-6β-hydroxycineole by cytochrome P450cin (CYP176A) is utilised as the initial step in the synthesis of a range of compounds, both novel and ones previously known only as racemates. The potential of P450cin to provide useful, enantiopure building blocks is thus demonstrated. In particular, hydroxylation by this enzyme was used as the initial step in the synthesis of a range of functionalised cineole derivatives that could be used as mechanistic probes to elucidate the effect of substrate structure on the transformations mediated by P450cin.

Cineole biodegradation: Molecular cloning, expression and characterisation of (1R)-6β-hydroxycineole dehydrogenase from Citrobacter braakii

The first steps in the biodegradation of 1,8-cineole involve the introduction of an alcohol and its subsequent oxidation to a ketone. In Citrobacter braakii, cytochrome P450cin has previously been demonstrated to perform the first oxidation to produce (1R)-6β-hydroxycineole. In this study, we have cloned cinD from C. braakii and expressed the gene product, which displays significant homology to a number of short-chain alcohol dehydrogenases. It was demonstrated that the gene product of cinD exhibits (1R)-6β-hydroxycineole dehydrogenase activity, the second step in the degradation of 1,8-cineole. All four isomers of 6-hydroxycineole were examined but only (1R)-6β-hydroxycineole was converted to (1R)-6-ketocineole. The (1R)-6β-hydroxycineole dehydrogenase exhibited a strict requirement for NAD(H), with no reaction observed in the presence of NADP(H). The enzyme also catalyses the reverse reaction, reducing (1R)-6-ketocineole to (1R)-6β-hydroxycineole. During this study the N-terminal His-tag used to assist protein purification was found to interfere with NAD(H) binding and lower enzyme activity. This could be recovered by the addition of Ni2+ ions or proteolytic removal of the His-tag.