38284-11-6

Basic information

• Product Name: 7-Oxabicyclo4.1.0heptane-2,5-dione, 1,3,3-trimethyl-
• Synonyms: 7-Oxabicyclo4.1.0heptane-2,5-dione, 1,3,3-trimethyl-;EPOXYOXOPHORONE
• CAS NO: 38284-11-6
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.19
• Mol File: 38284-11-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 265.5°C at 760 mmHg
• Flash Point: 114.1°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.0091mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 7-Oxabicyclo4.1.0heptane-2,5-dione, 1,3,3-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Oxabicyclo4.1.0heptane-2,5-dione, 1,3,3-trimethyl-(38284-11-6)
• EPA Substance Registry System: 7-Oxabicyclo4.1.0heptane-2,5-dione, 1,3,3-trimethyl-(38284-11-6)

Safety Data

• Hazardous Substances Data: 38284-11-6(Hazardous Substances Data)

Usage

Description

7-Oxabicyclo[4.1.0]heptane-2,5-dione, 1,3,3-trimethylis a colorless solid with a sweet camphoreous aroma. It has a medium strength odor and is characterized by its camphoreous type. This chemical compound is known for its unique properties and potential applications across various industries.

Uses

Used in Fragrance Industry:
7-Oxabicyclo[4.1.0]heptane-2,5-dione, 1,3,3-trimethylis used as a fragrance ingredient for its sweet camphoreous aroma. The medium strength odor makes it suitable for creating a pleasant and long-lasting scent in various perfumes, colognes, and other fragrance products.
Used in Flavor Industry:
In the flavor industry, 7-Oxabicyclo[4.1.0]heptane-2,5-dione, 1,3,3-trimethylis used as an additive to enhance the taste and aroma of various food and beverage products. Its sweet camphoreous flavor can be utilized to create unique and appealing flavors in candies, chewing gums, beverages, and other confectionery items.
Used in Pharmaceutical Industry:
7-Oxabicyclo[4.1.0]heptane-2,5-dione, 1,3,3-trimethylmay also find applications in the pharmaceutical industry, where its chemical properties can be harnessed for the development of new drugs or as an intermediate in the synthesis of existing medications. Its unique structure and properties make it a promising candidate for further research and development in this field.
Used in Chemical Research:
As a chemical compound with distinct properties, 7-Oxabicyclo[4.1.0]heptane-2,5-dione, 1,3,3-trimethylcan be used in various research applications, such as studying its reactivity, stability, and potential interactions with other compounds. This can lead to a better understanding of its properties and potential uses in different industries.

InChI:InChI=1/C9H12O3/c1-8(2)4-5(10)6-9(3,12-6)7(8)11/h6H,4H2,1-3H3

Upstream product

• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 

Downstream Products

• 35692-98-9 2-hydroxy-3,5,5-trimethylcyclohex-2-ene-1,4-dione 
• 41654-27-7 2-methoxy-3,5,5-trimethyl-cyclohex-2-ene-1,4-dione 

Relevant articles and documents

Stereoselective hydroxylation of isophorone by variants of the cytochromes P450 CYP102A1 and CYP101A1

The stereoselective oxidation of hydrocarbons is an area of research where enzyme biocatalysis can make a substantial impact. The cyclic ketone isophorone was stereoselectively hydroxylated (≥95%) by wild-type CYP102A1 to form (R)-4-hydroxyisophorone, an important chiral synthon and flavour and fragrance compound. CYP102A1 variants were also selective for 4-hydroxyisophorone formation and the product formation rate increased over the wild-type enzyme by up to 285-fold, with the best mutants being R47L/Y51F/I401P and A74G/F87V/L188Q. The latter variant, which contained mutations in the distal substrate binding pocket, was marginally less selective. Combining perfluorodecanoic acid decoy molecules with the rate accelerating variant R47L/Y51F/I401P engendered further improvement with the purified enzymes. However when the decoy molecules were used with A74G/F87V/L188Q the amount of product generated by the enzyme was reduced. Addition of decoy molecules to whole-cell turnovers did not improve the productivity of these CYP102A1 systems. WT CYP101A1 formed significant levels of 7-hydroxyisophorone as a minor product alongside 4-hydroxyisophorone. However the F87W/Y96F/L244A/V247L CYP101A1 mutant was ≥98% selective for (R)-4-hydroxyisophorone. A comparison of the two enzyme systems using whole-cell oxidation reactions showed that the best CYP101A1 variant was able to generate more product. We also characterised that the further oxidation metabolite 4-ketoisophorone was produced and then subsequently reduced to levodione by an endogenous Escherichia coli ene reductase.

Indium-promoted chemo- and diastereoselective allylation of α,β-epoxy ketones with potassium allyltrifluoroborate

A practical method for the chemo- and diastereoselective allylation of α,β-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,β-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.

Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. II. Ein neues Konzept fuer die Synthese von (3RS,3'RS)-Astaxanthin

Starting from 6-oxo-isophorone (2) a new concept for a seven-step synthesis of (3RS,3'RS)-astaxanthin (1) has been developed.As a key feature of the new approach, the oxidation state of astaxanthin (1) is adjusted already at an early stage of the synthesis.Thus, manipulation on more complex intermediates later in the synthesis is reduced to a minimum.Acetonide 10 or dimer 13 represent the key intermediates of this concept (Scheme 2).The whole sequence has been run on a kg scale with an overall yield of 52percent (s.Scheme 5).