18358-53-7

Basic information

• Product Name: 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
• Synonyms: 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one;Bicyclo3.1.1heptan-3-one, 2,6,6-trimethyl-;iso-Pinocamphone;Einecs 242-228-5
• CAS NO: 18358-53-7
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 242-228-5
• Mol File: 18358-53-7.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 212°Cat760mmHg
• Flash Point: 72.8°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(18358-53-7)
• EPA Substance Registry System: 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(18358-53-7)

Safety Data

• Hazardous Substances Data: 18358-53-7(Hazardous Substances Data)

Usage

Description

2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one is an organic compound that is found in various essential oils such as Hyssop oil, Hyssop oil CO2 extract, Cistus oil, and Labdanum leaf oil. It is a colorless liquid with a distinct cedar camphor aroma.

Uses

Used in Fragrance Industry:
2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one is used as a fragrance ingredient for its distinctive cedar camphor scent. It is particularly valued for its ability to add depth and complexity to perfumes and other fragrance products.
Used in Flavor Industry:
In the flavor industry, 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is used as an additive to enhance the taste and aroma of various food and beverage products. Its unique scent can contribute to the overall flavor profile, making it a valuable component in the creation of new and innovative flavors.
Used in Essential Oils:
2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one is also used in the production of essential oils, where it can be found in significant concentrations. These essential oils are then used in a variety of applications, including aromatherapy, massage, and as ingredients in various cosmetic and personal care products.
Used in Research and Development:
Due to its unique chemical properties and natural occurrence, 2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is also used in research and development for the study of its potential applications in various fields, such as pharmaceuticals, materials science, and biotechnology.

InChI:InChI=1/C10H16O/c1-6-8-4-7(9(6)11)5-10(8,2)3/h6-8H,4-5H2,1-3H3

Upstream product

• 555-31-7 aluminum isopropoxide 
• 1674-08-4 (-)-trans-pinocarveol 
• 80-56-8 Pinene 
• 4576-49-2 2,7,7-Trimethylbicyclo<3.1.1>heptane-3-carboxaldehyde oxime 
• 1196-00-5 d,l-Isopinocamphenol 
• 1686-14-2 α-pinene epoxide 
• 856335-07-4 2,6,6-trimethyl-3-methylene-norpinane 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 18680-27-8 pinanediol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 25488-94-2 5,7,7-trimethyl-3-oxa-tricyclo[4.1.1.0^2,4]octane 
• 473-61-0 (1RS:2SR:3RS)-Pinanol-⁽³⁾ 

Downstream Products

• 473-72-3 pinonic acid 
• 1196-00-5 d,l-Isopinocamphenol 
• 473-72-3 (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid 
• 17879-35-5 cis-pinonic acid 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 141243-74-5 (+)-(1R,2R)-2,7,7-Trimethyl-3-oxabicyclo<4.1.1>octan-4-one 

Relevant articles and documents

The thermolysis of α-pinene and verbenone epoxides in supercritical solvents

Thermal transformations of α-pinene and verbenone epoxides were studied in supercritical solvents with complex compositions, including CO 2, lower alcohols (ethanol and isopropanol), and water, over the temperature and pressure ranges 387-575 K and 135-215 atm. The main product from α-pinene epoxide in a supercritical solvent containing water was campholenic aldehyde and pinocamphone; the total content of these products in the reaction mixture was 80%. Suggestions concerning the mechanism of the thermal isomerization of α-pinene epoxide depending on the acidity of supercritical solvents were made. The direction of verbenone epoxide transformations was independent of the presence of water in the mixture. The main identified products were ketoalcohols with para-menthane and camphane frameworks.

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Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis

Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.

H- and Fe-modified zeolite beta catalysts for preparation of trans-carveol from α-pinene oxide

The isomerisation of a-pinene oxide has been intensively investigated for selective preparation of campholenic aldehyde, a compound used in the synthesis of fragrances. Selective preparation of another product of α-pinene oxide rearrangement, trans-carveol, still remains a challenging task. Trans-carveol is a highly valuable compound used in perfume bases, food flavour compositions and as an active pharmaceutical substance in chemoprevention of mammary carcinogenesis. In the present work zeolite beta with different SiO2/Al2O3 molar ratios was modified by iron, characterised and tested per se and in the modified form for trans-carveol preparation from a-pinene oxide. The isomerisation reaction was carried out in a polar basic solvent N, N-dimethylacetamide at 140 °C. The activities and selectivities of the catalysts were correlated with their acid properties and with the iron content.