35670-93-0

Usage

Uses

Used in Flavor and Fragrance Industry:
(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate is used as a flavoring agent and fragrance in various consumer products, including perfumes, colognes, and personal care products. Its pleasant, fruity odor makes it a desirable component in these products.
Used in Food and Beverage Industry:
In addition to its use in the flavor and fragrance industry, (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate is also used as a flavoring agent in food and beverage products. Its fruity aroma adds a unique taste and scent to these products.
Regulatory Approval:
(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate is considered relatively safe for use and has been approved for use in various applications by regulatory authorities. This approval ensures that the compound meets safety standards and can be used in a wide range of products.

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 105760-49-4 10-(trimethylstannyl)-α-pinene 
• 6712-78-3 myrtenol 
• 75-36-5 acetyl chloride 
• 111-55-7 ethylene glycol diacetate 
• 141-78-6 ethyl acetate 
• 7785-70-8 (+)-α-pinene 
• 108-24-7 acetic anhydride 
• 23516-38-3 β-pinene trans-epoxide 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 64-19-7 acetic acid 
• 1010824-89-1 (1S,5R)-2-(chloromethyl)-6,6-dimethyl-bicyclo[3.3.1]hept-2-ene 
• 6931-54-0 β-pinene oxide 
• 121508-12-1 Tributyl-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-stannane 

Downstream Products

• 4080-46-0 2⁽¹⁰⁾,3-pinadiene 
• 99-87-6 4-methylisopropylbenzene 

Relevant academic research and scientific papers

Scalable green approach toward fragrant acetates

The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.

Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification

Monoterpenic esters are very important flavor and fragrance compounds due to their organoleptic properties. Despite their importance, many drawbacks are found for the production of monoterpenic esters. Here in we report two different approach's (chemo and enzymatic) for the continuous production of monoterpenic esters with integrated purification arriving on the desired molecules with high yields (>95%) and short reaction times.

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs. Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin and rutin is presented. By simply tuning the MW heating program, polyols with chemical diverse -OH groups or thermolabile functionalities can be peracetylated to improve the biological activity without degradation of the natural starting molecules. An evaluation of the process greenness was performed. Conclusion: The method is potentially universally applicable for green acetylation of hydrophilic biological molecules, potentially easily scalable for industrial applications, including pharmaceutical, cosmetic and food industry.

Oxidation of α-pinene by atmospheric oxygen in the supercritical CO2-ethyl acetate system in the presence of Co(II) complexes

The reactivity of monoterpene α-pinene in a flow reactor in the presence of cobalt catalyst in a complex supercritical solvent consisting of CO2 and ethyl acetate is studied over the temperature range of 190-320°C and a pressure range of 110-125 atm. It was found that the main isomerization products include compounds with bicyclo[2.2.1]heptane and p-menthane backbones; the reaction is accompanied by partial racemization. The formation of oxidation products is observed in the presence of air, with epoxydation rather than allylic oxidation being the predominant process at the first stage. The oxidized products (campholenic aldehyde, verbenone, pinocamphone) are shown to be formed with a high enantioselectivity; the formation of acetoxylation products is observed at temperatures above 200°C.

Preparation and utilization of perillyl acetate

Perillyl acetate is a fragrance compound that was prepared by the reaction of β-pinenoxide with acetic anhydride and using acetic acid as an acid catalyst. Several selected catalysts were tested (homogenous: phosphoric acid, boric acid, acetic acid, and citric acid; heterogeneous: zeolite USY, SSA, and montmorillonite K-10) and the reaction conditions optimized for this reaction. The yield 78.7 % of perillyl acetate was obtained. Mayol (4- isopropylcyclohexylmethanol), a valuable fragrance compound, was further obtained by a two-step synthesis from perillyl acetate. Firstly, perillyl acetate was saponified to perillyl alcohol. The yield of alcohol was 94.4 %. The last step of the entire preparation was the hydrogenation of perillyl alcohol to Mayol. The yield of the desired product of this reaction was 94.6 %. Springer Science+Business Media B.V. 2012.

Reactions of epoxides prepared from some monoterpenes with acetic anhydride on aluminosilicate catalysts

Reactions of epoxides prepared from α-, β-pinenes and camphene with acetic anhydride on aluminosilicate catalysts (clay K-10, zeolite β) were investigated affording various products of skeleton rearrangements: mono- and diacetates with five- and six-membered rings, and also with norbornane and pinane cores.

First synthesis of hydroxy-pinonaldehyde and hydroxy-pinonic acid, monoterpene degradation products present in atmosphere

Hydroxy-pinonaldehyde and hydroxy-pinonic acid, monoterpene degradation products have been for the first time isolated by synthesis and fully characterized. The key step of the synthesis is an oxidation using the RuCl3/NaIO4 system.

OXIDATIVE SUBSTITUTION REACTION OF OLEFINIC TIN COMPOUNDS WITH LEAD TETRAACETATE

The oxidative substitution reaction of olefinic tin compounds with lead tetraacetate(LTA) was investigated.The oxidation is highly regioselective and gave a dipole inversed product (acetate) in good yield.

Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate

A new oxidative substitution reaction where an organotin group is replaced by an acetoxy group has been investigated; this reaction has been successfully applied to the synthesis of 4-ylidenebutenolides.

PALLADIUM-CATALYZED ALLYLIC OXIDATION OF OLEFINS BY t-BUTYL HYDROPEROXIDE AND TELLURIUM(IV) OXIDE

Treatment of several cyclic olefins, β-pinene, allylbenzene and estragole with palladium(II) salt in acetic acid in the presence of t-butyl hydroperoxide and tellurium(IV) oxide afforded mainly the corresponding allylic acetates.The reaction proceeded catalytically with palladium(II) salt, t-BuOOH working as a reoxidazing agent.