36203-31-3

Usage

Uses

Used in Flavor and Fragrance Industry:
(1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)methyl acetate is used as a flavoring agent and fragrance in various products, such as perfumes and food additives, due to its pleasant, fruity odor.
Used in Pharmaceutical Synthesis:
This chemical is also utilized in the synthesis of pharmaceuticals and other organic compounds because of its distinctive molecular structure, which offers potential applications in the development of new medications and treatments.

InChI:InChI=1/C12H18O2/c1-8(13)14-7-9-4-5-10-6-11(9)12(10,2)3/h4,10-11H,5-7H2,1-3H3

Upstream product

• 18172-67-3 beta-pinene 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 546-67-8 lead(IV) tetraacetate 
• 7785-26-4 (-)-α-pinene 
• 1010824-89-1 (1S,5R)-2-(chloromethyl)-6,6-dimethyl-bicyclo[3.3.1]hept-2-ene 
• 6712-78-3 myrtenol 
• 108-24-7 acetic anhydride 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 111-55-7 ethylene glycol diacetate 
• 7785-70-8 (+)-α-pinene 
• 56246-58-3 β-pinene oxide 
• 10300-01-3 trans-Pinocarvyl-methylether 
• 19894-97-4 (1R)-Myrtenol 

Downstream Products

• 7785-26-4 (-)-α-pinene 
• 4755-33-3 (1S)-(-)-cis-pinane 
• 54780-58-4 3-phenyl-β-pinene 
• 53318-08-4 2-benzyl-6,6-dimethylbicyclo<3.1.1>hept-2-ene 
• 15111-96-3 (4-isopropenyl-1-cyclohexen-1-yl)methyl acetate 

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.

The Allylic Acetoxylation of 1,1-Disubstituted Alkenes Catalyzed by a Palladium(II)/Monothiadiazole Ligand System

A palladium(II)/monothiadiazole ligand catalytic system and its application in catalyzing the acetoxylation of 1,1-disubstituted alkenes have been developed. With this newly designed monothiadiazole thioether ligand, the reaction showed a broad scope with respect to 1,1-disubstituted olefins, giving the corresponding products in yields of 30-86percent.

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.

Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers

We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl d-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.

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.

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.

An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.

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.