36203-31-3

Basic information

• Product Name: (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate
• Synonyms: (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate;(1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-methanol acetate;Acetic acid [(1R,5S)-6,6-dimethylbicyclo[3.1.1]hepta-2-ene-2-yl]methyl ester;Acetic acid [(1β,5β)-6,6-dimethylbicyclo[3.1.1]hepta-2-ene-2-yl]methyl ester;Bicyclo(3.1.1)hept-2-ene-2-methanol, 6,6-dimethyl-, acetate, (1theta)-;Einecs 252-909-9
• CAS NO: 36203-31-3
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.27012
• EINECS: 252-909-9
• Mol File: 36203-31-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 243.2°Cat760mmHg
• Flash Point: 98℃
• Appearance: /
• Density: 0.991 g/mL at 25 °C(lit.)
• Refractive Index: n20/D1.470-1.474
• Storage Temp.: 2-8°C
• BRN: 4309977
• CAS DataBase Reference: (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate(36203-31-3)
• EPA Substance Registry System: (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate(36203-31-3)

Safety Data

• WGK Germany: 2
• RTECS: DT6500000
• Hazardous Substances Data: 36203-31-3(Hazardous Substances Data)

Usage

General Description

The chemical (1R)-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl acetate is a compound with the molecular formula C12H18O2. It is a bicyclic compound with a unique structure, containing a bicycloheptane ring and an acetate functional group. This chemical is commonly used as a flavoring agent and fragrance in various products, such as perfumes and food additives. It has a pleasant, fruity odor and is often found in natural sources like fruits and essential oils. Additionally, it is also used in the synthesis of pharmaceuticals and other organic compounds due to its unique molecular structure.

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

• 7785-26-4 (-)-α-pinene 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 6712-78-3 myrtenol 
• 141-78-6 ethyl acetate 
• 111-55-7 ethylene glycol diacetate 
• 7785-70-8 (+)-α-pinene 
• 108-24-7 acetic anhydride 
• 23516-38-3 β-pinene trans-epoxide 
• 75-36-5 acetyl chloride 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 1010824-89-1 (1S,5R)-2-(chloromethyl)-6,6-dimethyl-bicyclo[3.3.1]hept-2-ene 
• 18172-67-3 beta-pinene 
• 56246-58-3 β-pinene oxide 

Downstream Products

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

Relevant articles and documents

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.