20347-65-3

Basic information

• Product Name: L-BORNYL ACETATE
• Synonyms: ACETIC ACID L-BORNYL ESTER;FEMA 2159;ENDO-(1R)-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPT-2-YL-ACETATE;ENDO-(1S)-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPT-2-YL ACETATE;BORNYL ACETATE, L-;L-BORNEOL ACETATE;L-(-)-BORNYL ACETATE;L-BORNYL ACETATE
• CAS NO: 20347-65-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 243-750-6
• Mol File: 20347-65-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 223 °C
• Flash Point: 85 °C
• Appearance: /
• Density: 0.984g/mL20°C
• Vapor Pressure: 0.0959mmHg at 25°C
• Refractive Index: n20/D 1.463
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: L-BORNYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: L-BORNYL ACETATE(20347-65-3)
• EPA Substance Registry System: L-BORNYL ACETATE(20347-65-3)

Safety Data

• Safety Statements: 23-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• Hazardous Substances Data: 20347-65-3(Hazardous Substances Data)

Usage

Description

L-BORNYL ACETATE, also known as (+)-Bornyl Acetate, is a chiral building block derived from essential oils, such as those found in Artemisia. It possesses a unique chemical structure that makes it a valuable component in the synthesis of various compounds. L-BORNYL ACETATE exhibits a range of biological activities, including antiviral, anti-stimulant, antidepressant, and stimulant bile flow properties. Additionally, it has been observed to influence the root growth of plants.

Uses

Used in Pharmaceutical Industry:
L-BORNYL ACETATE is used as a chiral building block for the synthesis of various compounds, contributing to the development of new drugs and therapeutic agents. Its unique chemical properties make it a valuable component in the creation of novel pharmaceuticals.
Used in Essential Oils Industry:
L-BORNYL ACETATE is used as a chemical constituent in the formulation of essential oils, such as those derived from Artemisia. Its presence in these oils contributes to their antiviral, anti-stimulant, antidepressant, and stimulant bile flow properties, making them beneficial for various applications.
Used in Agriculture:
L-BORNYL ACETATE is used as a growth regulator in the agricultural industry, specifically affecting the root growth of plants. By modulating the growth of plant roots, it can potentially enhance crop yields and improve overall plant health.

InChI:InChI=1/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3

Upstream product

• 464-43-7 d-borneol 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 7785-70-8 (+)-α-pinene 
• 108-24-7 acetic anhydride 
• 129594-60-1 endo-9-bromobornan-2-ol acetate 
• 108-05-4 vinyl acetate 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 10293-06-8 (1R)-3-endo-bromocamphor 
• 129704-41-2 endo-9-bromobornan-2-ol 
• 64474-56-2 (+)-9-bromocamphor 
• 85719-15-9 (+)-endo-3,9-dibromocamphor 
• 75-36-5 acetyl chloride 
• 6627-72-1 rac-endo-borneol 

Downstream Products

• 91839-99-5 dl-6-acetoxy-bornan-3-one 
• 76-22-2 Camphor 
• 39850-78-7 5-Ketoborneol 
• 565-00-4 dl-camphene 
• 74-85-1 ethene 
• 464-17-5 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene 
• 508-32-7 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane 
• 79-92-5 camphene 
• 4249-09-6 1,5,5-trimethyl-cyclopenta-1,3-diene 
• 64-19-7 acetic acid 
• 54717-80-5 bornyl acetoacetate 
• 464-43-7 borneol 
• 124-76-5 isoborneol 
• 28974-17-6 isobornyl acetate 

Relevant articles and documents

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Solvent-free Acetylation Procedure

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Simple Plug-In Synthetic Step for the Synthesis of (?)-Camphor from Renewable Starting Materials

Racemic camphor and isoborneol are readily available as industrial side products, whereas (1R)-camphor is available from natural sources. Optically pure (1S)-camphor, however, is much more difficult to obtain. The synthesis of racemic camphor from α-pinene proceeds via an intermediary racemic isobornyl ester, which is then hydrolyzed and oxidized to give camphor. We reasoned that enantioselective hydrolysis of isobornyl esters would give facile access to optically pure isoborneol and camphor isomers, respectively. While screening of a set of commercial lipases and esterases in the kinetic resolution of racemic monoterpenols did not lead to the identification of any enantioselective enzymes, the cephalosporin Esterase B from Burkholderia gladioli (EstB) and Esterase C (EstC) from Rhodococcus rhodochrous showed outstanding enantioselectivity (E>100) towards the butyryl esters of isoborneol, borneol and fenchol. The enantioselectivity was higher with increasing chain length of the acyl moiety of the substrate. The kinetic resolution of isobornyl butyrate can be easily integrated into the production of camphor from α-pinene and thus allows the facile synthesis of optically pure monoterpenols from a renewable side-product.

Synthesis, Characterisation, and Determination of Physical Properties of New Two-Protonic Acid Ionic Liquid and its Catalytic Application in the Esterification

A new ionic liquid was synthesised, and its chemical structure was elucidated by FT-IR, 1D NMR, 2D NMR, and mass analyses. Some physical properties, thermal behaviour, and thermal stability of this ionic liquid were investigated. The formation of a two-protonic acid salt namely 4,4′-trimethylene-N,N′-dipiperidinium sulfate instead of 4,4′-trimethylene-N,N′-dipiperidinium hydrogensulfate was evidenced by NMR analyses. The catalytic activity of this ionic liquid was demonstrated in the esterification reaction of n-butanol and glacial acetic acid under different conditions. The desired acetate was obtained in 62-88 % yield without using a Dean-Stark apparatus under optimal conditions of 10 mol-% of the ionic liquid, an alcohol to glacial acetic acid mole ratio of 1.3: 1.0, a temperature of 75-100°C, and a reaction time of 4 h. α-Tocopherol (α-TCP), a highly efficient form of vitamin E, was also treated with glacial acetic acid in the presence of the ionic liquid, and O-acetyl-α-tocopherol (Ac-TCP) was obtained in 88.4 % yield. The separation of esters was conducted during workup without the utilisation of high-cost column chromatography. The residue and ionic liquid were used in subsequent runs after the extraction of desired products. The ionic liquid exhibited high catalytic activity even after five runs with no significant change in its chemical structure and catalytic efficiency.