76-49-3

Basic information

• Product Name: Bornyl acetate
• Synonyms: (1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl) acetate;Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R,2S,4R)-;1,7,7-Trimethylbicyclo[2.2.1]heptane-2-yl=acetate;Acetic acid 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl;Acetic acid 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl ester;Acetic acid isobornyl;(1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl) ethanoate;acetic acid 2-bornyl ester
• CAS NO: 76-49-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 200-964-4
• Product Categories: Inhibitors;A-B;Alphabetical Listings;Flavors and Fragrances
• Mol File: 76-49-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 29°C
• Boiling Point: 228-231 °C(lit.)
• Flash Point: 192 °F
• Appearance: /
• Density: 0.985 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4635(lit.)
• Merck: 13,1329
• CAS DataBase Reference: Bornyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Bornyl acetate(76-49-3)
• EPA Substance Registry System: Bornyl acetate(76-49-3)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 76-49-3(Hazardous Substances Data)

Usage

Description

Bornyl acetate, also known as d-bornyl acetate, is an organic compound that occurs naturally in various essential oils derived from plants such as conifers, coriander, thyme, and valerian. It is an optically active ester with a characteristic pine-needle-like odor and a fresh, strong, piney taste. Bornyl acetate is prepared by the esterification of borneol with acetic anhydride or through a process involving borneol.

Uses

Used in Fragrance Industry:
Bornyl acetate is used as a fragrance ingredient for its camphoraceous, woody, mentholic, berry, and seedy scent with soapy and woody nuances. It is a characteristic component of most conifer oils, contributing to their distinct pine-needle-like aroma.
Used in Soaps and Bath Products:
Due to its fresh, strong, piney odor, bornyl acetate is used as a scent additive in soaps and bath products to provide a refreshing and invigorating experience for users.
Used in Room Sprays:
Bornyl acetate is used as an active ingredient in room sprays to impart a clean, pine-like fragrance, creating a pleasant and natural atmosphere in indoor spaces.
Used in Pharmaceutical Products:
Bornyl acetate is used in the pharmaceutical industry for its characteristic pine-needle odor, which can be incorporated into various medicinal products to enhance their scent and user experience.
Used in Essential Oils:
Bornyl acetate is found in the essential oils of various plants, such as Callitris glauca, C. robusta, C. gracilis, C. verrucosa, and C. calcarata. It contributes to the unique aroma and therapeutic properties of these essential oils, making them valuable for various applications in aromatherapy and alternative medicine.

Synthesis

l-Bornyl acetate occurs naturally in many oils distilled from the leaves of plants of the family Pinaceae; d-bornyl acetate is found in the oils distilled from plants of the family Cupressaceae; bornyl acetate, therefore may be isolated by distillation and crystallization from these; however, it is commonly prepared by direct acetylation of borneol; the first synthesis dates to 1889.

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

• 6627-72-1 rac-endo-borneol 
• 108-24-7 acetic anhydride 
• 79-92-5 camphene 
• 464-45-9 endo-borneol 
• 464-43-7 d-borneol 
• 75-36-5 acetyl chloride 
• 5813-49-0 nitrosyl acetate 
• 13293-47-5 2αH-pinan-3α-ylamine 
• 507-70-0 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol 
• 75-05-8 acetonitrile 
• 64-19-7 acetic acid 
• 80-56-8 Pinene 
• 7732-18-5 water 
• 98-11-3 benzenesulfonic acid 

Downstream Products

• 76-22-2 Camphor 
• 20347-65-3 (1R,2S,4R)-bornyl acetate 
• 464-45-9 endo-borneol 
• 464-43-7 d-borneol 
• 5655-61-8 bornyl acetate 
• 464-43-7 borneol 
• 28974-17-6 isobornyl acetate 
• 71424-71-0 iso-Bornyl acetate 
• 124-76-5 isoborneol 
• 565-00-4 dl-camphene 
• 64-19-7 acetic acid 
• 54717-80-5 bornyl acetoacetate 
• 6627-72-1 rac-endo-borneol 
• 74-85-1 ethene 

Relevant articles and documents

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.

Solvent-free Acetylation Procedure

-

Heterogeneous zeolite-based catalyst for esterification of α-pinene to α-terpinyl acetate

The purpose of this study is to determine the most effective type of heterogeneous catalyst such as natural zeolite (ZA), Zr-natural zeolite (Zr/ZA) and zeolite Y (H/ZY) in esterification of α-pinene. α-terpinyl acetate was successfully synthesized from α-pinene and acetic anhydride by their heterogeneous catalysts. The esterification reaction was carried out with reaction time, temperature and zeolite catalysts. The most effective catalysts used in the synthesis of α-terpinyl acetate is catalyst H/ZY with the yield is 52.83% at 40oC for the time 4 h with a selectivity of 61.38%. The results showed that the effective separation of catalyst could contribute to developing a new strategy for the synthesis of α-terpinyl acetate.