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

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

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 
• 72-89-9 acetylcoenzyme A 
• 141-78-6 ethyl acetate 
• 7785-70-8 (+)-α-pinene 
• 64-19-7 acetic acid 
• 464-17-5 (+-)-bornylene 
• 565-00-4 dl-camphene 
• 7664-93-9 sulfuric acid 
• 464-41-5 bornyl chloride 
• 557-34-6 zinc diacetate 
• 464-45-9 endo-borneol 
• 464-43-7 d-borneol 
• 13429-40-8 camphene hydrate 

Downstream Products

• 6627-72-1 rac-endo-borneol 
• 1686-28-8 (+/-)-Epiborneol 
• 565-00-4 dl-camphene 
• 54717-80-5 bornyl acetoacetate 
• 64-19-7 acetic acid 
• 91839-99-5 dl-6-acetoxy-bornan-3-one 
• 76-22-2 Camphor 
• 39850-78-7 5-Ketoborneol 
• 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 
• 464-43-7 borneol 

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.

Method for synthesizing bornyl acetate from turpentine

The invention discloses a method for synthesizing bornyl acetate from turpentine, which relates to the technical field of deep processing of turpentine. The preparation method comprises the followingsteps of proportioning titanium sulfate and hydroxycarboxylic acid to form a composite catalyst, mixing turpentine, acetic acid and the composite catalyst, and reacting in a stirring state, after thereaction is finished, filtering, and removing acetic acid from the filtrate to obtain a solution containing bornyl acetate, neutralizing the solution containing the bornyl acetate, and washing with water to obtain a bornyl acetate crude product, and then fractionating the crude product of the bornyl acetate to obtain the bornyl acetate. The synthesis method provided by the invention is high in catalytic activity, low in cost and high in selectivity on the borneol acetate, and does not need to use a raw material with too high pinene content.

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.

'Clean' hydrolase reactions using commercial washing powder

We report the use of commercial laundry powder as a biocatalyst for a range of lipase-catalysed reactions including (trans)esterification, ester hydrolysis and chemoenzymatic epoxidation reactions. The enzymatic laundry powder exhibited excellent stability and recyclability, making it a readily available and cheap biocatalyst for chemical transformations.

Method for synthesizing isobornyl acetate by camphene

The invention discloses a method for synthesizing isobornyl acetate by camphene. The method comprises the following steps of adding camphene, glacial acetic acid, a main catalyst (hydroxycarboxylic acid) and an additive into a reaction kettle according to a mass ratio of 100:(20 to 400):(1 to 50):(1 to 20), starting to stir, controlling the temperature to 40 to 100 DEG C, and reacting for 2 to 24h, so as to obtain a synthesized product; adding a small amount of water into the synthesized product, standing and delaminating, wherein the upper oil layer is a target product containing isobornyl acetate, the lower layer is acid water containing the catalyst and acetic acid, and the acid water is dewatered and recycled; adding the target product into a water washing tank, adding alkaline water to neutralize, and then adding water to wash, so as to obtain a crude product of the isobornyl acetate; relieving pressure and distilling, so as to obtain the refined isobornyl acetate. The method forsynthesizing the isobornyl acetate by catalyzing the camphene has the advantages that the obtained product has high yield and high purity, and is easy to separate; the used catalyst has high catalyzing activity; the preparation is simple, the repeatability is good, the toxicity is avoided, the corrosion property is low, the isobornyl acetate belongs to regeneration resources, and the industrialization product is easy.

Rice husk ash: A new, cheap, efficient, and reusable reagent for the protection of alcohols, phenols, amines, and thiols

Amild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. Copyright

Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes

Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.

Microwave-assisted α-pinene acidic catalytic isomerisation

A comparative study of microwave assisted α-pinene acidic catalytic isomerisation reactions with near-critical water procedure under microwave irradiation is presented. This study can be performed because in both cases the mechanism is similar, namely an acidiccatalyzed rearrangement. The non-critical method technique is milder using a lower temperature and pressure and a shorter reaction time than near-critical water conditions. The general aspect of the selectivity of the reaction products is changed, being higher for α-terpinolene and γ-terpinolene and lower for limonene and camphene compared to the non-critical conditions.

Liquid phase acetoxylation of α-pinene over Amberlyst-70 ion-exchange resin

Heterogeneously-catalyzed and solvent-catalyzed liquid phase acetoxylation of α-pinene with acetic acid acting as both a solvent and a reagent was studied. Both solvent-catalyzed and catalytic experiments were carried out and various reaction conditions were studied. The influence of temperature, pressure, solvent and gas milieu were taken into account. Bornyl, fenchyl, verbenyl as well as α-terpinyl acetates, limonene, camphene and γ-terpinene were found among reaction products. The addition of the catalyst allowed for maximization of the yield of bornyl acetate. The predominant products obtained were α-terpinyl, verbenyl and bornyl acetates. The reaction pathways were identified and evaluated. The aim of this work was to study the feasibility of batch acetoxylation of α-pinene. The analysis of the complex product distribution is not trivial and, consequently, resolving the reaction network was important. The optimized reaction conditions were searched for aiming at an efficient conversion of α-pinene to a mixture of valuable products.