84415-75-8

Basic information

• Product Name: (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate
• CAS NO: 84415-75-8
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.3923
• Mol File: 84415-75-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 286°C at 760 mmHg
• Flash Point: 133.4°C
• Density: 0.97g/cm³
• Vapor Pressure: 0.00272mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate(84415-75-8)
• EPA Substance Registry System: (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate(84415-75-8)

Safety Data

• Hazardous Substances Data: 84415-75-8(Hazardous Substances Data)

Usage

General Description

The chemical "(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate" is a bicyclic terpene ester with a molecular formula of C15H26O2. It is a colorless liquid with a fruity odor, commonly used in the fragrance and flavor industry. The compound is found in essential oils and has a wide range of applications in perfumes, soaps, and cosmetics. It is also used as a flavoring agent in food products. The chemical structure of "(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl hexanoate" gives it unique properties that make it valuable in the development of various scents and flavors.

Upstream product

• 24393-70-2 isoborneol 
• 142-61-0 Hexanoyl chloride 
• 464-43-7 d-borneol 
• 142-62-1 hexanoic acid 
• 464-45-9 endo-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.

Microwave-assisted synthesis of borneol esters and their antimicrobial activity

Seventeen borneol esters (1–17) were synthesised by conventional and microwave-assisted methodology using DIC/DMAP, and seven are described for the first time (8, 9, 10, 12, 13, 16 and 17). The microwave-assisted methodology was carried out without use of solvents, displayed short reaction times, and showed equal or higher yields for all the long-chain esters and three aromatic compounds (11, 12 and 14) when compared to the conventional approach. All the borneol esters were evaluated against the bacteria Streptococcus sanguinis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungus Candida albicans. Compounds 12, 13 and 14 displayed promising antibacterial activity with a MIC equal to ampicilin (62.5?mg?mL?1) for some microorganisms. In fact, bornyl 3′,4′-dimethoxybenzoate (13) was active against all tested bacteria and fungus.