Isobornyl acetate

Pinene hydrochloride is treated by one of the reagents which abstract-HCl, and so converted into camphene q.v.). This is heated with acetic and sulphuric acids, and so converted into isobornyl acetate. Canmhor results in the usual manner. 

The chemical structures of the majority of FMs that have been studied in wastewater treatment are given in Figs. 1-3. Figure 1 shows a variety of FM structures that include alcohols, aldehydes, and ketones, including benzyl acetate (phenylmethyl ester acetic acid), methyl salicylate (2-hydroxy-methyl ester benzoic acid), methyl dihydrojasmonate (3-oxo-2-pentyl-methyl ester cyclopentaneacetic acid), terpineol (4-trimethyl-3-cyclohexene-1-methanol), benzyl salicylate (2-hydroxy-phenylmethyl ester benzoic acid), isobornyl acetate... 

Primary+secondary removal benzyl acetate=86.4-99.9 methyl salicylate=92.0-99.9 methyl dihydrojasmonate=81.9-99.9 terpineol=95.4-99.9 benzyl salicylate=90.3-99.9 isobornyl acetate=84.5-99.9 g-methyl ionone=83.1-99.8 p-f-bucinal=84.8-99.3 hexylcinnamaldehyde=95.3-99.9 hexyl salicylate=96.4-99.9 OTNE=51.4-99.4 acetyl cedrene=71.3-99.9... 

Buchbauer G, Jager W, Jirovetz L, Meyer F, Dietrich H. (1992). [Effects of valerian root oil, borneol, isoborneol, bornyl acetate and isobornyl acetate on the motility of laboratory animals (mice) after inhalation]. Pharmazie. 1992 Aug. 47(8) 620-2. 

Alcohols are oxidized to aldehydes by the liver enzyme alcohol dehydrogenase, and aldehydes to carboxylic acids by aldehyde dehydrogenase. In mammals, monooxygenases can be induced by plant secondary metabolites such as a-pinene, caffeine, or isobornyl acetate. Reduction is less common and plays a role with ketones that cannot be further oxidized. Hydrolysis, the degradation of a compound with addition of water, is also less common than oxidation. 

Camphor is produced by fractional distillation and crystallization of camphor oil or, synthetically, by dehydrogenation of isoborneol (from isobornyl acetate, see p. 73) over a copper catalyst. 

Isobornyl acetate is used in large amounts for perfuming soap, bath products, and air fresheners. However, the major use of isobornyl acetate is as an intermediate in the production of camphor. 

The bornane-, camphane- and fenchane-type monoterpenes possess the [2.1.1] bicyclic skeleton formed by different cyclisation of the terpinyl cation. Important members include borneol 47, isobornyl acetate 48, camphene 49, camphor 50, fenchone 51 (Structure 4.12). 

This compound is isobornyl acetate which has an exo-oriented acetate group and therefore the compound will exist as two enantiomers, i.e., the R,R,R isomer and its non-superimposable mirror image S,S9S isomer. The name given in the question designates the racemate. 

Hexyl butanoate Butyl hexanoate Fenchyl acetate Menthyl acetate a-Terpinyl acetate Bornyl acetate Isobornyl acetate Linalyl acetate Citronellyl isobutyrate Phenethyl formate Anisyl formate Ethyl salicylate Pentyl salicylate isoamyl Salicylate hexyl Salicylate... 

The selectivity was useful in a synthesis of nojigku alcohol (8) from (—)-isobornyl acetate (4). Oxidation of 4 with CrOj gave a mixture of 5 and 6, which was converted into 7 in high yield by Riley oxidation and reduction. The conversion of 7 into 8 involves elimination of the 5-keto group and Wagner-Meerwein rearrangement. ... 

SYN BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, ACETATE, EXO- FEMA No. 2160 ISOBORNYL ACETATE PICHTOSIN PICHTOSINE... 

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