2500-83-6

Usage

Chemical Properties

TRICYCLODECENYL ACETATE is a colorless liquid with a herbal, fresh, woody odor. It consists of a mixture of isomers that is obtained by addition of acetic acid to dicyclopentadiene in the presence of an acid catalyst. It is used for perfuming soaps, detergents, and air fresheners.

Trade name

Cyclacet? (IFF), Jasmacyclene (Givaudan), Verdyl acetate (Kalp- Sutra), Verdyl acetate (Yinghai).

InChI:InChI=1/C12H16O2/c1-7(13)14-12-6-8-5-11(12)10-4-2-3-9(8)10/h2,4,8-12H,3,5-6H2,1H3

Upstream product

• 1755-01-7 endo-Dicyclopentadien 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 77-73-6 exo-tricyclo[5.2.1.0^2,6]deca-3,8-diene 
• 108-05-4 vinyl acetate 
• 933-60-8 exo-dicyclopentadiene 
• 93818-38-3 (1RS,2RS,6RS,7RS,8SR)-tricyclo[5.2.1.0^2,6]dec-4-en-8-yl 4-nitrobenzoate 
• 133-21-1 (1RS,2RS,6RS,7RS,8SR)-tricyclo[5.2.1.0^2,6]dec-4-en-8-ol 
• 77-73-6 bi(cyclopentadiene) 
• 13080-96-1 methylaceto acetate 

Downstream Products

• 501929-86-8 (1S,2S,6S,7S,8R)-tricyclo[5.2.1.0^2,6]dec-4-en-8-ol 
• 501929-84-6 (1R,2R,6R,7R,8S)-tricyclo[5.2.1.0^2,6]dec-4-en-8-ol 

Relevant academic research and scientific papers

Stereoselective exo-addition to norbornenes of acetic acid generated from vinyl acetate in the presence of rhodium complexes

Rhodium complexes catalyzed decomposition of vinyl acetate with liberation of acetic acid and subsequent stereoselective exo-addition of the latter to norbornene and its derivatives under mild conditions.

Process for making tricyclodecenyl esters

A process for making tricyclodecenyl esters is disclosed. A C2-C4 carboxylic acid and a dicyclopentadiene react in the presence of triflic acid under conditions effective to produce the ester. The process gives tricyclodecenyl esters in good yield while avoiding the need to use a large excess of the carboxylic acid. The process efficiently provides fragrance-quality tricyclodecenyl esters from technical grade dicyclopentadienes and/or recycled carboxylic acids.

Synthesis of esters from cage-like unsaturated hydrocarbons, carboxylic acid anhydrides, and water

A convenient method for the preparation of esters was developed on the basis of reaction of cage-like polycyclic olefins with carboxylic acid anhydrides and water. Mixed anhydrides were found to give rise to the corresponding low-molecular acid esters. Among the obtained esters, acetates possess a pleasant odor, and they can be used as components of synthetic fragrant substances.

Enantioselectivity in odor perception synthesis and olfactory properties of the new tricyclic sandalwood odorant Fleursandol

The 3-methyl-4-(tricyclo[5.2.1.02,6]dec-4-en-8-ylidene)butan-2- ols (=Fleursandol; rac-10), a new class of sandalwood odorants, were synthesized in their enantiomerically pure forms by use of tricyclo[5.2.1.0 2,6]dec-4-en-8-ones 17 and ent-17 and (tetrahydro-2H-pyran-2-yl)- protected 4-bromo-3-methylbutan-2-ols 22 and ent-22 as starting materials (Schemes 2-4). Only four of 16 possible stereoisomers of rac-10 possess the typical, very pleasant, long-lasting sandalwood odor (Table 1). The (2S,3R,4E,1′R,2′R,6′R,7′R)-isomer ent-10a is by far the most important representative, with an odor threshold of 5 μg/l in H 2O.

Production of "dicylate" perfume

The method for producing "dicylate" - tricyclo[5,2,1,02,6]dec-3-enyl-8(9)-acetate -from acetic acid and tricyclo[5,2,1,02,6]deca-3,8-diene has been improved. The reaction is carried out at a temperature of 130-170°C and spontaneous pressure, which enables the use of strong acids as catalysts to be discarded.

Synthesis of esters by addition of carboxylic acids to cage cycloolefins

The thermal addition of monocarboxylic acids to cage bi-, tri-, tetra-, and pentacyclic hydrocarbons was carried out, and a highly efficient wasteless method of preparing esters of the corresponding alcohols was developed. The reaction has no need for Lewis acids as special catalysts since the initial acids themselves function as both catalyst and reagent. Orientation of the formyloxy and acyloxy groups in cycloolefin hydrocarbons was found, and the degree of regio- and stereoselectivity of the reaction was determined. A number of new esters of polycyclic alcohols were prepared. Some of them are of interest for perfumes.

Synthesis and Reactions of Tricyclic Monocarboxylic Acid Esters

A convenient and efficient method for preparing tricyclic esters has been developed on the basis of addition of C1-C3 monocarboxylic acids to tricyclo2,6>deca-3,8-diene and its dimethyl derivatives in the presence of p-toluenesulfonic acid.The orientation of the ester group in the products has been determined.Some reactions of the resulting esters have been studied, and their possible applications have been proposed.

Photooxidation and 13C N.M.R. Spectroscopic Investigation of 5,6-Dihydrodicyclopentadiene Derivatives

The sensitized photooxidation of endo-5,6-dihydrodicyclopentadiene (2) by singulet oxygen gives via the corresponding hydroperoxide (10) exo-1-hydroxy-5,6-dihydrodicyclopentadiene (7a).Starting from exo-5,6-dihydrodicyclopentadiene (6) exo-5,6-dihydrodicyclopentadien-1-one (12) is formed.The 13C n.m.r. spectroscopical data of these compounds and of other hydroxy, alkoxy and acyloxy dihydrodicyclopentadiene derivatives are discussed in relation on their structure.