Reference

https://pubchem.ncbi.nlm.nih.gov/compound/linalyl_acetate#section=Top A. Martin, V. Silva, L. Perez, J. Garcia-Serna, M. J. Cocero, Direct Synthesis of Linalyl Acetate from Linalool in Supercritical Carbon Dioxide: A Thermodynamic Study, Chemical Engineering & Technology, 2007, vol. 30, pp. 726-731 H. Surbung, J. Panten, Common Fragrance and Flavor Materials: Preparation, Properties und Uses, 2006, ISBN 978-3-527-31315-0 C. S. Letizia, J. Cocchiara, J. Lalko, A. M. Api, Fragrance material review on linalyl acetate, Food and Chemical Toxicology, 2003, vol. 41, pp. 965-976

Preparation

Linalyl acetate is synthesized by two methods: 1) Esterification of linalool requires special reaction conditions since it tends to undergo dehydration and cyclization as it is an unsaturated tertiary alcohol. These reactions can be avoided as follows: esterification with ketene in the presence of an acidic esterification catalyst below 30 °C results in the formation of linalyl acetate without any by-products. Esterification can be achieved in good yield, with boiling acetic anhydride, whereby the acetic acid is distilled off as it is formed; a large excess of acetic anhydride must be maintained by continuous addition of anhydride to the still vessel. Highly pure linalyl acetate can be obtained by transesterification of tert-butyl acetate with linalool in the presence of sodium methylate and by continuous removal of the tert-butanol formed in the process. 2) Dehydrolinalool, obtained by ethynylation of 6-methyl-5-hepten-2-one, can be converted into dehydrolinalyl acetatewith acetic anhydride in the presence of an acidic esterification catalyst. Partial hydrogenation of the triple bond to linalyl acetate can be carried out with, for example, palladium catalysts deactivated with lead.

Contact allergens

Structurally close to linalool, linalyl acetate is the main component of lavender oil and is commonly used in fragrances and toiletries, and in household cleaners and detergents as well. By autoxidation, it leads mainly to hydroperoxides, with a high sensitizing potent.

Synthesis

Normally prepared by direct acetylation of linalool; another method starts from myrcene hydrochloride, anhydrous sodium acetate and acetate anhydride in the presence of a catalyst; all synthetic methods tend to avoid the simultaneous formation (because of isomerization) of terpenyl and geranyl acetate.

Aroma threshold values

Detection: 1 ppm

Taste threshold values

Taste characteristics at 5 ppm: floral, green, waxy, terpy, citrus, herbal and spicy nuances.

General Description

Linalyl acetate is a monoterpene ester mainly found in lavandula essential oil. It is used as a flavoring agent in food industries, as well as a preservative additive in cosmetics and fragrances such as soaps, colognes, perfumes, and skin lotions.