Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review

Abstract

Currently, a shift towards chemical products derived from renewable, biological feedstocks is observed more and more. However, substantial differences with traditional feedstocks, such as their "hyperfunctionalization," ethical problems caused by competition with foods, and problems with a constant qualitative/quantitative availability of the natural products, occasionally complicate the large-scale market entry of renewable resources. In this context the vast family of terpenes is often not taken into consideration, although the terpenes have been known for hundreds of years as components of essential oils obtained from leaves, flowers, and fruits of many plants. The simple acyclic monoterpenes, particularly the industrially available myrcene, provide a classical chemistry similar to unsaturated hydrocarbons already known from oil and gas. Hence, this Review is aimed at reviving myrcene as a renewable compound suitable for sustainable chemistry in the area of fine chemicals. The versatility of the unsaturated C(10)-hydrocarbon myrcene, leading to products with several different areas of application, is pointed out.

Essential Oils Chemistry

“…This compound is very relevant in perfumery as an important intermediate in the synthesis of menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool as well as vitamins A and E (Behr and Johnen 2009). The isomer α does not occur in nature.…”

Volatile compounds profile of Bromeliaceae flowers

“…It is widely used in the cosmetic and pharmaceutical industries, as described by Behr and Johnen (2009). Linalool has been observed in tangerines and is responsible for their taste and aroma (Sawamura, Minhtu, Onishi, Ogawa, & Choi, 2004).…”

Novel Palladium‐Catalysed Hydroamination of Myrcene and Catalyst Separation by Thermomorphic Solvent Systems

“…A comprehensive overview of the versatile product network based on myrcene amine derivatives was shown in a recent review article. [9] Other metals, especially transition metals, are more expensive but do afford a higher total product yield, if effective catalyst recycling is realised. Until now only one process using transition metal catalysts has been described by Rhône-Poulenc with a TOF of 27 h À1 .…”

“…Its high and versatile reactivity allows access to a wide product platform ranging from flavours and fragrances to polymers and pharmaceuticals. [9] In the first step of the Takasago process, myrcene is converted to N,N-diethylgeranylamine via lithium-catalysed hydroamination with diethylamine. After four further steps, mostly homogeneous catalysed reactions, the desired (À)-menthol is obtained, which is more and more sought because of its peppermint flavour and refreshing properties.…”