Irregular mnoterpenes in essential oils with special emphasis on ortho-Menthane derivatives

ACEITES ESENCIALES

DERIVADOS DE ORTO-MENTANO

BIBLIOGRAFIA NACIONAL QUIMICA

2022

Monoterpenes are frequently the most common and distinctive components of essential oils. Most of them (the so-called regular monoterpenes) obey the Ruzicka’s Isoprene Biogenetic Rule, which means that the assembly of the bioactive isoprene building blocks (IPP and DMAPP) takes place in a head-to tail fashion. However, in some cases, the occurrence of completely different biogenetic assemblies gives rise to irregular monoterpenes that do not go from head-to-tail. The most common representatives of this type being artemisyl, chrysanthemyl, lavandulyl, and santolinyl skeletons. In addition, rearrangements from regular compounds are also frequently observed giving rise to a new category of irregular monoterpenes, the rearranged ones. Finally, other closely related group is made up by the degraded monoterpenes (or nor-monoterpenes or homoterpenes),compounds that lose carbon atoms during their biosynthesis and that can be considered also as “irregulars”. This chapter discusses the role of these three groups of compounds as all of them have eventually been identified in essential oils. Emphasis will be placed on rearranged monoterpenes, especially ortho-menthane derivatives, due to the paucity of literature dealing with this topic. Carquejol and piquerols, and some of their derivatives are reviewed according to their occurrence, possible biosynthesis, and biological properties. Semi-synthesis will also be discussed, as potentially bioactive compounds could be obtained. Finally, some practical aspects for the preparation of carquejol oxide (7,8-epoxy carquejol), a novel derivative of the ortho-menthane family, will be presented.

Flavors and Fragrances in Food Processing: Preparation and Characterization Methods / Balakrishnan, Preetha y Gopi, Sreerag, eds. -- s.l. : ACS Publications, 2022. -- pp. 361-383

ACS Publications

2022

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23 p.

Inglés

Capítulo

10.1021/bk-2022-1433.ch009

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