Linalool rosemary

The enantiomeric differentiation of linalool is useful in the quality control of essential oils and oleoresins, as it was found to provide an important indication of the authenticity of many herbs and spices. The enantiomeric composition of linalool has been determined in many essential oils, including basil, bergamot, rosemary, lavandin, lavender, balm, coriander, mace. Pelargonium, rose, Cymbopogon, lemon, mandarin, Osman-thus, davana, jasmine, Lippia alba and orange, as well as in many fruit... 

A recent survey about essential oils and their pure constituents used to control Varroa jacobsoni, contained three interesting tables that reported the toxicity of essential oils for V. jacobsoni and Apis mellifera after 24, 48 and 72 hours in a topical application and in an evaporation test, and the effects of essential oils on behavior and reproduction of V jacobsoni and on the bee brood [63]. The most interesting oils were those of cinnamon and clove, with 100% mite mortality after 24 h and no significant toxicity on honey bees. Furthermore, clove essential oil produced small brood mortality, and it was an inhibitor of mite reproduction. Other effective oils were anise, fennel, lavender, rosemary and wintergreen, which killed 100% mites after 48-72 hours. On the contrary, the oils obtained from garlic, onion, oregano and thyme, were found to be very toxic for honey bees. Among pure constituents, camphor, linalool, linalyl acetate and pinene resulted small brood mortality and inhibited mite reproduction. 

Oxides in essential oils have an oxygen atom within a ring structure, usually made from an alcohol, and are named after the alcohol with the termination oxide, e.g. linalool oxide (Fig. 3.12). They are found in a wide range of essences, especially those of a camphoraceous nature, e.g. eucalyptus, rosemary, tea tree and cajeput. 

The rosemary extracts were collected as separate samples succesively in time. Each of them was analysed separatively and the results are listed in Table 4. The concentrations of a-pinene, champhene, p-cimene and limonene decreased with extraction time, while that of the oxygeneted derivatives (cineol, linalool, camphor, bomeol and verbenon) increased significantly. 

Composition Up to 55% 1,8-cineole, camphor, bomeol and its acetate, a-terpineol, terpinene-4-ol, linalool, verbenone, 3-octanone and terpene hydrocarbons. For detailed analyses see e.g. [254, 255, 256[. Even if different chemotypes of rosemary exist, only two qualities are of commercial interest (ISO and European Pharmacopoeia give almost identical specifications) ... 

Enantioselective GC has found a wide variety of applications, for instance, studies of citronellol (Ravid et al., 1992) and a-terpineol (Ravid et al., 1995) in a variety of species and verbenone in rosemary oils (Ravid et al., 1997). Chiral phases were applied to the separation of linalool and linalyl acetate in a variety of plant species (Konig et al., 1992 Cassabianca et al., 1998), extracts of Angelica seeds and roots (Holm et al., 1997) and other monoterpenoids in geranium oils (Kreis Mosandl, 1993). Separation of monoterpenes in Scots pine and juniper oils (Hiltunen Laakso, 1995), Abies (Holm et al., 1994) and Picea (Persson et al., 1996) oils and limonene, linalool, citronellal and P-citronellol Cymbopogon winterianus)... 

ISO standard 4719 shows character and data for that oil. Adulteration is done by white camphor oil, 1,8-cineole distilled from eucalyptus oil, synthetic camphor, and linalool. Blending is done with ter-penes from eucalyptus oil, turpentine oil, n-bornyl acetate, lavandin, rosemary oil, HO leaf oil, and a terpineol. Detection can be made by GC MS and by multidimensional chiral separation. Ravid (1992) mentions the chiral ratio of terpinen 4 ol as (4S) (+) terpinen-4-ol 93% (4I -(-)-terpinen 4-ol 7%. 

The technique has also been successfully applied to the authenticity assessment of various commercially available rosemary oils [111]. The ER of a-pinene, camphene, P-pinene, limonene, borneol, terpinen-4-ol, a-terpineol, linalool, and camphor were measured moreover, (IS)-(-)-borneol of high enantiomeric purity (higher than 90%) has been defined as a reliable indicator of... 

Linalool is one of the main compounds (up to 15%) of the EO obtained from Rosmarinus officinalis L. (rosemary, Lamiaceae). The EO was tested using two different methods radical scavenging with the DPPH assay and the p-carotene bleaching test. The oil was able to reduce the stable free radical DPPH and showed a slightly weaker scavenging activity than the standard trolox. But the efficiency of rosemary oil was clearly weaker than that of the reference oil Thymus porlock. By the P-carotene bleaching test it could be shown that this EO has the ability to prevent the lipid peroxidation with a capacity close to the used standards. 

Determination of the following constituents are specifically mentioned in some monographs for quality assessment of the essential oils that will be discussed subsequently anethole in anise and star anise oils carvone in caraway, dill, and spearmint oils 1,8-cineole in cardamom, rosemary, and sage oils and linalool in coriander and basil oils. 

---