Linalyl acetate lavender

Other. Lavaudiu oil is sometimes used as a source of linalool and linalyl acetate. Lavender oil is sometimes used externally as an insect repellent (martindale). 

Aroma chemicals are isolates, or chemically treated oils or components of oils. Some components are removed physically, others chemically. In most cases, they are further purified by distillation. For example, Bois de Rose (rosewood) oil may be distilled to isolate linalool, which may be then further treated chemically to yield derivatives such as linalyl acetate, an important fragrance ingredient and a primary component in its own right of lavender and lavandin oils. Vetiver oil Haiti, although containing only 70% alcohols, is treated with acetic anhydride, then carefully distilled to include valuable odor components in the distillate, even though they may not be esters. 

L v ndin. Lavandin, Lavandula hjbrida as a plant species is of recent origin, unknown until the late 1920s. It is a hybrid of two common lavenders, l vandula officinalis and l vandula latifolia. Lavandin is cultivated mainly ia southern France and has become one of the most produced and used natural perfumery materials. The flowering tops of the shmb are used to produce a concrete, an absolute, and a steam-distilled oil the last is by far the most used. Low cost and refreshing odor quaUty allow lavandin to be employed ia a wide variety of perfume appHcations and at high concentrations. Chemically it is comprised of 30—32% linalool (3) and linalyl acetate (1), along with numerous other substances, mosdy terpenic. 

Uses ndReactions. Linalool can be estetified to linalyl acetate by reaction with acetic anhydride. Linalyl acetate [115-95-7] has a floral-fmity odor, reminiscent of bergamot and lavender. The price of the acetate in 1995 was 14.30/kg (45). Linalool is subject to dehydration and to isomerization to nerol and geraniol during the esterification. However, if the acetic acid formed during the esterification is removed in a distillation column, the isomerization can be minimized and good yields of the acetate obtained (130). 

Esters, or salts of alkyl radicles, such as linalyl acetate, etc., are frequently the most important constituents of essential oils. Their importance is especially noteworthy in such cases as lavender , bergamot, peppermint, and wintergreen oils, and their estimation is very frequently necessary. The principle upon which this depends is the fact that most esters are decomposed by solution of caustic alkali (preferably in alcohol) according to the equation—... 

As the free acids present in essential oils consist in the main of acetic acid, they are, when necessary, calculated in terms of acetic acid in the same way the esters are conventionally calculated from the alkali required for their hydrolysis, in terms of the principal ester present, for example, linalyl acetate in the case of lavender and bergamot oUs, and geranyl tiglate in the case of geranium oil. 

Linalyl acetate is the principal constituent of the essential oils of bergamot, clary sage, lavender and lavandin. It is also present in the essential oils of Salvia officinalis, petitgrain, sassafras, neroli, lemon, lime, a few Mentha species and others. 

Optically pure (3i )(—)-linalyl acetate was detected in the oils of clary sage Salvia sclarea). Salvia dominica, lavender and lavandin using H-NMR spectroscopy with a chiral lanthanide shift reagent, Eu(hfc)3. This enantiomer was also detected in the oils of lavender, lavandin and bergamot using complexation gas chromatography on Ni(hfc) 2, and... 

Ravid U, Putievsky E, BassatM, Ikan R, Weinstein V, Isolation of optically pure (—)-linalyl acetate from clary sage, Salvia dominica L., lavender and lavandin,... 

Mosandl A, Schubert V, Stereoisomeric flavour compounds XXXIX Chiral constituents of essential oils (I), stereo differentiation of linalyl acetate — A new possibility for quality evaluation of lavender oil, Z Lebensm Unters Frosch 190 506-510, 1990. 

Uses. Linalyl acetate is used extensively in perfumery. It is an excellent fragrance material for, among others, bergamot, lilac, lavender, linden, neroli, ylang-ylang, and phantasy notes (particularly chypre). Smaller amounts are used in other citrus products. Since linalyl acetate is fairly stable toward alkali, it can also be employed in soaps and detergents. 

True French lavender grows in the Flaute Provence at an altitude of 600 1500 m. The plants are grown from seeds of the wild lavender ( population lavender). Lavender oil is produced in a yield of 10 25kg/ha. It has the following typical composition (%) m-ocimene (4 10), trans-odimene (1.5-6), 1,8-cineole (<1), camphor (<0.5), linalool (25-38), linalyl acetate (25-45), 1-terpinen-4-ol (2-6), and lavandulyl acetate (>2) [574-583a]. 

Lavandin plants are sterile and can be propagated only by using cuttings. The oils from the most important varieties, abrial and grosso, contain linalool (26-38/ 24-35%) and linalyl acetate (20-29/28-38%) as major constituents as well as 1,8-cineole (6-11/4-7%) and camphor (7-11/6-8%) [594-601]. A third variety is called super because its oil contains a high concentration of linalyl acetate (35-47%), and, thus, resembles lavender oil most closely. 

Lavender Lavandula angustifolia MUler Linalyl acetate (25-46), linalool (20-45)... 

Other activities on the gastrointestinal system included antidiarrhoeal and gastroprotective effects. Satureja hortensis and Aloysia triphylla EOs inhibited castor oil induced diarrhoea in rodents [225, 255]. The EO of lavender and its components (linalool, linalyl acetate) and the EO of Cryptomeria japonica (ter-pin-4-ol and elemol) showed protective activities against acute ethanol/aspirin-induced gastric ulcers in rodents [200,254]. 

For hundreds of years the essential oil of lavender has been well appreciated for perfumery purposes [72]. Lavender oil is obtained by steam distillation from the fresh-flowering tops of Lavandula angustifolia Miller (Lavandula officinalis Chaix) [73]. It is a colourless or pale yellow, clear liquid, with a fresh, sweet, floral, herbaceous odour on a woody balsamic base [73, 74]. According to the European Pharmacopoeia, characteristic components of lavender oils are limonene, cineol, 3-octanone, camphor, linalool, linalyl acetate, terpinen-4-ol, lavandulyl acetate, lavandulol and a-terpineol. Adulterations commonly include blends of lavender oils with lavandin oil or spike oil, and the addition of synthetic linalool and linalyl acetate. In contrast, genuine lavender oils contain as main constituents (i )-linalyl acetate and (i )-linalool of high enantiomeric purity (Fig. 17.14). 

A reliable authenticity assessment is concluded from the simultaneous consideration of multielement IRMS and enantioselective analysis. The differences of the stable isotope ratios of linalool and linalyl acetate are depicted as a three-dimensional plot of A values (d values of linalool minus d values of linalyl acetate for oxygen, hydrogen and carbon) (Fig. 17.15). This plot shows that the commercial samples S1-S5 are different from all the other samples investigated. Linalool and linalyl acetate of S1-S5 definitely are not genuine lavender oil compounds. 

Fig. 17.15 Multielement IRMS analysis of lavender oil main compounds. Differential diagram (h = linalool - linalyl acetate ) authentic (black circles) and commercial (white circles) samples commercial non-authentic (circles with a line through) and special aberrations (circles with a cross) [82]...

Bilke S, Mosandl A (2002) Authenticity assessment of lavender oil i ing GC-P-IRMS H/ H-ratios of linalool and linalyl acetate. Eur Food Res Technol 214 532... 

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. 

The ester number for any essential oil may vary within more or less wide limits (see Table XXXIV), but its determination is of importance in the identification of an oil, the detection of adulteration, and for judging of the quality of the oil. With some oils, the esters represent the odoriferous principle, e.g., linalyl acetate in bergamot, lavender and petit-grain oils, bomyl acetate in pine-needle oil and menthyl acetate in mint oil, the value of these Oils being deduced from the ester content. 

Linalyl acetate (3,7-dimethyl-1,6-octadien-3-yl acetate) Found in essential oils of bergamot, lavender, lavandin, spike lavender, Clary sage, neroli and petitgrain. Floral, fruity, sweet and herbaceous odour. 

For an essential oil such as lavender, the same major components will be present these are linalool, linalyl acetate and 1,8-cineole. This is the qualitative knowledge. The different types of lavender essential oils will contain different amounts of constituent compounds. Spike lavender, Lavandula latifolia, has high amounts of 1,8-cineole (25-37%), while true lavender, Lavandula angustifolia, has very small amounts (0-5%). Lavandula latifolia may contain up to 60% camphor, while Lavandula angustifolia has only up to about 12%. This is quantitative information. A quantitative analysis is needed to help identify different types of oil and can distinguish chemotypes. 

In lavender essential oils, linalool and linalyl acetate are sedative and antispasmodic compounds when lavender is used in blends with other essential oils, these effects can be enhanced. 

Chemically, all forms contain linalyl acetate, linalool and 1,8-cineole, along with many other compounds. Further analysis of each type reveals their differences in amounts of chemical components. The situation is illustrated by comparing published data for principal constituents and then seeing how these are reinforced by an actual GC chromatogram. This is shown in Table 7.1 the main figure is the published data while figures in brackets are those taken from the GC analysis of actual oil samples (cis- and trans-ocimene are minor hydrocarbon components, but are included as they are often used as markers for the authenticity of lavender oils). In all cases the amounts of compounds in the hybrid (Lavandula intermedia) are in between those of the true (Lavandula angustifolia) and the spike (Lavandula latifolia). 

Figure 7.3 Lavender. A good-quality French lavender, true lavender Lavandula angustifolia. This shows a high linalyl acetate content (33.29%) and low camphor content (0.21%). This oil would meet the ISO standards. Courtesy of Jenny Warden, Traceability.

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