Citrus fragrances

Citrus Fix Citrus fragrances Citrus juices Citrus odor Citrus oils... 

Features Strong oily citrus fragrance Trade Name Synonyms Tridecen-2-nitrile 3/076791 t[Dragoco http //www.dragoco.com, http //www.symrise. com]... 

Komori, T, Fujiwara, R, Tanida, M, Nomura, J., and Yokoyama, M, M, 1995b, Effects of citrus fragrance on immune function and depressive states. Neuroimmunomodulation (2) 174-180. 

The structure of sesquiterpenoid (+)-l(10)-aristolene (=calarene) (36) from the crude drug Nardostachys chinensis was similar to that of nootkatone. 2-Oxo-l(10)-aristolene (38) shows antimelanin-inducing activity and excellent citrus fragrance. On the other hand, the enantiomer (37)... 

Using Figure 10.5, draw the structure of (S)-limonene, which is isolated from pine needles and has a turpentine-like odor. Explain how it can smell differently from the R isomer, which has a citrus fragrance. 

It has a powerful, sweet, lemon-peel type odor of medium tenacity and is used in all types of citrus - fragrances as one of the main odor contributors. In other fragrance types it reinforces fresh, natural citrus topnotes (-+odor description) and sparkle. Widespread use in citrus - flavors and other fruit flavors, such as apple, cherry or grape. 

In fragrances, traces are used to give lift and pungency to pine, herbal and citrus fragrances. 

Citrus Family. This is a popular fragrance group noted for its refreshing brisk quaUty. Lemon, lime, orange, and bergamot are important ingredients. These oils combine well with lavender and amber accords. 

Crude turpentine is distilled to obtain refined products used in the fragrance and flavour industry. Only the unsaturated mono- and bicyclic terpenes are of interest for resin production. These are mainly a-pinene, p-pinene and dipentcne (D,L-limonene) (Fig. 17). D-Limonene is obtained by extraction of orange peel in citrus fruits. 

An example of commercial interest is the synthesis of citronitrile (Scheme 17), a compound with a citrus-like odor, which is used in the cosmetics and fragrance industries. The first step in the synthesis of citronitrile is the Knoevenagel condensation of benzyl acetone and ethyl cyanoacetate. This condensation has been carried out with MgO and Al-Mg calcined hydrotalcites as catalysts (148). Similar results were obtained with the two solid catalysts, with yields of 75% of the Knoevenagel adduct. 

CH3(CH2)iiCHO, C13H26O, Mr 198.34, i pijkPa 128 °C, df 0.8356, nf 1.4384, occurs in lemon oil and has been identified as a volatile constituent of cucumber. It is a colorless liquid having a fatty-waxy, slightly citrus-like odor. Addition of tridecanal to fragrance compositions imparts fresh nuances in the top note as well as in the dry out. 

Uses. Citronellol is one of the most widely used fragrance materials, particularly for rose notes and for floral compositions in general. As flavor material, citronellol is added for bouquetting purposes to citrus compositions. It is the starting material for numerous citronellyl esters and for hydroxydihydrocitronellol, an intermediate in the production of hydroxydihydrocitronellal. 

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. 

C12H22O2, Mr 198.30, Z PlOl.SkPa 240 °C, d 0.8901, Wp 1.4515, occurs in many essential oils either as one of its optical isomers or as the racemate. The odor of racemic citronellyl acetate differs little from that of the optical isomers. ( )-Citronellyl acetate is a liquid with a fresh-fruity rose odor. It is often used as a fragrance, for example, for rose, lavender, and geranium notes as well as for eau de cologne with citrus nuances. Since it is relatively stable to alkali, it can be used in soaps and detergents. Citrus flavors acquire speciflc character through the addition of citronellyl acetate it is also used to round off other fruit flavors. 

It is used in a large number of blossom fragrances. However, its use in perfumes for soap and cosmetics is limited because it causes discoloration. It is used in aroma compositions (e.g., in grape and citrus flavors). 

The flavour and fragrance business has always been very research driven and innovative. All larger companies spend about 7-8% of their total sales per annum on research and development. They all have large research centres, usually centred in their headquarters, as well as development and innovation centres around the globe. The general focus of their research is on new products, offering better performance at the lowest cost. This can be new molecules but also a new technique to concentrate (fold) a citrus oil, or a new way to encapsu-... 

Mondello, L., Casilli, A., Tranchida, P.Q., Dugo, R, Dugo, G. (2005) Comprehensive two-dimensional GC for the analysis of citrus essential oils. Flavour Fragrance J. 20 136-140. 

The products have the characteristic lemon odor of citral and also have greater odor strength and chemical stability than citral. As the need for more stable citrus-like fragrances for use in bleach developed, other nitrile compounds have been made available commercially. Citronellyl nitrile is made from citronellal dimethyloctanenitrile is produced from dimethyloctanal by the oximation method. 

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