Geranyl esters

Some oils consist almost entirely of esters for example, those of Oaultheria procumhens and Betula lenta contain about 99 per cent, of methyl salicylate. Bergamot and lavender owe the greater part of their perfume value to esters of linalol, of which the acetate predominates. Geranium oil owes its fragrance chiefly to geranyl esters, of which the tiglate is the chief. On the other hand, oils such as spike lavender, sandalwood, lemon-grass, and citronella contain but small quantities of esters, and owe their perfume value to entirely different types of compounds. 

The rose odour is still further modified by the presence of the five carbon acid radicle, and judicious blending of the various geranyl esters is capable of giving numerous characteristic bouquets to the various rose odours. This ester boils at 135° to 138° at 10 mm. pressure. 

A product with a higher geraniol content and slightly different odor quality for use in fine fragrances is obtained by fractionating palmarosa oil after saponification of the geranyl esters. 

It is an important intermediate in the manufacture of geranyl esters, citronellol,... 

Synthesis of short-chain geranyl esters catalysed by esterase from Fusarium oxysporum in an organic solvent was reported by Stamatis et al. [39]. 

Geranyl esters Citronellyl esters T etrahy drogerani ol Rholiate... 

Uses. Geraniol is one of the most frequently used terpenoid fragrance materials. It can be used in all flowery-roselike compositions and does not discolor soaps. In flavor compositions, geraniol is used in small quantities to accentuate citrus notes. It is an important intermediate in the manufacture of geranyl esters, citronellol, and citral. 

Geranyl ester, C SHM01P liquid pleasant odor djf 0.9279 bp, 149-151. ... 

Synonyms (E)-3,7-Dimethyl-2,6-octadien-1 -ol propionate (E)-3,7-Dimethyl-2,6-octadienyl propanoate 3,7-Dimethyl-2,6-octadien-1-yl propionate trans-3,7-Dimethyl-2,6-octadien-1-yl propionate Geraniol propionate 2,6-Octadien-1-ol, 3,7-dimethyl-, propionate, (E)- Propionic acid, geranyl ester Definition Ester of geraniol and propionic acid Empirical C13H22O2 Formula C2H5COOC10H17 Properties Colorless liq. fruity flowery odor bitter taste sol. in fixed oils, alcohol insol. in water, glycerol, propylene glycol m.w. 210.31 sp.gr. 0.896-0.913 b.p. 253 C flash pt. 99 C ref. index 1.4570-1.4650... 

Propionic acid, geranyl ester. See Geranyl propionate... 

Monoterpenes are important constituents of essential oils. These complex mixtures of compounds, as well as individual monoterpenes are used in medicine (F 2) and industry (F 4). Commercially important monoterpenes are, for instance, menthol, camphor, carvone, thymol, fenchone, and oc-pinene. Monoterpenes flavor foodstuffs and beverages (F 1). Citral, for example, is an important constituent of the smell of lemon. Thymol is involved in the flavor of mandarin oranges. Other monoterpenes, e.g., limonene and geraniol, are constituents of flower scents and attract plant pollinators (E 5.5.1). High monoterpene concentrations in plants will repel most potential predators, but my attract some animals (E 5.5.3). Animals use citronellal, citral, and oc- and jS-pinene als feeding deterrents (E 5.1) and geraniol, geranyl esters, myrcene, and terpinolene as pheromones (E 4). Some monoterpenes, e.g., 1,8-cineole and camphor, are also involved in plant-plant interactions (E 5.3). 

Whiie the esters (and lactones) mentioned above may (or may not) be mixtures, the farnesyl and geranyl esters found in Andrena are not. They appear to all be of all-tra/is-farnesol and devoid of esters of the other farnesol isomers. Simiiarly the geranyl esters are free of their neryl counterparts. The specific isomer of dihydrofarnesyl acetate from Melissodes is unknown although 2,3-dihydro-6-tra 5-farnesol has been found in a Bombus jonellus cephalic gland (Bergstrom and Svensson, 1973a). 

Bergstrdm, G. and Tengd, J. (1974) Studies on natural odoriferous compounds IX. Farnesyl- and geranyl esters as main volatile constituents of the secretion from Dufour s gland in 6 species of Andrena (Hymenoptera, Apidae). Chem, Scr.y 5, 28-38. 

Recent clinical trials have revealed that two terpenoid derivatives of quite different chemical constitutions may hold some promise as useful chemotherapeutic agents in the treatment of gastric ulcers, although accurate assessment of their therapeutic potentialities must await the fullness of time. These compounds are the disodium salt of the hemisuccinate ester (LXVIII) of 18 -glycyr-rhetinic acid (approved name Carbenoxolone sodium) [505 a] and the geranyl ester (LXIX) of farnesylacetic acid (approved name Gefarnate). 

The leaf oil is practically a terpene oil, the principal constituents being pinene, dipentene, and laevo-limonene. Bornyl and geranyl esters are present in very small amount. Two samples gave the following values —... 

Two grms. of the oil are heated with 2 grms. of phthalic anhydride and 2 c.c. of benzene for two hours on a water-bath. The mixture is allowed to cool, and shaken for ten minutes with 60 c.c. of semi-normal aqueous caustic potash, in a stoppered flask. At the end of this time the anhydride is converted into neutral phthalate, and the acid geranyl ester into its potassium salt. The excess of alkali is titrated with seminormal sulphuric acid. By deducting from the proportion of alkali absorbed by the quantity of phthalic anhydride used, the quantity of alkali used up in the experiment, the quantity of alkali absorbed by the geranyl ester is obtained, and hence the percentage of geitiniol can be calculated. The results of this method applied to the above mixtures were as follows —... 

They found present in the oil cineol, linalol, geraniol, and geranyl esters. 

The principal constituent is citral, with some geraniol, geranyl esters, and a terpene. 

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