Geraniol propionate

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... 

However, the lower fatty acid esters (particularly the acetates) of the acyclic terpene alcohols geraniol, linalool, and citronellol are extremely important both as fragrance and as flavor substances. The acetates occur in many essential oils, sometimes in rather high amounts. Formates, propionates, and butyrates occur less frequently. As a result of the development of large-scale production processes for terpenes, the esters of acyclic terpene alcohols are nearly always made synthetically. All acyclic terpene esters that are used as fragrance and flavor materials can be prepared by direct esterification of the appropriate alcohols. However, special precautions are required for the esterification of linalool. 

CIC The basic Muscat note is produced from linalool, balanced with further terpene alcohols, geraniol and linalool oxides. The catty odour of the concord grape is based on methyl anthranilate, combined with ethyl-3-mercapto propionate, benzaldehyde adds the touch of a seedy character. 

A word about the synthesis of the a-series, a-geraniol (73) and a-nerol (74), is warranted because they are often intermediates in the synthesis of 1-hydroxylated compounds (e.g., some diols described below). Weiler has continued his exploitation of the dianion of methyl acetoacetate to this end. Instead of prenylation (Vol. 4, p. 461, Ref. 73) he carried out a similar series of operations by alkylating the dianion with 4-bromo-2-methyl-l-butene, thus arriving at compounds of the a-series via the keto ester 75, methylating the enol phosphate to 76. He also prepared the double methylene isomer 77 (R = COEt) of geranyl propionate from the intermediate 75. The purpose of synthesizing this propionate was to prepare the pheromone of the San Jose scale, Quadraspidiotus pernicious, which is a mixture of the propionates of 73, 74,... 

The antibacterial compounds used in packaging materials are either synthetic or of namral origin and include (a) Organics allyl isothiocyanate, propionate, benzoate, sorbate, ethanol, linalool, methyl chavicol (l-allyl-4-methoxybenzene), dtral (3,7-dimethylocta-2,6-dienal ), methylcinnamate, methyleugenol, geraniol, 1,8-cineole, tra/is-a-bergamolene, carvacrol (5-isopropyl-2-methylphenol), thymol (2-isopropyl-5-methylphenol), l-octen-3-one, 3-octanol, ethyl pyruvate (ethyl... 

Citronellol has a fresh rosy odor that finds extensive use in floral fragrances and also in flavors for citrus and other fruit notes. Its improved stability over geraniol, nerol, and linalool makes it particularly useful in fragrances for soaps, detergents, and other household products. The odor of the levorotatory isomer is much finer than that of the racemate. Citronellyl acetate [150-84-5], also known as Cephreine, has a fresh rosy and fruity note and is also a significant perfumery ingredient. The formate, propionate, butyrate, and isobutyrate esters are also used. Citronellol is also important as an intermediate in the synthesis of a number of other aroma chemicals. 

Other constituents include esters (acetates, propionates, etc.) of geraniol, citronellol, and linalool monoterpenes (limonene, pinene, camphene, etc.) sesquiterpenes and alcohols (bourbonene, caryophyllene, elemol, famesol, etc.) phenols (eugenol, methyl eugenol, etc.) and free acids, among others. Java citronella oil contains higher amounts of sesquiterpenes, while the Ceylon type contains much larger amounts of monoterpenes (arctander list... 

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