Citronellyl ester

Citronellol undergoes the typical reactions of primary alcohols. Compared with geraniol, which contains one more double bond, citronellol is relatively stable. Citronellol is converted into citronellal by dehydrogenation or oxidation hydrogenation yields 3,7-dimethyloctan-l-ol. Citronellyl esters are easily prepared by esterification with acid anhydrides. 

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. 

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

FORMIC ACID, CITRONELLYL ESTER FORMIC ACID-3,7-DLMETHYL-6-OCTEN-l-YL ESTER... 

ACETIC ACID, CINNAMYL ESTER see CMQ730 ACETIC ACID, CITRONELLYL ESTER see AAUOOO ACETIC ACID, COBALT(2+) SALT see CNCOOO ACETIC ACID, COBALT(2+) S. LT, TETRAHYDIL TE see CNA500... 

FORMIC ACID, CINNAMYL ESTER see CMR500 FORi nC ACID, CITRONELLYL ESTER see CMT750 FORMIC ACID-3,7-DIMETHYL-6-OCTEN-1-YL ESTER see CMT750... 

Beilstein Handbook Reference) Acetic acid, 3,7-dimethyl-6-octen-1-yl ester Acetic acid, citronellyl ester 1-Acetoxy-... 

Use Perfume and cosmetic industry. C. serve as starting materials for the production of citronellyl esters formates (fruity, flowery), acetates (bergamot, lavender), propionates (roses, lily of the valley), isobutyrates (sweet, fruity), isovalerates (herby), tiglates (fungus-like). 

Acetic acid, citronellyl ester. See Citronellyl acetate... 

Synonyms Citronellyl methanoate 3,7-Dimethyl-6-octen-1-ol formate 2,6-Dimethyl-2-octen-8-yl formate 3,7-Dimethyl-6-octen-1-yl formate Formic acid, citronellyl ester Formic acid-3,7-dimethyl-6-octen-1-yl ester Empirical C11H20O2 Formula C10H19OOCH... 

Citronellyl Acetate.—The odour of the acetic ester of citronellol recalls to some extent that of hergamot. It is a natural constituent of geranium oil, and is useful in small amounts for blending with rose and geranium odours. It is prepared hy the action of acetic anhydride on citronellol. When pure it has the following characters —... 

Hydrogenation of the carbon-carbon double bond occurs without alteration of the ester function when citronellyl acetate is treated with 2.5 equivalents of trifluoroacetic acid and two equivalents of triethylsilane in 2-nitropropane.205 The reduced product is obtained in 90% yield after 22 hours at room temperature in the presence of one equivalent of added lithium perchlorate (Eq. 82). The yields are lower in the absence of this added salt. Similar reduction of an unsaturated phenolic chroman derivative occurs to give an 85% yield of product with only the carbon-carbon double bond reduced (Eq. 83).205... 

Uses and Reactions. The main use for citronellol is for use in soaps, deteigents, and other household products. It is also important as an intermediate in the synthesis of other important fragrance compounds, such as citronellyl acetate and other esters, citronellal, hydroxycitronellal, and menthol. 

Citronellol is easily esterified with acid anhydrides or carboxylic acids, catalyzed by mineral acids. The price of citronellyl acetate [150-84-5] in 1995 was 10.45/kg (45). Other esters such as the formate and isobutyrate are also used. 

Examples of significant esters include benzyl acetate, linalyl acetate, gera-nyl acetate and citronellyl formate. 

SYNS ACETIC ACID-3,7-DIMETHYL-6-OCTEN-I-YL ESTER CITRONELLYL ACETATE (FCC) 2,6-DIMETHYL-2-OCTEN-8-OL ACETATE 3,7-DIMETHYL-6-OCTEN-l-YL ACETATE FEMA No. 2311... 

Group 4 lists compounds with leaf-like notes such as (Z)-3-hexen-l-ol (Flavis 02.056, FEMA 2563) and (Z)-3-hexenal (Flavis 05.075, FEMA 2561) as well as esters such as citronellyl acetate (Flavis 09.012, FEMA 2311) with rose-like, floral profile. 

Ester has a fruity note. When the initial alkyl group in alcohol or acid or both is relatively large in molecular size or with its own characteristic note, the resulting ester maintains this note in addition to the fruity note. Examples include citronellyl acetate, having a fresh rosy-fruity odor, which inherits the rosy note from citronellol and bomyl acetate, having a sweet herbaceous-piney odor with a balsamic undertone, which maintains the odor of bomeol. 

Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl ester citronellyl isobutyrate ... 

Passion fruit Red Rf. (Passiflora edulis) . The flowery-fruity flavor is due in particular to (Z)-3-hexenyl esters, (Z)-3-octenyl acetate, citronellyl and geranyl acetate. Yellow P.f. (P. edulis flavicarpa). 2-Methy 1-4-propyl-1,3-oxathiane, 3-mercapto-l-hexanol (CjHuOS, Mr 134.24, CAS [51755-83-0]) and the corresponding esters are mainly responsible for the exotic-fruity flavor. In both sorts about 30 Cu-noriso-prenoids, including fl ionone, )3- damascenone and edulane (2,5,5,8a-tetramethyl-l-benzopyran) make major contributions to the aroma. 

The oxidative dehydrogenation of alcohols represents key steps in the synthesis of aldehyde, ketone, ester, and acid intermediates employed within the fine chemical, pharmaceutical, and agrochemical sectors, with allylic aldehydes in particular high-value components used in the perfume and fiavoring industries [1]. For example, crotonaldehyde is an important agrochemical and a valuable precursor for the food preservative sorbic acid, while citronellyl acetate and cinnamaldehyde confer rose/fruity and cinnamon flavors and aromas, respectively. There is also considerable interest in the exploitation of biomass-derived feedstocks such as glycerol (a by-product of biodiesel synthesis from plant or... 

Benzeneacetic acid, 3,7-dimethyl-6-octenyl ester. See Citronellyl phenylacetate Benzeneacetic acid, 3,7-dimethyl-7-octenyl ester, (S)-. See Rhodinyl phenylacetate Benzeneacetic acid, ethyl ester. See Ethyl phenylacetate... 

Butenoic acid, 2-methyl-, 3,7-dlmethyl-2,6-octadienyl ester (E,E)-. See Geranyl tiglate 2-Butenoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl ester, (E)-. See Citronellyl tiglate 2-Butenoic acid, methyl ester, (E)- trans-2-Butenoic acid methyl ester. See Methyl crotonate... 

Beeswax, white Beeswax, yellow Benzoic, acid Benzyl tiglate y-Bisabolene Brominated vegetable oil 3-Butylidenephthalide Butyloxepanone 3-Butylphthalide Calcium lactate Caramel Castor (Ricinus communis) oil Citronellyl isovalerate Citronellyloxy acetaldehyde p-Cresyl isovalerate p-Cresyl octanoate Crotonic acid p-Cyclocitral p-Damascenone 9-Decenal trans-4-Decenal Diacetyl tartaric acid esters of mono- and diglycerides Diethyl malate Difurfuryl disulfide Dihydroeugenol Dihydro-a-ionone Dihydrojasmone Diisobutyl ketone Diisopropyl disulfide 3,4-Dimethylcyclopentane-1,2-dione Dimethyl dicarbonate 2,5 Dimethyl-3-furanthiol p-a-Dimethylstyrene Diphenyl oxide Ethyl acetate... 

Phytochemistry See Ferula foetida for general information on the genus Ferula. The roots contain up to 21.5 % resins containing phytosterin, vanillic acid, umbelliferone, fatty acids (including isovaleric), up to 4 % essential oil, consisting of linalyl acetate, citronellyl acetate, ferulene, sesquiterpenes, doremon, doremol and its acetic ester, as well as the sesquiterpene sambulene and up to 24.41 % total sugars (Tsukurvanik and Simkhaev 1948 Khalmatov 1964). The dried roots contained many different coumarins and sesquiterpene lactones (Zhou et al. 2000 El-Razek et al. 2001). 

Many different ester compounds are released to the atmosphere by plants as shown by the following example of citronellyl formate. Although the quantities of esters released are small, they are largely responsible for the fragrances of plants and their flowers and fruits. 

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