| Chemical Properties | clear light yellow liquid |
| Chemical Properties | Ceylon citronella (C. nardus) and Java citronella (C. winterianus) are both perennial grasses growing more than 1 m high. The herb is harvested two to three times a year in Ceylon. The freshly cut or partially dried herb is steam distilled. The plant yields the largest amount of essential oil at about its third year of growth. Citronella is also cultivated and distilled in Java, Guatemala, Taiwan, Hainan, Argentina and New Guinea. The Java-type essential oil is considered to be of superior quality over the Ceylon type. Citronella has a characteristic citronella, rose- and lemon-like odor. The Council of Europe (CoE, 2000) has described Ceylon citronella and Java Citronella separately. |
| Chemical Properties | Citronellal has an intense, lemon-, citronella-, rose-type odor. |
| Chemical Properties | (?)-Citronellal occurs in Java citronella oil at a concentration of 35%. Racemic citronellal is the main constituent of E. citriodora oil with a content of up to 85%.
Pure citronellal is a colorless liquid with a refreshing odor, reminiscent of lemon balm. Upon catalytic hydrogenation, citronellal yields dihydrocitronellal, citronellol, or dihydrocitronellol, depending on the reaction conditions. Protection of the aldehyde group, followed by addition of water to the double bond in the presence of mineral acids or ion-exchange resins results in the formation of 3,7-dimethyl-7-hydroxy-octan-l-al (hydroxydihydrocitronellal). Acid-catalyzed cyclization to isopulegol is an important step in the synthesis of (?)-menthol. |
| Occurrence | The d-form of citronellal has been reported in the oil of citronella (Ceylon, Jammus, Kaschmis), in the oil from leaves of Barosma pulchella, in the oil from roots of Phebalium nudum and in the oils of Eucalyptus citriodora, Leptospermum citratum and Baeckea citriodora. The /-form is present in the oils of Backhousia citriodora var. A, E. citriodora, Litsea cubeba (fruits) and lemongrass. Citronellal is generally present also in the oils of lemon, mandarin, Lavandula delphinensis, Ocimum canum f. citrata and many others (Fenarolis Handbook of Flavor Ingredients, 1971). |
| Uses | rac-Citronellal is a monoterpenoid and the major isolate in citronella oil. Citronella oil is an essential oil bearing insecticidal properties. rac-Citronellal is also often used as a fragrance ingred ient. |
| Uses | citronella is used primarily as a fragrance (perfuming and masking), it also has tonic properties. It is derived from the essential oil of the Cymbopogon nardus plant, and its constituents include geraniol (approximately 60 percent), citronellal, camphene, limonene, linalool, and borneol. |
| Uses | Citronellal is a flavoring agent that is a liquid, faintly yellow with an intense odor resembling lemon, citronella, and rose. it is soluble in alcohol and most fixed oils, slightly soluble in mineral oil and pro- pylene glycol, and insoluble in water and glycerin. it is obtained by chemical synthesis; the aldehyde may be obtained from natural oils, such as citronella oil. it is also termed 3,7-dimethyl-6-octen-1-a1. |
| Definition | ChEBI: A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma. |
| Preparation | Citronellal is still isolated from essential oils in considerable quantities; it is also produced synthetically.
1) Isolation from essential oils:(+)-Citronellal is obtained from citronella oils by fractional distillation. Racemic citronellal is isolated from E. citriodora oil; when necessary, it is purified by using an addition compound, for example, the bisulfite derivative.
2) Synthesis from geraniol or nerol: Racemic citronellal can be obtained by vaporphase rearrangement of geraniol or nerol in the presence of, for example, a barium-containing copper–chromium oxide catalyst.
3) Synthesis from citronellol: Racemic citronellal can also be obtained by dehydrogenation of citronellol under reduced pressure with a copper chromite catalyst.
4) Synthesis from citral: Selective hydrogenation of citral to citronellal can be accomplished in the presence of a palladium catalyst in an alkaline alcoholic reaction medium. A continuously operating process for the hydrogenation on a palladium catalyst in the presence of trimethylamine has been developed.
5) Synthesis from myrcene: (+)- and (?)-Citronellal are available from myrcene via geranyldiethylamine, which is enantioselectively isomerized to (+)- or (?)-citronellalenamine. Hydrolysis yields pure (+)- or (?)-citronellal; see monograph menthol. |
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