Chemical Properties
CLEAR COLOURLESS TO PALE YELLOW LIQUID
Uses
(
S)-(-)-Citronellal may be used in the synthesis of bioactive compounds like (+)-hexahydrocannabinol, (
S)-isopulegol, machaeriols A and B.
Definition
ChEBI: The (3S)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).
General Description
(
S)-(-)-Citronellal is a monoterpenoid compound mainly found in
Corymbia citriodora and
Cymbopogon nardus essential oils.
Purification Methods
Fractionally distil it. Alternatively extract it with NaHSO3 solution, wash it with Et2O, then acidify it to decompose the bisulfite adduct and extract with Et2O, dry (Na2SO4), evaporate and distil. Check for purity by hydroxylamine titration. The ORD in MeOH (c 0.167) is: []700 +9o, []589 +11o, []275 +12o and []260 +12o. The semicarbazone has m 85o, and the 2,4-dinitrophenylhydrazone has m 79-80o. [(+)-compound: Tietze & Beifuss Org Synth 71 167 1993, IR: Carroll et al. J Chem Soc 3457 1950, ORD: Djerassi & Krakower J Am Chem Soc 81 237 1959, Beilstein 1 IV 3515.]
