Spectrometric identifications of sesquiterpene alcohols from niaouli (Melaleuca quinquenervia) essential oil

• Published in: Analytica chimica acta Vol. 447; no. 1-2; pp. 113 - 123
• Main Authors: Bombarda, Isabelle, Raharivelomanana, Phila, Ramanoelina, Panja A.R, Faure, Robert, Bianchini, Jean-Pierre, Gaydou, Emile M
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 26.11.2001; Elsevier
• Subjects: 2D-NMR; Alloaromadendrene; Analytical chemistry; Applied sciences; Chemical industry and chemicals; Chemistry; Essential oils, perfumes; Exact sciences and technology; Ledol; Oxidation; Reduction; Sesquiterpene aldehydes; Sesquiterpene epoxides; Sesquiterpenol; Spectrometric and optical methods; Viridiflorol; Washing products. Cosmetics and toiletries. Perfumes; Reduction; Sesquiterpenol; Sesquiterpene aldehydes; Ledol; MS; Sesquiterpene epoxides; Oxidation; Viridiflorol; 2D-NMR; Alloaromadendrene; Chemical analysis; Molecular structure; Alcohol; NMR spectrometry; Aldehyde; Two dimension spectrometry; Chemical reduction; Multicomponent analysis; Sesquiterpenes; Oxidative degradation; Epoxide; Qualitative analysis; Chemical composition; Essential oil; Mass spectrometry; Carbon 13
• ISSN: 0003-2670; 1873-4324
• DOI: 10.1016/S0003-2670(01)01307-1

Oxidation and reduction reactions on alloaromadendrene and aromadendrene sesquiterpene hydrocarbons have been investigated in order to produce alcohols with an aromadendrene skeleton for checking the chemical structure and therefore the identity of one main alcohol present in niaouli (Melaleuca quinquenervia) essential oil. Oxidation using m-chloroperbenzoic acid was carried out to produce two diastereoisomer epoxides and two corresponding aldehyde isomers for each sesquiterpene. Epoxide reductions yielded two alcohols ledol and viridiflorol, from alloaromadendrene and globulol and epiglobulol from aromadendrene. The structure determination of all compounds, i.e. epoxides, aldehydes, and alcohols, was achieved using spectrometric methods: 2D-NMR and mass spectroscopy. The stereochemistry of known sesquiterpenic alcohols, viridiflorol and ledol, has been unambiguously established.