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Towards a complete characterisation of guaiacwood oil

Published on May 1, 2018in Phytochemistry2.90
· DOI :10.1016/j.phytochem.2018.02.007
Loïc Tissandié1
Estimated H-index: 1
(CNRS: Centre national de la recherche scientifique),
Stéphane Viciana1
Estimated H-index: 1
(CNRS: Centre national de la recherche scientifique)
+ 2 AuthorsJean-Jacques Filippi13
Estimated H-index: 13
(CNRS: Centre national de la recherche scientifique)
Cite
Abstract
Abstract Guaiacwood oil is a common perfume ingredient used in modern compositions for its suave woody-rosy scent. This essential oil is a byproduct of the timber industry obtained by hydrodistillation of the heartwood of Bulnesia sarmientoi , a tree native from Latin America. Despite being widely used in perfumery, guaiacwood oil has been poorly described in the past. This study aims at giving an in-depth characterisation of its chemical composition as well as disclosing the odorant compounds responsible for its characteristic fragrance. Our methodology was based on a combination of fractionation and analytical techniques, including comprehensive two-dimensional gas chromatography coupled to mass spectrometry and preparative capillary-gas chromatography. The entire analytical work led to the isolation of 20 constituents among which 14 have never been reported so far in natural extracts. Each isolated compound was fully characterised by spectroscopic methods. Finally, the accurate knowledge of the chemical composition permitted the identification of the odour-active constituents by gas chromatography-olfactometry.
  • References (44)
  • Citations (1)
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References44
Newest
Published on Jan 1, 2018in Flavour and Fragrance Journal1.38
Teris A. van Beek31
Estimated H-index: 31
(WUR: Wageningen University and Research Centre),
Daniel Joulain13
Estimated H-index: 13
(SIDI)
The leaves of Pogostemon cablin (Blanco) Benth. (Lamiaceae) are the source of patchouli essential oil, which is - with an annual production of about 1300 tonnes - an important and unique commodity in the fragrance industry. All the literature pertaining to patchouli was critically reviewed with an emphasis on the qualitative and quantitative chemical analysis of the oil but also harvesting, fermentation, drying, distillation, used analytical techniques, sensory aspects including molecules respon...
Published on Feb 24, 2017in Journal of Natural Products4.26
Loïc Tissandié1
Estimated H-index: 1
,
Marc Gaysinski3
Estimated H-index: 3
+ 2 AuthorsJean-Jacques Filippi13
Estimated H-index: 13
Guaiacwood oil from Bulnesia sarmientoi Lorentz ex. Griseb is a common natural ingredient of the perfume industry used in both domestic and luxury fragrances for its highly appreciated woody-rosy odor, as well as its excellent fixative properties. Despite its long and traditional use as a perfume ingredient, guaiacwood oil has not been extensively studied. Thus, the chemical characterization of its constituents by using a full array of GC-hyphenated techniques (GC-MS, GC × GC-MS, and pc-GC) comb...
Published on May 1, 2016in Flavour and Fragrance Journal1.38
T. Cachet2
Estimated H-index: 2
,
Hugues Brevard9
Estimated H-index: 9
+ 14 AuthorsP. Liddle2
Estimated H-index: 2
This recommended practice enables the quantification of volatile compounds in flavourings to be made by gas chromatography with flame-ionization detection, without having authentic compounds available, and also in many cases it can avoid time-consuming calibration procedures. The relative-response factors (RRF) can be predicted from the molecular formula of the compound, and this approach can be applied to compounds containing the atoms C, H, O, N, S, F, Cl, Br, I, and Si, providing that the mol...
Published on Feb 1, 2015in Industrial Crops and Products4.19
Beatriz Lima11
Estimated H-index: 11
(National University of San Juan),
Marianela Sánchez5
Estimated H-index: 5
(Facultad de Ciencias Exactas y Naturales)
+ 3 AuthorsGabriela Egly Feresin21
Estimated H-index: 21
(National University of San Juan)
Abstract Azorella cryptantha (Clos) Reiche, Apiaceae, vernacular name “yerba del soldado or cuerno de cabra” is a medicinal herb that grows in the Andean mountains (Argentina). An infusion or decoction of the leaves is employed as cholagogue and digestive, usually to treat food-borne illnesses associated with enterobacteria. Extracts and compounds from two Argentinean populations were subjected to antibacterial assays against pathogenic bacteria ( Escherichia coli , Pseudomonas aeruginosa , Salm...
Published on Jan 1, 2015in Flavour and Fragrance Journal1.38
Emilie Belhassen4
Estimated H-index: 4
(CNRS: Centre national de la recherche scientifique),
Jean-Jacques Filippi13
Estimated H-index: 13
(CNRS: Centre national de la recherche scientifique)
+ 2 AuthorsNicolas Baldovini13
Estimated H-index: 13
(CNRS: Centre national de la recherche scientifique)
A comprehensive and critical compilation of the volatile constituents of vetiver root (Chrysopogon zizanioides L.) is presented, including those present in its essential oil. This extremely complex material has stimulated analytical research for many decades in the hope of unravelling the secrets of its composition. Up to now, more than 300 molecules have been reported, mostly sesquiterpenoids possessing a large variety of skeletons, together with their norterpenic counterparts. This review atte...
Published on Nov 26, 2014in Journal of Natural Products4.26
An-Cheng Huang6
Estimated H-index: 6
,
Christopher J. Sumby24
Estimated H-index: 24
+ 1 AuthorsDennis K. Taylor18
Estimated H-index: 18
The diastereomeric ratio of epoxidation of the internally bridged carbon–carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products g...
Published on Nov 1, 2013in Phytochemistry2.90
Sofia Mendes1
Estimated H-index: 1
(University of Lisbon),
Tayyab A. Mansoor13
Estimated H-index: 13
(University of Lisbon)
+ 2 AuthorsMaria-José U. Ferreira25
Estimated H-index: 25
(University of Lisbon)
Abstract Two unprecedented guaiane-type sesquiterpene glycosides (undulatumosides A and B) were isolated by bioassay-guided fractionation from the MeOH extract of Pittosporum undulatum fruits, along with six known compounds, including the guaiane isomers 5-guaien-11-ol and 4-guaien-11-ol. The structures of the compounds were established as 4-guaiene-11- O -β- d -(3′-angeloxy-6′-deoxy)-glucopyranoside and 1(5)-guaiene-11- O -β- d -(3′-angeloxy-6′-deoxy)-glucopyranoside by spectroscopic methods, i...
Published on May 1, 2013in Journal of Chromatography A3.86
Jean-Jacques Filippi13
Estimated H-index: 13
(University of Nice Sophia Antipolis),
Emilie Belhassen4
Estimated H-index: 4
(University of Nice Sophia Antipolis)
+ 2 AuthorsUwe J. Meierhenrich29
Estimated H-index: 29
(University of Nice Sophia Antipolis)
Abstract Vetiver essential oils (VEO) are important raw ingredients used in perfume industry, entering the formula of numerous modern fragrances. Vetiver oils are considered to be among the most complex essential oils, resulting most of the time in highly coeluted chromatograms whatever the analytical technique. In this context, conventional gas chromatography has failed to provide a routine tool for the accurate qualitative and quantitative analysis of their constituents. Applying comprehensive...
Published on Nov 27, 2012in Molecules3.06
Marcos D. P. Pereira2
Estimated H-index: 2
,
Tito da Silva4
Estimated H-index: 4
+ 3 AuthorsJulio Zukerman-Schpector1
Estimated H-index: 1
(UNESP: Sao Paulo State University)
Root extracts of Holostylis reniformis (Aristolochiaceae) yielded three new natural sesquiterpenes, a sesquiterpene with an unusual carbon skeleton, 4,5-seco-guaiane (7-epi-11-hydroxychabrolidione A, 1), a nine-membered lactone with new carbon skeleton (holostylactone, 2), and a new megastigmane [(6S ,7 E )-6,9-dihydroxy-10-(2'-hydroxy-ethoxy)-4,7-megastigmadien-3-one, 3], together with bulnesol and sitosterol-3-O-β- D- glucopyranoside. The structures of these compounds were determined by spectr...
Published on Aug 1, 2012in Journal of Essential Oil Research1.23
S. G. De Lima3
Estimated H-index: 3
,
L.B.P. Medeiros1
Estimated H-index: 1
+ 7 AuthorsF.de A.M. Reis3
Estimated H-index: 3
(State University of Campinas)
The essential oils from the fresh leaves of Croton hirtus from two locations, Teresina and Simoes in Piaui State, located in northeastern Brazil were obtained by hydrodistillation and analyzed by gas chromatography–flame ionization detection (GC–FID) and gas chromatography–mass spectrometry (GC–MS) techniques and further confirmed by 1H and 13C NMR. The main compounds found in the oil of the leaves from C. hirtus collected at Simoes were spathulenol (26.7%), E-caryophyllene (10.0%), bicyclogerma...
Cited By1
Newest
Published on Aug 1, 2019in Phytochemistry2.90
Marina Ayubova , Zahra Osman Guelleh + 2 AuthorsNicolas Baldovini13
Estimated H-index: 13
Abstract Three samples of Boswellia occulta gum resin (Grades I, II and III) were analyzed by GC-MS and GC-FID. Fifty constituents could be identified, and several of them were isolated by flash chromatography and characterized by NMR. The combinatorial synthesis of homologous series of reference constituents permitted the unambiguous identification of five 1-methoxyalkanes and one 1-methoxyalkene. In addition, we measured the 14 C content of one sample of essential oil and of a methoxyalkanes r...
Published on Jan 1, 2019in Molecules3.06
Michelle S. S. Amaral1
Estimated H-index: 1
,
Philip J. Marriott46
Estimated H-index: 46
Multidimensional approaches in gas chromatography have been established as potent tools to (almost) attain fully resolved analyses. Flavours and odours are important application fields for these techniques since they include complex matrices, and are of interest for both scientific study and to consumers. This article is a review of the main research studies in the above theme, discussing the achievements and challenges that demonstrate a maturing of analytical separation technology.
Published on Oct 1, 2018in Journal of Chromatography A3.86
Loïc Tissandié1
Estimated H-index: 1
(CNRS: Centre national de la recherche scientifique),
Hugues Brevard9
Estimated H-index: 9
(SIDI)
+ 3 AuthorsJean-Jacques Filippi13
Estimated H-index: 13
(CNRS: Centre national de la recherche scientifique)
Abstract Vetiveryl acetate is a common ingredient of the perfume industry highly prized by perfumers for its crisp vetiver note and thus often used in high-end perfume compositions. Vetiveryl acetate is currently manufactured from vetiver oil by means of various industrial processes that result in the conversion of the main vetiver alcohols into their corresponding acetates. Despite being used for decades as perfume ingredient, vetiveryl acetate has barely been studied in the past, therefore its...