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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 responsible for the odour, adulteration and toxicological aspects, i.e., skin sensitisation, are discussed. In total 72 constituents have been convincingly identified in the oil and another 58 tentatively. The main constituent is the sesquiterpene patchoulol. For this review over 600 papers were consulted and in the supplementary information all patchouli-related references not relevant enough to be cited in the paper itself are listed.

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 attempts to clarify some of the discrepancies related to the characterization of these constituents, which were often due to the misuses of analytical methods without enough critical consideration of the literature. The identification of the main odour impact components of vetiver is also discussed, because much contradictory information appears in the literature on this subject. Copyright © 2014 John Wiley & Sons, Ltd.

A comprehensive review is presented on the constituents of the heartwood from fragrant sandalwood species, including Santalum album, S. spicatum and S. austrocaledonicum, which are important raw materials in the fragrance industry, and S. insulare, a closely related species. Analytical aspects are discussed in detail, both on qualitative and quantitative standpoints, and sensory properties are also reviewed. It is shown that more than 230 constituents have been identified so far in the heartwood of these sandalwood species. These components belong to many different chemical classes and are mainly terpenoids, but some other families are also represented. Copyright © 2010 John Wiley & Sons, Ltd.

This is a comprehensive review of extracts from the lichen Pseudevernia furfuracea (treemoss) that are used in the fragrance industry. Qualitative and quantitative analytical aspects are critically reviewed and the results are compared to those of the related oakmoss extracts. It is shown that more than 90 constituents have been identified so far in treemoss extracts, including 42 depsides, depsidones or depside-derived compounds, and 42 triterpenes or steroids. Constituents of certain host trees, mainly Pinus species, generate specific analytical and toxicological issues which need to be considered in addition to those related to the known degradation products of lichen compounds. A new classification of lichen extracts used as raw materials in fragrance compounding is proposed. Copyright © 2009 John Wiley & Sons, Ltd.

Volatile extracts of two wild cabbages, Brassica cretica and Brassica insularis, were studied by GC–MS, GC/FID, and GC–olfactometry/aroma extract dilution analysis (GC–O/AEDA). Major compounds were 3-butenyl cyanide (70% of the total GC/FID area) and 3-butenyl isothiocyanate (29%) in B. cretica and 2-phenylethyl cyanide (53%) and 2-phenylethyl isothiocyanate (21%) in B. insularis. AEDA revealed the impact of five heteroatomic trace compounds (diacetyl, methional, furfuryl thiol, 1-octen-3-one and skatole) with moderate to high flavour dilution (FD) factors that were detected only due to GC–O analyses. Copyright © 2008 John Wiley & Sons, Ltd.

International audience; Indian cress (Tropaeolum majus L.) absolute was studied by GC-olfactometry (VIDEO-Sniff method) in order to identify odor-active aroma compounds. Because of its fruity-sulfury odor note, a compound that has never been identified in plant extracts before stood out: O,S-diethyl thiocarbonate, present at 0.1% (percentage of the total GC/FID area) in the extract. GCxGC-TOFMS allowed for a clean mass spectrum to be obtained, and isolation by preparative GC followed by NMR studies allowed its identification. Here, we report on the first detection of O,S-diethyl thiocarbonate in Indian cress absolute by GC-olfactometry/VIDEO-Sniff and on its isolation and identification. The synthesis and odor evaluation of its homologues are presented.

For a long time, exotic scents from the islands of the South Pacific have universally been appreciated. Most frequently, fragrant flowers (e.g., frangipani, jasmine sambac, tiaré, pua kenikeni) are used locally for ornamental purposes such as flower garlands (leis). Despite their powerful and delightful fragrance, very few of these flowers have been commercially employed in this part of the world for perfume manufacturing. Creative perfumers are nevertheless strongly interested to better understand these fragrances and to use them, either genuine or artificially reconstituted. Analytical results on the fragrance of these flowers are reported, together with some economical considerations.

New, odorant nitrogen- and sulfur-containing compounds are identified in cress extracts. Cress belongs to the botanical order Brassicales and produces glucosinolates, which are important precursors of nitrogen- and sulfur-containing compounds. Those compounds often present low perception thresholds and various olfactive notes and are thus of interest to the flavor and fragrance chemistry. When the study of organonitrogen and organosulfur compounds is undertaken, Brassicale extracts are one of the matrices of choice. Cress extracts were studied by analytical (GC-MS, GC-FPD) and chemical (fractionation) means to identify new interesting odorant compounds. Two compounds that have never been reported in cress extracts, containing both nitrogen and sulfur, were discovered: N-benzyl O-ethyl thiocarbamate and N-phenethyl O-ethyl thiocarbamate. These two molecules being of organoleptic interest, their homologues were synthesized and submitted to organoleptic tests (static and GC-sniffing). Their odors evolve from garlic and onion over green, mushroom- and cress-like to fresh, spearmint-like. This paper presents the origin, chemical synthesis, and organoleptic properties of a series of O-alkyl thiocarbamates.

The volatile flavor components of Mobola plum (Parinari curatellifolia), a native fruit of Southern Africa, have been isolated by a vacuum headspace concentration method. The concentrate was analyzed by hyphenated gas chromatographic techniques, including gas chromatography (GC)/mass spectrometry (MS) and GC/Fourier transform infrared (FTIR), together with other GC-coupled detection devices for the specific and selective detection of nitrogen- and sulfur-containing compounds. A total of 88 components were identified. Of these compounds, 12 contain nitrogen, including 2-aminobenzaldehyde and phenylacetaldoxime, which are detected for the first time in an edible fruit. In addition, two unusual nitrated compounds have been identified, including optically active (2-nitrobutyl)benzene, which is a new natural product. Quantitative and sensory data of the new compounds are provided.

(-)-2,6-Dimethyl-10-(p-tolyl)-2,6(E)-undecadiene (1) is a major constituent in the essential oil of Cistus monspeliensis, an aromatic shrub common in Mediterranian countries. 1 was isolated by column chromatography, subjected to ozonolyses, and the absolute configuration was determined by enantioselective gas chromatographic correlation with the ozonolysis product of the sesquiterpene hydrocarbon ar-curcumene with known absolute configuration.

The components in essential oils of Dalmatian sage, Salvia officinalis L., were identified by 1 H- and 13 C-NMR spectroscopy and by GC-MS. The diterpene manool was identified for the first time in steam-distilled oil from Dalmatian sage. Several sesquiterpenes were also identified for the first time in Dalmatian sage oils. A rapid GC method was developed and used to analyse 13 oils from a preliminary study of Dalmatian sage accessions. Oil yields from pilot-scale distillations in summer were significantly higher from non-flowering accessions than from flowering accessions. Oils from flowering and non-flowering accessions had different compositions, with significantly higher levels of thujones, β-caryophyllene and viridiflorol in oils from flowering accessions

Yeast extract-mediated reduction of 4-(4-hydroxyphenyl)-but-3-en-2-one 3 to raspberry ketone 1 occurs with transfer β to the carbonyl group of HR from NADPH and of an hydrogen atom from the solvent at α position, as indicated by experiments with (4R) and (4S) [4-2H]-NADPH and with deuterated solvent. The same extract converts 3 in 1 in the presence of NADH, but much less efficiently. In this latter case HS and not HR is transferred from the reduced cofactor to position 4 of 1. Horse liver alcohol dehydrogenase-mediated reduction of 1, bearing deuterium labelling at positions 1, 3 and 4 and obtained from 3 using the whole-cell system in the presence of D2O, gave an S carbinol possessing 0.95 ee, shown by 2H NMR studies onto the diacetate 7 to contain an excess of the (3S,4S) diastereoisomer, thus suggesting a prevalent β re-face.syn addition of hydrogen across the double bond of 3 in the whole-cell mediated conversion into 1

Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-2H2]-4-(4-hydroxyphenyl)butan-2-ol (15) and (2R,3R)-[1,3-2H4]-4-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (1R)-[1-2H]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6−C-4 framework of the intermediate raspberry ketone 1 to give the C-6−C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.

In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4‘-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4‘-hydroxyphenyl)butan-2-one (raspberry ketone, 1), and of the S and R,S forms of 4-(4‘-hydroxyphenyl)butan-2-ol (2) yields 2-(4‘-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer−Villiger-type degradation is raspberry ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4‘-hydroxyphenyl)butan-2-ol (2). Keywords: Raspberry ketone; tyrosol; degradation; Beauveria bassiana; Baeyer−Villiger oxidation; stereochemistry

The absolute prepared from an Indian commercial concrete from flowers of Jasminum auriculatum Vahl was examined. Column and molecular distillations, column chromatography and chemical function separations were carried out. GC-MS and GC-FTIR of numerous fractions thus obtained allowed the identification of 198 compounds. Among them, methyl, ethyl, (Z)-hex-3-enyl, benzyl, 2-phenylethyl and (E,E)-farnesyl esters were found, in addition to phenols and nitrogen compounds.

International audience; Odor impact compounds of Tagetes minuta L. essential oil were studied by gas chromatography (GC)-olfactometry using aroma extract dilution analysis (AEDA) and vocabulary-intensity-duration of elementary odors by sniffing (VIDEO-Sniff). AEDA was conducted by direct injection and revealed the presence of 43 odorant zones. Highest flavor dilution (FD) values were obtained for ethyl 2-methylpropanoate, ethyl 3-methylbutanoate, (E)-ocimenone, two tentatively identified thiols, and two yet unknown compounds. VIDEO-Sniff was realized by dynamic headspace sampling (D-HS) combined with 8W-GC-olfactometry where eight sniffers simultaneously detect volatile compounds obtained from a single chromatographic separation and revealed the presence of 42 odorant zones. Odorant trace compounds detected by GC-O that were present in quantities inferior to the GC-qMS system’s detection limit and those subject to coelutions were identified by GC×GC-time-of-flight mass spectrometry (TOFMS). A total amount of 37 odorant components could be identified by VIDEO-Sniff, and the strong influence of the fruity notes of numerous esters stood out. Highest olfactory signals were obtained for ethyl 2-methylpropanoate, ethyl 2- and 3-methylbutanoate, and oct-1-en-3-one. Both methods hence come to the conclusion that ethyl 2-methylpropanoate and ethyl 2- and 3-methylbutanoate are among the main odorants in Tagetes minuta L. essential oil. Differences, advantages, and drawbacks of both GC-O methods are discussed.

Forty-one compounds have been identified in the essential oil of Ruta angustifolia. Besides the already known compounds, seven derivatives possessing the 3,4-methylenedioxyphenyl moiety were identified, including piperonyl acetone and a novel olefinic derivative 8-(3,4-methylenedioxyphenyl)-1-octene.

Four sesquiterpenes (1-4) with the africanane skeleton [of which only 5-africanene (1) has been previously reported] and the new asteriscane derivative asterisca-3(15),6-diene (5) were isolated from the essential oil of Lippia integrifolia. A further new compound, african-2(6)-ene (7), was obtained as a semisynthetic product by derivatization of isoafricanol (6). The structures of the new compounds were assigned on the basis of spectroscopic data, enantioselective gas chromatography, and by chemical correlations.

A targeted search for heliotropin (or piperonal) in the flower fragrance of heliotrope and in cured vanilla beans of Tahitian origin is reported. Heliotropin is not detected in the fragrance emitted by heliotrope, using dynamic headspace SBSE sampling, followed by thermal desorption and analysis by conventional GC-MS. Main constituents are anisaldehyde and benzaldehyde, which confirms previous findings. Less than one part per million of heliotropin is accurately detected in authentic Tahitian vanilla bean, in using both GC-MS and LC-MS/MS. This confirms previous observations, which had shown that 4-methoxyaromatic compounds are the characteristic elements in the flavor of Tahitian vanilla, with p-anisaldehyde as the the main aroma donator. We suggest that heliotropin was named after the discovery of piperonal by degradation of piperine, the odor of which was reminiscent of the heliotrope flower. Later, its identification in vanilla extracts was the result of either a wrong interpretation of analytical data, or, much more probably, adulterations of these extracts. As a result, heliotropin should not be cited any longer as a characteristic consituent of Tahitian vanilla.

Among the character-donating components of the fragrance of Wisteria sinensis flowers, two new β-chromenes were detected by GC-MS and GC-FTIR of

The essential oil of Ruta graveolens produced in Malaysia was subjected to analysis by GC/MS. Thirty compounds representing ca. 82% of the oil were identified. The major compounds were 2-undecanone (30.73%), 2-nonanone (18.06%) and 2-nonyl acetate (11.03%). Psoralen (1.28%) and bergaptene or xanthotoxin (7.24%) also were identified in the oil.

The fragrance given off by certain springtime flowers was the subject of a previous communication. We now present the results from further analyses of flower headspaces from cultivated and wild plants (including trees), which bloom at the end of spring and in summer in the Grasse region: Sambucus nigra L. (elder), Ligustrum ovalifolium (privet), Ligustrum vulgare L. (common-privet), Ailantus glandulosa Desf., Magnolia grandiflora L. and Trachelospermum jasminoides. We bring further information about the composition of the headspace from Philadelphia coronarius L. flowers (seringat), which were only briefly reported in our first communication. We confirm that the odoriferous emissions from flowers contain some chemical substances which are not readily detected in the corresponding extraction or hydrodistillation products. Such constituents include, for example, terpenoids and aliphatic amino acid derivatives, some of which may be considered as new natural products.