WO2025045859A1 - Method for the ecological extraction of volatile organic compounds from fragrant plant matter by virtue of the plant fibre of ceiba pentandra - Google Patents

Abstract

The invention relates to the field of the extraction of natural fragrances used in cosmetics and in perfumery. In particular, the invention relates to a method for the ecological extraction of volatile compounds from fragrant matter by virtue of the fibre of Ceiba <i /> pentandra. The fragrant matter is in particular plant matter such as flowers.

Description

ECOLOGICAL EXTRACTION PROCESS OF ORGANIC VOLATILE COMPOUNDS FROM ODORAL PLANT MATTER USING CEIBA P ENTANDRA PLANT FIBER

The invention relates to the field of extraction of natural scents used in cosmetics and perfumery. More particularly, the invention relates to a method for eco-extraction of volatile compounds from odorous matter using Ceiba fiber. pentandra . The fragrant matter is particularly plant matter such as flowers.

Field of invention

The history of perfumes dates back to Antiquity with the use of the still and raw materials such as flowers, aromatic plants and resins.

In the Middle Ages, after a decline in perfumery due to the barbarian invasions, the reopening of Roman trade routes allowed the discovery of many fragrances, including those from spices. In addition, the discovery of alcohol and the distillation technique greatly contributed to the rise of perfumery.

The Renaissance was very marked by perfumery, with in particular the use of amber, musk, jasmine and tuberose. New raw materials (cocoa, vanilla, tobacco, pepper and cardamom) brought back by the great explorers were used. It was also at this time that Paris began to welcome the first perfumers and the great perfume houses.

In the century of Louis XIV, perfumery was omnipresent, French production of raw materials developed with the installation of large-scale plantations of rose, jasmine, tuberose (among others) in the Grasse region. This city then became, and still is today, the "World Capital of Perfume". The International Perfume Museum is also located in Grasse.

In the ^19th century, the French Revolution led to a further decline in perfumery. But from the Consulate and the Empire of Napoleon and Empress Josephine, perfumery came back in force.

At the end of the ^19th century and the beginning of the 20th ^century , the first industries were set up in Grasse (Chiris, Roure, Tournaire, Charabot, Robertet, etc.) and the first synthetic molecules appeared. This was the beginning of perfumery as we know it today. Since then, we have witnessed a real democratization of perfumes. It should be noted that modern perfumery has developed considerably, it is marked by several trends (mixed fragrances, niche perfumes, room fragrances, etc.).

The field of perfumery undoubtedly still has a bright future due, on the one hand, to the many technical advances that continue to be recorded in the field of extraction (extraction by supercritical fluid CO ₂ , extractions assisted by microwaves and ultrasounds, micro-extraction on solid phase, etc.) and analytics (gas chromatography coupled with mass spectrometry and olfactometry, etc.) and, on the other hand, to the use and appreciation of perfumes on a global scale. Indeed, two bottles of perfume are sold every second and the global perfume market is expected to reach more than 50 billion dollars by 2024.

Several techniques for extracting odorous compounds have been developed over the centuries in the cosmetics and perfumery industry. Some, such as enfleurage, are rarely or no longer used. On the other hand , supercritical _CO2 extraction is booming, while hydrodistillation and volatile solvent extraction are the two most common techniques.

Volatile solvent extraction consists of macerating flowers in an organic solvent such as cyclohexane in order to obtain a perfumed ointment/paste called “concrete”. This is then “washed” with ethanol to obtain the “absolute” which is a concentrate of odorous volatile compounds. However, this technique has drawbacks. Indeed, hexane is a petroleum-based solvent (therefore non-renewable) which turns out to be harmful, irritating, CMR (Carcinogenic Mutagenic Reprotoxic), toxic to aquatic organisms and whose liquids and vapors are flammable.

It is therefore necessary to find a more environmentally friendly alternative solution to extract the odorous compounds present in plant and animal materials used in perfumery and cosmetics.

The present invention addresses this problem by proposing an ecological process for extracting volatile organic compounds (VOCs) from an odorous material using a plant fiber from the Ceiba species. pentandra including the steps of:

- Obtaining plant fiber surrounding the fruits of the Ceiba species pentandra

- Removal of the wax present on said fiber by washing with absolute ethanol, then drying

- Capture of VOCs by bringing said odorous material into contact with said plant fiber

- Desorption of VOCs from said plant fiber in an absolute ethanol bath

- Filtration to obtain an ethanolic extract containing the VOCs

Advantages of the invention

The only organic solvent used during the process is absolute ethanol, a green solvent, non-toxic to humans and the environment. This makes it possible to obtain odorous products free of petrochemical solvent residues, which is an innovative result. Thus, the process provides access to odorous products of high olfactory quality and safe for consumers. These high added value products are intended for the fields of perfumery and cosmetics.

The VOC capture step by kapok fiber can be carried out using two distinct methods, static extraction and dynamic extraction. The olfactory profile of the extracts obtained by these two methods differs from those obtained by conventional methods (extraction by organic solvents of petrochemical origin in particular), but also from each other. These odorous extracts are different, chemically and olfactorily, from the absolutes and concretes used by perfumers. The process according to the invention therefore makes it possible to offer new natural olfactory extracts that enrich the range of perfumery raw materials.

The method according to the invention can be implemented on a large scale, the method based on dynamic extraction being particularly suitable for industrial exploitation.

Unlike state-of-the-art processes, the process according to the invention does not require separation of the concrete into waxes/absolutes. The final odorous product can be offered in the form of dry matter or absolute, the concentration of which is controlled (by dissolution of the dry matter).

After desorption, the fiber can be reused several times, which reinforces the ecological aspect of the process.

The process is applicable to any odorous material, of plant or animal origin. The process parameters can be adapted according to the odorous material considered in order to optimize the extraction of VOCs and the olfactory rendering of the extract. Flowers, whose odors are highly sought after, can be treated specifically according to their fragility, their fermentation speed, but also the time of harvest which will influence the characteristics of the extract obtained.

DETAILED DESCRIPTION OF THE INVENTION

The subject of the present invention concerns an ecological process for extracting VOCs from an odorous material using a plant fiber from the Ceiba species. pentandra including the steps of:

- Obtaining plant fiber surrounding the fruits of the Ceiba species pentandra

- Removal of the wax present on said fiber by washing with absolute ethanol, then drying

- Capture of VOCs by bringing said odorous material into contact with said plant fiber

- Desorption of VOCs from said plant fiber in an absolute ethanol bath

- Filtration to obtain an ethanolic extract containing the VOCs

By "volatile organic compounds - or VOCs -" we mean compounds which, due to their physicochemical characteristics, have a very low boiling point and which can therefore evaporate easily; this is called volatility. The higher the vapor pressure of a compound, the more volatile it is. This term VOC covers a wide variety of chemical substances which have in common that they are carbon compounds and are volatile at room temperature. 80% of volatile compounds emitted into the atmosphere are of natural origin, mainly emitted by plants. All parts of a plant, i.e. the leaves, flowers and roots, can emit VOCs. In the context of the present invention, the VOCs (odorous molecules) described are emitted by flowers and are therefore of natural origin. These volatile odorous molecules are responsible for the characteristic odor of each flower. These are mainly terpene compounds (monoterpenes and sesquiterpenes), fatty acid derivatives and phenylpropanoids and benzenoids (phenylalanine and tryptophan derivatives).

The plant fiber used in the process comes from the Ceiba fruit pentandra . The fruits should be harvested and then the fiber called "kapok fiber" should be separated from the seed. Since the fiber is covered with a waxy substance, this wax should be removed; this step is carried out by washing in absolute ethanol. The washed fiber is then dried. Drying can be carried out by any method known to those skilled in the art, such as air drying or drying in a blower, in a healthy environment free of contaminating VOCs.

The removal of wax helps ensure that the fiber is free of any contaminating VOCs. Indeed, the wax present on the fiber has been in contact with many odorous compounds throughout the fruit’s development phase, up until its harvest and after (transport, storage, etc.).

“Contaminating VOC” means any VOC originating from an odorant source other than the odorant material from which the extract is prepared.

The washed and dried fiber is ready to be used for VOC extraction.

The quality of the fiber as a "VOC receptacle" is based on the absence of contamination by odors other than those sought and coming from the odorous material of interest. This quality is obtained by removing the wax and then ensuring that the fiber is dried, handled, transported, stored, etc. in an environment containing a minimum, or even the absence (depending on the level of requirement applied) of contaminating VOCs. These precautions will avoid the presence of artifacts in the odorous extract obtained.

Thus, in a preferred embodiment of the invention, the drying of the fiber is carried out in an environment free of contaminating VOCs. This absence of contaminating VOCs can be obtained for example by drying the fiber in air if it is clean (odorless), under an extractor hood, or in a clean blower.

The capture of VOCs from the odorous material by the plant fiber can be carried out by static or dynamic extraction.

In a first embodiment, the capture step is carried out in static conditions in a non-hermetically sealed container for a period of between 3 and 30 hours.

The odorant is simply placed in a container with the fiber. The container will be closed to promote the concentration of VOCs in the enclosed space so as to optimize their capture by the fiber. The container will be closed in a non-hermetic manner so that air can pass through and prevent the degradation of the odorant by fermentation.

When it comes to flowers, you can place them in the container and cover them with plant fiber.

The duration of contact between the odorous material and the fiber will be determined according to the nature of the odorous material and the desired olfactory result.

In a second embodiment, the capture step is carried out under dynamic conditions in a reactor having a means of circulating air, namely:

- the odorous material is placed in the reactor tank, and the plant fiber is placed in a separate compartment, the whole being subjected to an air flow circulating from the odorous material to the fiber,

- the duration of contact between the odorous material and the plant fiber is between 1 hour and 5 hours.

The means of circulating air may be a vacuum pump or any other equivalent device.

VOC capture is faster by the dynamic extraction method than by static extraction, the air flow accelerating the passage of VOCs towards the fiber. This method can be considered advantageous and is more easily industrialized. However, comparative tests show that the extracts obtained are chemically and olfactorily different (see Example 4). These two methods are therefore alternatives, allowing access to qualitatively different extracts.

The duration of contact between the odorous material and the fiber will be determined according to the nature of the odorous material and the desired olfactory result.

Once captured by the plant fiber, the VOCs are recovered by desorption in a bath of absolute ethanol. The fiber is thus immersed to allow the transfer of VOCs to the absolute ethanol. The mixture is then filtered to recover the fiber, remove the fluffy residues from the fiber and obtain a clear extract: the ethanolic extract containing the VOCs.

Filtration can be microfiltration or ultrafiltration, depending on the level of purity required for the intended use, this does not change the quantity/nature of VOCs present in the extract. The odorous ethanolic extract can be used as is.

The process may include an additional step of evaporating the absolute ethanol at a temperature less than or equal to 40°C.

Evaporation can be promoted using a rotary evaporator under reduced pressure (in this embodiment the pressure is calibrated at 58 mbar) and/or under nitrogen flow. In practice, the evaporation flow rate is preferably reduced to limit the evaporation of highly volatile odorous compounds. For example, it is possible to first use a rotary evaporator to remove most of the ethanol and then, once the amount of ethanol has been reduced, to finalize the evaporation under nitrogen flow until a dry material is obtained.

The dry matter thus obtained can either be used as is, as a finished product, or be resuspended in absolute ethanol to obtain an absolute whose concentration is defined. The dry matter and absolute thus obtained are two high-quality odorous raw materials for perfumery and cosmetics.

The starting odorant material can be a plant material or an animal material. Plant odors are particularly sought after and the process is suitable for the extraction of VOCs from plant material such as flowers, bark, resins and leaves.

The present invention will be better understood from the following examples, provided for illustration purposes and in no way to be considered as limiting the scope of the present invention.

DESCRIPTION OF FIGURES

: Scanning electron microscopy (SEM) images of kapok fibers (a) and degreased cotton fibers (b).

 : Treatment of Ceiba pentandra fibers (© FLOR).

: Static mode VOC extraction steps using kapok fiber.

: Dynamic mode VOC extraction system (© FLOR).

: Chromatogram of the “static” kapok extract of Cananga odorata from February 1, 2022.

: Chromatogram of the “dynamic” kapok extract of Cananga odorata from April 28, 2022.

: Distributions (in %) of families of molecules identified in the “static” kapok extract (left) and in the dynamic kapok extract (right) of Cananga odorata.

: Radar diagrams grouping the olfactory descriptors of static (left) and dynamic (right) kapok extracts of Cananga odorata.

: Chromatogram of the “static” kapok extract of Michelia champaca from Dec. 27, 2021.

: Chromatogram of the “dynamic” kapok extract of Michelia champaca from January 5, 2022.

: Distributions (in %) of families of molecules identified in the “static” kapok extract (left) and in the dynamic kapok extract (right) of Michelia champaca.

: Radar diagrams grouping the olfactory descriptors of the static kapok (left) and dynamic kapok (right) extracts of Michelia champaca.

: Chromatogram of the “static” kapok extract of Plumeria alba from December 21, 2021.

: Chromatogram of the “dynamic” kapok extract of Plumeria alba from December 15, 2021.

: Distribution (in %) of families of molecules identified in the “static” kapok extract (left) and in the dynamic kapok extract (right) of Plumeria alba.

: Radar diagrams grouping the olfactory descriptors of the static kapok (left) and dynamic kapok (right) extracts of Plumeria alba

EXAMPLES EXAMPLE 1: Description of kapok fiber

The plant fiber used in the VOC extraction process is the fiber from the fruits of Ceiba pentandra . These were collected at the Parc de la Trinité on Reunion Island in October and November 2021 and 2022.

• Ceiba occidentalis (Spreng.) Burkill
• Bombax pentandrum L.
• Eriodendron anfractuosum DC.
• Eriodendron pentandrum (L.) Kurz
• Xylon pentandrum (L.) Kuntze

The scientific name of this tree is Ceiba pentandra (L.) Gaertn. (WFO, 2023). This species has several synonyms according to WFO (WFO, 2023) and the Tropicos Base of the Missouri Botanical Garden (Tropicos, 2023), the best known being:

• Ceiba occidentalis (Spreng.) Burkill
• Bombax pentandrum L.
• Eriodendron anfractuosum DC.
• Eriodendron pentandrum (L.) Kurz
• Xylon pentandrum (L.) Kuntze

The vernacular names associated with Ceiba pentandra are Ouatier, Fromager, Kapokier, Kapok, Lovers' tree, Bois coton, Arbre à boure, Mapou, Bois diable (Tropicos, 2023; Plantnet, 2023).

The taxonomy of the genus Ceiba is presented in Table I below.

Gender classification Ceiba Reign Plantae Sub-kingdom Viridiplantae Class Equisetopsida Subclass Magnoliidae Order Malvales Family Malvaceae Gender Ceiba

Table 1 : Taxonomy of the genus Ceiba (Tropicos, 2023).

Ceiba pentandra is native to tropical regions of the Americas, including Central and South America.

This tree has become pantropical and is currently present in tropical rainforests and savannahs. Thus, it is found distributed on several continents, notably in East Africa and in the forests of Southeast Asia (Indonesia, Cambodia, Philippines, Thailand). It has also been introduced to the Antilles and the Pacific Islands and is known to be invasive in certain regions of the globe.

In the Mascarene archipelago, particularly in Reunion and Mauritius, it is only present in a cultivated state and is distributed over a large part of the island (in gardens, parks and urban spaces). However, it is planted less and less in private gardens because it is a tree that takes up a lot of space. It is considered exotic and non-invasive in these islands (CBNM, 2023).

Ceiba pentandra is an imposing tree dominating the canopy and can reach up to 60 m in height and 2 m in diameter. Its fruits are large elliptical capsules 20 cm long. Each of them can contain 60 to 250 ovoid seeds 4 to 6 mm in diameter, surrounded by the "kapok fibers", used in the present invention. This fiber is covered with a waxy substance that makes the fruits waterproof. This configuration is particularly suitable for dispersal by wind and water.

Kapok is a very light, yellowish-white natural plant fiber that has a texture similar to cotton. It consists of single-cell fibers that are themselves composed of cellulose (64%), pentosan (23%), and lignin (13%) on their lignocellulosic systems (Ying YT et al. , 2012; Lorelei A. et al. , 2013; Zheng Y. et al. , 2015). Kapok fiber, with low density, has a cylindrical shape, a smooth surface with a thick wax layer, and a thin cell wall (8–10 μm in diameter and 0.8–1.0 in wall thickness) (Zheng Y. et al ., 2015). In addition, it has a hollow structure that gives it a strong ability to transmit light and a high porosity (80%). All these characteristics distinguish it from other fibers (Zheng Y. et al ., 2015). shows the physical difference between kapok fibers (a) and cotton fibers (b) (Zheng Y. et al ., 2015). Indeed, cotton fibers have a helical structure while kapok fibers are smooth.

E EXAMPLE 2: Extraction of VOCs grace to Kapok fiber

Odorous raw material

For the implementation of this eco-extraction technique of new scents, three plants were chosen: Cananga odorata (Ylang-Ylang), Michelia champaca (Champac) and Plumeria alba (White frangipani). The extraction can be carried out from several organs of the plant (leaves, flowers, fruits, etc.) but for this study we chose to use flowers only.

The three flowers were collected in Reunion Island during their flowering period, between November and April during the years 2021, 2022 and 2023.

Fiber processing

It is necessary to treat the fiber in order to remove as much as possible the waxes present on the surface of the fibers which would otherwise be found in too great a quantity in the extract. To do this, the plant fiber was removed from the fruits and then separated from the seeds. It was then introduced into an Erlenmeyer flask and ethanol was added so as to cover it completely (approximately 500 mL for 2g of fiber). The washing was carried out under magnetic stirring for 24 hours. After these 24 hours, the solution was filtered (using filter paper) to remove the alcohol and the washed fiber was distributed in several crystallizing dishes in order to dry. Once dry, it was stretched in order to increase its contact surface and then stored in a glass jar before use. These fiber treatment steps are presented in .

Extraction of volatile odorous compounds and desorption of fibers in the EtOH

For the two protocols described below, flowers were used. However, it is quite possible to use other odorous raw materials (resins, leaves, roots, fruits, etc.). The extraction of volatile compounds is carried out according to two capture modes: a so-called “static” capture and another so-called “dynamic” capture, each followed by the desorption of the fibers by ethanol.

“Static” extraction

Freshly picked (not wet) flowers were arranged in a thin layer in a crystallizer. The kapok fibers were then arranged so as to cover the flowers completely and homogeneously (i.e. approximately 2g of kapok fiber per 100g of flowers).

Then, the crystallizer was covered with aluminum foil (to limit the evaporation of volatile compounds and avoid external contamination) which is pierced to prevent the fermentation of the flowers (container closed in a non-hermetic manner). The crystallizer is then placed in a non-odorous place for the duration of the extraction. This generally varies between 3h and 23h and can be repeated once depending on the physical state of the flower.

After extracting the VOCs by static capture, the kapok fiber was placed in an Erlenmeyer flask, then covered with absolute ethanol and stirred magnetically for 1 to 3 hours. The whole was then filtered (on filter paper) and the fiber was pressed above this filter in order to recover a maximum of ethanolic solution. Finally, the fiber was dried in a crystallizer under a hood before being stored for further use.

The ethanol containing the volatile odorous compounds was then evaporated using a rotary evaporator. The bath temperature should not exceed 40 °C and the evaporation rate should be reduced to limit the evaporation of highly volatile odorous compounds. It is important to monitor the evaporation to avoid evaporating the product to dryness. A few milliliters of extract should be left in the flask, then the remainder should be transferred to an amber pillbox using a glass pipette. The steps for extracting VOCs in static mode using kapok fiber are presented in .

“Dynamic” extraction

The “dynamic” extraction was carried out using a reactor (IKA LR 1000 Basic) and is presented in . For this, a known mass of fresh flowers (not wet) was introduced into this reactor and then the kapok fiber was inserted into a glass tube connected on one side to the reactor and on the other to the vacuum pump. Thus, with the suction created by the pump, the volatile compounds of the flowers contained in the reactor were adsorbed on the fiber. The extraction duration was 3 hours and can be repeated depending on the physical state of the flower.

The step of desorption of the odorous fiber with ethanol as well as the evaporation of the latter are the same as for “static” extraction.

The samples obtained from both extraction methods were then dried under nitrogen flow to calculate the yield, then kept cool (4°C) pending analysis.

EXAMPLE 3: Methods for c characteristics ation excerpts odorous obtained

Sample preparation : In order to be analyzed by gas chromatography and olfactory, the extracts were filtered with a PTFE filter (Sartorius stedium biotech, pore size: 0.20 μm, filter diameter 25 mm) before being dried under nitrogen flow. Then, they were diluted to 10% in absolute ethanol.

GC-MS analysis : Qualitative analyses of samples obtained by gas chromatography (GC) were performed on an Agilent 8890N system equipped with an SPB-5 capillary column and coupled to an Agilent 5977B mass spectrometer (MS). The system is completed by a Gerstel automatic sample changer (Liq., HS, Twister desorption).

The analysis conditions are detailed below:

Gas chromatography

Column: SPB-5 (L = 60 m, di = 0.32 mm, e = 0.25 μm)

Carrier gas & flow rate: helium, 0.5 mL/min

Injector type: Split / Splitless (SSL)

Injection mode: Splitless

Injector temperature: 250°C

Injected volume: 5 μL

Temperature programming: from 60°C to 250°C (at 4°C/min) with a final level of 15 min

Runtime: 62.5 min

Mass spectrometry

Ionization mode: electronic ionization

Ionization current: 70 eV

Mass range: 30 to 300 amu

A table of alkanes (C8 to C22) was injected under the same conditions in order to calculate the Relative Retention Indices (RRI) of each compound. The RRI was calculated according to the following equation defined in temperature programming:

With :

X: compound to be identified

C: hydrocarbon

n and n+1: number of carbon atoms of the two paraffins which surround the compound X

t(X): retention time of compound X

t(C _n ) and t(C _n+1 ): retention time of the two paraffins surrounding compound X

In order to identify the molecules present in the extracts, two parameters were taken into account. These are the mass spectra and the calculated retention indices (IRR) of each compound. The latter were compared to those of the Nist02 and Wiley7n databases and the literature (Adams, 2017). The identification was validated if the experimental IRR is close to that of the databases and if the mass spectra are identical.

The contents (in percentage) of each molecule were obtained with the mass spectrometer (MS). The entire chromatogram is integrated by reprocessing software. Thus, the contents are calculated by calculating the ratio (in %) between the peak area of the molecule of interest and the total area of the chromatogram.

GC-O/MS analysis : The olfactory analysis of the samples obtained was performed on a Perkin Elmer GC system coupled in series to a SQ 8T Single Quadrupole MS mass spectrometer and a SNFR Olfactometry Port GC olfactometer. The GC oven was equipped with an Elite-5 MS capillary column. The volatile compounds were identified by comparing their mass spectra with the Nist20 database and by comparing the olfactory descriptors obtained during the analysis with those of the reference website “The Good Scents company” for a given molecule.

During the GC-O analysis, the olfactory intensities were also recorded (light, medium, strong, very strong).

Olfactory characterization of extracts

Olfactory characterization is a crucial step in the development of perfumes or cosmetic products. It consists of assigning olfactory descriptors and then evaluating them.

In this case, the extracts obtained with the two capture techniques were evaluated by an independent perfumer from Grasse and by two research engineers (specially trained for this purpose). The olfactory descriptors were proposed by taking into account the chemical composition of the sample and using a language specific to perfumery. Then, for each descriptor, a score from 0 to 6 was assigned in order to establish radar graphs for each extract (0 being an absence of olfactory impact and 6 being a strong olfactory impact).

EXAMPLE 4 : Characterization of VOCs obtained by the two extraction methods, static and dynamic, for 3 different flower species

The new technique for extracting odorous VOCs, with two modes of capture “static” and “dynamic” was applied to three flowers: Cananga odorata , Michelia champaca and Plumeria alba . The extraction was carried out in triplicate to verify the reproducibility of the technique and validate the results. However, only the results of the analysis of a single “static” and “dynamic” extract are presented for each flower.

Study of volatile compounds from flowers of Cananga odorata

Cananga Kapok Extracts odorata were obtained using two batches of flowers picked in 2022 in Sainte-Clotilde: that of January 31 was used for the static capture technique, and that of April 28 for the dynamic capture technique.

The static extraction was carried out for 3 hours and then for 17h30 with renewal of the kapok fibers. As for the dynamic extraction, it lasted twice 3 hours with also a change of the fibers between the two extractions. Then, the fibers were desorbed in ethanol for 3 hours. The GC-MS chromatograms are presented below and are followed by the summary tables of the compounds identified for the two extracts (with their respective contents).

The results obtained using the two extraction methods, static and dynamic, are presented in Figures 5 and 6 respectively in the form of chromatograms.

Tables 2 and 3 below report the chemical compositions of the extracts obtained by static extraction and dynamic extraction. Table 3 compares the chemical compositions of these same extracts obtained by static extraction and dynamic extraction with an extract by solid phase microextraction (SPME) with regard to the majority compounds.

Compounds % of CG-MS areas Olfactory descriptors (The good scents & Flavor base) Kapok st.
010222 Dynamic kapok.
280422 Alcohols 2,3-butanediol (isomer) 1.5 - Fruity, creamy, smooth diethylene glycol - 0.8 - Ketones 3-hydroxy-2-butanone 0.3 - Sweet, buttery, creamy, milky, fatty ( Z )-jasmone - 0.5 Woody, herbaceous, floral, spicy; scent of jasmine, celery Oxygenated monoterpenes eucalyptol - m (0.2) Fresh, herbaceous, camphoraceous; eucalyptus scent linalool m (2.3) m (16.7) Floral, woody; citrus scent α-terpineol - 1.4 Woody, resinous, floral, refreshing, citrus; scent of pine, lilac nerol - 0.3 Sweet, citrus; smell of neroli, magnolia general - 0.9 Sweet, citrus; smell of lemon, lemon zest geraniol - 6.9 Sweet, floral, fruity, waxy, citrus; rose scent geranial - 1.1 Citrus; lemon smell geranyl acetate m (0.2) 10.0 Sweet fruity, floral, pink, green; smell of apple, lavender cinnamaldehyde diethyl acetal - - Spicy; smell of cinnamon geranial diethyl acetal - 0.3 Green, fresh, waxy, citrus; smell of lemon zest Hydrocarbon sesquiterpenes α-copaene 0.7 - Woody, spicy β-ylangene 0.8 - - ( E )-caryophyllene 1.7 - Woody, spicy, dry β-copaene 0.6 - Sweet; smell of lilac, lemon α-humulene 0.8 - Woody, sweet, slightly spicy germacrene D 8.6 0.6 Woody, minty, hay, tea, tobacco smell α-farnesene 13.3 3.3 Herbaceous, green, citrus 0.2 - Dry, woody; slight burnt smell Oxygenated sesquiterpenes germacrene D-4-ol 0.8 0.3 - ( 2Z , 6E )-farnesol 0.4 - Light, soft, delicate, oily, slightly floral ( 2E , 6E )-farnesyl acetate 1.4 0.2 Oily, waxy Aromatic compounds prenyl acetate - - Fruity, sweet, fresh, smell of banana, jasmine p -methylanisole - 0.1 Acrid, spicy, sweet, floral (in dilution green-hazelnut note) benzyl alcohol 17.7 8.4 + m (0.1) Light, soft, fruity, sweet phenylacetaldehyde - - Strong, floral, green; smell of rose, hyacinth p -Cresol 0.5 0.7 Phenolic, animal, medicinal; smell of narcissus, tar o -guaiacol 0.7 1.8 Oily, floral, waxy; smell of rose, lemon (in dilution) methyl benzoate m (4.0) m (7.3) Pungent, sweet, floral, fruity phenylethyl alcohol 1.5 0.7 Floral; scent of rose, dried rose benzene acetonitrile - - - benzyl acetate 7.1 7.1 Sweet, floral, fruity; scent of jasmine, gardenia ethyl benzoate 0.6 - Sweet, balsamic, slightly bitter, fruity creosol 0.3 - Spicy, phenolic, medicinal, leathery, woody, smoky, burnt; smell of cloves, vanilla methyl salicylate 0.2 0.7 Warm, sweet; smell of wintergreen 2-phenylethyl acetate 0.4 0.8 Sweet, fruity, smell of rose, honey ( E )-cinnamaldehyde - 0.4 Woody, spicy, dry p -anisic alcohol 0.2 - Sweet, powdery, floral; scent of hawthorn, lilac, rose, hyacinth ( E )-anethole 0.3 0.4 Sweet, herbaceous, aniseed indole 1.2 1.6 Floral, powerful, diffuse 2-phenylnitroethane 6.5 10.1 Sweet, floral, warm-spicy; vanilla scent ( E )-cinnamic alcohol 2.9 1.6 Sweet, floral, fresh, spicy 2-methyl methoxybenzoate 1.6 1.3 Herbaceous, sweet; smell of anise, green vegetables, red currants benzyl butanoate - - Fresh, fruity, tropical; scent of jasmine, apricot, pineapple, apple, loganberry methyl anthranilate 0.3 0.5 Fruity, smell of grape, wine, orange blossom, neroli eugenol 0.2 - Sweet, spicy, woody; smell of cloves p -methyl anisate m (0.5) - Sweet, aniseed, vanilla p-anisyl acetate 0.3 0.2 Sweet, powdery, balsamic, vanilla, fruity; smell of plum, cherry, tonka ( E )-cinnamyl acetate 5.4 7.5 Sweet, balsamic, floral, fruity ( E )-isoeugenol 5.4 0.9 Warm, spicy; smell of cloves prenyl benzoate 1.1 - Balsamic, fruity; smell of chocolate, ylang-ylang, tea cinnamaldehyde diethyl acetal - 0.1 Spicy; smell of cinnamon ( E )-isoeugenol acetate - - Spicy; clove scent coniferyl alcohol 0.5 0.2 - benzyl benzoate 2.8 1.9 Sweet, balsamic with slight bitter notes benzyl salicylate 1.8 0.3 Sweet, floral, balsamic verimol K - - - % total of compounds identified 97.5 98.1   Number of compounds n.i. 8 5   % of n.i. compounds 2.5 1.9   Alcohols 1.5 0.8 st. : static Ketones 0.3 0.5 dyn.: dynamic Oxygenated monoterpenes 2.5 37.7 n.i.: unidentified Hydrocarbon sesquiterpenes 26.8 3.9 m: mixture Oxygenated sesquiterpenes 2.6 0.6 Majority compound Aromatic compounds 63.8 54.6 % of compound > 4% neither. 2.5 1.9 TOTAL 100.0 100.0

Table 2 : Chemical compositions (% of MS areas) and distribution by family of the molecules identified in the “static” and “dynamic” kapok extracts from Cananga smell - Majority compounds.

Compounds % of CG-MS areas Olfactory descriptors (The good scents & Flavor base) SPME Kapok st.
010222 Dynamic kapok.
280422 linalool - m (2.3) m (16.7) Floral, woody; citrus scent geraniol - - 6.9 Sweet, floral, fruity, waxy, citrus; rose scent geranyl acetate m (0.6) m (0.2) 10.0 Sweet fruity, floral, pink, green; smell of apple, lavender ( E )-caryophyllene 4.1 1.7 - Woody, spicy, dry germacrene D 28.8 8.6 0.6 Woody, minty, hay, tea, tobacco smell α-farnesene 30.2 13.3 3.3 Herbaceous, green, citrus p -methylanisole 0.4 - 0.1 Acrid, spicy, sweet, floral (in dilution green-hazelnut note) benzyl alcohol 0.2 17.7 8.4 + m (0.1) Light, soft, fruity, sweet methyl benzoate 1.2 m (4.0) m (7.3) Pungent, sweet, floral, fruity benzyl acetate 2.9 7.1 7.1 Sweet, floral, fruity; scent of jasmine, gardenia 2-phenylnitroethane 1.8 6.5 10.1 Sweet, floral, warm-spicy; vanilla scent ( E )-cinnamyl acetate 5.6 5.4 7.5 Sweet, balsamic, floral, fruity ( E )-isoeugenol 0.2 5.4 0.9 Warm, spicy; smell of cloves benzyl benzoate 7.5 2.8 1.9 Sweet, balsamic with slight bitter notes benzyl salicylate 0.9 1.8 0.3 Sweet, floral, balsamic % total of compounds identified 96.6 97.5 98.1   Number of compounds n.i. 8 5   % of n.i. compounds 3.4 2.5 1.9  

Table 3 : Chemical compositions (% of MS areas) and distribution by family of the majority molecules in the “static” and “dynamic” kapok extracts and SPME from Cananga smell .

There presents the distribution (in %) of the families of molecules identified in the extracts from Cananga flowers odorata depending on the extraction mode applied .

Descriptors Associated olfactory molecules Kapok st. 010222 Dynamic Kapok 280422 Animal fecal indole 1 0 horse animal p-cresol, creosol, guaiacol 1 3 Citrus lemon neral, geranial, geranial diethyl acetal 0 2 Almond balsamic cinnamic alcohol 3 0 Fruity green geranyl acetate, benzyl acetate, benzyl alcohol 3 1 Cooling flowers methyl salicylate, methyl benzoate, ethyl benzoate 3 3 Spicy (hot) eugenol, isoeugenol, cinnamaldehyde 5 1 Solar floral benzyl salicylate, benzyl benzoate 4 1 Dust / 2 1

Values ranging from 0 (no impact) to 6 (very strong olfactory impact)

Table 4 : Olfactory descriptors characterizing the “static” kapok extract and the “dynamic” kapok extract of Cananga smell .

Compounds Kapok st. 010222 Dynamic Kapok 280422 CG-O olfactory descriptors % of CG-MS areas Perceived intensity
CG-O % of areas
CG-SM Perceived intensity
CG-O Alcohols           2,3-butanediol (isomer) 1.5 - - - - diethylene glycol - - 0.8 - - Ketones           furanone derivative - intense - - Caramel, sugar 3-hydroxy-2-butanone 0.3 - - - - ( Z )-jasmone - - 0.5 - Dried herb Oxygenated monoterpenes           eucalyptol - - m (0.2) - Cleaning product, fresh, citrus fruits linalool m (2.3) average m (16.7) - Fresh, floral, citrus α-terpineol - - 1.4 - - nerol - - 0.3 - - general - - 0.9 - - geraniol - - 6.9 - Pink floral geranial - - 1.1 - - geranyl acetate m (0.2) - 10.0 - Floral, sweet, fruity geranial diethyl acetal - - 0.3 - - Hydrocarbon sesquiterpenes           α-copaene 0.7 - - - - β-ylangene 0.8 - - - - ( E )-caryophyllene 1.7 - - - - β-copaene 0.6 - - - - α-humulene 0.8 - - - - germacrene D 8.6 - 0.6 - - α-farnesene 13.3 - 3.3 - - δ-cadinene 0.2 - - - - Oxygenated sesquiterpenes           germacrene D-4-ol 0.8 - 0.3 - - ( 2Z , 6E )-farnesol 0.4 - - - - ( 2E , 6E )-farnesyl acetate 1.4 - 0.2 - - Aromatic compounds           p -methylanisole - - 0.1 - Floral, powerful, fresh, medicinal, medicine cabinet, disinfectant benzyl alcohol 17.7 forte 8.4 + m(0.1) - Floral, pink, honey phenylacetaldehyde - forte - - Floral, white flowers, honey, stem p -Cresol 0.5 very strong 0.7 - Burnt plastic, animal, marker o -guaiacol 0.7 forte 1.8 - Spicy, warm, vanilla pod, antiseptic, round, gourmand methyl benzoate m (4.0) - m (7.3) - Rustic, stem green, plastic phenylethyl alcohol 1.5 average 0.7 - Pink floral benzene acetonitrile - forte - - Neutral, aqueous, maintenance product benzyl acetate 7.1 light 7.1 - Candy, banana, ylang-ylang, tutti-frutti, fresh, floral ethyl benzoate 0.6 - - - - creosol 0.3 average - - Hot, fatty, vanilla bean, antiseptic, spicy hot methyl salicylate 0.2 - 0.7 - - 2-phenylethyl acetate 0.4 - 0.8 - Pink floral ( E )-cinnamaldehyde - - 0.4 - Biscuit, cereal, muesli, tasty, gourmet, hot, cake p -anisic alcohol 0.2 - - - - ( E )-anethole 0.3 - 0.4 - Aromatic, mint, basil indole 1.2 light 1.6 - Floral, white flowers, animal, jasmine 2-phenylnitroethane 6.5 - 10.1 - - ( E )-cinnamic alcohol 2.9 - 1.6 - - 2-methyl methoxybenzoate 1.6 - 1.3 - - methyl anthranilate 0.3 average 0.5 - Orange blossom eugenol 0.2 - - - - p -methyl anisate m (0.5) average - - Honey, sweet p -anisyl acetate 0.3 - 0.2 - - ( E )-cinnamyl acetate 5.4 - 7.5 - Round, candy, like benzyl acetate ( E )-isoeugenol 5.4 - 0.9 - - prenyl benzoate 1.1 - - - - cinnamaldehyde diethyl acetal - - 0.1 - - coniferyl alcohol 0.5 - 0.2 - - benzyl benzoate 2.8 - 1.9 - Floral benzyl salicylate 1.8 - 0.3 - Neutral, floral Miscellaneous           furanose derivative? - intense - - Bread crust, burnt, plastic % total of compounds identified 97.5 - 98.1 - - Number of compounds n.i. 8 - 5 - - % of n.i. compounds 2.5 - 1.9 - -

Table 5 : Chemical compositions (% of MS areas) and intensities perceived in GC-Olfactory for the “static” and “dynamic” kapok extracts of Cananga smell - Olfactory impacts.

The results presented for the two kapok extracts prove the effectiveness of the technique. Indeed, odorous compounds were identified in all the extracts obtained.

Tables 4 and 5 illustrate that these two extraction methods produce extracts that are chemically and olfactorily different from those obtained by the classic SPME extraction method.

Aromatic compounds (benzyl alcohol, benzyl acetate, methyl benzoate, benzyl benzoate, etc.) are the majority and are, for the most part, found in both extracts with similar contents. The differences between the two extracts lie in the second majority family: hydrocarbon sesquiterpenes (germacrene D, alpha-farnesene) for the static kapok extract and oxygenated monoterpenes (linalool, geranyl acetate) for the dynamic kapok extract.

These disparities are also perceived olfactorily. Indeed, the radar diagrams of the two extracts show that the extract with static kapok has dominant “warm spicy” and “solar floral” notes while the extract with dynamic kapok is less “rich” olfactorily ( and Table 5). This can be explained by differences in extraction techniques, seasonality, terroir, etc.

Study of volatile compounds from flowers of Michelia champaca

Michelia 's Kapok Extracts champaca were obtained using two batches of flowers: those which were picked on December 27, 2021 in Saint Benoît for the static capture technique, and those which were collected on January 5, 2022 in Bras Panon for the dynamic capture technique.

The static extraction was carried out for 3 hours and then for 17h30 with renewal of the kapok fibers. As for the dynamic extraction, it lasted twice 3 hours with also a change of the fibers between the two extractions. Then, the fibers were desorbed in ethanol for 3 hours. The GC-MS chromatograms are presented below and are followed by the summary tables of the compounds identified for the two extracts (with their respective contents).

The results obtained using the two extraction methods, static and dynamic, are presented in Figures 9 and 10 respectively in the form of chromatograms.

Compounds % of CG-MS areas Olfactory descriptors (The good scents & Flavor base) Kapok st. 271221 Dynamic Kapok 050122 C13 isoprenoids (E)- α-ionone 0.6 - Woody, balsamic, scent of violets dihydro-β-ionone 0.8 - Woody, fruity, scent of violet (E) -β-ionone 2.0 1.0 Woody, fruity, scent of violet Hydrocarbon sesquiterpenes (E,E)- α-farnesene 1.2 - Herbaceous, citrus, juniper berry and apple scent Aromatic compounds benzyl alcohol 1.2 0.5 Light, soft, fruity, sweet phenylacetaldehyde - 0.5 Strong, floral, green, smell of rose, hyacinth phenylethyl alcohol 41.9 44.1 Floral, rose scent benzene acetonitrile 6.5 5.1 Floral, spicy, bitter almond scent syn- phenylacetaldoxime 3.8 2.3 - anti -phenylacetaldoxime 3.3 1.9 - indole 36.1 32.3 Floral, powerful, diffuse methyl anthranilate 1.0 11.8 Fruity, scent of grape, orange blossom, neroli (E)- coniferyl alcohol 0.5 - - % total of compounds identified 98.8 99.4 Number of compounds n.i. 3 1 % of n.i. compounds 1.2 0.6
C13 isoprenoids 3.4 1.0 st. : static Hydrocarbon sesquiterpenes 1.2 0.0 dyn.: dynamic Aromatic compounds 94.2 98.5 n.i.: unidentified neither. 1.2 0.6 m: mixture TOTAL 100.0 100.0 Majority compound % of compound > 4%

Table 6 : Chemical compositions (% of MS areas) and distribution by family of the molecules identified in the “static” and “dynamic” kapok extracts of Michelia champaca .

There presents the distribution (in %) of the families of molecules identified in the extracts from Michelia flowers champaca depending on the extraction method applied .

Descriptors Associated olfactory molecules Kapok st. 271221 Dynamic Kapok 050122 Animal fecal indole 6 2 Floral violet alpha, beta & dihydrobeta ionones 3 5 Hyacinth phenylacetaldehyde 1 2 Almond balsamic benzaldehyde 1 1 Straw dust ? 2 2 Orange blossom methyl anthranilate 1 5 Powdered balsamic vanillin 2 2 Cooling flowers methyl benzoate 1 1 Pink floral phenylethyl alcohol 2 3

Values ranging from 0 (no impact) to 6 (very strong olfactory impact)

Table 7 : Olfactory descriptors characterizing the “static” kapok extract and the “dynamic” kapok extract of Michelia champaca .

Compounds Kapok st. 271221 Dynamic Kapok 050122 CG-O olfactory descriptors % of CG-MS areas Perceived intensity
GC-O % GC-SM areas Perceived intensity
GC-O Aldehydes hexanal - light - light Fruity green, cut grass, green, stem C13 isoprenoids (E)- α-ionone 0.6 average - light Honey, floral dihydro-β-ionone 0.8 - - light Floral (E)- β-ionone 2.0 - 1.0 light Honey, sweet, candy, gourmet 3-oxo-7,8-dihydro-α-ionone - - - light Floral Oxygenated monoterpenes ( Z )-linalool oxide - forte - - Burnt plastic, rubber ( E )-linalool oxide - light - - Moldy, fermented linalool - light - - Floral, fresh, wet, pleasant, plastic Hydrocarbon sesquiterpenes (E,E)- α-farnesene 1.2 - - - Aromatic compounds benzyl alcohol 1.2 average 0.5 - Floral, very fresh, green, fruity, citrus, pleasant phenylacetaldehyde - - 0.5 average Floral, honey, Murraya , petal pink p -cresol - forte - forte Urine, animal, ammonia phenylethyl alcohol 41.9 very strong 44.1 very strong Pink, floral, petal benzene acetonitrile 6.5 average 5.1 average Wet, neutral, clean, new, cold, burnt, smoked, maintenance product syn- phenylacetaldoxime 3.8 - 2.3 - - anti -phenylacetaldoxime 3.3 - 1.9 - - indole 36.1 - 32.3 very strong Floral, jasmine, white flower, animal, lily of the valley methyl anthranilate 1.0 average 11.8 average Orange blossom (E)- coniferyl alcohol 0.5 - - - - % total of compounds identified 98.8 99.4 Number of compounds n.i. 3 1 % of n.i. compounds 1.2 0.6

Compounds with olfactory impact in static and/or dynamic kapok extract (in bold).

Table 8 : Chemical compositions (% of MS areas) and intensities perceived in GC-Olfactory for the “static” and “dynamic” kapok extracts of Michelia champaca - Olfactory impacts.

Analysis of the two extracts from Michelia champaca using a new extraction technique has allowed to identify more than 95% of their composition. The extracts consist mainly of aromatic compounds (> 90%), among which phenylethyl alcohol, benzene acetonitrile, indole and methyl anthranilate, which are raw materials widely used in perfumery, constitute the majority compounds.

Despite the differences observed in the chromatographic profiles of the two samples, the major compounds are identical but their concentrations remain slightly variable. However, the extraction in static mode generated an extract more concentrated in compounds than that carried out in dynamic mode. This disparity can be explained by the fact that the fiber is in direct contact with the flowers during the static extraction.

The olfactory characterization of the two extracts reveals that both share pink and violet floral notes ( ). However, there is a difference in the additional notes present in each extract. The static kapok extract has a more animalic note, which can give it a wilder feel. In contrast, the dynamic kapok extract is dominated by an orange blossom note, which can give it a softer and more refined impression, creating unique scent profiles for each extract.

The GC-O analyses (Table 8) support the results of the olfactory characterization and the GC-MS. Indeed, the pink floral note perceived very intensely in both extracts is attributed to the high content of phenylethyl alcohol (> 40%) in these 2 extracts, which is confirmed by the GC-O analyses. The strong animal note in the static kapok extract is justified by the presence of a significant amount of indoles in this extract, which is also corroborated by the GC-O analyses. Similarly, the strong orange blossom note in the dynamic kapok extract is explained by the presence of a significant amount of methyl anthranilate in this extract.

Study volatile compounds from flowers of Plumeria alba

The kapok extracts of Plumeria alba were obtained using two batches of flowers from 2021: that of December 20 from Saint-Paul was used for the static capture technique, and that of December 14 from Sainte-Clotilde for the dynamic capture technique.

The static extraction was carried out for 3 hours and then for 17 hours with renewal of the kapok fibers. As for the dynamic extraction, it lasted twice for 3 hours with also a change of the fibers between the two extractions. Then, the fibers were desorbed in ethanol for 3 hours. The GC-MS chromatograms are presented below and are followed by the summary tables of the compounds identified for the two extracts (with their respective contents).

The results obtained using the two extraction methods, static and dynamic, are presented in Figures 13 and 14 respectively in the form of chromatograms.

Compounds % of CG-MS areas Olfactory descriptors (The good scents & Flavor base) Kapok st. 211221 Dynamic Kapok 151221 Alcohols octadecanol 0.3 0.5 Fade smell Esters γ-decalactone 0.3 - Fruity, fresh, oily, waxy, buttery, sweet; smell of peach, coconut δ-decalactone 1.1 - Fruity, fresh, sweet, creamy; smell of coconut, peach Hydrocarbons heptadecane 0.2 - - Oxygenated monoterpenes trans -linalool oxide (furanoid) 0.4 - Powerful, fresh, sweet, woody, floral linalool oxide (pyranoid) 1.4 - Floral, fresh general - 0.5 Sweet; smell of citrus, lemon, lemon peel geraniol - 5.3 Floral, fruity, sweet; smell of rose, citrus geranial - 0.6 Smell of citrus, lemon linalool m (4.4) > 1.2 m (4.1) > 0.6 Floral, sweet, woody, green; citrus, rosewood scent Oxygenated sesquiterpenes ( E )-nerolidol 0.2 2.9 Floral, green, woody, waxy; citrus scent dendrolasin 0.2 - - Aromatic compounds benzaldehyde 0.6 0.5 Smell of bitter almonds benzyl alcohol 3.9 40.8 Light, soft, fruity, sweet phenylacetaldehyde 3.0 - Green, sweet, floral; smell of hyacinth, honey, cocoa - 0.1 Oily, floral, waxy; smell of rose, lemon (in dilution) methyl benzoate m (4.4) > 3.2 m (4.1) > 3.5 Pungent, sweet, floral, fruity phenylethyl alcohol 18.2 - Floral; rose scent benzene acetonitrile 19.0 - - benzyl acetate m (0.2) > 0.1 - Sweet, floral, fruity; jasmine scent ethyl benzoate m (0.2) > 0.1 - Minty, fruity, dry, musty; wintergreen smell methyl salicylate 2.0 1.9 Warm, soft syn -phenylacetaldoxime 16.5 - - anti-phenylacetaldoxime 14.3 - - indole 0.3 - Floral, powerful, diffuse 1-nitro-2-phenylethane 8.8 - Sweet, floral, warm, spicy; cinnamon scent ( E )-methyl cinnamate - 7.3 Balsamic, sweet; smell of strawberry, cherry benzyl benzoate 0.4 15.4 Sweet, balsamic, slightly bitter benzyl salicylate - 17.0 Sweet, floral, balsamic geranyl benzoate - 2.3 Amber; scent of rose, ylang-ylang ( E )-coniferyl alcohol 0.8 - - % total of compounds identified 96.5 99.1 Number of compounds n.i. 11 1 % of n.i. compounds 3.5 0.9 Alcohols 0.3 0.5 st. : static Esters 1.4 - dyn.: dynamic Hydrocarbons 0.2 - n.i.: unidentified Oxygenated monoterpenes 3.0 7.0 m: mix Oxygenated sesquiterpenes 0.4 2.9 Majority compound Aromatic compounds 91.2 88.7 % of compound > 4% neither. 3.5 0.9 TOTAL 100.0 100.0

Table 9 : Chemical compositions (% of MS areas) and distribution by family of the molecules identified in the “static” and “dynamic” kapok extracts of Plumeria alba - Majority compounds.

There presents the distribution (in %) of the families of molecules identified in the extracts from Plumeria alba flowers according to the extraction method applied .

Descriptors Associated olfactory molecules Kapok st. 211221 Dynamic Kapok 151221 Green banana fruit benzyl acetate, benzyl alcohol 1 3 Fruity yellow gamma decalactone, delta decalactone 5 0 Citrus lemon neral, geranial 0 4 Hyacinth phenylacetaldehyde 5 0 Almond balsamic benzaldehyde, methyl cinnamate 0 2 Cooling flowers methyl salicylate, methyl benzoate 3 3 Solar floral benzyl benzoate, benzyl salicylate 0 6 Pink floral phenylethyl alcohol, geraniol 3 6

Values ranging from 0 (no impact) to 6 (very strong olfactory impact)

Table 10 : Olfactory descriptors characterizing the “static” kapok extract and the “dynamic” kapok extract of Plumeria alba.

Compounds Kapok st. 211221 Dynamic Kapok 151221 CG-O olfactory descriptors % of CG-MS areas Perceived intensity
CG-O % of CG-MS areas Perceived intensity
CG-O Alcohols octadecanol 0.3 - 0.5 - - Aldehydes isovaleraldehyde derivative - light - - Sock Esters butyrolactone - average - average Hazelnut, pyrazine, toasted, sock, taste, toasted almond furanone derivative - average - intense Caramel pyranone derivative - average - forte Caramelized, smoky, hot γ-decalactone 0.3 - - - - δ-decalactone 1.1 - - - - Hydrocarbons heptadecane 0.2 - - - - Oxygenated monoterpenes trans -linalool oxide (furanoid) 0.4 - - - - linalool oxide (pyranoid) 1.4 - - - - general - - 0.5 - - geraniol - - 5.3 light Fresh, lemongrass, green, airy geranial - - 0.6 - - linalool m (4.4) > 1.2 light m (4.1) > 0.6 average Floral, fresh Oxygenated sesquiterpenes ( E )-nerolidol 0.2 - 2.9 - - dendrolasin 0.2 - - - - Aromatic compounds p -methylanisole - - tr light animal, horse benzaldehyde 0.6 - 0.5 - - benzyl alcohol 3.9 light 40.8 light Fresh, moist, floral phenylacetaldehyde 3.0 forte - - White flower, honeyed guaiacol - - 0.1 forte Spicy, warm, leathery, animal methyl benzoate m (4.4) > 3.2 light m (4.1) > 3.5 - Floral, medicinal, warm phenylethyl alcohol 18.2 average - light Pink floral benzene acetonitrile 19.0 forte - - Aqueous, neutral, burnt plastic, new benzyl acetate m (0.2) > 0.1 - - light Honeyed, sweet ethyl benzoate m (0.2) > 0.1 strong? - - Neutral, clean, watery, soft, transparent methyl salicylate 2.0 average 1.9 - Floral, warm or fresh, round syn -phenylacetaldoxime 16.5 - - - - anti-phenylacetaldoxime 14.3 - - - - indole 0.3 - - - - 1-nitro-2-phenylethane 8.8 - - - - ( E )-methyl cinnamate - - 7.3 average Warm, floral benzyl benzoate 0.4 - 15.4 - - benzyl salicylate - - 17.0 - - geranyl benzoate - - 2.3 - - ( E )-coniferyl alcohol 0.8 - - - - Miscellaneous butyl lactate - light - average Cooked, moldy, fermented vegetable % total of compounds identified 96.3 - 99.1 - - number of compounds n.i. 11 - 1 - - % of n.i. compounds 3.5 - 0.9 - -

Compounds with olfactory impact in static and/or dynamic kapok extract (in bold).

Table 1 1 : Chemical compositions (% of MS areas) and intensities perceived in GC-Olfactory for the “static” and “dynamic” kapok extracts of Plumeria alba - Olfactory impacts.

The results presented for the two kapok extracts prove the effectiveness of the technique: odorous compounds were identified in all the extracts obtained.

Aromatic compounds (benzyl alcohol, methyl benzoate, benzyl benzoate, etc.) are predominant in both extracts but with very different contents. Indeed, the predominant compound in the dynamic kapok extract is benzyl alcohol while for the static kapok extract it is phenylethyl alcohol which is one of the predominant compounds.

These disparities are also perceived olfactorily. Radar charts of the two extracts show that the static kapok extract has dominant “yellow fruity” and “hyacinth” notes while the dynamic kapok extract is described as “solar floral” and “pink floral” ( ). This can be explained by differences in extraction techniques, seasonality, terroir, etc.

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Claims (7)

Ecological process for extracting VOCs from an odorous material using a plant fiber from the Ceiba species pentandra including the steps of:
- Obtaining plant fiber surrounding the fruits of the Ceiba species pentandra
- Removal of the wax present on said fiber by washing with absolute ethanol, then drying
- Capture of VOCs by bringing said odorous material into contact with said plant fiber
- Desorption of VOCs from said plant fiber in an absolute ethanol bath
- Filtration to obtain an ethanolic extract containing the VOCs The method of claim 1 wherein the fiber drying step is carried out in an environment free of contaminating VOCs. Method according to one of the preceding claims, in which the capture step is carried out in static conditions in a non-hermetically sealed container for a period of between 3 hours and 30 hours. Method according to one of the preceding claims, in which the capture step is carried out under dynamic conditions in a reactor having a means of circulating air, namely that:
- the odorous material is placed in the reactor tank, and the plant fiber is placed in a separate compartment, the whole being subjected to an air flow circulating from the odorous material to the fiber,
- the duration of contact between the odorous material and the plant fiber is between 1 hour and 5 hours. Method according to one of the preceding claims, further comprising a step of evaporation of the absolute ethanol at a temperature less than or equal to 40°C. 6. Method according to one of the preceding claims in which said odorous material is chosen from a plant material or an animal material. 7. A method according to claim 6 wherein said odorous material is a plant material selected from flowers, barks, resins and leaves.

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