Preparation method of perfume component

Abstract

The present invention relates to a method for preparing a perfume component, the method comprising a step of extracting an extract using an alkanediol, and a step of recovering the wax thus obtained using a specific solvent. The invention also relates to a perfume ingredient which can be obtained according to the above method, and a perfuming composition comprising the perfume ingredient, in particular a blending liquid or a perfume liquid.

Description

Technical Field

[0001] This invention relates to a method for preparing a fragrance ingredient, the method comprising the steps of extracting a concrete using alkyldiol and recovering the wax using a specific solvent. The invention also relates to a fragrance ingredient obtainable according to the above method, and a fragrance composition comprising the fragrance ingredient, particularly an aromatic accord or fragranced liquor. Background Technology

[0002] The perfume industry employs various methods to extract aromatic molecules, such as enfleurage, steam distillation, pressing, atomization, and supercritical CO2 extraction. These techniques are used to obtain different extracts, particularly essential oils, extracts, and absolutes.

[0003] Absolute oils are particularly prized in the perfume world because of their more complex olfactory characteristics compared to essential oils. They combine top notes with base notes derived from non-volatile molecules that cannot be extracted by water distillation or steam distillation. The aromatic molecules contained in absolute oils are mainly terpenes and terpenoids, but they also contain esters, alcohols, ketones, aldehydes, as well as phenylpropanes and phenolic compounds.

[0004] Pure oils are typically obtained by immersing starting plant material in a volatile organic solvent at room temperature for a period of time, followed by separation of the liquid phase from the plant material. After removing the solvent by distillation, a residue in solid or paste form rich in waxes, pigments, and aromatic molecules is obtained. This residue, called an extract, is then dissolved in ethanol at high temperature, and the waxes are removed by cold precipitation. After evaporating the ethanol from the filtrate, the pure oil is obtained, which can then be subjected to molecular distillation steps to improve its olfactory characteristics or color. Such methods for preparing pure oils are particularly described in WO 2022 / 197576 and FR 3110 417.

[0005] However, it has been observed that some of the target aromatic molecules may be trapped in the precipitated wax, thus resulting in loss. The applicant has also observed that during the evaporation step, ethanol carries away certain volatile compounds that contribute to the complexity and subtlety of plant aromas.

[0006] The applicant considered an alternative solution: replacing ethanol with 1,3-propanediol and not evaporating it to obtain a liquid fragrance ingredient. This solution was also not entirely satisfactory, especially in terms of olfactory properties.

[0007] Therefore, research was conducted and an alternative method was proposed to prepare a fragrance ingredient similar to absolute oil, but with better olfactory properties than the aforementioned extracts, especially a more natural floral scent and base note, giving the fragrance a stronger and longer-lasting effect.

[0008] Therefore, there is a need for a new method for preparing absolute alternatives that is environmentally friendly, allows the use of potentially bio-based solvents (especially those compliant with Ecocert), and does not impair the aroma of the extracted material. A method that can produce a fragrance component with improved olfactory characteristics compared to traditional absolutes and is easily formulated into fragrance compositions in effective quantities (i.e., miscible with solvents commonly used in the perfume industry) would be particularly useful.

[0009] It is against this backdrop that the method according to the present invention was developed. Summary of the Invention

[0010] The applicant has demonstrated that the fragrance ingredients that meet the above requirements can be obtained by following a method comprising the following steps: extracting the extract using alkyldiol, and recovering the wax obtained therefrom using a specific solvent.

[0011] Therefore, one aspect of the present invention is a method for preparing a fragrance ingredient, the method comprising the following steps:

[0012] (a) The extract is contacted with a first solvent containing at least one C3-C6 alkyldiol at a temperature sufficient to obtain a first liquid phase and a wax phase for a period of time.

[0013] (b) Separating the wax phase and the first liquid phase, preferably by decantation.

[0014] (c1) The wax phase is contacted with the second solvent at a temperature sufficient to obtain the second liquid phase and the solid phase for a period of time.

[0015] (c2) The second liquid phase is mixed with a third solvent, the third solvent being selected from the C8-C group of alcohols or polyols. 20 Fatty acid esters,

[0016] (c3) Perform molecular distillation on the mixture obtained in step (c2) to obtain a residue, a first volatile phase, and a first distillate.

[0017] (c4) Optionally, the residue is subjected to molecular distillation to obtain a second distillate and a second volatile phase.

[0018] (d) Mixing the first liquid phase with the first volatile phase and the first distillate, or, in the case of step (c4), mixing the first liquid phase with the first volatile phase and the second volatile phase, as well as the first distillate and the second distillate.

[0019] (e) Residual wax present in the mixture obtained in step (d) is preferably separated by winterization, followed by centrifugation and / or filtration.

[0020] (f) Recover the flavoring components obtained therefrom.

[0021] The subject of this invention also relates to a fragrance ingredient obtainable according to the above method, comprising 1% to 10% by weight of an aromatic substance and a solvent mixture, said solvent mixture comprising:

[0022] - 25% to 60% by weight, preferably 30% to 50% by weight of alkyldiols

[0023] - 40% to 75% by weight, preferably 50% to 70% by weight, of a second solvent.

[0024] - Optionally, 3% to 10% by weight, preferably 4% to 6% by weight, of compatibilizer.

[0025] The subject of this invention also lies in a fragrance composition comprising the fragrance ingredient, particularly an aromatic blend or fragrance liquid. Invention Overview

[0027] As previously stated, the present invention relates to a method for preparing a flavoring ingredient.

[0028] The term "fragrance component" refers to any aromatic plant extract, i.e., an extract containing aromatic molecules and having olfactory characteristics suitable for a fragrance composition and free of any waxes. The term "aromatic molecule" refers to a volatile molecule present in the starting plant material, capable of producing a perceptible odor alone or in combination. In this invention, aromatic molecules include, but are not limited to, terpenes and terpenoids commonly found in plant materials. Examples of monoterpenes that may be mentioned include ocimene, limonene, α-pinene, β-pinene, camphene, and p-cymene. Examples of monoterpenoids that may be mentioned include terpene alcohols, such as linalool, eucalyptol, menthol, nerol, geraniol, citronellol, terpineol, and their acetates, or even terpene ketones and aldehydes, such as citral, geraniol, citronellol, camphor, and carvone.

[0029] The term "plant material" refers to any type of plant material from any type of plant species. The term "plant material" depends on the plant species under consideration, including fruits, vegetables, and grains, including berries, nuts, buds, flowers, shoots, leaves, stems, branches, wood, bark, pericarps, roots, rhizomes, seeds, kernels, and combinations and parts thereof.

[0030] In some embodiments, plant materials include flowers, buds, shoots, and combinations thereof, or are composed of them. Examples of plant materials may include vanilla, yerba mate, vetiver, chamomile, magnolia, myrrh, iris, benzoin, cocoa, coffee, rockrose, labdanum, fenugreek, hay, sandalwood, ginger, tree moss, nutmeg, pepper, saffron, tea, cardamom, daffodil, sage, galangal, blackcurrant buds, amaryllis, basil, broom, immortelle, frankincense, marigold, osmanthus, grapefruit, mint, styrax, oak, tiare flower, violet, lavender, hybrid lavender, rose, daffodil, blackcurrant buds, narcissus, mimosa, lily, hyacinth, carnation, tuberose, jasmine such as Jasminum sambac or grandiflorum, vanilla, ylang-ylang, or orange blossom.

[0031] The method according to the invention includes a first step of contacting the extract with a first solvent containing at least one C3-C6 alkyldiol.

[0032] The extracts used in this invention are typically in the form of a paste or solid rich in aromatic molecules and waxes. The extracts are commercially available or can be prepared by first contacting plant material, such as the aforementioned plant material, with at least one nonpolar solvent, such as hexane or dimethyl ether.

[0033] The plant material used in the preparation of the extract can be fresh (i.e., freshly harvested), or dried, pulverized (including cryogenically pulverized), freeze-dried, or frozen. Prior to the preparation of the extract, the plant material may have undergone one or more treatments selected from: washing, cutting or pulverizing steps (e.g., cryogenic pulverization), drying, and combinations thereof. In some embodiments, the plant material is dried and / or subjected to heat treatment, particularly heating, prior to the preparation of the extract. In other embodiments, the plant material is washed and may be pulverized prior to the preparation of the extract.

[0034] In the first step of the method according to the invention, the solvent in contact with the extract comprises at least one C3-C6 alkyldiol, and preferably does not contain solvents other than C3-C6 alkyldiols, wherein the C3-C6 alkyldiol has a melting point below 90°C, preferably below 50°C, and more preferably below 20°C. For example, it may be selected from: 1,2-propanediol (propylene glycol), 1,3-propanediol, 1,3-butanediol (butanediol), 2,3-butanediol, 1,4-butanediol, 1,2-butanediol, 1,5-pentanediol, 1,4-pentanediol, 1,2-pentanediol (pentanediol), 2-methyl-2,4-pentanediol, and mixtures thereof. In a preferred embodiment of the invention, the alkyldiol is selected from 1,3-propanediol, 1,3-butanediol (butanediol), and 2,3-butanediol. More preferably, it is 2,3-butanediol.

[0035] Those skilled in the art can determine the amount of the first solvent to be used based on the content of volatile components in the extract and the weight ratio of the volatile fraction to the alkanediol that is desired to be obtained in the fragrance component. The content of volatile compounds in the extract can itself be assessed, for example, by thermogravimetric analysis or by gas chromatography (GC / FID) (GC-FID) coupled with a flame ionization detector on a hydrophobic column.

[0036] Extraction of the extract using alkyldiol can be carried out, for example, at a temperature of 50 to 90°C (especially 60 to 80°C) for a period of time ranging from 30 minutes to 2 hours (especially 1 to 2 hours). This step can be carried out at least partially with stirring, followed by cooling, especially cooling to room temperature (20-25°C), to allow the wax to precipitate.

[0037] At the end of the first step of the method according to the invention, a wax phase and a first liquid phase are obtained, and then they are separated, preferably by decantation.

[0038] During the wax phase treatment described below, the liquid phase can be maintained at a temperature of, for example, 1 to 10°C.

[0039] The wax phase is contacted with the second solvent at a temperature sufficient to obtain a second liquid and solid phase for a period of time, for example, at 50 to 90°C, preferably 60 to 80°C, for example, for 30 minutes to 4 hours, particularly in the range of 1 to 2 hours. The amount of the second solvent relative to the total weight of the wax phase can be determined in advance according to the method described above, based on the content of volatile compounds present in the extract used and the proportion of volatile compounds that are desired to be transferred to the fragrance component. The second solvent is particularly selectable from: dimethyl isosorbide ester, diesters such as diisobutyl succinate, triesters such as triethyl citrate, monoesters such as isononyl isononanoate, branched and / or unsaturated fatty acids, branched and / or unsaturated fatty alcohols such as octyl dodecanol or hexyl decanol, propylene carbonate, and mixtures thereof. It is advantageously selected from odorless, biodegradable compounds with a vapor pressure of 1-10 Pa at 25°C. Triethyl citrate is preferred.

[0040] The second liquid phase and the solid phase can then be optionally separated, preferably by filtration, and the second liquid phase is then mixed with a third solvent selected from the C8-C group of alcohols or polyols. 24 Fatty acid esters, such as caprylic / capric triglycerides, C8-C 24 Fatty acid triglycerides, such as C 16 -C 22 Fatty acid triglycerides, and vegetable oils containing them.

[0041] This solvent acts as a fluidizing agent, designed to facilitate subsequent molecular distillation steps by preventing the wax from clumping together (which would disrupt the vacuum and interrupt distillation). It can be added at a ratio of 50% to 150% by weight relative to the initial weight of the extract, preferably at a 1:1 weight ratio.

[0042] The mixture of the second liquid phase and the third solvent is then subjected to molecular distillation to reduce the amount of waxes (fatty acids and triglycerides) present in the second liquid phase. Those skilled in the art can easily adjust the distillation conditions according to the properties of the extract used. For example, the following conditions can be applied:

[0043] Inlet temperature: 60-70℃

[0044] Column temperature: 65-75℃

[0045] Condenser temperature: 5-10℃

[0046] Stirring: 300-500 rpm

[0047] Pressure: 0.1-1 mbar.

[0048] This results in residues, a first volatile phase, and a first distillate. The volatile phase is typically recovered by condensation in a trap, for example, using liquid nitrogen.

[0049] The residue is then optionally subjected to a new molecular distillation step under more stringent conditions than the previous step, such as reducing the pressure to 0.01–0.1 mbar, while other conditions are generally kept constant. This produces a residue containing a third solvent, a second distillate containing a second solvent, and a second volatile phase. The volatile phase is typically recovered by condensation in a trap, for example, using liquid nitrogen.

[0050] The method according to the invention further includes the step of mixing the first liquid phase with the volatile phase and the distillate. Then, any residual wax present in the mixture is removed, preferably by winterization (e.g., at 2-6°C), followed by centrifugation and / or filtration.

[0051] In certain cases, particularly when alkyldiols are poorly miscible with the first solvent (e.g., in the case of 1,3-propanediol and triethyl citrate), the method according to the invention may further include, after the winterization and centrifugation and / or filtration steps, a step of mixing the product obtained from these steps with at least one compatibilizer (i.e., a solvent miscible with both the first and second solvents, such as isopropylidene glycerol or pentanediol). The amount of the compatibilizer may particularly be from 1% to 10% by weight, preferably from 3% to 8% by weight, relative to the total weight of the flavoring components.

[0052] This yields a fragrance ingredient comprising 1% to 10% by weight of an aromatic substance and a solvent mixture, wherein the solvent mixture comprises:

[0053] - 25% to 60% by weight, preferably 30% to 50% by weight of alkyldiols

[0054] - 40% to 75% by weight, preferably 50% to 70% by weight, of a second solvent.

[0055] - Optionally, 3% to 10% by weight, preferably 4% to 6% by weight, of compatibilizer.

[0056] This flavoring ingredient is preferably free of ethanol.

[0057] Due to their superior olfactory characteristics, the fragrance ingredients according to the present invention can be formulated into fragrance compositions, which can be aromatic blends or liquids. The term "aromatic blend" refers to a combination of fragrance ingredients with possible other ingredients that produces a specific aroma that cannot be obtained with a single ingredient or a single essential oil. The fragrance composition typically contains at least one other fragrance ingredient and one or more solvents, such as those selected from: ethanol, esters (e.g., triethyl citrate or methyl dihydrojasmonate), glycols (e.g., dipropylene glycol), and mixtures thereof.

[0058] Fragrance compositions are particularly suitable for incorporation into fragrances, cosmetic compositions, household detergents, or fabric softeners. Fragrances can be used to produce pleasant odors, mask unpleasant odors, induce a certain mental state (relaxation, stimulation, etc.) through inhalation, and / or suggest the properties of products containing them (freshness, cleanliness, etc.). The term "cosmetic composition" refers to a composition containing a physiologically acceptable medium, which is compatible with skin and / or its appendages and preferably "cosmetically acceptable," i.e., a medium that is unlikely to cause redness, itching, or stinging when applied to the skin or its appendages. Cosmetic compositions typically have the effect of modifying and / or improving the appearance of skin or appendages (especially hair), and even preventing and / or correcting non-pathological changes in the skin or its appendages. Examples of cosmetic compositions that may be specifically mentioned include facial and / or body care products, shampoos, and conditioners. Household detergents that may be specifically mentioned include laundry detergents, hard surface cleaners, and dishwashing liquids.

[0059] The fragrance components according to the invention may advantageously account for 0.1% to 20% by weight, preferably 0.5% to 15% by weight, and more preferably 1% to 10% by weight, relative to the total weight of the fragrance composition. Attached Figure Description

[0060] Figure 1 The chromatogram of the fragrance components according to the invention, obtained by extracting rose extract with 1,3-propanediol and injected into a GC-FID chromatograph in pure form, is shown.

[0061] Figure 2 The chromatogram of rose absolute injected into a GC-FID chromatograph in pure form is shown.

[0062] Figure 3 The chromatogram of the fragrance components according to the invention, obtained by extracting rose extract with 1,3-propanediol and injected into a GC-FID chromatograph in the form of a 10% THF dilution, is shown.

[0063] Figure 4 The chromatogram of rose absolute oil injected into a GC-FID chromatograph in the form of a 10% THF dilution is shown.

[0064] Figure 5 The chromatogram of the fragrance components according to the invention, obtained by extracting rose extract with 2,3-butanediol and injected into a GC-FID chromatograph in pure form, is shown.

[0065] Figure 6 The chromatogram of the fragrance components according to the invention, obtained by extracting rose extract with 2,3-butanediol and injected into a GC-FID chromatograph in the form of a 10% THF dilution, is shown. Detailed Implementation

[0066] Example

[0067] The invention can be better understood through the following examples, which are given for illustrative purposes only and are not intended to limit the scope of the invention as defined by the claims.

[0068] Example 1 Preparation of the fragrance ingredients according to the present invention

[0069] Materials and methods

[0070] TGA: Thermogravimetric analysis was performed on a 25 mg sample placed in a 70 µL alumina crucible using a Mettler Toledo instrument coupled with a horizontal mode data acquisition system. The temperature gradient used was: 10°C / min, from 25°C to 200°C; then, 20°C / min, from 200°C to 700°C, with two isotherms: held at 50°C for 30 min, then at 200°C for 30 min, and then at 150°C for 5 min. The nitrogen flow rate was set at 20 mL / min throughout the temperature gradient.

[0071] 1A – Preparation method using 1,3-propanediol

[0072] The following methods were applied to various commercial extracts.

[0073] First, the extract was analyzed by TGA to determine its volatile compound content, and the amounts of the first and second solvents to be used were calculated to obtain a solvent mixture containing 5% by weight of volatile compounds in a first solvent to second solvent weight ratio of 50 / 50 to 30 / 65.

[0074] The extract was then melted at 50°C, and a first solvent consisting of 1,3-propanediol was added. The mixture was maintained at this temperature for 1 to 2 hours. After cooling at room temperature for 24 hours, the wax precipitated, yielding a liquid phase and a wax phase. The liquid phase was separated by decantation and stored at 4°C.

[0075] The wax phase was then extracted at 70°C for 1–2 hours using a second solvent consisting of triethyl citrate. Caprylic / capric triglycerides were then added, and the mixture was homogenized for 30 minutes. The mixture was then introduced into a molecular distillation apparatus under the following conditions:

[0076] Inlet temperature: 60-70℃

[0077] Column temperature: 65-75℃

[0078] Condenser temperature: 5-10℃

[0079] Stirring: 300-500 rpm

[0080] Pressure: 0.1-1 mbar.

[0081] The obtained distillate (or first distillate) is recovered, and the volatile phase (or first volatile phase) is collected in a liquid nitrogen trap. The residue is then subjected to a second molecular distillation under the same conditions, except that the pressure is adjusted to 0.01–0.1 mbar. The second distillate and the second volatile phase are then recovered.

[0082] All volatile phases, distillates, and the first liquid phase were mixed at room temperature and then cooled at 4°C for 4 hours to precipitate residual wax. The mixture was then filtered through a 5 to 8 µm filter under nitrogen pressure of 2 bar.

[0083] Isopropylidene glycerol is then added to the mixture at a ratio of approximately 5% by weight relative to the total weight of the first and second solvents.

[0084] Thus, the fragrance ingredients according to the present invention are obtained.

[0085] 1B – Preparation method using 2,3-butanediol

[0086] The fragrance ingredients prepared using this solvent are obtained as described above, except that no compatibilizer is added at the end of the method because the first and second solvents are miscible with each other.

[0087] Example 2 Characterization of extracts

[0088] 2-1: Rose extract

[0089] The components obtained from rose extract according to Example 1B were compared with rose absolute oil prepared conventionally by ethanol extraction.

[0090] Materials and methods :

[0091] GC-FID: Liquid samples were diluted to 10% in THF before injection. Volatile compounds were analyzed using an Agilent 7890B GC system. Separation was performed on a polar column (DB-wax, 30 m x 0.25 mm, 0.25 µm, Agilent) and a non-polar column (DB1-MS, 30 m x 0.25 mm, 0.25 µm, Agilent) using the following temperature gradient: constant temperature at 50°C for 5 min, then ramped at 3°C / min to 120°C and then at 5°C / min to 250°C, followed by constant helium flow (1.6 mL / min). The injector temperature was set to 250°C. The injection volume was 1 µl, and the split ratio was set to 50:1. The detection was performed on a 5977B mass spectrometer with the following parameters: initial temperature 250℃, quadrupole temperature 150℃, scan parameters between mass-to-charge ratio (m / z) 50 and 550, and flame ionization detector operated under the following conditions: temperature 250℃, H2 / air ratio 10%, and air flow rate 450 mL / min.

[0092] Solubility: The solubility of the fragrance components according to the present invention in different solvents at three concentrations was tested. The appearance of each solution was observed and any changes were recorded. If no precipitation, phase separation, or turbidity was observed, the test result was considered correct; otherwise, the test result was considered inaccurate.

[0093] Olfactory assessment:

[0094] The initial assessment was conducted by a trained team using a descriptive approach. Fragrance ingredients were placed on strips, which were then placed in a room with controlled temperature and humidity. Team members smelled these strips daily until they could no longer detect any odors beyond their known range.

[0095] The perfumer will conduct a second evaluation.

[0096] result

[0097] GC-FID: such as Figure 1 and Figure 2As shown, according to component 1A of the present invention ( Figure 1 It contains volatile compounds, more specifically terpenes (α-pinene, γ-terpinene, β-pinene, myrcene, limonene), while rose absolute ( Figure 2 It does not contain these compounds. On the other hand, with Figure 4 compared to, Figure 3 The results show that it contains no heavy alkanes or alkenes (heptadecane, nonadecane, nonadecane), and it contains even fewer terpene alcohols. These compounds present in the absolute do not represent the scent of the flower.

[0098] at last, Figure 5 and Figure 6 The chromatogram of component 1B is shown. Figure 6 and Figure 3 The comparison shows that components 1A and 1B according to the present invention have the same overall chromatogram. However, by Figure 5 and Figure 1 A more detailed analysis obtained through comparison revealed that component 1B ( Figure 5 The complexity is greater, evident in the presence of citronellol, β-caryophyllene, α-guaiacene, and α-humulene. This results in a more lasting effect on the olfactory perception of fragrances, as observed by the group.

[0099] Solubility:

[0100] [Table 1]

[0101]

[0102] As shown in Table 1, the fragrance components according to the present invention are dissolved in common fragrance solvents at a level of at least 10% by weight.

[0103] The perfumer noted that, unlike absolutes which only have middle notes (floral, rose, sweet and alluring), component 1B not only has middle notes (hay, clove) but also top notes (floral, juicy, spicy). Therefore, the components according to the present invention are more representative of the aroma of plants.

[0104] 2-2: Jasmine extract

[0105] The perfumer was given the ingredients obtained from jasmine extract according to Example 1B, as well as jasmine absolute prepared conventionally by ethanol extraction.

[0106] The perfumer noted that component 1B not only has middle notes (rich, animalic) but also top notes (floral, fruity, green), while the absolute only has middle notes (floral, rich, fruity, animalic). Therefore, the components according to the present invention are more representative of plant aromas.

Claims

1. A method for preparing a fragrance ingredient, the method comprising the following steps: (a) The extract is contacted with a first solvent containing at least one C3-C6 alkyldiol at a temperature sufficient to obtain a first liquid phase and a wax phase for a period of time. (b) Separating the wax phase and the first liquid phase, preferably by decantation. (c1) The wax phase is contacted with the second solvent at a temperature sufficient to obtain the second liquid phase and the solid phase for a period of time. (c2) The second liquid phase is mixed with a third solvent, the third solvent being selected from the C8-C group of alcohols or polyols. 24 Fatty acid esters, (c3) Perform molecular distillation on the mixture obtained in step (c2) to obtain a residue, a first volatile phase, and a first distillate. (c4) Optionally, the residue is subjected to molecular distillation to obtain a second distillate and a second volatile phase. (d) Mixing the first liquid phase with the first volatile phase and the first distillate, or, in the case of step (c4), mixing the first liquid phase with the first volatile phase and the second volatile phase, as well as the first distillate and the second distillate. (e) The residual wax present in the mixture obtained in step (d) is preferably separated by winterization, followed by centrifugation and / or filtration. (f) Recover the flavoring components obtained therefrom.

2. The method according to claim 1, characterized in that, The second solvent is selected from: dimethyl isosorbide diester, diesters such as diisobutyl succinate, teresters such as triethyl citrate, monoesters such as isononyl isononanoate, branched and / or unsaturated fatty acids, branched and / or unsaturated fatty alcohols such as octyl dodecanol or hexyl decyl alcohol, propylene carbonate and mixtures thereof; preferably, the first solvent is triethyl citrate.

3. The method according to claim 1 or 2, characterized in that, The third solvent is selected from caprylic / capric triglyceride, C8-C 24 Fatty acid triglycerides and vegetable oils containing them.

4. The method according to any one of claims 1 to 3, characterized in that, The C3-C6 alkyldiol is selected from: 1,2-propanediol (propylene glycol), 1,3-propanediol, 1,3-butanediol (butanediol), 2,3-butanediol, 1,4-butanediol, 1,2-butanediol, 1,5-pentanediol, 1,4-pentanediol, 1,2-pentanediol (pentanediol), 2-methyl-2,4-pentanediol and mixtures thereof, preferably selected from 1,3-propanediol, 1,3-butanediol (butanediol) and 2,3-butanediol, more preferably composed of 2,3-butanediol.

5. The method according to any one of claims 1 to 4, characterized in that, The method is used to obtain extracts by impregnating the flowers of plants selected from the following in a volatile organic solvent: vanilla, yerba mate, vetiver, chamomile, magnolia, myrrh, iris, benzoin, cocoa, coffee, rockrose, labdanum, fenugreek, hay, sandalwood, ginger, tree moss, nutmeg, pepper, saffron, tea, cardamom, daffodil, sage, galbanum, blackcurrant bud, ambrette, basil, broom, immortelle, frankincense, marigold, osmanthus, grapefruit, pepper, styrax, oak, tiare flower, violet, lavender, hybrid lavender, rose, daffodil, blackcurrant bud, narcissus, mimosa, lily, hyacinth, carnation, tuberose, jasmine (e.g., Jasminum sambac or grandiflorum), vanilla, ylang-ylang, and orange blossom.

6. The method according to any one of claims 1 to 5, characterized in that, The method further includes, after the winterization and centrifugation and / or filtration steps, a step of mixing the product obtained from these steps with at least one compatibilizer, said compatibilizer being a solvent miscible with both a first solvent and a second solvent, such as isopropylidene glycerol or pentylene glycol.

7. A fragrance ingredient obtainable by the method according to any one of claims 1 to 6, comprising 1% to 10% by weight of an aromatic substance and a solvent mixture, said solvent mixture comprising: - 25% to 60% by weight, preferably 30% to 50% by weight of alkyldiols - 40% to 75% by weight, preferably 50% to 70% by weight, of a second solvent. - Optionally, 3% to 10% by weight, preferably 4% to 6% by weight, of compatibilizer.

8. A fragrance composition, particularly an aromatic blend or fragrance liquid, characterized in that, It contains the flavoring ingredient according to claim 7, wherein the flavoring ingredient is preferably 0.1% to 20% by weight, more preferably 0.5% to 15% by weight, and even more preferably 1% to 10% by weight, relative to the total weight of the flavoring composition.

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