Fermented essential oil

Abstract

The present invention relates to a method for adjusting the odor profile of an essential oil; an essential oil obtained or obtainable by such a method; a fragrance composition comprising such an essential oil; a fragrance product, preferably a pharmaceutical, cosmetic or a formulation for the provision of nutrition or pleasure, comprising such an essential oil or such a fragrance composition; and the use of a yeast of the genus Yarrowia for adjusting the odor profile of an essential oil.

Description

Technical Field

[0001] The present invention relates to a method for adjusting the odor characteristics of an essential oil; an essential oil obtained or obtainable by such method; a fragrance composition comprising such an essential oil; an aromatic product comprising such an essential oil or such fragrance composition, preferably a pharmaceutical preparation, a cosmetic preparation or a preparation for providing nutrition or pleasure; and the use of a yeast of the genus *Yarlium* for adjusting the odor characteristics of an essential oil. Background Technology

[0002] Essential oils are liquids containing concentrated forms of volatile fragrances, and are mostly hydrophobic. Generally, essential oils are obtained from plants as plant extracts, which contain the characteristic aromas of their source plants.

[0003] Essential oils generally refer to any concentrated hydrophobic liquid containing volatile compounds derived from plants. They are also known as volatile oils, ether oils, aetheroleum, or simply the oil from which essential oils are extracted. Essential oils are called "essential" because they contain the essence of the plant's fragrance—the characteristic aroma of the plant from which they are derived. The term "essential" in essential oils does not imply that they are indispensable or usable by the human body, unlike terms such as essential amino acids or essential fatty acids, which are used for nutritional purposes. Essential oils are commonly used in perfumes, cosmetics, soaps, air fresheners, and other products to add fragrance to aromatherapy and household cleaning products.

[0004] However, obtaining these essential oils requires an extraction process. This extraction process is typically laborious and yields only limited quantities of essential oil. Therefore, these essential oils are quite expensive and precious.

[0005] When essential oils are used, for example, in the fragrance industry, large quantities are needed to provide a strong aroma in scented products. Therefore, it is desirable to adjust the odor of essential oils, such as enhancing one or more odors and / or increasing the complexity of their odor characteristics.

[0006] Furthermore, existing fragrance compositions offer only low complexity and olfactory versatility, and typically include olfactory odors that need to be removed or reduced.

[0007] In addition, existing processes typically require significant time and / or high concentrations of enzymes, which also necessitates improvement.

[0008] Therefore, there is a strong need to provide optimized methods and optimized flavor compositions compared to those available in the prior art. Summary of the Invention

[0009] Therefore, a primary objective of this invention is to provide improved possibilities for obtaining fragrance compositions. Another objective of this invention is to provide fragrance compositions with improved complexity and olfactory versatility.

[0010] These objectives are achieved by a method for adjusting the odor characteristics of essential oils, the method comprising the following steps:

[0011] i) Provide one or more essential oils, preferably wherein the one, two, three or more or all of the essential oils are plant extracts selected from plants of the genus comprising the group consisting of jasmine, rose, magnolia and mixtures thereof;

[0012] ii) Provide an aqueous culture of one or more yeasts of the genus *Yarlium*, preferably wherein the cell density of the aqueous culture is at least 7 × 10⁻⁶ cells per milliliter of the aqueous culture. 7 The yeast cells described;

[0013] iii) Mix the essential oil provided in step i) and the aqueous culture provided in step ii) to obtain a mixture;

[0014] iv) Incubate the mixture obtained in step iii) under conditions that allow the essential oil to ferment to obtain a fermentation mixture containing a liquid phase;

[0015] v) Separating the liquid phase from the fermented biomass to obtain a fermented mixture containing fermented essential oils;

[0016] vi) Extract the fermented essential oil from the fermented mixture.

[0017] Surprisingly, it has been found that the aroma characteristics of the provided essential oil can be adjusted by the method according to the invention. A particularly pleasant (fermented) essential oil has been obtained by the method according to the invention. Surprisingly, it has been found that several aromas of the provided essential oil can be enhanced.

[0018] Preferably, the one, two, three or more or all essential oils provided in step i) refer to oils obtained by steam distillation, water distillation and / or pressing of fruit peels; and / or reprocessed essential oils, such as distilled oils, decolorized oils, low furanocoumarin oils, terpene fraction oils, deterpene fraction oils, hypoallergenic crude oils, and non-hypoallergenic crude oils.

[0019] In the method according to the invention, preferably, the one, two, three or more, or all of the essential oils provided in step i) are selected from the group consisting of: basil oil, caraway oil, carrot seed oil, celery seed oil, clary sage oil, dill oil, dill seed oil, tarragon oil, fennel oil, gabone oil, hesperidin oil, marjoram oil, parsley seed oil, parsley leaf oil, star anise oil, star anise, tea tree oil, Brazilian sandalwood oil, geranium oil, linalool leaf oil, jasmine, lavender oil, mixed lavender oil, magnolia oil, magnolia leaf oil, neroli oil, orange flower oil, orris root resin, palmarosa oil, petitgrain mandarin oil, petitgrain orange oil, petitgrain orange bitter orange oil. Oils including rose oil, rosewood oil, rosewood leaf oil, linalool oil, marigold oil, ylang-ylang oil, bhullia leaf oil, carrot oil, artemisia oil, galangal oil, laurel oil, black pepper oil, cardamom oil, cinnamon oil, cinnamon leaf oil, cinnamon bark oil, coriander leaf oil, coriander seed oil, cumin oil, cumin seed oil, ginger oil, ginger herb oil, green pepper oil, angelica leaf oil, angelica root oil, nutmeg bark oil, nutmeg oil, perilla oil, allspice oil, pink pepper oil, and pink pepper berries (Peruvian pink pepper (Schinus molle L.)).Oils including: white pepper oil, schinus molle oil, turmeric oil, litsea cubeba oil, myrrh oil, frankincense oil, red myrrh oil, Peruvian balsam oil, styrax oil, turmeric balsam oil, bergamot oil, citron oil, lemongrass oil, lemon eucalyptus oil, grapefruit oil, lemon oil, lemongrass oil, litsea cubeba oil, lime oil, mandarin orange oil, orange oil, bitter orange oil, petitgrain lemon oil, mandarin orange oil, allspice oil, artemisia oil, balsamita oil, calamus oil, catnip oil, cedarwood oil, blue chamomile oil, Roman chamomile oil, clove bud oil, clove leaf oil, clove stem oil, cornmint oil, cypress oil, elegans oil, eucalyptus oil, fir oil, fusel oil, immortelle oil, hop oil, juniper oil, bay leaf oil, and mentha arvensis oil. Peppermint oil, myrtle oil, oregano oil, peppermint oil, allspice leaf oil, pine needle oil, punida oil, rosemary oil, rosemary extract, sage oil, spearmint oil, spruce oil, thyme oil, wintergreen oil, wormwood oil, agarwood oil, sandalwood oil, boya oil, Atlantic cedarwood oil, Chinese cedarwood oil, Texas cedarwood oil, Virginia cedarwood oil, Cuban oil, Cuban balsam oil, sedge oil, alligator wood agarwood oil, guaiac oil, ancient rue balsam oil, Alaskan nootka tree oil, patchouli oil, sandalwood oil, vetiver oil, rockrose oil, ambrette seed oil, and mixtures thereof. The term "mixtures thereof" preferably refers to a mixture of two or more of these oils, such as a mixture of vetiver oil and patchouli oil.

[0020] Preferably, the essential oil provided in step i) contains one or more fragrances.

[0021] In the method according to the invention, preferably, the one, two, three or more, or all of the fragrances in the essential oil provided in step i) are selected from the group consisting of: primary alcohols, secondary alcohols, tertiary alcohols, straight-chain alcohols, branched-chain alcohols, monocyclic alcohols, bicyclic alcohols, tricyclic alcohols, monools, diols, triols, saturated alcohols, monounsaturated alcohols, diunsaturated alcohols, triunsaturated alcohols, polyunsaturated alcohols, alcohols further containing aldehyde groups, alcohols further containing ketone groups, alcohols further containing carbonate groups, alcohols further containing ether groups, alcohols further containing epoxy groups, alcohols further containing acetal groups, alcohols further containing hemiacetal groups, alcohols further containing ester groups, alcohols further containing amino groups, and alcohols further containing one or more heteroatoms.

[0022] Preferably, the essential oil provided in step i) contains one, two, three or more, or all of the fragrances selected from the group consisting of: benzyl alcohol, bisabolol, borneol, fennelol, isopreneol, terpineol, verbenaenoyl alcohol, ambroxol, aphidicolin, betulinol, juniperol, carvacrol, carvacrol, cedrol, citronellol, p-cresol, lentinanol, cuminol, and cyclohexane. Atenol, dihydrocarvol, elemol, eugenol, farnesol, geraniol, geraniol, 1-hexanol, hexenol, beetledienol, isophytol, isomenthol, khusimol, lanosterol, linalool, lupeol, menthol, myrceneol, nerol, nerolidol, perillol, phenethyl alcohol, phytol, rose alcohol, perillol, eucalyptol, terpineol, thymol.

[0023] Alternatively or preferably, the one, two, three or more or all of the fragrances in the essential oil provided in step i) are selected from the group consisting of alcohols with a molecular weight in the range of 50 g / mol to 500 g / mol, preferably 100 g / mol to 300 g / mol, and particularly preferably 120 g / mol to 230 g / mol.

[0024] Preferably, the one, two, three or more or all of the fragrances or alcohols in the essential oil provided in step i) are selected from the group consisting of alcohols with a molecular weight in the range of 50 g / mol to 500 g / mol, preferably 100 g / mol to 300 g / mol, and particularly preferably 120 g / mol to 230 g / mol.

[0025] Furthermore, in the method according to the invention, it is preferred that the essential oil provided in step i) contains additional fragrance, wherein one, two, three or more, or all of the additional fragrance are selected from the group consisting of aldehydes, alkenes, and carbonic acids. Preferably, the additional fragrance is not an alcohol.

[0026] Preferably, the one, two, three or more or all of the essential oils provided in step i) are essential oils of plants selected from the genus of the group consisting of jasmine, rose, magnolia and mixtures thereof.

[0027] Preferably, the one, two, three or more, or all of the essential oils provided in step i) are essential oils of the Rosa genus.

[0028] Preferably, the one, two, three or more or all of the essential oils provided in step i) are essential oils of plants selected from the genus of the group consisting of jasmine, magnolia and mixtures thereof.

[0029] Preferably, the term "essential oil of plants of a genus selected from [...] and mixtures thereof" refers to a mixture of two or more essential oils from different genera, or a mixture of different essential oils from the same genus, or a mixture thereof.

[0030] Essential oils are typically produced by distillation, boiling, or pressing. Generally, compositions produced by solvent extraction or enfleurage are described as "pure oils." Preferably, the term "essential oil" also includes pure oils.

[0031] In the method according to the invention, preferably, the one, two, three or more or all of the essential oils provided in step i) are plant extracts.

[0032] Preferably, the plant extracts, one, two, three or more, or all of them, are selected from the group consisting of: flowers, stems, leaves, fruits, pericarps, roots, needles, and branches.

[0033] Alternatively or preferably, the one, two, three or more, or all of the plant extracts are selected from the group consisting of: basil extract, caraway extract, carrot seed extract, celery seed extract, celery extract, clary sage extract, tarragon extract, daylily extract, galangal extract, heather extract, licorice extract, immortelle extract, frankincense extract, flaxseed extract, yerba mate extract, star anise extract, tobacco extract, violet leaf extract, wheat bran extract, broom extract, carnation extract, acacia extract, pea extract, geranium extract, hyacinth extract, and jasmine extract. Extracts of various herbs and plants, including jasmine extract, daffodil extract, lavender extract, mixed lavender extract, mimosa extract, narcissus extract, orange blossom extract, orange leaf extract, iris extract, sweet osmanthus extract, rose extract, marigold extract, tuberose extract, ylang-ylang extract, apple extract, beeswax extract, blackcurrant bud extract, wheat bran extract, broom extract, black pepper extract, cardamom extract, fenugreek seed extract, ginger extract, nutmeg extract, pink pepper extract, frankincense extract, Sichuan pepper extract, tonka bean extract, turmeric extract, benzoin extract, myrrh extract, frankincense extract, red myrrh extract, styrax extract, turmeric extract, vanilla extract, orange extract, clove bud extract, elemi extract, eucalyptus extract, balsam fir extract, gentian extract, bay leaf extract, peppermint extract, pine needle extract, thyme extract, castoreum extract, civet extract, oakmoss extract, and tree moss extract. cextract), patchouli extract, rockrose extract, labdanum extract, okra seed extract, and mixtures thereof,

[0034] Preferably, the one, two, three or more, or all of the plant extracts are extracts from plants of the genus selected from the group consisting of jasmine, rose, magnolia and mixtures thereof.

[0035] Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus Rosa. Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus Jasmine. Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus Magnolia.

[0036] Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of a genus selected from the group consisting of jasmine, magnolia and mixtures thereof.

[0037] The information about essential oils in this article can be applied to plant extracts, and vice versa.

[0038] Preferably, an aqueous culture of one or more yeasts of the genus *Yarlosporium* is obtained by mixing the one or more yeasts with water. Preferably, the yeasts provided in step ii) are selected from the group consisting of: Yarrowia bubula, Yarrowia deformans, Yarrowia lipolytica, Yarrowia porcina, Yarrowia yakushimensis, Yarrowia parophonii, Yarrowia galli, Yarrowia oslonensis, Yarrowia alimentaria, Yarrowia hollandica, and Yarrowia phangngaensis. Particularly preferably, one or more of the yeasts is Yarrowia lipolytica, and more preferably, one or more of the yeasts is Yarrowia lipolytica (DSM 1345, DSMZ GmbH).

[0039] Particularly preferably, the cell density of the aqueous culture provided in step ii) is at least 7.5 × 10⁻⁶ cells per milliliter of the aqueous culture. 7 Preferably at least 10×10 7 Preferably at least 15×10 7 Preferably, it should be at least 19×10 7 The yeast cells mentioned above.

[0040] Surprisingly, it was found that at least 7 × 10⁻⁶ ppm was present per milliliter of the aqueous culture. 7 At cell densities of 1,000 cells, and further at densities preferred as described above, the adjustment of odor characteristics and the change in compound amounts are more pronounced as described herein.

[0041] Preferably, when determining the cell density, the total number of cells is taken into account.

[0042] Preferably, when determining the cell density, only living or viable cells are taken into account.

[0043] The cell density in the aqueous culture can be determined by cell counting (e.g., via a counting chamber), automated cell counter, or flow cytometry based on autofluorescence, staining (e.g., propidium iodide), or side-scattered light.

[0044] Alternatively, or at another location, the OD can be determined. 600 (Optical density of the sample measured at a wavelength of 600 nm in a 1 cm optical path), and the cell density can be calculated based on this and using a correction factor described in Worland et al., “Analysis of Yarrowia lipolytica growth, catabolism, and terpenoid biosynthesis during utilization of lipid-derived feedstock”, Metabolic Engineering Communications 11 (2020) e00130, https: / / doi.org / 10.1016 / j.mec.2020.e00130.

[0045] In the method according to the invention, preferably, the yeast in the aqueous culture provided in step ii) is not permeabilized. Preferably, the yeast in the aqueous culture provided in step ii) is not permeabilized using one or more cationic surfactants. Preferably, the yeast in the aqueous culture provided in step ii) is not permeabilized using cetrimonium bromide (CTAB).

[0046] In the method according to the invention, the yeast, particularly *Yarrowia lipolytica*, is capable of secreting enzymes from inside the cell into the environment. However, permeabilization alters the interaction between the yeast cell and the surrounding compounds, thus changing the transformations that may occur during fermentation in step iv). Therefore, such flavoring compositions differ in molecular composition from flavoring compositions obtained using unpermeabilized yeast or yeast permeated in a different manner.

[0047] Therefore, using permeabilized yeast cells, especially permeabilized yeast cells treated with one or more cationic surfactants, and particularly permeabilized yeast cells treated with cetrimonium bromide (CTAB), produces fragrance compositions with odor characteristics different from those obtained from unpermeabilized yeast cells or yeast cells treated in different ways. It has been found that the odor characteristics of fragrance compositions obtained using unpermeabilized yeast cells or yeast cells treated in different ways are particularly advantageous.

[0048] Preferably, the conditions for allowing fermentation in step iv) include an incubation temperature in the range of 20°C to 30°C, preferably 22.5°C to 27.5°C, and particularly preferably 24°C to 26°C.

[0049] Alternatively or alternatively, preferably, the conditions for allowing fermentation in step iv) include an incubation time of 1 to 168 hours, preferably 2 to 144 hours, particularly preferably 3 to 120 hours, further preferably 4 to 96 hours, even more preferably 5 to 72 hours, more preferably 8 to 48 hours, especially preferably 12 to 36 hours, and even more preferably 18 to 30 hours.

[0050] Alternatively or preferably, the conditions for allowing fermentation to occur in step iv) include a stirring speed in the range of 50 rpm to 300 rpm, preferably 75 rpm to 250 rpm, more preferably 100 rpm to 200 rpm, and even more preferably 125 rpm to 175 rpm.

[0051] The incubation described in step iv) typically results in the formation of a liquid phase and a phase containing fermented biomass (including yeast culture).

[0052] The term "separation of the liquid phase from the fermentation mixture" includes the partial or complete separation of the liquid phase from the fermentation mixture, wherein the residue is or contains fermented essential oils.

[0053] Preferably, the separation in step v) includes one or more methods selected from centrifugation, lyophilization, filtration, preferably membrane filtration, and combinations thereof.

[0054] The term "extracting the fermented essential oil from the fermentation mixture" refers to the step of separating the fermented essential oil from other components in the mixture, such as components already present during incubation in step iv), like the culture medium used for culturing yeast cultures. This separation can be complete or partial. The extraction can include one or more methods selected from liquid-liquid extraction, maceration, remaceration, digestion, stirred maceration, vortex extraction, ultrasonic extraction, countercurrent extraction, percolation, re-percolation, evacolation (reduced pressure extraction), extraction using supercritical carbon dioxide, diacolation, and solid / liquid extraction (preferably under continuous reflux).

[0055] Preferably, the extraction can be aqueous, alcoholic, or aqueous / alcoholic extraction.

[0056] Particularly preferably, the extraction is performed using methyl tert-butyl ether (MTBE), hexane, cyclohexane, diethyl ether, pentane, heptane, toluene, ethyl acetate, dichloromethane, chloroform, or mixtures thereof.

[0057] The extraction process is preferably carried out at a temperature in the range of 5°C to 50°C, more preferably 25°C to 35°C. Particularly preferably, the extraction is carried out in an inert gas atmosphere to avoid oxidation of the components of the extract.

[0058] Following the extraction process, the resulting crude extract may optionally undergo other typical steps, such as purification, concentration, and / or decolorization. The extraction process can proceed to any extent, but typically continues until exhaustion.

[0059] Furthermore, in the method according to the invention, it is preferred that the total concentration of the essential oil provided in step i) is based on 1×10⁻⁶ provided in step ii). 7 One yeast cell, in the range of 0.1 mL to 20 mL, preferably 0.5 mL to 15 mL, more preferably 1 mL to 10 mL, and particularly preferably 2 mL to 7.5 mL.

[0060] The term "fermented essential oil" refers to an essential oil obtained after steps iv), v), or vi) of the method according to the invention, wherein the essential oil may be present in the composition together with other components according to the method. For example, the essential oil obtained after step iv) is present in a fermentation mixture that also contains a liquid phase.

[0061] Preferably, the term "fermented essential oil" refers to an oil that has been fermented as described in step iv) of the method according to the invention.

[0062] Particularly preferred, the term "adjusting the odor characteristics" refers to adjusting one or more odors selected from floral, fruity, sweet, woody, and herbal scents.

[0063] More preferably, the term "adjusting the odor characteristics" means increasing the complexity of the odor characteristics and / or increasing the intensity of one or more odors preferably selected from floral, fruity, sweet, woody, and herbal scents.

[0064] Surprisingly, it has been found that several compounds, which provide floral, fruity, sweet, woody, and / or herbal aromas, are produced or enriched by the method according to the invention.

[0065] Surprisingly, it was found that by altering the amount of compounds such as benzyl acetate, phytol, methyl 2-methylbutyrate, caryophyllene, caryophyllene oxide, benzyl benzoate, isophytol, benzyl alcohol, methyl benzoate, (E)-isoeugenol, linalool, linalool oxide, linolenic acid benzoate, 2-phenylethanol, 2-phenylethyl acetate, citronellol, nerol, geraniol, limonene, jasmine lactone, methyl jasmonate, cis-jasmone, p-cresol, α-pinene, indole, and methyl stearate in the fermented essential oil according to the method of the invention.

[0066] Therefore, preferably, in the incubation in step iv), and more preferably in the fermentation in step iv), one, two, three or more, or all of the compounds in the essential oil selected from the group consisting of:

[0067] Benzyl acetate, phytol, methyl 2-methylbutyrate, caryophyllene, caryophyllene oxide, benzyl benzoate, isophytol, benzyl alcohol, methyl benzoate, (E)-isoeugenol, linalool, linalool oxide, linolenic acid benzoate, 2-phenylethyl acetate, citronellol, nerol, nerol, geraniol, limonene, jasmine lactone, methyl jasmonic acid, cis-jasmone, p-cresol, α-pinene, indole, and methyl stearate.

[0068] Preferably, the essential oil is or comprises a plant extract of the genus Jasmine, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of the following is changed when compared with the essential oil provided in step i) of the method according to the invention:

[0069] Linolenic acid benzoate, benzyl alcohol, methyl stearate, jasmine lactone, p-cresol, benzyl benzoate, isophytol, indole, benzyl acetate, phytol, methyl jasmone, linalool, cis-jasmone, methyl benzoate, (E)-isoeugenol.

[0070] Particularly preferably, the essential oil is or comprises an extract of a plant of the genus Jasmine, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of the following increases when compared with the essential oil provided in step i) of the method according to the invention:

[0071] Linolenic acid benzoate, benzyl alcohol, methyl stearate, jasmine lactone, p-cresol, benzyl benzoate, isophytol,

[0072] And / or

[0073] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0074] Indole, benzyl acetate, phytol, methyl jasmone, linalool, cis-jasmone, methyl benzoate, (E)-isoeugenol.

[0075] Preferably, the essential oil is or comprises an extract of a plant from the genus Rosa, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of Rosa changes when compared with the essential oil provided in step i) of the method according to the invention:

[0076] Benzyl alcohol, 2-phenylethyl acetate, neraldehyde, caryophyllene, citronellol.

[0077] Particularly preferably, the essential oil is or contains an extract of a plant of the genus Rosaceae, wherein the amount of benzyl alcohol in the essential oil increases compared to the essential oil provided in step i) of the method according to the invention.

[0078] And / or

[0079] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0080] 2-Phenylethyl acetate, neraldehyde, caryophyllene, citronellol.

[0081] Preferably, the essential oil is or comprises an extract of a plant of the genus *Magnolia*, wherein the amount of one, two, three, or more compounds selected from the group consisting of the following is altered when compared with the essential oil provided in step i) of the method according to the invention:

[0082] Linalool, methyl 2-methylbutyrate, caryophyllene, benzyl alcohol, benzyl acetate, α-pinene, limonene, nerol, geraniol, linalool oxide, caryophyllene oxide.

[0083] Particularly preferably, the essential oil is or comprises a plant extract of the genus *Magnolia*, wherein the amount of linalool in the essential oil increases compared to the essential oil provided in step i) of the method according to the invention.

[0084] And / or

[0085] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0086] 2-Methylbutyrate, caryophyllene, benzyl alcohol, benzyl acetate, α-pinene, limonene, nerol, geraniol, linalool oxide, caryophyllene oxide.

[0087] Benzyl acetate (preferably CAS Registry No. 140-11-4) has been described as providing an odor with the following characteristics: sweet, floral, fruity, jasmine and fresh.

[0088] Phytol (preferably CAS Registry No. 150-86-7 or 7541-49-3) has been described as providing an odor with floral, balsamic, powdery and waxy notes.

[0089] 2-Methylbutyrate (preferably CAS Registry No. 868-57-5), (S)-2-methylbutyrate (preferably CAS Registry No. 10307-60-5), and (R)-2-methylbutyrate (preferably CAS Registry No. 55449-44-0) have been described as providing an odor with the following characteristics: fruity, green, apple, lily, powdery, and oily.

[0090] Caryophyllene has been described as providing an odor with the following characteristics: sweet, woody, spicy, clove-like, and dry. Preferably, the term "caryophyllene" refers to α-caryophyllene (preferably CAS Registry No. 6753-98-6), β-caryophyllene (preferably CAS Registry No. 87-44-5), and / or γ-caryophyllene (preferably CAS Registry No. 118-65-0).

[0091] Caryophyllene oxide (preferably CAS Registry No. 1139-30-6) has been described as providing an odor with the following characteristics: sweet, fresh, dry, woody and spicy.

[0092] Benzyl benzoate (preferably CAS Registry No. 120-51-4) has been described as providing an odor that is sweet, balsamic, oily, and herbal.

[0093] Isophyll (preferably CAS Registry No. 505-32-8) has been described as providing an aroma that is floral, herbal and green.

[0094] Benzyl alcohol (preferably CAS Registry No. 100-51-6) has been described as having an odor that is sweet, floral and fruity.

[0095] Methyl benzoate (preferably CAS Registry No. 93-58-3) has been described as providing an odor with the following characteristics: phenolic, wintergreen, almond, floral, and cananaga aroma.

[0096] (E)-Isoeugenol (preferably CAS Registry No. 5932-68-3) has been described as providing an odor with the following characteristics: sweet, spicy, carnation-like, phenolic, and floral.

[0097] Linalool (preferably CAS Registry No. 78-70-6), preferably (R)-linalool (preferably CAS Registry No. 126-91-0), and preferably (S)-linalool (preferably CAS Registry No. 126-90-9) have been described as providing an odor with the following characteristics: citrus, orange, floral, terpene, waxy, and rose.

[0098] Linalool oxide (preferably CAS Registry No. 1365-19-1) has been described as providing an odor with the following characteristics: floral, herbal, earthy and green.

[0099] 2-Phenylacetyl alcohol (preferably CAS Registry No. 60-12-8) has been described as providing an odor such as sweet, floral, fresh, bread, rose and honey.

[0100] 2-Phenylethyl acetate (preferably CAS Registry No. 103-45-7) has been described as providing an odor such as floral, rose, sweet, honey, fruity and tropical.

[0101] Citronellol (preferably CAS Registry No. 106-22-9), (R)-citronellol (preferably CAS Registry No. 1117-61-9), and (S)-citronellol (preferably CAS Registry No. 7540-51-4) have been described as providing an aroma that is floral, rose-like, sweet, citrus-like, green, oily, and terpene-like.

[0102] Neraldehyde (preferably CAS Registry No. 106-26-3) has been described as providing an odor with the following characteristics: sweet, citral, and lemon peel.

[0103] Neroli (preferably CAS Registry No. 106-25-2) has been described as providing an aroma that is sweet, natural, orange blossom, citrus and magnolia.

[0104] Geraniol (preferably CAS Registry No. 106-24-1) has been described as providing an aroma that is sweet, floral, fruity, rose-like, waxy, and citrus-like.

[0105] Limonene (preferably CAS Registry No. 138-86-3) has been described as providing an odor with the following characteristics: citrus, herbal, terpene and camphor.

[0106] Jasmine lactone (preferably CAS Registry No. 34686-71-0) has been described as providing an aroma that is oily, fruity, petal-like, floral, jasmine-like, tuberose-like, peach-like, apricot-like, and coconut-like.

[0107] Methyl jasmonate (preferably CAS Registry No. 39924-52-2) has been described as providing an odor as follows: jasmine, oily, green, petal, soft and greasy.

[0108] Cis-jasmone (preferably CAS Registry No. 488-10-8) has been described as providing an aroma that is woody, herbal, floral, spicy, jasmine, and celery.

[0109] p-Cresol (preferably CAS Registry No. 106-44-5) has been described as providing an odor as follows: phenolic, daffodil, animal and mimosa.

[0110] α-Pinene (preferably CAS Registry No. 80-56-8) has been described as providing an odor such as fresh, camphor, sweet, pine, earthy and woody.

[0111] Indole (preferably CAS Registry No. 120-72-9) has been described as providing an odor such as animalic, floral, moth odor, and naphthalene.

[0112] Methyl stearate (preferably CAS Registry No. 112-61-8) has been described as having an odor that is both oily and waxy.

[0113] The present invention also relates to an essential oil that is obtained or can be obtained by the method according to the present invention.

[0114] Preferably, the amount of one, two, three or more, or all of the compounds selected from the group consisting of the following is changed when compared with the essential oil provided in step i) of the method according to the invention:

[0115] Benzyl acetate, phytol, methyl 2-methylbutyrate, caryophyllene, caryophyllene oxide, benzyl benzoate, isophytol, benzyl alcohol, methyl benzoate, (E)-isoeugenol, linalool, linalool oxide, linolenic acid benzoate, 2-phenylethyl acetate, citronellol, nerol, nerol, geraniol, limonene, jasmine lactone, methyl jasmonic acid, cis-jasmone, p-cresol, α-pinene, indole, and methyl stearate.

[0116] The foregoing description of the method according to the invention, particularly the preferred features, applies accordingly to the essential oils according to the invention.

[0117] Preferably, the essential oil is or comprises one or more plant extracts of one, two, or all of the genera selected from the group consisting of jasmine, rose, magnolia, and mixtures thereof. Preferably, the essential oil is or comprises plant extracts from the genus *Jasmine*. Preferably, the essential oil is or comprises plant extracts from the genus *Rosa*. Preferably, the essential oil is or comprises plant extracts from the genus *Magnolia*.

[0118] Preferably, the term "the essential oil is a plant extract" refers to a plant extract that has been processed by the method according to the invention.

[0119] Preferably, the essential oil is or comprises a plant extract of the genus Jasmine, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of the following is changed when compared with the essential oil provided in step i) of the method according to the invention:

[0120] Linolenic acid benzoate, benzyl alcohol, methyl stearate, jasmine lactone, p-cresol, benzyl benzoate, isophytol, indole, benzyl acetate, phytol, methyl jasmone, linalool, cis-jasmone, methyl benzoate, (E)-isoeugenol.

[0121] Particularly preferably, the essential oil is or comprises an extract of a plant of the genus Jasmine, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of the following increases when compared with the essential oil provided in step i) of the method according to the invention:

[0122] Linolenic acid benzoate, benzyl alcohol, methyl stearate, jasmine lactone, p-cresol, benzyl benzoate, isophytol,

[0123] And / or

[0124] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0125] Indole, benzyl acetate, phytol, methyl jasmone, linalool, cis-jasmone, methyl benzoate, (E)-isoeugenol.

[0126] Preferably, the essential oil is or comprises an extract of a plant from the genus Rosa, wherein the amount of one, two, three or more, or all of the compounds selected from the group consisting of Rosa changes when compared with the essential oil provided in step i) of the method according to the invention:

[0127] Benzyl alcohol, 2-phenylethyl acetate, neraldehyde, caryophyllene, citronellol.

[0128] Particularly preferably, the essential oil is or contains an extract of a plant of the genus Rosaceae, wherein the amount of benzyl alcohol in the essential oil increases compared to the essential oil provided in step i) of the method according to the invention.

[0129] And / or

[0130] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0131] 2-Phenylethyl acetate, neraldehyde, caryophyllene, citronellol.

[0132] Preferably, the essential oil is or comprises an extract of a plant of the genus *Magnolia*, wherein the amount of one, two, three, or more compounds selected from the group consisting of the following is altered when compared with the essential oil provided in step i) of the method according to the invention:

[0133] Linalool, methyl 2-methylbutyrate, caryophyllene, benzyl alcohol, benzyl acetate, α-pinene, limonene, nerol, geraniol, linalool oxide, caryophyllene oxide.

[0134] Particularly preferably, the essential oil is or comprises a plant extract of the genus *Magnolia*, wherein the amount of linalool in the essential oil increases compared to the essential oil provided in step i) of the method according to the invention.

[0135] And / or

[0136] Wherein, the amount of one, two, three or more, or all of the compounds selected from the group consisting of in the essential oil is reduced compared with the essential oil provided in step i) of the method according to the invention:

[0137] 2-Methylbutyrate, caryophyllene, benzyl alcohol, benzyl acetate, α-pinene, limonene, nerol, geraniol, linalool oxide, caryophyllene oxide.

[0138] As described above, it has been surprisingly found that the aroma characteristics of the provided essential oils can be adjusted by the method according to the invention. Particularly pleasant (fermented) essential oils have been obtained by the method according to the invention. It has been surprisingly found that several aromas of the provided essential oils can be enhanced. Therefore, the essential oils obtained or obtainable by the method according to the invention differ in aroma characteristics from both existing and known essential oils.

[0139] Surprisingly, several odors were detected in the essential oils (fermented essential oils) obtained or available by the method according to the invention, which were absent or weak in the originally provided essential oils.

[0140] However, it was also surprising to find that several odors in the essential oils (fermented essential oils) obtained or available by the method according to the invention were weaker than those in the originally provided essential oils.

[0141] As described above, it was surprisingly found that the odor characteristics in the essential oils obtained or available according to the method of the invention were adjusted compared to the starting materials. Increased complexity and olfactory versatility were observed, while no off-odors or only weak off-odors were observed. Therefore, the fragrance compositions according to the invention provide particularly advantageous odor characteristics.

[0142] Surprisingly, it was found that the intensity of at least four scents selected from floral, green, fruity, animalic, and sweet notes in the fragrance composition varied compared to the pure oil provided.

[0143] Therefore, for the essential oil according to the invention, it is preferred that the intensity of at least four scents selected from the group consisting of floral, green, fruity, animalic, and sweet scents changes compared to the essential oil provided in step i) of the method according to the invention.

[0144] Those skilled in the art are familiar with floral, green, fruity, animalic, and sweet scents, as well as their understanding, definition, and characterization. Preferably, these scents are understood, defined, and / or characterized as described, for example, in S. Arctander, Perfume and Flavor Chemicals, Volumes I and II, Montclair, NJ, 1969, author's edition, or H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 5th edition, Wiley-VCH, Weinheim 2006.

[0145] Preferably, the intensity of the floral, fruity, animalic, and sweet notes varies compared to the essential oil provided in step i) of the method according to the invention.

[0146] Preferably, the intensity of the floral, green, fruity, animalic, and sweet notes varies compared to the essential oil provided in step i) of the method according to the invention.

[0147] Surprisingly, it was further discovered that in all flavoring compositions, the intensity of two or three scents selected from floral, green, fruity, animalic, and sweet notes increased compared to the provided absolute oil. Furthermore, it was found that in all flavoring compositions, the intensity of two scents selected from floral, fruity, animalic, and sweet notes increased compared to the provided absolute oil.

[0148] Therefore, for the essential oil according to the invention, it is preferable that the intensity of two or three scents selected from the group consisting of floral, green, fruity, animalic, and sweet scents is increased compared to the essential oil provided in step i) of the method according to the invention.

[0149] Particularly preferably, the intensity of two scents selected from the group consisting of floral, fruity, animalic, and sweet scents is increased compared to the essential oil provided in step i) of the method according to the invention.

[0150] Preferably, the intensity of the fruity aroma and sweetness is increased compared to the essential oil provided in step i) of the method according to the invention.

[0151] Preferably, the intensity of the fruity and animalic aromas is increased compared to the essential oil provided in step i) of the method according to the invention.

[0152] Preferably, the intensity of the floral, green, and animalic notes is increased compared to the essential oil provided in step i) of the method according to the invention.

[0153] Surprisingly, it was further discovered that in all the flavor compositions, the intensity of two aromas selected from floral, fruity, animalic, and sweet notes was reduced compared to the pure oils provided.

[0154] Therefore, for the essential oil according to the invention, it is preferred that the intensity of the two scents selected from the group consisting of selected floral, fruity, animalic and sweet scents is reduced compared to the essential oil provided in step i) of the method according to the invention.

[0155] Preferably, the intensity of the floral and animalic notes is reduced compared to the essential oil provided in step i) of the method according to the invention.

[0156] Preferably, the intensity of the floral and sweet notes is reduced compared to the essential oil provided in step i) of the method according to the invention.

[0157] Preferably, the intensity of the fruity aroma and sweetness is reduced compared to the essential oil provided in step i) of the method according to the invention.

[0158] Preferably, the term "two odors" as used herein should be understood as "at least two odors". This also applies accordingly to any other number of odors described.

[0159] Preferably, the term "two odors" as used herein should be understood to mean at least two odors, but not more than two odors. This also applies accordingly to any other number of odors described.

[0160] Typically, to assess whether an odor has changed, preferably increased or decreased, a trained team performs sensory evaluations, as is well known to technicians. Typically, the tested odor is evaluated based on a nominal scale, where changes are observed as different scores are obtained.

[0161] The present invention also relates to a fragrance composition comprising an essential oil according to the present invention.

[0162] Preferably, the fragrance composition according to the invention comprises the essential oil (preferably an extract) according to the invention, as well as other components commonly used in fragrance compositions, such as fragrances, solvents, stabilizers, UV filters, and emulsifiers.

[0163] Furthermore, preferably, the content of the essential oil (preferably extract) in the fragrance composition according to the invention is in the range of 0.0001 wt.-% to 10 wt.-%, preferably 0.001 wt.-% to 5 wt.-%, and particularly preferably 0.01 wt.-% to 1 wt.-% based on the total weight of the fragrance composition.

[0164] Furthermore, the present invention relates to an aromatic product comprising an essential oil according to the invention or a fragrance composition according to the invention, preferably a pharmaceutical preparation, a cosmetic preparation, or a preparation for nutrition or pleasure.

[0165] Preferably, the fragrance product is selected from the group consisting of detergents and cleaning agents, hygiene or care products preferably in the fields of body and hair care, cosmetics and household care, and preferably from the group consisting of: perfume extracts; perfumes; eau de toilette; aftershave; cologne; preshave products; splash cologne; fragrance-freshening tissues; acidic, alkaline or neutral detergents; textile fresheners; ironing aids; liquid detergents; powdered detergents; garment pretreatments; fabric softeners; laundry soaps; laundry sheets; disinfectants; surface disinfectants; air fresheners; aerosols; waxes and polishes; body care products; hand creams and hand lotions; shower gels; foot creams and foot lotions; depilatory creams and depilatory lotions; aftershave creams and aftershave lotions; tanning creams and tanning lotions; hair care products; shampoos; deodorants; antiperspirants; cosmetic products; candles; lamp oil; incense sticks; insecticides; insect repellents; and sprays.

[0166] Preferably, the pharmaceutical preparations according to the invention are in the form of emulsions, powders, solutions, pastes or other swallowable or chewable preparations, such as capsules, tablets (uncoated tablets and coated tablets, such as tablets with gastric juice resistant coatings), sugar-coated tablets, granules, pills, solid mixtures, liquid dispersions, and are preferably used as medicines or other medicines that can only be obtained by prescription or from a pharmacy, or as food supplements.

[0167] The cosmetic formulations described herein are particularly suitable for formulations that are applied topically to human skin, especially for the purpose of achieving cosmetic effects.

[0168] Cosmetic or pharmaceutical preparations as described herein may also contain one, two, three, or more substances selected from the group consisting of: fragrance substances, perfume oils, fatty oils, fatty acids, ceramides, ceramide-like substances, sterols, hydrocarbons, phytosterols, anti-acne active ingredients, anti-dandruff active ingredients, antimicrobial active ingredients, preservatives, antiperspirants, antiirritants, antipruritic active ingredients, cooling active ingredients, anti-aging active ingredients, skin whitening and tanning active ingredients, skin moisturizing regulators, and osmotic regulators. Agents, insect repellents, enzyme inhibitors, odor absorbers, dyes, abrasives, anti-acne agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, irritant preventatives, irritant inhibitors, antioxidants, astringents, antiperspirants, antibacterial agents, antistatic agents, adhesives, buffers, carrier materials, chelating agents, cell stimulants, detergents, conditioning agents, depilatory agents, surfactants, deodorants, antiperspirants, emulsifiers, enzymes, fibers, film-forming agents, fixatives, foam forming agents, foam stabilizers, antifoaming substances, foam Accelerators, gelling agents, gelling agents, hair conditioning agents, hair styling agents, hair straighteners, moisturizers, humectants, water-retaining substances, bleaching agents, strengthening agents, detergents, optical brighteners, impregnating agents, anti-fouling agents, friction reducers, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, covering agents, polishing agents, gloss agents, polymers, powders, proteins, re-oiling agents, abrasives, silicones, skin soothing agents, skin cleansers, skin care products, skin healing agents, skin whitening agents, skin protectants, skin softeners. Hair growth promoters, coolants, skin coolants, warming agents, skin warming agents, stabilizers, ultraviolet absorbers, ultraviolet filters, detergents, fabric conditioners, suspending agents, skin tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, monounsaturated or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color protectants, pigments, corrosion resistant agents, fragrances, perfumery substances, aroma-generating substances, polyols, surfactants, electrolytes, organic solvents, and silicone derivatives.

[0169] Preferably, the compositions provided for food or pleasure as described herein can be selected from the group consisting of: (low-calorie) baked goods (e.g., bread, biscuits, cakes, other baked goods); confectionery (e.g., cereal bar products, chocolate, chocolate bars, other bar-shaped products, fruit gummies, sugar-coated pills, hard and soft caramel, chewing gum); non-alcoholic beverages (e.g., cocoa, coffee, green tea, black tea, (green, black) tea beverages rich in (green, black) tea extracts, rooibos tea, other herbal teas, fruit-containing soft drinks, isotonic beverages, stimulant drinks, fruit juice beverages, fruit and vegetable juices, fruit... Juice preparations or vegetable juice preparations); instant beverages (e.g., instant cocoa beverages, instant tea beverages, instant coffee beverages); meat products (e.g., ham, fresh sausage or raw sausage preparations, fresh or salted meat products with spices or cured); eggs or egg products (dried eggs, egg whites, egg yolks); cereal products (e.g., breakfast cereals, cereal bars, pre-cooked instant rice products); dairy products (e.g., whole or low-fat or skim milk beverages, rice pudding, yogurt, kefir, cream cheese, soft cheese, hard cheese, milk powder, whey, butter, buttermilk, ice cream, products containing partially or completely hydrolyzed milk proteins); products made from soy protein or Other products derived from soybean fractions (e.g., soy milk and products made therefrom, beverages containing isolated or enzymatically treated soy protein, beverages containing soy flour, preparations containing soy lecithin, fermented products such as tofu or tempeh, and mixtures with fruit preparations and optionally flavorings); dairy-like preparations (milk-type, yogurt-type, dessert-type, ice cream-type) derived from protein-rich plant materials (e.g., materials derived from oat, almond, pea, lupin, lentil, broad bean, chickpea, rice, rapeseed seeds); non-dairy beverages rich in plant protein; fruit preparations ( Examples include: jams, ice cream, fruit sauces, fruit fillings; vegetable preparations (e.g., tomato sauces, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, concentrated cooked vegetables); snacks (e.g., baked or fried potato chips or potato cake products, corn-based or peanut-based extrudates); fat-based and oil-based products or their emulsions (e.g., mayonnaise, remola sauce, seasonings, each in full-fat or low-fat form); other prepared meals and soups (e.g., dry soups, instant soups, pre-cooked soups); spices; spice mixtures, especially seasonings for the snack food sector; sweetener preparations, tablets or sachets; other preparations for sweetening or whitening beverages.

[0170] Preferably, the formulations according to the invention can be selected from the group consisting of: toothpaste, tooth gel, mouthwash, mouthwash, gargle, oral or pharyngeal spray (pump or aerosol spray), lozenges, candy, chewing gum, soft candy and dental care chewing gum.

[0171] Furthermore, preferably, the content of the fragrance composition according to the invention in the formulation according to the invention is in the range of 0.0001 wt.-% to 1 wt.-%, preferably 0.001 wt.-% to 0.5 wt.-%, and particularly preferably 0.01 wt.-% to 0.1 wt.-%, based on the total weight of the fragrance composition according to the invention.

[0172] Furthermore, preferably, the content of the essential oil in the formulation according to the invention is in the range of 0.000001 wt.-% to 1 wt.-%, preferably 0.00001 wt.-% to 0.5 wt.-%, particularly preferably 0.0001 wt.-% to 0.1 wt.-%, and even more preferably 0.001 wt.-% to 0.01 wt.-%.

[0173] The present invention also relates to the use of yeasts of the genus Yarrow for adjusting the odor characteristics of essential oils, preferably in the method according to the present invention.

[0174] The foregoing description of the method according to the invention, particularly the preferred features, applies accordingly to the uses of the invention.

[0175] In the intended use according to the invention, preferably, the one, two, three or more, or all yeasts are selected from the group consisting of: *Yaruosia buxiflora*, *Yaruosia var. mutata*, *Yaruosia lipolytica*, *Yaruosia stolonifera*, *Yaruosia yakushima*, *Yaruosia parofonnia*, *Yaruosia foetida*, *Yaruosia osloensis*, *Yaruosia suspensa*, *Yaruosia hologramma*, and *Yaruosia phanga*.

[0176] Preferably, the yeast is *Yarrowia lipolytica*, and particularly preferably, the yeast is selected from the group consisting of: *Yarrowia lipolytica* (DSM 1345, DSMZ GmbH), *Yarrowia lipolytica* (DSM 3286, DSMZ GmbH), *Yarrowia lipolytica* (DSM 8218, DSMZ GmbH), *Yarrowia lipolytica* (DSM 16126, DSMZ GmbH), *Yarrowia lipolytica* (DSM 21175, DSMZ GmbH), and *Yarrowia lipolytica* (DSM70562, DSMZ GmbH), and particularly preferably, the yeast is *Yarrowia lipolytica* (DSM 1345, DSMZ GmbH).

[0177] Further aspects and advantages of the invention arise from the following description of preferred embodiments. Detailed Implementation

[0178] Example

[0179] Example 1: Modification of essential oils

[0180] Cultures of *Yarrowia lipolytica* (DSM 1345, DSMZ GmbH) were grown in YPD medium at 25°C and 150 rpm for 24 hours to reach a minimum 7.5 × 10⁻⁶ ppm. 7 The cell density of CFU was determined. Subsequently, essential oil was added, with 100 mL of essential oil added to 2.3 L of cell culture. The resulting mixture was then incubated at 25°C and 150 rpm for 24 hours.

[0181] After incubation, the mixture is centrifuged at 3800 rpm to separate the yeast cells (precipitate) from the mixture.

[0182] The liquid phase was collected and extracted with methyl tert-butyl ether at 25°C.

[0183] The obtained extract is a fermented essential oil.

[0184] After obtaining the fermented essential oils, a trained team compared the provided oils and fermented oils based on their sensory evaluations.

[0185] Example 2: Jasmine

[0186] Perform the method as described in Example 1 using jasmine absolute oil.

[0187] A portion of the initial jasmine absolute oil and a portion of the obtained fermented essential oil were collected, and their component contents were determined by GC-MS:

[0188]

[0189]

[0190]

[0191]

[0192] The composition of fermented essential oils differs from that of unfermented oils. Surprisingly, fermented jasmine absolute oil offered notes of alcohol, whiskey, and champagne. Furthermore, licorice and chocolate notes were also detected. These notes were not observed in jasmine absolute oil.

[0193] Example 3: Rose

[0194] Perform the method as described in Example 1 using rose absolute oil.

[0195] A portion of the initial rose absolute oil and a portion of the obtained fermented essential oil were collected, and their component contents were determined by GCMS:

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] The composition of fermented essential oils differs from that of unfermented oils. Surprisingly, fermented rose absolute oil was found to offer an alcoholic aroma. Additionally, chocolate and geranium notes were detected. These aromas were not observed in rose absolute oil. Fermented oils are described as more sparkling and lighter than rose absolute oil.

[0202] Example 4: Magnolia

[0203] Perform the method as described in Example 1 using magnolia oil.

[0204] A portion of the initial magnolia absinthe and a portion of the obtained fermented essential oil were collected, and their component contents were determined by GCMS:

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] The composition of fermented essential oils differs from that of unfermented oils. Surprisingly, fermented magnolia absolute oil offered a milder fruity aroma. However, spicy, cinnamon, and hay-like notes were detected. These aromas were not observed in magnolia absolute oil.

[0213] Example 5: Olfactory Evaluation

[0214] Fragrance compositions according to Examples 2, 3 and 4 were prepared and their olfactory properties were evaluated by perfumers (n=2).

[0215] The following results were obtained:

[0216]

[0217]

[0218]

[0219] It was found that in all the flavor compositions, the intensity of at least four aromas selected from floral, green, fruity, animalic, and sweet notes varied compared to the absolute oil provided.

[0220] Further investigation revealed that in all flavoring compositions, the intensity of two or three aromas selected from floral, green, fruity, animalic, and sweet notes increased compared to the provided absolute oil. Additionally, it was found that in all flavoring compositions, the intensity of two aromas selected from floral, fruity, animalic, and sweet notes increased compared to the provided absolute oil.

[0221] Further investigation revealed that, among all the flavor compositions, the intensity of two aromas selected from floral, fruity, animalic, and sweet notes was reduced compared to the pure oils provided.

Claims

1. A method for adjusting the odor characteristics of essential oils, the method comprising the following steps: i) Provide one or more essential oils, wherein the one, two, three or more or all of the essential oils are plant extracts selected from plants of the genus that make up the group consisting of jasmine, rose, magnolia and mixtures thereof; ii) Provide an aqueous culture of one or more yeasts of the genus Yarrow; The cell density of the aqueous culture is at least 7 × 10⁶ cells per milliliter of the aqueous culture. 7 The yeast cells described; iii) Mix the essential oil provided in step i) and the aqueous culture provided in step ii) to obtain a mixture; iv) Incubate the mixture obtained in step iii) under conditions that allow the essential oil to ferment to obtain a fermentation mixture containing a liquid phase; v) Separating the liquid phase from the fermented biomass to obtain a fermented mixture containing fermented essential oils; vi) Extract the fermented essential oil from the fermented mixture.

2. The method according to claim 1, wherein, The one, two, three or more, or all of the yeasts provided in step ii) are selected from the group consisting of: Yarrowia bubula, Yarrowia deformans, Yarrowia lipolytica, Yarrowia porcina, Yarrowia yakushimensis, Yarrowia parophonii, Yarrowia galli, Yarrowia oslonensis, Yarrowia alimentaria, Yarrowia hollandica, and Yarrowia phangngaensis. Preferably, The yeast mentioned is *Yarrowia lipophila*.

3. The method according to claim 1 or 2, wherein, Adjusting the odor characteristics refers to adjusting one or more odors selected from floral, fruity, sweet, woody, and herbal scents.

4. The method according to any one of the preceding claims, wherein, Adjusting the odor characteristics means increasing the complexity of the odor characteristics and / or increasing the intensity of one or more odors preferably selected from floral, fruity, sweet, woody, and herbal scents.

5. The method according to any one of the preceding claims, wherein, The conditions for allowing fermentation to occur in step iv) include: a) The incubation temperature is in the range of 20°C to 30°C, preferably 22.5°C to 27.5°C, and particularly preferably 24°C to 26°C; and / or b) The incubation time is in the range of 1 hour to 168 hours, preferably 2 hours to 144 hours, particularly preferably 3 hours to 120 hours, further preferably 4 hours to 96 hours, even more preferably 5 hours to 72 hours, more preferably 8 hours to 48 hours, especially preferably 12 hours to 36 hours, and even more preferably 18 hours to 30 hours; and / or c) The stirring speed is in the range of 50 rpm to 300 rpm, preferably 75 rpm to 250 rpm, more preferably 100 rpm to 200 rpm, and even more preferably 125 rpm to 175 rpm.

6. The method according to any one of the preceding claims, wherein, The cell density of the aqueous culture provided in step ii) is at least 7.5 × 10⁻⁶ cells per milliliter of the aqueous culture. 7 Preferably at least 10×10 7 Preferably at least 15×10 7 Preferably, it should be at least 19×10 7 The yeast cells mentioned above.

7. The method according to any one of the preceding claims, wherein, The total concentration of essential oils provided in step i) is based on 1×10⁻⁶ provided in step ii). 7 The amount of yeast cells ranges from 0.1 mL to 20 mL, preferably from 0.5 mL to 15 mL, more preferably from 1 mL to 10 mL, and particularly preferably from 2 mL to 7.5 mL.

8. The method according to any one of the preceding claims, wherein, The separation in step v) includes one or more methods selected from centrifugation, lyophilization, liquid-liquid extraction, filtration, preferably membrane filtration, reverse osmosis, and combinations thereof. Preferably, the separation in step v) includes one or more methods selected from centrifugation, lyophilization, liquid-liquid extraction, preferably using methyl tert-butyl ether (MTBE), hexane, cyclohexane, diethyl ether, pentane, heptane, toluene, ethyl acetate, dichloromethane and / or chloroform, filtration, preferably membrane filtration, reverse osmosis and combinations thereof.

9. An essential oil, said essential oil being obtained or obtainable by the method according to any one of the preceding claims, in, The amount of one, two, three or more, or all of the compounds selected from the group consisting of the following changes when compared with the essential oil provided in step i) of the method: Benzyl acetate, phytol, methyl 2-methylbutyrate, caryophyllene, caryophyllene oxide, benzyl benzoate, isophytol, benzyl alcohol, methyl benzoate, (E)-isoeugenol, linalool, linalool oxide, linolenic acid benzoate, 2-phenylethyl acetate, citronellol, nerol, nerol, geraniol, limonene, jasmine lactone, methyl jasmonic acid, cis-jasmone, p-cresol, α-pinene, indole, and methyl stearate. Preferably, The intensity of at least four scents selected from the group consisting of floral, green, fruity, animalic, and sweet scents, preferably the four scents, varies compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

10. The essential oil according to claim 9, wherein, The intensity of two or three of the aromas selected from the group consisting of floral, green, fruity, animalic, and sweet notes is increased compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8. Particularly preferred, wherein, The intensity of two scents selected from the group consisting of floral, fruity, animalic, and sweet scents is increased compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

11. The essential oil according to claim 9 or 10, wherein, The intensity of two scents selected from the group consisting of selected floral, fruity, animalic, and sweet scents is reduced compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

12. A fragrance composition comprising an essential oil according to any one of claims 9 to 11.

13. An aromatic product, preferably a pharmaceutical preparation, a cosmetic preparation, or a preparation for nutrition or pleasure, said aromatic product comprising an essential oil according to any one of claims 9 to 11 or a fragrance composition according to claim 12.

14. Use of a yeast of the genus *Yarlium* for adjusting the odor characteristics of essential oils, preferably in the method according to any one of claims 1 to 8. Preferably, the one, two, three or more, or all yeasts are selected from the group consisting of: *Yaruoia oxensis*, *Yaruoia morphologica*, *Yaruoia lipolytica*, *Yaruoia sporeina*, *Yaruoia yakushima*, *Yaruoia parofonia*, *Yaruoia chickenina*, *Yaruoia osloa*, *Yaruoia foodina*, *Yaruoia holmica*, and *Yaruoia phanga*. Preferably, The yeast mentioned is *Yarrowia lipophila*.

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