WO2025176705A1

WO2025176705A1 - Fermented essential oils

Info

Publication number: WO2025176705A1
Application number: PCT/EP2025/054410
Authority: WO
Inventors: Pia Rebecca BARTON; Benoît Join
Original assignee: Symrise AG
Current assignee: Symrise AG
Priority date: 2024-02-19
Filing date: 2025-02-19
Publication date: 2025-08-28
Anticipated expiration: 2026-08-19
Also published as: WO2025176277A1

Abstract

The present invention relates to a method for modifying the odour profile of an essential oil, to an essential oil obtained or obtainable by such a method, to a fragrance composition comprising such an essential oil, to a perfumed product, preferably a pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure comprising such an essential oil or such a fragrance composition, and to the use of a yeast of the genus Yarrowia, for modifying the odour profile of an essential oil.

Description

Fermented essential oils

Essential oils are liquids, often hydrophobic liquids, comprising volatile, fragrances in concentrated form. Typically, essential oils are obtained from plants as plant extracts, wherein such plant extracts contain the characteristic fragrance of the plant it is derived from. Essential oils typically mean any concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted. An essential oil is essential in the sense that it contains the essence of the plant's fragrance, i.e. the characteristic fragrance of the plant from which it is derived. The term "essential" in essen- tial oil does not mean indispensable or usable by the human body, as e.g. with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism. Essential oils are often used in perfumes, cosmetics, soaps, air fresheners and other products for adding scents to incense and household cleaning products.

However, for obtaining such essential oils, extraction processes are required. Such extraction processes are often laborious and provide only a limited amount of essential oils. Thus, essential oils are rather expensive and valuable.

When applying essential oils e.g. in the fragrance industry, large amounts of the oils are necessary to provide an intense fragrance in a scented product. Consequently, it is desired to modify the odour of essential oils, such as intensifying one or more odours of the essential oil and/or increasing the complexity of its odour profile.

Furthermore, the fragrance compositions in the prior art provide only low complexity and olfactory versatility and often include olfactory off-notes, which need to be removed or reduced.

Moreover, the processes in the prior art typically require much time and/or high concentrations of applied enzymes, which also requires improvement.

There is thus a strong need to provide optimized methods and optimized fragrance compositions compared to the methods and compositions available in the prior art.

A primary object of the present invention is thus to provide an improved possibility obtaining fragrance compositions. A further object of the present invention is to provide fragrance compositions with improved complexity and olfactory versatility.

The objects are solved by a method for modifying the odour profile of an essential oil, comprising the steps i) providing one or more essential oil(s), preferably wherein the, one, two, three or more or all essential oil(s) is/are plant extract(s) of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof, ii) providing an aqueous culture of one or more yeast(s) of the genus Yarrowia, preferably wherein the aqueous culture has a cell density of at least 7 x 10⁷ of the yeast cells per mL of the aqueous culture, iii) mixing the essential oil(s) provided in step i) and the aqueous culture provided in step ii) to obtain a mixture, iv) incubating the mixture obtained in step iii) at conditions allowing a fermentation of the essential oil(s) to obtain a fermented mixture comprising a liquid phase, v) separating the liquid phase from the fermented biomass to obtain a fermented mixture containing a fermented essential oil, vi) extracting the fermented essential oil from the fermented mixture.

It was surprisingly found that the provided essential oils can be modified in their odour profile with the method according to the invention. With the method according to the invention, a particularly pleasant (fermented) essential oil is obtained. It was surprisingly found that several odours of the provided essential oil can be increased.

Preferably, the, one, two, three or more or all essential oil(s) provided in step i) refers to oils obtained per steam distillation, hydrodistillation, and/or pressing peel, and/orto reworked essential oils such as rectified-, colour reduced-, furocoumarine reduced-, terpene fractions-, deterpened fraction-, allergen reduced-, allergen free-oils.

It is preferred in the method according to the invention that the, one, two, three or more or all essential oil(s) provided in step i) is/are selected from the group consisting of basil oil, caraway oil, carrot seed oil, celery seed oil, clary sage oil, dill weed oil, dill seed oil, estragon oil, fennel oil, galbanum oil, hyssop oil, marjoram oil, parsley seed oil, parsley leaf oil, star anise oil, star anise, teatree oil, cabreuva oil, geranium oil, ho leaf oil, jasmin, lavender oil, lavandin oil, magnolia flower oil, magnolia leaf oil, neroli oil, orange flower oil, orris butter, palmarosa oil, petit grain mandarine oil, petit grain orange oil, petit grain orange bitter oil, rose oil, rosewood oil, rosewood leaf oil, shiu oil, tagetes oil, ylang ylang oil, buchu leaf oil, carrot oil, davana oil, alpinia oil, bay oil, black pepper oil, cardamom oil, cascarilla oil, cassia oil, cinnamon leaf oil, cinnamon bark oil, coriander leaf oil, coriander seed oil, cumin oil, cumin seed oil, ginger oil, gingergrass oil, green pepper oil, longoza oil, lovage leaf oil, lovage root oil, mace oil, nutmeg oil, perilla oil, pimento berry oil, pink pepper oil, pink pepper berries (Schinus molle L.) oil white pepper oil, schinus mole oil, turmeric oil, litsea cubeba oil, myrrh oil, olibanum oil, opoponax oil, peru balsam oil, styrax oil, tolu balsam oil, bergamote oil, cedrat oil, citronella oil, eucalyptus citriodora oil, grapefruit oil, lemon oil, lemongrass oil, litsea cubeba oil, lime oil, mandarin oil, orange oil, orange bitter oil, petit grain lemon oil, tangerine oil, allspices oil, artemisia oil, balsamite oil, calamus oil, catnip oil, cedar leaf oil, chamomile oil blue, chamomile oil roman, clove bud oil, clove leaf oil, clove stem oil, cornmint oil, cypress oil, elemi oil, eucalyptus oil, fir needle oil, fusel oil, helichrysum oil, hop oil, juniper berry oil, laurel leaf oil, mentha arvensis oil, mentha pip- perita oil, myrtle oil, oregano oil, pennyroyal oil, pimento leaf oil, pine needle oil, punida oil, rosemary oil, rosemary extact, sage oil, spearmint oil, spruce oil thyme oil, Wintergreen oil, wormwood oil, agarwood oil, amyris oil, boya oil, cedar-wood oil atlas, cedarwood oil china, cedarwood oil texas, cedarwood oil Virginia, copaiba oil, copaiba balm oil, cypriol oil, gaharu buaya oil, guaiac oil, gurjun balsam oil, nootka tree oil, patchouli oil, sandalwood oil, vetiver oil, cistus oil, ambrette seed oil, and mixtures thereof. The term “mixtures thereof’ preferably refers to a mixture of two or more of such oils, e.g. a mixture of vetiver oil and patchouli oil.

Preferably, the essential oil(s) provided in step i) comprise one or more fragrance(s).

It is preferred in the method according to the invention that the, one, two, three or more or all fragrance(s) in the essential oil(s) provided in step i) is/are selected from the group consisting of primary alcohols, secondary alcohols, tertiary alcohols, linear alcohols, branched alcohols, monocyclic alcohols, bicyclic alcohols, tricyclic alcohols, monoalcohols, diols, triols, saturated alcohols, mono-unsaturated alcohols, double-unsaturated alcohols, tripleunsaturated alcohols, poly-unsaturated alcohols, alcohols further comprising an aldehyde group, alcohols further comprising a ketone group, alcohols further comprising a carbonic acid group, alcohols further comprising an ether group, alcohols further comprising an epoxide group, alcohols further comprising an acetal group, alcohols further comprising a hemiacetal group, alcohols further comprising an ester group, alcohols further comprising an amine group, and alcohols further comprising one or more heteroatoms, preferably wherein the, one, two, three or more or all fragrance(s) in the essential oil(s) provided in step i) is/are selected from the group consisting of benzyl alcohol, bisabolols, borneols, fenchols, isopulegols, terpineols, verbenols, ambrein, aphidicolin, betulin, ca- dinol, carveol, cavacrol, cedrol, citronellol, p-cresol, cubebol, cumin alcohol, cycloartenol, dihydrocarveol, elemol, eugenol, farnesol, geraniol, geranylgeraniol, 1 -hexanol, hexenol, ipsdienol, isophytol, isopulegol, khusimol, lanosterol, ledol, linalool, lupeol, menthol, myrceneol, nerol, nerolidol, perilla alcohol, phenylethyl alcohol, phytol, rhodinol, sclareol, spathulenol, terpineol, thymol.

Additionally or alternatively, it is preferred that the, one, two, three or more or all fragrance^) in the essential oil(s) provided in step i) is/are selected from the group consisting of alcohols with a molecular mass in the range of from 50 to 500 g/mol, preferably of from 100 to 300 g/mol, particularly preferably 120 to 230 g/mol. Preferably, the, one, two, three or more or all fragrance(s) in the essential oil(s) provided in step i), which are alcohols, is/are selected from the group consisting of alcohols with a molecular mass in the range of from 50 to 500 g/mol, preferably of from 100 to 300 g/mol, particularly preferably 120 to 230 g/mol.

Furthermore, it is preferred in the method according to the invention that the essential oil(s) provided in step i) comprise further fragrance(s), wherein the, one, two, three or more or all further fragrance(s) is I are selected from the group consisting of aldehydes, olefins, and carbonic acids. Preferably, the further fragrance(s) is/are not alcohols.

It is preferred that the, one, two, three or more or all essential oil(s) provided in step i) is I are essential oil(s) of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

It is preferred that the, one, two, three or more or all essential oil(s) provided in step i) is I are essential oil(s) of the genus Rosa.

It is preferred that the, one, two, three or more or all essential oil(s) provided in step i) is I are essential oil(s) of a plant of the genus selected from the group consisting of Jasminum, Magnolia, and mixtures thereof.

Preferably, the term “essential oil(s) of a plant of the genus selected from the group consisting of [...] and mixtures thereof’ refers to a mixture of two or more essential oils of different genera or different essential oils of the same genus or a mixture thereof.

Essential oils are usually produced by distillation, boiling or pressing. Typically, compositions produced by solvent extraction or enfleurage are described as “absolutes”. Preferably, the term “essential oil” also includes absolutes.

It is preferred in the method according to the invention that the, one, two, three or more or all essential oil(s) provided in step i) is/are plant extract(s).

It is preferred that the, one, two, three or more or all plant extracts) is/are selected from the group consisting of extracts of blossoms, stems, leaves, fruits, fruit peels, roots, needles and branches. Additionally or alternatively, it is preferred that the, one, two, three or more or all plant extract(s) is I are selected from the group consisting of basil extract, caraway extract, carrot seed extract, celery seed extract, celery extract, clary sage extract, estragon extract, flouve extract, galbanum extract, heather extract, hay extract, immortelle extract, len- tisque extract, lin seed extract, mate extract, star anise extract, tobacco extract, violet leaf extract, wheat bran extract, broom extract, carnation extract, cassie extract, genet extract, geranium extract, hyacinthe extract, jasmin sambac extract, jasmin extract, jon- quille extract, lavender extract, lavandin extract, mimosa extract, narcisse extract, orange flower extract, orange leaf extract, orris extract, osmanthus extract, rose extract, tagetes extract, tuberose extract, ylang ylang extract, apple extract, beeswax extract, black currant bud extract, bran extract, buchu extract, black pepper extract, cardamom extract, fenugrec seed extract, ginger extract, nutmeg extract, pink pepper extract, schi- nus mole extract, sichuan pepper extract, tonka bean extract, turmeric extract, benzoin extract, myrrh extract, olibanum extract, opoponax extract, styrax extract, tolu balsam extract, vanilla extract, orange extract, clove bud extract, elemi extract, eucalyptus extract, fir balsam extract, gentiane extract, laurel leaf extract, mentha piperita extract, pine needle extract, thyme extract, castoreum extract, civet extract, moss a extract, moss c extract, patchouli extract, cistus extract, labdanum extract, ambrette seed extract, and mixtures thereof, preferably wherein the, one, two, three or more or all plant extract(s) is I are extract(s) of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

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 Jasminum. Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus Magnolia.

Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus selected from the group consisting of Jasminum, Magnolia, and mixtures thereof.

What is said herein with regard to essential oil(s) may apply accordingly to plant extracts) and vice versa. Preferably, the aqueous culture of one or more yeast(s) of the genus Yarrowia is obtained by mixing the one or more yeast(s) with water. Preferably, the, one, two, three or more or all yeast(s) provided in step ii) is/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 hol- landica, and Yarrowia phangngaensis, particularly preferably wherein the or one yeast is Yarrowia lipolytica, more preferably wherein the or one yeast is Yarrowia lipolytica (DSM 1345, DSMZ GmbH).

Particularly preferably, the aqueous culture provided in step ii) has a cell density of at least 7.5 x 10⁷, preferably at least 10 x 10⁷, preferably at least 15 x 10⁷, preferably at least 19 x 10⁷ of the yeast cells per mL of the aqueous culture.

It was surprisingly found that with a cell density of at least 7 x 10⁷ cells per mL of the aqueous culture and even further with the densities described as preferred above, the modification of the odour profile and the alteration of the amount(s) of the compounds, each as described herein, was even more pronounced.

Preferably, when determining the cell density, the total cells are considered.

Preferably, when determining the cell density, only the living or viable cells are considered.

The cell density in the aqueous culture may be determined by cell counting (e.g. via counting chambers), automated cell counters, or flow cytometry methods based on autofluorescence, stainings (e.g. propidium iodide) or side scattered light.

Additionally or alternatively, the ODeoo (optical density of a sample measured at a wavelength of 600 nm in 1 cm light path) may be determined and based thereon, the cell density can be calculated with the correcting factors described in Worland et al., “Analysis of Yarrowia lipolytica growth, catabolism, and terpenoid biosynthesis during utilization of lipidderived feedstock", Metabolic Engineering Communications 11 (2020) e00130, https://doi.Org/10.1016/j.mec.2020.e00130.

It is preferred in the method according to the invention that the yeast(s) in the aqueous culture provided in step ii) were not permeabilized. Preferably, the yeast(s) in the aqueous culture provided in step ii) were not permeabilized with one or more kationic surfactants. Preferably, the yeast(s) in the aqueous culture provided in step ii) were not permeabilized with cetrimonium bromide (CTAB).

The yeasts in the method according to the invention, particularly Yarrowia lipolytica, are capable of secreting enzymes from a cell interior into the environment. However, permea- bilizing yeasts alters the interaction of the yeast cells with the compounds in their surrounding and thus the possible conversion of compounds during the fermentation in step iv). Thus, the molecular composition of such fragrance compositions is different than those fragrance compositions obtained with non-permeabilized or differently-permeabilized yeasts.

Consequently, using permeabilized yeast cells, particularly yeasts permeabilized with one or more kationic surfactants, especially yeasts permeabilized with cetrimonium bromide (CTAB), leads to fragrance compositions with different odour profiles than fragrance compositions obtained with non-permeabilized or differently-permeabilized yeasts. It was found that the odour profile of the fragrance compositions obtained with non-permeabilized or differently-permeabilized yeasts is particularly advantageous.

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

Additionally or alternatively, it is preferred that the conditions allowing a fermentation in step iv) include an incubation time in the range of from 1 to 168 h, preferably of from 2 to 144 h, particularly preferably of from 3 to 120 h, further preferably of from 4 to 96 h, even further preferably of from 5 to 72 h, more preferably of from 8 to 48 h, especially preferably of from 12 to 36 h, even more preferably of from 18 to 30 h.

Additionally or alternatively, it is preferred that the conditions allowing a fermentation in step iv) include stirring at a speed in the range of from 50 to 300 rpm, preferably of from 75 to 250 rpm, further preferably of from 100 to 200 rpm, even further preferably of from 125 to 175 rpm.

The incubation in step iv) typically leads to the formation of a liquid phase and a phase comprising the fermented biomass (including the yeast culture(s)). The term “separating the liquid phase from the fermented mixture” includes a partial or complete separation of the liquid phase from the fermented mixture, wherein the residue is or comprises the fermented essential oil.

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

The term “extracting the fermented essential oil from the fermented mixture” refers to a step to separate the fermented essential oil from further components in the mixture, e.g. such components, which have been present during the incubation in step iv), such as the medium in which the yeast culture was cultured. The separation may be a complete or partial separation. The extraction may include one or more methods selected from liquid-liquid extraction, maceration, re-maceration, digestion, agitation maceration, vortex extraction, ultrasonic extraction, counter current extraction, percolation, re-percolation, evacolation (extraction under reduced pressure), extraction using supercritical carbon dioxide, diacola- tion and solid/liquid extraction (preferably under continuous reflux).

Preferably, the extraction may be an aqueous, alcoholic or aqueous/alcoholic extraction.

Particularly preferably, the extraction is performed using methyl tert-butyl ether (MTBE), hexane, cyclohexane, diethylether, pentane, heptane, toluene, ethylacetate, methylene chloride, chloroform, or mixtures thereof.

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

After the extraction process, the crude extracts obtained may optionally be subjected to other typical steps, such as for example purification, concentration and/or decoloration. The extraction process may be carried out to any degree, but is usually continued to exhaustion.

Moreover, it is preferred in the method according to the invention that the total concentration of essential oil(s) provided in step i) is in a range of from 0.1 to 20 mL, preferably of from 0.5 to 15 mL, further preferably of from 1 to 10 mL, particularly preferably of from 2 to 7.5 mL, based on 1 x 10⁷ yeast cells provided in step ii). The term “fermented essential oil” refers to the essential oil obtained after step iv), v) or vi) of the method according to the invention, wherein the essential oil may be present in a composition with further components of the method according to the invention. For example, the essential oil obtained after step iv) is present in the fermented mixture, which further comprises a liquid phase.

Preferably, the term “fermented essential oil” refers to an oil, which was incubated as described in step iv) of the method according to the invention.

Particularly preferably, the term “modifying the odour profile” refers to modifying one or more odour(s) selected from flowery, fruity, sweet, woody and herbal.

It is further preferred that the term “modifying the odour profile” refers to increasing the complexity of the odour profile and/or increasing the intensity of one or more odours, preferably selected from flowery, fruity, sweet, woody, and herbal.

It was surprisingly found that with the method according to the invention several compounds were produced or enriched, which provide a flowery, fruity, sweet, woody, and/or herbal odour.

It was surprisingly found that with the method according to the invention the amounts of compounds such as Benzyl acetate, Phytol, Methyl-2-methylbutyrate, Caryophyllene, Caryophyllene oxide, Benzyl benzoate, Isophytol, Benzyl alcohol, Methyl benzoate, (E)-lsoeu- genol, Linalool, Linalool oxide, Linolenic acid benzoic ester, 2-Phenylethanol, 2-Phe- nylethyl acetate, Citronellol, Neral, Nerol, Geraniol, Limonene, Jasmin lactone, Methyl jasmonate, Cis-jasmone, p-Cresol, a-Pinene, Indole, and Methyl stearate were altered in the fermented essential oils.

It is thus preferred that in the incubation in step iv), preferably the fermentation in step iv), one, two, three or more or all compounds selected from the group consisting of

Benzyl acetate, Phytol, Methyl-2-methylbutyrate, Caryophyllene, Caryophyllene oxide, Benzyl benzoate, Isophytol, Benzyl alcohol, Methyl benzoate, (E)-lsoeugenol, Linalool, Linalool oxide, Linolenic acid benzoic ester, 2-Phenylethyl acetate, Citronellol, Neral, Nerol, Geraniol, Limonene, Jasmin lactone, Methyl jasmonate, Cisjasmone, p-Cresol, a-Pinene, Indole, and Methyl stearate is/are altered in the essential oil, when compared to the essential oil provided in step i).

Preferably, the essential oil is or comprises a plant extract of Jasminum, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Linolenic acid benzoic ester, Benzyl alcohol, Methyl stearate, Jasmin lactone, p-Cre- sol, Benzyl benzoate, Isophytol, Indole, Benzyl acetate, Phytol, Methyl jasmonate, Linalool, Cis-jasmone, Methyl benzoate, (E)-lsoeugenol, is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Particularly preferably, the essential oil is or comprises a plant extract of Jasminum, wherein the amounts) of one, two, three or more or all compounds selected from the group consisting of

Linolenic acid benzoic ester, Benzyl alcohol, Methyl stearate, Jasmin lactone, p-Cre- sol, Benzyl benzoate, Isophytol is/are increased in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention, and/or wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Indole, Benzyl acetate, Phytol, Methyl jasmonate, Linalool, Cis-jasmone, Methyl benzoate, (E)-lsoeugenol, is/are reduced in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the essential oil is or comprises a plant extract of Rosa, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of Benzyl alcohol, 2-Phenylethyl acetate, Neral, Caryophyllene, Citronellol, is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Particularly preferably, the essential oil is or comprises a plant extract of Rosa, wherein the amount of Benzyl alcohol is increased in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention, and/or wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

2-Phenylethyl acetate, Neral, Caryophyllene, Citronellol, is/are reduced in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the essential oil is or comprises a plant extract of Magnolia, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Linalool, Methyl-2-methylbutyrate, Caryophyllene, Benzyl alcohol, Benzyl acetate, a- Pinene, Limonene, Nerol, Geraniol, Linalool oxide, Caryophyllene oxide, is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Particularly preferably, the essential oil is or comprises a plant extract of Magnolia, wherein the amount of Linalool is increased in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention, and/or wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of Methyl-2-methylbutyrate, Caryophyllene, Benzyl alcohol, Benzyl acetate, a-Pinene, Limonene, Nerol, Geraniol, Linalool oxide, Caryophyllene oxide is/are reduced in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Benzyl acetate (preferably CAS-No. 140-11-4) has been described as providing a sweet, floral, fruity, jasmin, and fresh odour.

Phytol (preferably CAS-No. 150-86-7 or 7541-49-3) has been described as providing a floral, balsamic, powdery, and waxy odour.

Methyl-2-methylbutyrate (preferably CAS-No. 868-57-5), preferably (S)-methyl-2-methyl- butyrate (preferably CAS-No. 10307-60-5), preferably (R)-methyl-2-methylbutyrate (preferably CAS-No. 55449-44-0) has been described as providing a fruity, green, apple, lily, powdery, and fatty odour.

Caryophyllene has been described as providing a sweet, woody, spice, clove and dry odour. Preferably, the term “caryophyllene” refers to a-caryophyllene (preferably CAS-No. 6753-98-6), p-caryophyllene (preferably CAS-No. 87-44-5), and/or y-caryophyllene (preferably CAS-No. 118-65-0).

Caryophyllene oxide (preferably CAS-No. 1139-30-6) has been described as providing a sweet, fresh, dry, woody, and spicy odour.

Benzyl benzoate (preferably CAS-No. 120-51-4) has been described as providing a sweet, balsam, oily, and herbal odour.

Isophytol (preferably CAS-No. 505-32-8) has been described as providing a floral, herbal, and green odour.

Benzyl alcohol (preferably CAS-No. 100-51-6) has been described as providing a sweet, floral, and fruity odour.

Methyl benzoate (preferably CAS-No. 93-58-3) has been described as providing a phenolic, Wintergreen, almond, floral, and cananga odour. (E)-lsoeugenol (preferably CAS-No. 5932-68-3) has been described as providing a sweet, spicy, carnation, phenolic, and floral odour.

Linalool (preferably CAS-No. 78-70-6), preferably (R)-Linalool (preferably CAS-No. 126- 91-0), preferably (S)-Linalool (preferably CAS-No. 126-90-9) has been described as providing a citrus, orange, floral, terpenic, waxy, and rose odour.

Linalool oxide (preferably CAS-No. 1365-19-1) has been described as providing a floral, herbal, earthy, and green odour.

2-Phenylethanol (preferably CAS-No. 60-12-8) has been described as providing a sweet, floral, fresh, bready, rose, and honey odour.

2-Phenylethyl acetate (preferably CAS-No. 103-45-7) has been described as providing a floral, rose, sweet, honey, fruity, and tropical odour.

Citronellol (preferably CAS-No. 106-22-9), preferably (R)-Citronellol (preferably CAS-No. 1117-61-9), preferably (S)-Citronellol (preferably CAS-No. 7540-51-4) has been described as providing a floral, rose, sweet, citrus, green, fatty, and terpenic odour.

Neral (preferably CAS-No. 106-26-3) has been described as providing a sweet, citral, and lemon peel odour.

Nerol (preferably CAS-No. 106-25-2) has been described as providing a sweet, natural, neroli, citrus, and magnolia odour.

Geraniol (preferably CAS-No. 106-24-1) has been described as providing a sweet, floral, fruity, rose, waxy, and citrus odour.

Limonene (preferably CAS-No. 138-86-3) has been described as providing a citrus, herbal, terpene, and camphor odour.

Jasmin lactone (preferably CAS-No. 34686-71-0) has been described as providing an oily, fruity, petal, floral, jasmin, tuberose, peach, apricot, and coconut odour.

Methyl jasmonate (preferably CAS-No. 39924-52-2) has been described as providing a jasmin flower, oily, green, petal, soft, and greasy odour. Cis-jasmone (preferably CAS-No. 488-10-8) has been described as providing a woody, herbal, floral, spicy, jasmin, and celery odour.

P-Cresol (preferably CAS-No. 106-44-5) has been described as providing a phenolic, narcissus, animal, and mimosa odour. a-Pinene (preferably CAS-No. 80-56-8) has been described as providing a fresh, camphor, sweet, pine, earthy, and woody odour.

Indole (preferably CAS-No. 120-72-9) has been described as providing an animal, floral, moth, and naphthelene odour.

Methyl stearate (preferably CAS-No. 112-61-8) has been described as providing an oily, and waxy odour.

The present invention further relates to an essential oil obtained or obtainable by a method according to the invention, preferably wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Benzyl acetate, Phytol, Methyl-2-methylbutyrate, Caryophyllene, Caryophyllene oxide, Benzyl benzoate, Isophytol, Benzyl alcohol, Methyl benzoate, (E)-lsoeugenol, Linalool, Linalool oxide, Linolenic acid benzoic ester, 2-Phenylethyl acetate, Citronellol, Neral, Nerol, Geraniol, Limonene, Jasmin lactone, Methyl jasmonate, Cisjasmone, p-Cresol, a-Pinene, Indole, and Methyl stearate is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

What was said above with regard to the method according to the invention applies accordingly to the essential oil according to the invention, particularly with regard to preferred features.

Preferably, the essential oil is or comprises one or more plant extract(s) of one, two or all plant(s) of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof. Preferably, the essential oil is or comprises a plant extract of Jasminum. Preferably, the essential oil is or comprises a plant extract of Rosa. Preferably, the essential oil is or comprises a plant extract of Magnolia.

Preferably, the term “the essential oil is a plant extract” refers to a plant extract, which has been treated with the method according to the invention.

Linolenic acid benzoic ester, Benzyl alcohol, Methyl stearate, Jasmin lactone, p-Cre- sol, Benzyl benzoate, Isophytol, Indole, Benzyl acetate, Phytol, Methyl jasmonate, Linalool, Cis-jasmone, Methyl benzoate, (E)-lsoeugenol is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Particularly preferably, the essential oil is or comprises a plant extract of Jasminum, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Indole, Benzyl acetate, Phytol, Methyl jasmonate, Linalool, Cis-jasmone, Methyl benzoate, (E)-lsoeugenol, is/are reduced in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention. Preferably, the essential oil is or comprises a plant extract of Rosa, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Benzyl alcohol, 2-Phenylethyl acetate, Neral, Caryophyllene, Citronellol, is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

Particularly preferably, the essential oil is or comprises a plant extract of Magnolia, wherein the amount of Linalool is increased in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention, and/or wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Methyl-2-methylbutyrate, Caryophyllene, Benzyl alcohol, Benzyl acetate, a-Pinene, Limonene, Nerol, Geraniol, Linalool oxide, Caryophyllene oxide is/are reduced in the essential oil, when compared to the essential oil provided in step i) of the method according to the invention.

As described above, it was surprisingly found that the provided essential oils can be modified in their odour profile with the method according to the invention. With the method according to the invention, a particularly pleasant (fermented) essential oil is obtained. It was surprisingly found that several odours of the provided essential oil can be increased. Thus, the essential oil obtained or obtainable by a method according to the invention differs in its odour profile from the provided essential oil and known essential oils.

It was surprisingly found that in an essential oil which is obtained or obtainable by a method according to the invention (fermented essential oil) several odours were detected, which were not present or weaker in the essential oil, which was initially provided.

However, simultaneously, it was surprisingly found that in an essential oil which is obtained or obtainable by a method according to the invention (fermented essential oil) several odours were weaker than in the essential oil, which was initially provided.

As described above, it was surprisingly found that in an essential oil which is obtained or obtainable by a method according to the invention the odour profile is modified in comparison to the starting material. It was found that the complexity and the olfactory versatility was increased, whereas no or only low off-notes were observed. The fragrance compositions according to the invention thus provide a particularly advantageous odour profile.

It was surprisingly found that in the fragrance compositions, at least 4 odours selected from floral, green, fruity, animalic and sweet are changed in their intensity compared to the provided absolute.

It is thus preferred for the essential oil according to the invention that at least 4 odours, preferably 4 odours, selected from the group consisting of floral, green, fruity, animalic and sweet are changed in their intensity compared to the essential oil provided in step i) of the method according to the invention.

A skilled person working in this field knows the odours floral, green, fruity, animalic and sweet and their understanding, definition and characterization. Preferably, the odours are understood, defined and/or characterized as described in e.g. S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N. J., 1969, author’s edition or H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 5th Ed., Wiley-VCH, Weinheim 2006.

Preferably, the odours floral, fruity, animalic and sweet are changed in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours floral, green, fruity, animalic and sweet are changed in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Surprisingly, it was further found that in all fragrance compositions, 2 or 3 odours selected floral, green, fruity, animalic and sweet are increased in their intensity compared to the provided absolute. Further, it was found that in all fragrance compositions, 2 odours selected floral, fruity, animalic and sweet are increased in their intensity compared to the provided absolute.

It is thus preferred for the essential oil according to the invention that 2 or 3 odours selected from the group consisting of floral, green, fruity, animalic and sweet are increased in their intensity compared to the essential oil provided in step i) of the method according to the invention, particularly preferably wherein 2 odours selected from the group consisting of floral, fruity, animalic and sweet are increased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours fruity and sweet are increased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours fruity and animalic are increased in their intensity compared to the essential oil provided in step i) of the method according to the invention. Preferably, the odours floral, green, and animalic are increased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Surprisingly, it was further found that in all fragrance compositions, 2 odours selected floral, fruity, animalic and sweet are decreased in their intensity compared to the provided absolute.

It is thus preferred for the essential oil according to the invention that 2 odours selected from the group consisting of selected floral, fruity, animalic and sweet are decreased in their intensity compared to compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours floral and animalic are decreased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours floral and sweet are decreased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the odours fruity and sweet are decreased in their intensity compared to the essential oil provided in step i) of the method according to the invention.

Preferably, the term “2 odours”, as used herein is to be understood as “at least 2 odours”. The same applies accordingly to any other described number of odours.

Preferably, the term “2 odours”, as used herein is to be understood as at least but not more than 2 odours. The same applies accordingly to any other described number of odours.

Typically, for evaluating whether an odour is changed, preferably increased or decreased, a trained panel performs a sensorial evaluation, which is well-known to a skilled person. Usually, the tested odours are evaluated on a nominal scale, wherein a change is observed in case a different score is obtained.

The present invention further relates to a fragrance composition comprising an essential oil according to the invention.

It is preferred that the fragrance composition according to the invention comprises the essential oil (preferably extract) according to the invention, as well as further components typical for a fragrance composition, such as fragrances, solvents, stabilizers, UV-filters, and emulsifiers.

Furthermore, it is preferred that the fragrance composition according to the invention comprises the essential oil (preferably extract) in an amount in the range of from 0.0001 to 10 wt.-%, preferably of from 0.001 to 5 wt.-%, particularly preferably of from 0.01 to 1 wt.-%, based on the total weight of the fragrance composition.

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

Preferably, a perfumed product is selected from the group consisting of washing and cleaning agents, hygiene or care products, preferably in the field of body and hair care, cosmetics and home care, preferably selected from the group consisting of perfume extracts, perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave-products, splash-colognes, perfumed refreshing tissues, acid, alkaline or neutral cleaning agents, textile refreshing agents, ironing aids, liquid washing agents, washing agents in powder form, laundry pre-treatment agents, fabric softeners, laundry soap, laundry tablets, disinfectants, surface disinfectants, air refreshers, aerosols, waxes and polishes, body care agents, hand creams and lotions, shower gels, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair-care products, shampoos, deodorants, anti-perspirants, products of decorative cosmetics, candles, lamp oils, joss sticks, insecticides, repellents and propellants.

Preferably, pharmaceutical preparations according to the invention are in the form of capsules, tablets (uncoated and coated tablets, for example having coatings resistant to gastric juices), sugar-coated tablets, granules, pellets, mixtures of solids, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations and are preferably used as medicines only available by prescription, from pharmacies or other medicines or as food supplements.

Cosmetic preparations, as described herein, are in particular preparations, which are suitable for topical application to the skin of a human, in particular to achieve a cosmetic effect. Cosmetic preparations or pharmaceutical preparations, as described herein, may further comprise one, two, three or more or all substances selected from the group consisting of odoriferous substances, perfume oils, fatty oils, fatty acids, ceramides, pseudoceramides, sterols, hydrocarbons phytosterols, anti-acne active ingredients, antidandruff active ingredients, antimicrobial active ingredients, preservatives, antiperspirants, anti-irritants, pruritus-relieving active ingredients, cooling active ingredients, antiaging active ingredients, skin-lightening and skin-tanning active ingredients, skin moisture regulators, osmolytes, insect repellents, enzyme inhibitors, odour absorbers, dyes, abrasives, anti-acne agents, anti-cellulitis agents, antidandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, astringents, perspiration-inhibiting agents, antiseptic agents, ant-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, care agents, depilatory agents, surface-active substances, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, fibres, film-forming agents, fixatives, foam-forming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents, gel-forming agents, hair care agents, hair-setting agents, hair-straightening agents, moisture-donating agents, moisturizing substances, moisture-retaining substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, impregnating agents, dirtrepellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifying agents, plasticizing agents, covering agents, polish, gloss agents, polymers, powders, proteins, re-oiling agents, abrading agents, silicones, skin-soothing agents, skin-cleansing agents, skin care agents, skin-healing agents, skin-lightening agents, skin-protecting agents, skin-softening agents, hair promotion agents, cooling agents, skin-cooling agents, warming agents, skinwarming agents, stabilizers, UV-absorbing agents, UV filters, detergents, fabric conditioning agents, suspending agents, skin-tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, a-hydroxy acids, poly hydroxyfatty acids, liquefiers, dyestuffs, colour-protecting agents, pigments, anticorrosives, aromas, flavouring substances, odoriferous substances, polyols, surfactants, electrolytes, organic solvents, and silicone derivatives.

Preferably, a composition serving for food or pleasure, as described herein, may be selected from the group consisting of (reduced-calorie) baked goods (e.g. bread, dry biscuits, cakes, other baked articles), confectionery (e.g. muesli bar products, chocolates, chocolate bars, other products in bar form, fruit gums, dragees, hard and soft caramels, chewing gum), non-alcoholic drinks (e.g. cocoa, coffee, green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooibos tea, other herbal teas, fruit-containing soft drinks, isotonic drinks, refreshing drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salt meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, muesli bars, precooked ready- to-eat rice products), dairy products (e.g. full-fat or reduced-fat or fat-free milk drinks, rice pudding, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, ice-cream, partially or completely hydrolysed milk-protein-containing products), products made from soy protein or other soybean fractions (e.g. soy milk and products produced therefrom, drinks containing isolated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, fermented products such as tofu or tempeh or products produced therefrom and mixtures with fruit preparations and optionally flavours), dairy-like preparations (milk-type, yoghurt-type, dessert-type, ice cream) from protein rich plant materials (e.g. from seed materials of oat, almond, pea, lupine, lentils, faba beans, chickpea, rice, canola), plant protein-enriched non-dairy drinks, fruit preparations (e .g. jams, sorbets, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, precooked vegetables, boiled- down vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, maize- or groundnut-based extrudates), fat- and oil-based products or emulsions thereof (e.g. mayonnaise, remoulade, dressings, in each case full-fat or reduced-fat), other readymade dishes and soups (e.g. dried soups, instant soups, precooked soups), spices, spice mixtures and in particular seasonings which are used, for example, in the snacks field, sweetener preparations, tablets or sachets, other preparations for sweetening or whitening drinks.

Preferably, the preparation according to the invention may be selected from the group consisting of toothpastes, toothpastes, tooth gels, mouthwashes, mouth rinses, liquids for gargling, oral or pharyngeal sprays (pump or aerosol spray), lozenges, lozenges, candies, chewing gums, chewy candies and dental care chewing gums.

Furthermore, it is preferred that the preparation according to the invention comprises the fragrance composition according to the invention in an amount in the range of from 0.0001 to 1 wt.-%, preferably of from 0.001 to 0.5 wt.-%, particularly preferably of from 0.01 to 0.1 wt.-%, based on the total weight of the fragrance composition.

Furthermore, it is preferred that the preparation according to the invention comprises the essential oil in an amount in the range of from 0.000001 to 1 wt.-%, preferably of from 0.00001 to 0.5 wt.-%, particularly preferably of from 0.0001 to 0.1 wt.-%, further preferably of from 0.001 to 0.01 wt.-% based on the total weight of the fragrance composition.

The present invention further relates to the use of a yeast of the genus Yarrowia, for modifying the odour profile of an essential oil, preferably in a method according to the invention.

What was said above with regard to the method according to the invention applies accordingly to the use according to the invention, particularly with regard to preferred features.

It is preferred in the use according to the invention that the, one, two, three or more or all yeast(s) is I 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 wherein the or one yeast is Yarrowia lipolytica, particularly preferably wherein the, one, two, three or more or all yeast(s) is/are 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 (DSM 70562, DSMZ GmbH), particularly preferably wherein the or one yeast is Yarrowia lipolytica (DSM 1345, DSMZ GmbH).

Further aspects and advantages of the invention result from the subsequent description of preferred examples.

Examples

Example 1 : Modification of essential oils

A culture of Yarrowia lipolytica (DSM 1345, DSMZ GmbH) was grown for 24 h at 25 °C and at 150 rpm in YPD-medium to a cell density of at least 7.5x10⁷ CFU. Subsequently, the essential oil is added, wherein 100 mL essential oil was added to 2,3 L of the cell culture.

The obtained mixture was incubated for further 24 h at 25 °C and at 150 rpm.

After the incubation, the mixture is centrifuged at 3800 rpm to separate the yeast cells (pellet) from the mixture.

The liquid phase is collected and extracted with methyl tert-butyl ether at 25 °C. The obtained extract is the fermented essential oil.

After obtaining the fermented essential oil, the provided oil and the fermented oil were compared in view of their sensorial evaluation by a trained panel.

Example 2: Jasmine

The method as described in Example 1 was performed with Jasmin absolute. A portion of the initial Jasmin absolute and of the obtained fermented essential oil was collected and their contents were determined by GCMS:

The fermented essential oil had a different composition than the oil before fermentation. It was surprisingly found that the fermented Jasmine absolute provided an alcoholic, whisky and champagne note. Furthermore a licorice and chocolate note was detected. These notes were not observed in the Jasmine absolute.

Example 3: Rose

The method as described in Example 1 was performed with Rose absolute. A portion of the initial Rose absolute and of the obtained fermented essential oil was collected and their contents were determined by GCMS:

The fermented essential oil had a different composition than the oil before fermentation. It was surprisingly found that the fermented Rose absolute provided an alcoholic note. Furthermore a chocolate note and a geranium note were detected. These notes were not ob- served in the Rose absolute. The fermented oil was described as more sparkling and less heavy than the Rose absolute.

Example 4: Magnolia

The method as described in Example 1 was performed with Magnolia absolute.

A portion of the initial Magnolia absolute and of the obtained fermented essential oil was collected and their contents were determined by GCMS:

The fermented essential oil had a different composition than the oil before fermentation. It was surprisingly found that the fermented Magnolia absolute provided a less fruity note. However, a spicy and cinnamic note, as well as a hey note were detected. These notes were not observed in the Magnolia absolute.

Example 5: Olfactory evaluation

The fragrance compositions according to Examples 2, 3 and 4 were prepared and their olfactory characteristics were evaluated by perfumers (n = 2).

The following results were obtained:

It was found that in all fragrance compositions, at least 4 odours selected from floral, green, fruity, animalic and sweet are changed in their intensity compared to the provided absolute.

It was further found that in all fragrance compositions, 2 or 3 odours selected floral, green, fruity, animalic and sweet are increased in their intensity compared to the provided absolute. Further, it was found that in all fragrance compositions, 2 odours selected floral, fruity, animalic and sweet are increased in their intensity compared to the provided absolute.

It was further found that in all fragrance compositions, 2 odours selected floral, fruity, animalic and sweet are decreased in their intensity compared to the provided absolute.

Claims

1 . Method for modifying the odour profile of an essential oil, comprising the steps i) providing one or more essential oil(s), wherein the, one, two, three or more or all essential oil(s) is/are plant extract(s) of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof, ii) providing an aqueous culture of one or more yeast(s) of the genus Yarrowia, wherein the aqueous culture has a cell density of at least 7 x 10⁷ of the yeast cells per mL of the aqueous culture, iii) mixing the essential oil(s) provided in step i) and the aqueous culture provided in step ii) to obtain a mixture, iv) incubating the mixture obtained in step iii) at conditions allowing a fermentation of the essential oil(s) to obtain a fermented mixture comprising a liquid phase, v) separating the liquid phase from the fermented biomass to obtain a fermented mixture containing a fermented essential oil, vi) extracting the fermented essential oil from the fermented mixture.

2. Method according to claim 1 , wherein the, one, two, three or more or all yeast(s) provided in step ii) is/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 wherein the or one yeast is Yarrowia lipolytica.

3. Method according to claim 1 or 2, wherein modifying the odour profile refers to modifying one or more odour(s) selected from flowery, fruity, sweet, woody and herbal.

4. Method according to any one of the preceding claims, wherein modifying the odour profile refers to increasing the complexity of the odour profile and/or increasing the intensity of one or more odours, preferably selected from flowery, fruity, sweet, woody, and herbal.

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

6. Method according to any one of the preceding claims, wherein the aqueous culture provided in step ii) has a cell density of at least 7.5 x 10⁷, preferably at least 10 x 10⁷, preferably at least 15 x 10⁷, preferably at least 19 x 10⁷ of the yeast cells per mL of the aqueous culture.

7. Method according to any one of the preceding claims, wherein the total concentration of essential oil(s) provided in step i) is in a range of from 0.1 to 20 mL, preferably of from 0.5 to 15 mL, further preferably of from 1 to 10 mL, particularly preferably of from 2 to 7.5 mL, based on 1 x 10⁷ yeast cells provided in step ii).

8. Method according to any one of the preceding claims, wherein the separation in step v) includes one or more methods selected from centrifugation, lyophilisation, liquidliquid extraction, filtration, preferably membrane filtration, reverse osmosis, and combinations thereof, preferably wherein the separation in step v) includes one or more methods selected from centrifugation, lyophilization, liquid-liquid extraction extraction, preferably liquidliquid extraction extraction using methyl tert-butyl ether (MTBE), hexane, cyclohexane, diethylether, pentane, heptane, toluene, ethylacetate, methylene chloride, and/or chloroform, filtration, preferably membrane filtration, reverse osmosis, and combinations thereof.

9. Essential oil obtained or obtainable by a method according to any one of the previous claims, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of

Benzyl acetate, Phytol, Methyl-2-methylbutyrate, Caryophyllene, Caryophyllene oxide, Benzyl benzoate, Isophytol, Benzyl alcohol, Methyl benzoate, (E)-lsoeugenol, Linalool, Linalool oxide, Linolenic acid benzoic ester, 2-Phe- nylethyl acetate, Citronellol, Neral, Nerol, Geraniol, Limonene, Jasmin lactone, Methyl jasmonate, Cis-jasmone, p-Cresol, a-Pinene, Indole, and Methyl stearate is/are altered in the essential oil, when compared to the essential oil provided in step i) of the method, preferably wherein at least 4 odours, preferably 4 odours, selected from the group consisting of floral, green, fruity, animalic and sweet are changed in their intensity compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

10. Essential oil according to claim 9, wherein 2 or 3 odours selected from the group consisting of floral, green, fruity, animalic and sweet are increased in their intensity compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8, particularly preferably wherein 2 odours selected from the group consisting of floral, fruity, animalic and sweet are increased in their intensity compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

11. Essential oil according to claim 9 or 10, wherein 2 odours selected from the group consisting of selected floral, fruity, animalic and sweet are decreased in their intensity compared to compared to the essential oil provided in step i) of the method according to any one of claims 1 to 8.

12. Fragrance composition comprising an essential oil according to any one of claim 9 to 11.

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

14. Use of a yeast of the genus Yarrowia, for modifying the odour profile of an essential oil, preferably in a method according to any one of claims 1 to 8, preferably wherein the, one, two, three or more or all yeast(s) is I 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 wherein the or one yeast is Yarrowia lipolytica.