Biotransformation of plant extracts

Abstract

The present invention relates to a method for obtaining a fragrance composition, to a fragrance composition obtained or obtainable by such a method and to a perfumed product, preferably a pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure comprising such a fragrance composition. The method for obtaining a fragrance composition comprises the steps of i) providing a plant extract comprising one or more fragrance(s), wherein said fragrance(s) in the plant extract provided in step i) are selected from the group consisting of alcohols, wherein the plant extract is an essential oil or an absolute, ii) providing an esterase, iii) providing an ester, iv) mixing the plant extract provided in step i) with the esterase provided in step ii) and the ester provided in step iii) to obtain a reaction mixture and reacting the fragrance(s) in the reaction mixture under conditions allowing a transesterification of the carboxylic acid moiety of the ester provided in step iii) to the fragrance(s), to obtain a mixture comprising an esterified fragrance, v) optionally: drying the mixture comprising an esterified fragrance obtained in step iv) to obtain the fragrance composition.

Description

[0001] Biotransformation of plant extracts

[0002] The present invention relates to a method for obtaining a fragrance composition, to a fragrance composition obtained or obtainable by such a method and to a perfumed product, preferably a pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure comprising such a fragrance composition.

[0003] 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.

[0004] 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 essential 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.

[0005] 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.

[0006] WO 2016 / 193208 discloses a method for treating essential vetiver oil to obtain a fragrance composition comprising vetiveryl esters, which may be used for the preparation of a perfumed product.

[0007] However, the stability of the fragrance compositions in the prior art requires improvement.

[0008] 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.

[0009] Moreover, the processes in the prior art typically require much time and / or high concentrations of applied enzymes, which also requires improvement.

[0010] 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.

[0011] 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.

[0012] The objects are solved by a method for obtaining a fragrance composition, comprising the steps i) providing a plant extract comprising one or more fragrance(s), wherein the, one, two, three or more or all fragrance(s) in the plant extract provided in step i) is I are selected from the group consisting of alcohols, preferably wherein the plant extract is an essential oil or an absolute, preferably wherein the, one, two, three or more or all plant extracts) provided in step i) is / are extract(s) of a plant of the genus Jasminum, and / or preferably wherein the, one, two, three or more or all plant extracts) provided in step i) is / are extract(s) of a plant of the genus Rosa, and / or preferably wherein the, one, two, three or more or all plant extracts) provided in step i) is I are extract(s) of a plant of the genus Magnolia, ii) providing an esterase, preferably one or more lipase(s), iii) providing an ester, preferably wherein the ester is an acetic acid ester, particularly preferably selected from the group consisting of ethyl acetate, vinyl acetate, isopropenyl acetate, ace- tonenole acetate, and mixtures thereof, further preferably selected from the group consisting of ethyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, iv) mixing the plant extract provided in step i) with the esterase provided in step ii) and the ester provided in step iii) to obtain a reaction mixture and reacting the fragrance(s) in the reaction mixture under conditions allowing a transesterification of the carboxylic acid moiety of the ester provided in step iii) to the fragrance(s), to obtain a mixture comprising an esterified fragrance, v) optionally drying the mixture comprising an esterified fragrance obtained in step iv) to obtain the fragrance composition, wherein in step iv), the conditions allowing the transesterification include a water content in the range of from 0.1 to 7.5 wt.-%, preferably of from 0.1 to 5 wt.-%, particularly preferably 0.1 to 2.5 wt.-%, further preferably 0.1 to 1 wt.-%, based on the total weight of the reaction mixture.

[0013] It was surprisingly found that a water content in the reaction in step iv) allows chemical reactions providing compounds, which are beneficial for the resulting fragrance composition. It was surprisingly found that with such a water content, the obtained fragrance composition provides improved complexity and olfactory versatility compared to known fragrance compositions. This was particularly surprising, since WO 2016 / 193208 suggests to dry the vetiver oil to completely remove the present water. It is described in WO 2016 / 193208 that the water content leads to an undesired production of carboxylic acid, such as acetic acid, which reduce the olfactory quality of the obtained fragrance compositions.

[0014] However, with the method according to the invention, no or only low amounts of such carboxylic acids are produced. To avoid the production of such carboxylic acids after the reaction in step iv), the obtained mixture is optionally dried in step v). For example, in case the mixture obtained after step iv) already has a low water content, the obtained mixture does not need to be further dried (but may be further dried).

[0015] Preferably, in case step v) is not performed, the mixture obtained after step vi) is considered a fragrance composition. Preferably, the, one, two, three or more or all plant extract(s) provided in step i) refers to extracts) obtained by solvent extraction of a natural raw material. Preferably such extract(s) refer to concretes, absolutes, resinoides, tinctures, CO2 extracts, and / or rectified or re-extracted versions thereof.

[0016] Preferably, the, one, two, three or more or all plant extracts) provided in step i) 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, lentisque 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, jonquille extract, lavender extract, lavandin extract, mimosa extract, narcisse extract, orange flower extract, orange leaf extract, orris extract, osman-thus 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, schinus 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, the, one, two, three or more or all plant extracts) provided in step i) is / are essential oil(s), preferably essential oil(s) 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.

[0017] Preferably, the, one, two, three or more or all plant extracts) provided in step i) is I are essential oil(s) 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 (Schi- nus 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 pipperita 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, am- brette 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.

[0018] Preferably, the term “esterase” as used herein refers to an enzyme, which catalyses the separation of an ester into an acid and an alcohol. Preferably, the term “esterase” as used herein refers to an enzyme classified according to the Enzyme Commission number (EC number), with the EC class E.C. 3.1 preferably E.C. 3.1 .1 .

[0019] Preferably, the term “lipase” as used herein refers to an enzyme, which catalyses the hydrolysis of fats. Preferably, the term “lipase” as used herein refers to an enzyme classified according to the Enzyme Commission number (EC number), with the EC class E.C. 3.1 .1 , preferably E.C. 3.1 .1 .3.

[0020] Preferably, the, one, two, three or more or all lipases is / are lipase(s) from the genus Candida or Aspergillus, particularly a lipase(s) from the species Candida Antarctica, Candida rugosa, Aspergillus oryzae, Aspergillus niger, Rhizopus oryzae, Mucor miehei, and Burkholderia cepacia.

[0021] In case the plant extract provided in step i) comprises an ester, it is preferred that step i) already includes step iii) of the method according to the invention.

[0022] In case the plant extract provided in step i) comprises an esterase, preferably a lipase, it is preferred that step i) already includes step ii) of the method according to the invention.

[0023] In step iv) of the method according to the invention, the plant extract provided in step i) are mixed with the esterase provided in step ii) and the ester provided in step iii). The components may be mixed simultaneously or subsequently, preferably in any order.

[0024] The esterified fragrance(s) obtained in step iv) is / are obtained by a transesterification as described in step iv). The ester provided in step iii) comprises a carboxylic acid moiety, which is transferred in the transesterification. The carboxylic acid moiety is transferred to the or a fragrance present in the plant extract provided in step i). However, in case such fragrance(s) is / are added in the method in addition to the fragrance(s) present in the plant extract provided in step i), a corresponding transesterification may be obtained.

[0025] Thus, the term “esterified fragrance” refers to a fragrance, which was present as an educt in the reaction, preferably present in the plant extract provided in step i), and which was converted to an ester, such as described above. The reaction educts and products can be analysed by methods in the art, e.g. mass spectrometry, to determine such fragrances and esterified fragrances. As described above, it was surprisingly found that a water content in the reaction in step iv) in the range as described for the method according to the invention allows the production of esterified fragrances and simultaneously provides improved complexity and olfactory versatility compared to known fragrance compositions, whereas at the same time the production of carboxylic acids as described in WO 2016 / 193208 is prevented I reduced.

[0026] It is preferred that step v) is present and in step v) of the method according to the invention, the mixture is dried to a water content of at most 5 wt.-%, preferably at most 2.5 wt.-%, further preferably at most 1 wt.-%, even further preferably at most 0.5 wt.%, more preferably at most 0.25 wt.-%, based on the total weight of the dried mixture.

[0027] It is preferred that step v) is present and in step v) of the method according to the invention, the mixture is dried to a water content in a range of from 0.001 to 5 wt.-%, preferably of from 0.01 to 5 wt.-%, particularly preferably of from 0.025 to 2.5 wt.-%, further preferably of from 0.05 to 1 wt.-%, more preferably of from 0.075 to 0.5 wt.-%, based on the total weight of the dried mixture.

[0028] Preferably, the dried mixture represents the produced fragrance composition.

[0029] Preferably, a water content, as described herein, is determined by the dry-loss-method or Karl-Fischer titration.

[0030] It is preferred in the method according to the invention that the, one, two, three or more or all fragrance(s) in the plant extract 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 plant extract provided in step i) is / are selected from the group consisting of benzyl alcohol, bisabolols, borneols, fenchols, isopulegols, terpineols, verbenols, ambrein, aphidicolin, betulin, cadinol, carveol, cavacrol, cedrol, citronellol, p-cresol, cubebol, cumin alcohol, cycloartenol, dihy- drocarveol, 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.

[0031] Additionally or alternatively, it is preferred that the, one, two, three or more or all fragrance^) in the plant extract 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.

[0032] Preferably, the, one, two, three or more or all fragrance(s) in the plant extract 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.

[0033] Furthermore, it is preferred in the method according to the invention that the plant extract provided in step i) comprises 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.

[0034] It is further preferred in the method according to the invention that in step iv), the conditions allowing the transesterification include a reaction temperature in the range of from 25 to 60 °C, preferably of from 30 to 50 °C, particularly preferably of from 35 to 45 °C.

[0035] Additionally or alternatively, it is preferred that in step iv), the conditions allowing the transesterification include a reaction time in the range of from 8 to 240 hours, preferably of from 10 to 216 hours, particularly preferably of from 12 to 192 hours.

[0036] Additionally or alternatively, it is preferred that in step iv), the conditions allowing the transesterification include stirring at a speed in the range of from 100 to 2,000 rpm, preferably in the range of from 200 to 1 ,800 rpm, further preferably in the range of from 250 to 1 ,750 rpm, more preferably in the range of from 500 to 1 ,500 rpm, particularly preferably in the range of from 750 to 1 ,250 rpm.

[0037] Preferably, the drying in step v) of the method according to the invention is present and is achieved by or includes a method selected from the group consisting of heat drying, sun drying, hot air drying, combined air and heat pump drying, vacuum oven drying, belt drying, vacuum belt drying, freeze drying, adding one or more drying agent(s), and combinations thereof. The term “combinations thereof’ refers to situations, in which two or more of such methods are performed, either simultaneously or subsequently.

[0038] A drying agent, as described herein, may refer to a salt selected from the group consisting of lithium fluoride, sodium fluoride, potassium fluoride, magnesium fluoride, calcium fluoride, lithium chloride, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, lithium bromide, sodium bromide, potassium bromide, calcium bromide, magnesium bromide, lithium iodide, sodium iodide, potassium iodide, calcium iodide, magnesium iodide, lithium sulfate, sodium sulfate, potassium sulfate, calcium sulfate, magnesium sulfate, calcium oxide, lithium nitrate, sodium nitrate, potassium nitrate, calcium nitrate, magnesium nitrate, lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, lithium acetate, sodium acetate, potassium acetate, magnesium acetate, calcium acetate, lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, lithium phosphate, sodium phosphate, potassium phosphate, magnesium phosphate, calcium phosphate, lithium chlorate, sodium chlorate, potassium chlorate, calcium chlorate, magnesium chlorate, lithium perchlorate, sodium perchlorate, potassium perchlorate, calcium perchlorate, magnesium perchlorate, lithium thiocyanate, sodium thiocyanate, potassium thiocyanate, calcium thiocyanate, and magnesium thiocyanate.

[0039] A drying agent may be added as such, but also as a solution, preferably a saturated solution, for the drying step.

[0040] It is thus preferred in the method according to the invention that the drying in step v) consists of or includes adding one or more drying agent(s) to the mixture comprising an ester- ified fragrance obtained in step iv), preferably wherein the drying agent(s) is / are added as a solution, preferably saturated solution, comprising the, one, two, three or more drying agent(s), preferably wherein the, one, two, three or more drying agent(s) is / are salt(s), particularly preferably wherein the, one, two, three or more drying agent(s) is / are salt(s) selected from the group consisting of lithium fluoride, sodium fluoride, potassium fluoride, magnesium fluoride, calcium fluoride, lithium chloride, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, lithium bromide, sodium bromide, potassium bromide, calcium bromide, magnesium bromide, lithium iodide, sodium iodide, potassium iodide, calcium iodide, magnesium iodide, lithium sulfate, sodium sulfate, potassium sulfate, calcium sulfate, magnesium sulfate, calcium oxide, lithium nitrate, sodium nitrate, potassium nitrate, calcium nitrate, magnesium nitrate, lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, lithium acetate, sodium acetate, potassium acetate, magnesium acetate, calcium acetate, lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, lithium phosphate, sodium phosphate, potassium phosphate, magnesium phosphate, calcium phosphate, lithium chlorate, sodium chlorate, potassium chlorate, calcium chlorate, magnesium chlorate, lithium perchlorate, sodium perchlorate, potassium perchlorate, calcium perchlorate, magnesium perchlorate, lithium thiocyanate, sodium thiocyanate, potassium thiocyanate, calcium thiocyanate, and magnesium thiocyanate.

[0041] Furthermore, it is preferred that the plant extract provided in step i) is an extract of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

[0042] Particularly preferably, the plant extract provided in step i) is or comprises an extract of a plant of the genus Rosa.

[0043] 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.

[0044] Preferably, the term “extract of a plant of the genus selected from the group consisting of [...] and mixtures thereof’ refers to a mixture of two or more plant extracts of different genera or different plant extracts of the same genus or a mixture thereof.

[0045] It is further preferred in the method according to the invention that the method further comprises the step iv.b) removing esterase, preferably the esterase, and / or acyl donor, preferably the acyl donor, from the mixture comprising an esterified fragrance obtained in step iv), and / or vi) removing esterase, preferably the esterase, and / or acyl donor, preferably the acyl donor, from the mixture obtained after step iv) or the dried mixture obtained in step v), preferably wherein the removing in step iv.b) and / or vi) includes a distillation step.

[0046] It is advantageous to remove esterase, preferably the esterase, from the mixture to control, e.g. stop, the reaction of step iv).

[0047] Preferably, the term “removing esterase” refers to removing some of or all of the esterase, wherein the term “removing the esterase” refers to removing all of the esterase.

[0048] Particularly, step iv.b) is performed after step iv).

[0049] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the summed amount of calcium hydride, calcium chloride, calcium sulfate, magnesium sulfate, sodium carbonate, sodium sulfate, phosphorus pentoxide and microporous aluminosilicate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0050] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of calcium hydride is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0051] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of calcium chloride is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0052] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of calcium sulfate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0053] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of magnesium sulfate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0054] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of sodium carbonate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0055] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of sodium sulfate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0056] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of phosphorus pentoxide is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0057] It is further preferred in the method according to the invention that in the reaction mixture obtained in step iv) the amount of microporous aluminosilicate is below 5 wt.-%, preferably below 2.5 wt.-%, particularly preferably below 1 wt.-%, further preferably below 0.5 wt.-%, even further preferably below 0.1 wt.-%, more preferably below 0.01 wt.-%, especially preferably below 0.001 wt.-%.

[0058] It is preferred that in the reaction in step iv), preferably the transesterification in step iv), one, two, three or more or all compounds selected from the group consisting of 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D, Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid, Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Linalooloxide, 2-Methyl-methyl butyrate, Limonene is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0059] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Rosa, wherein one, two, three or more or all compounds selected from the group consisting of

[0060] 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D, Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0061] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Rosa, wherein one, two, three or more or all compounds selected from the group consisting of

[0062] 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D is / are increased in the fragrance composition, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of

[0063] Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid is / are reduced in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0064] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Jasminum, wherein one, two, three or more or all compounds selected from the group consisting of Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, Ethyl palmitate, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Neophytadiene is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0065] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Jasminum, wherein one, two, three or more or all compounds selected from the group consisting of

[0066] Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, Ethyl palmitate, 2-Phenylethyl acetate is / are increased in the fragrance composition, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of

[0067] Phytol, Phytol acetate E, Isophytol, Neophytadiene is / are reduced in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0068] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Magnolia, wherein one, two, three or more or all compounds selected from the group consisting of

[0069] 2-Phenylethyl acetate, Germacrene D, Linalooloxide, Trans-Jasmone, 2-Methyl-methyl butyrate, Limonene, Neophytadiene is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0070] Preferably, the plant extract provided in step i) of the method is or comprises an extract of a plant of the genus Magnolia, wherein one, two, three or more or all compounds selected from the group consisting of 2-Phenylethyl acetate, Germacrene D, Linalooloxide, Trans-Jasmone is / are increased in the fragrance composition, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of 2-Methyl-methyl butyrate, Limonene, Neophytadiene is / are reduced in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0071] Furthermore, the present invention relates to a fragrance composition 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

[0072] 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D, Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid, Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Linalooloxide, 2-Methyl-methyl butyrate, Limonene is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

[0073] 2-Phenylethyl acetate preferably refers to a compound of the CAS no.: 103-45-7.

[0074] Citronellyl acetate preferably refers to a compound of the CAS no.: 150-84-5.

[0075] Ethyl linoleate preferably refers to a compound of the CAS no.: 544-35-4. Ethyl palmitate preferably refers to a compound of the CAS no.: 628-97-7.

[0076] Germacrene D preferably refers to a compound of the CAS no.: 23986-74-5. Citronellol preferably refers to a compound of the CAS no.: 106-22-9, preferably 11 17-61- 9, preferably 7540-51-4.

[0077] Benzyl alcohol preferably refers to a compound of the CAS no.: 100-51-6.

[0078] Neophytadiene preferably refers to a compound of the CAS no.: 504-96-1 , preferably as described in PubChem (https: / / pubchem.ncbi.nlm.nih.gov / ).

[0079] Geranic acid preferably refers to a compound of the CAS no.: 459-80-3, preferably 4698- 08-2.

[0080] Methyl hexadecanoate preferably refers to a compound of the CAS no.: 112-39-0.

[0081] Jasmin lactone preferably refers to a compound of the CAS no.: 34686-71-0, preferably 25524-95-2, preferably 32764-98-0.

[0082] Trans-Nerolidol preferably refers to a compound of the CAS no.: 40716-66-3, preferably 7212-44-4.

[0083] Trans-Jasmone preferably refers to a compound of the CAS no.: 6261-18-3.

[0084] 2-Phenylethyl acetate preferably refers to a compound of the CAS no.: 103-45-7.

[0085] Phytol preferably refers to a compound of the CAS no.: 150-86-7, preferably 7541-49-3.

[0086] Phytol acetate E preferably refers to a compound of the CAS no.: 10236-16-5.

[0087] Isophytol preferably refers to a compound of the CAS no.: 505-32-8.

[0088] Linalooloxide preferably refers to a compound of the CAS no.: 1365-19-1 , preferably 68892-15-9, preferably 60047-17-8.

[0089] 2-Methyl-methyl butyrate preferably refers to a compound of the CAS no.: 7452-79-1 , preferably 10307-61-6, preferably 40917-00-8 (e.g. as described in https: / / www.chemical- book.com / ). Limonene preferably refers to a compound of the CAS no.: 138-86-3, preferably 5989-27- 5, preferably 5989-54-8.

[0090] Preferably the CAS nos. refer to the compounds listed under the respective numbers in https: / / commonchemistrv.cas.org / , if not indicated otherwise. Preferably in case more than one CAS number is indicated for a compound, the compound may refer to any of the CAS numbers and / or a combination thereof.

[0091] Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Rosa, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0092] 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D, Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid, Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Linalooloxide, 2-Methyl-methyl butyrate, Limonene is / are altered in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method.

[0093] Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Rosa, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0094] 2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Germacrene D is / are increased in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of

[0095] Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid is / are reduced in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method. Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Jasminum, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0096] Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, Ethyl palmitate, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Neophytadiene is / are altered in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method.

[0097] Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Jasminum, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0098] Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, Ethyl palmitate, 2-Phenylethyl acetate is / are increased in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of

[0099] Phytol, Phytol acetate E, Isophytol, Neophytadiene is / are reduced in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method.

[0100] Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Magnolia, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0101] 2-Phenylethyl acetate, Germacrene D, Linalooloxide, Trans-Jasmone, 2-Methyl-methyl butyrate, Limonene, Neophytadiene is / are altered in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method. Preferably, the fragrance composition is or comprises a (dried) plant extract, preferably essential oil and / or absolute, of a plant of the genus Magnolia, wherein the amount(s) of the, one, two, three or more or all compounds selected from the group consisting of

[0102] 2-Phenylethyl acetate, Germacrene D, Linalooloxide, Trans-Jasmone is / are increased in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method, and / or wherein one, two, three or more or all compounds selected from the group consisting of

[0103] 2-Methyl-methyl butyrate, Limonene, Neophytadiene is / are reduced in the fragrance composition, preferably essential oil and / or absolute, when compared to the plant extract provided in step i) of the method.

[0104] Preferably, the water content in the fragrance composition according to the invention is at most 5 wt.-%, preferably at most 2.5 wt.-%, further preferably at most 1 wt.-%, even further preferably at most 0.5 wt.%, more preferably at most 0.25 wt.-%, based on the total weight of the fragrance composition, preferably wherein the water content in the fragrance composition is in a range of from 0.001 to 5 wt.-%, preferably of from 0.01 to 5 wt.-%, particularly preferably of from 0.025 to 2.5 wt.-%, further preferably of from 0.05 to 1 wt.-%, more preferably of from 0.075 to 0.5 wt.-%, based on the total weight of the reaction mixture.

[0105] It was surprisingly found that a fragrance composition which is obtained or obtainable by a method according to the invention and is thus produced from a plant extract comprises compounds, particularly fragrances, which are known from plant extracts of other plant genera or species but not from the genus or species of the used plant extract. For example, it was surprisingly found that a fragrance composition, which was produced from a plant extract of the genus Jasminum, comprises compounds, which were not known for Jas- minum but rather from e.g. Rosa or Magnolia, and vice versa.

[0106] It was surprisingly found that in a fragrance composition which is obtained or obtainable by a method according to the invention three odours selected from the group consisting of floral, green, fruity and sweet are changed in their intensity compared to the plant extract. The term “changed”, as used herein, describes increased or decreased, wherein one odour may be increased whereas another may be decreased.

[0107] 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 10 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.

[0108] Essential oils are usually produced by distillation, boiling or pressing plant material. Typically, compositions produced by solvent extraction or enfleurage of plant material are described as “absolutes”. Preferably, the term “plant extract” also includes essential oils and / or absolutes.

[0109] When comparing odours, the term “plant extract”, as used herein, preferably refers to the plant extract provided in step i) of the method according to the invention, which is used to obtain a fragrance composition according to the invention.

[0110] Moreover, it was surprisingly found that in a fragrance composition which is obtained or obtainable by a method according to the invention one or two odours selected from the group consisting of floral, green, fruity and sweet is increased in its intensity compared to the plant extract. Preferably, at least one but at most two odours selected from the group consisting of floral, green, fruity and sweet are increased in its intensity compared to the plant extract.

[0111] Further, it was surprisingly found that in a fragrance composition which is obtained or obtainable by a method according to the invention one or both odours selected from fruity and sweet is decreased in its intensity compared to the plant extract.

[0112] Furthermore, it was surprisingly found that although the odours floral, green, fruity and sweet are changed, the odour animalic was not changed in its intensity compared to the plant extract.

[0113] It is thus preferred in the fragrance composition according to the invention that three odours selected from the group consisting of floral, green, fruity and sweet are changed in their intensity compared to the plant extract. It is particularly preferred in the fragrance composition according to the invention that one or two odours selected from the group consisting of floral, green, fruity and sweet is increased in its intensity compared to the plant extract, particularly preferably at least one but at most two odours selected from the group consisting of floral, green, fruity and sweet are increased in its intensity compared to the plant extract.

[0114] It is particularly preferred in the fragrance composition according to the invention that one or both odours selected from fruity and sweet is decreased in its intensity compared to the plant extract.

[0115] Furthermore, it is preferred in the fragrance composition according to the invention that the odour animalic is not changed in its intensity compared to the plant extract.

[0116] It is further preferred in the fragrance composition according to the invention that three odours selected from the group consisting of floral, green, fruity and sweet are changed in their intensity compared to the plant extract, and one ortwo odours selected from the group consisting of floral, green, fruity and sweet is increased in its intensity compared to the plant extract, particularly preferably at least one but at most two odours selected from the group consisting of floral, green, fruity and sweet are increased in its intensity compared to the plant extract, and one or both odours selected from fruity and sweet is decreased in its intensity compared to the plant extract, and preferably the odour animalic is not changed in its intensity compared to the plant extract.

[0117] It is clear to a skilled person that the odours fruity and sweet cannot be increased and decreased at the same time. Thus, it is preferred in a fragrance composition according to the invention that in case two odours selected from the group consisting of floral, green, fruity and sweet are increased in their intensity compared to the plant extract and in case one or both odours selected from fruity and sweet is decreased in its intensity compared to the plant extract, then the two increased odours are not fruity and sweet together. Instead, in such a case, only one or none of the odours fruity and sweet is increased in the fragrance composition according to the invention. As described above, it was surprisingly found that in a fragrance composition which is obtained or obtainable by a method according to the invention the odour profile is modified in comparison to the plant extract. 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.

[0118] What was said above with regard to the method according to the invention applies accordingly to the fragrance composition according to the invention.

[0119] It is preferred in the fragrance composition obtained or obtainable by a method according to the invention that the water content in the fragrance composition is at most 5 wt.-%, preferably at most 2.5 wt.-%, further preferably at most 1 wt.-%, even further preferably at most 0.5 wt.%, more preferably at most 0.25 wt.-%, based on the total weight of the fragrance composition, preferably wherein the water content in the fragrance composition is in a range of from 0.001 to 5 wt.-%, preferably of from 0.01 to 5 wt.-%, particularly preferably of from 0.025 to 2.5 wt.-%, further preferably of from 0.05 to 1 wt.-%, more preferably of from 0.075 to 0.5 wt.-%, based on the total weight of the fragrance composition.

[0120] Additionally, it is preferred that the fragrance composition comprises the ester provided in step iii) of the method according to the invention, preferably wherein the ester is an acetic acid ester, particularly preferably selected from the group consisting of ethyl acetate, vinyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, further preferably selected from the group consisting of ethyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, and / or wherein the plant extract provided in step i) of the method according to the invention is an extract of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

[0121] It is preferred that the fragrance composition according to the invention further comprises components typical for a fragrance composition, such as fragrances, solvents, stabilizers, UV-filters, and / or emulsifiers. The present invention further relates to a perfumed product, preferably a pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure comprising a fragrance composition according to the invention.

[0122] 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.

[0123] 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.

[0124] Cosmetic preparations, as described herein, are in particular preparations, which are suitable for topical application to the skin and / or hair of a human, in particular to achieve a cosmetic effect.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] What was said above with regard to the method according to the invention and the fragrance composition according to the invention applies accordingly to the pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure according to the invention.

[0130] Further aspects and advantages of the invention result from the subsequent description of preferred examples. Examples

[0131] Example 1 : Rose

[0132] 150 g of Rose absolute are provided and mixed with 150 g ethyl acetate and 1.5 g Lipase acrylic resin from Candida Antarctica (> 5,000 U / g, recombinant, expressed in Aspergillus niger, Sigma-Aldrich, L4777). The water content of the mixture was determined by Karl- Fischer titration and was 0.16 wt.-%. The reaction mixture is incubated at 40 °C at 400 rpm and for 24 h in a fermenter.

[0133] After 24 h, 150 ml saturated NaCI-solution was added to the reaction mixture to stop the reaction. The enzyme is shaken out in a separating funnel and the reaction mixture is dried. In the separating funnel, the aqueous phase is separated from the organic phase. The organic phase was washed twice with 100 ml water.

[0134] The aqueous phases were mixed and extracted with 100 ml ethyl acetate to obtain another aqueous phase and organic phase. The obtained organic phase was mixed with the washed organic phase obtained above and the ethyl acetate was distilled of under reduced pressure (water bath 45 °C, 170 mbar, 30 min, then: water bath 50 °C, 0 mbar, 35 min).

[0135] The obtained fragrance composition had a water content of 0.00 vol.-%, which was determined by Karl-Fischer titration.

[0136] The contents of the fragrance composition were determined by GCMS.

[0137] Example 2: Jasmin

[0138] 150 g of Jasmin absolute are provided and mixed with 150 g acetonenole acetate and 1.5 g Lipase resin from Candida rugosa (> 700 U / mg, Type VII, from Candida rugosa, Sigma- Aldrich, L1754). The water content of the mixture was determined by Karl-Fischer titration and was 0.19 wt.-%. The reaction mixture is incubated at 40 °C at 400 rpm and for 7 days in a fermenter. After 7 days, 150 ml saturated NaCI-solution was added to the reaction mixture to stop the reaction. The enzyme is shaken out in a separating funnel and the reaction mixture is dried. In the separating funnel, the aqueous phase is separated from the organic phase. The organic phase was washed twice with 100 ml water. The aqueous phases were mixed and extracted with 100 ml acetonenole acetate to obtain another aqueous phase and organic phase. The obtained organic phase was mixed with the washed organic phase obtained above and the acetonenole acetate was distilled of under reduced pressure (water bath 45 °C, 170 mbar, 30 min, then: water bath 50 °C, 0 mbar, 35 min). The obtained fragrance composition had a water content of 0.09 vol.-%, which was determined by Karl-Fischer titration.

[0139] The contents of the fragrance composition were determined by GCMS. Example 3: Magnolia

[0140] 150 g of Magnolia absolute are provided and mixed with 150 g acetonenole acetate and 1.5 g Lipase resin from Aspergillus niger (200 U / g, from Aspergillus niger, Sigma-Aldrich, 62301). The water content of the mixture was determined by Karl-Fischer titration and was 0.85 wt.-%. The reaction mixture is incubated at 40 °C at 400 rpm and for 7 days in a fermenter.

[0141] After 7 days, 150 ml saturated NaCI-solution was added to the reaction mixture to stop the reaction. The enzyme is shaken out in a separating funnel and the reaction mixture is dried. In the separating funnel, the aqueous phase is separated from the organic phase. The organic phase was washed twice with 100 ml water. The aqueous phases were mixed and extracted with 100 ml acetonenole acetate to obtain another aqueous phase and organic phase. The obtained organic phase was mixed with the washed organic phase obtained above and the acetonenole acetate was distilled of under reduced pressure (water bath 45 °C, 170 mbar, 30 min, then: water bath 50 °C, 0 mbar, 35 min). The obtained fragrance composition had a water content of 0.12 vol.-%, which was determined by Karl-Fischer titration.

[0142] The contents of the fragrance composition were determined by GCMS.

[0143] Example 4: Olfactory evaluation

[0144] The fragrance compositions according to Examples 1 , 2 and 3 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, 3 odours selected from floral, green, fruity and sweet are changed in their intensity compared to the provided absolute.

[0145] It was further found that in all fragrance compositions, 1 or 2 odours selected from floral, green, fruity and sweet are increased in their intensity compared to the provided absolute.

[0146] It was further found that in all fragrance compositions, 1 or 2 odours selected from fruity and sweet are decreased in their intensity compared to the provided absolute.

[0147] In all examples, the odour animalic remained unchanged in its intensity compared to the provided absolute.

[0148] Example 5: Water content

[0149] The fragrance compositions as described in Examples 1 to 3 were provided. As described in the Examples, the water content of the reaction mixture, with which a transesterification is obtained, was 0.16 % (Rose), 0.19 % (Jasmin) or, respectively, 0.85 % (Magnolia).

[0150] Parallel approaches were performed for each sample (Rose, Jasmin, Magnolia), however wherein the water content of the reaction mixture was 0 % and in another sample, wherein the water content of the reaction mixture was 10 %, as a comparison.

[0151] For each of the samples, the contents were determined by GCMS. As shown below, the samples according to the invention differ from the controls. It was found that the samples according to the invention provided the most likeable odour compared to the controls.

[0152] Example 5.1 : Rose

[0153] The contents determined by GCMS were each normalized to the 0 % water control. It was found that e.g. Citronellyl acetate, Ethyl linoleate, and Ethyl palmitate were particularly increased in the 0.16 water sample, with regard to the provided plant extract and when compared to the 0 % or 10 % water control:

[0154] Thus, the 0.16 % water sample was different from the controls. Further, the 0.16 % water sample provided the most likeable odour compared to the controls.

[0155] Example 5.2: Jasmin The contents determined by GCMS were each normalized to the 0 % water control. It was found that e.g. Methyl hexadecanoate, Phytone, and Ethyl linoleate were particularly increased and linalool was particularly decreased in the 0.19 water sample, with regard to the provided plant extract and when compared to the 0 % or 10 % water control: Thus, the 0.19 % water sample was different from the controls. Further, the 0.19 % water sample provided the most likeable odour compared to the controls. Example 5.3: Magnolia

[0156] The contents determined by GCMS were each normalized to the 0 % water control. It was found that e.g. Linalooloxide, and Caryophyllene oxide, were particularly increased and Caryophyllene beta was particularly decreased in the 0.85 water sample, with regard to the provided plant extract and when compared to the 0 % or 10 % water control:

[0157] Thus, the 0.85 % water sample was different from the controls. Further, the 0.19 % water sample provided the most likeable odour compared to the controls.

Claims

Claims1 . Method for obtaining a fragrance composition, comprising the steps i) providing a plant extract comprising one or more fragrance(s), wherein the, one, two, three or more or all fragrance(s) in the plant extract provided in step i) is I are selected from the group consisting of alcohols, wherein the plant extract is an essential oil or an absolute, preferably wherein the, one, two, three or more or all plant extract(s) provided in step i) is I are extract(s) of a plant of the genus Jasminum, and / or preferably wherein the, one, two, three or more or all plant extract(s) provided in step i) is I are extract(s) of a plant of the genus Rosa, and / or preferably wherein the, one, two, three or more or all plant extracts) provided in step i) is I are extract(s) of a plant of the genus Magnolia, ii) providing an esterase, preferably one or more lipase(s), iii) providing an ester, preferably wherein the ester is an acetic acid ester, particularly preferably selected from the group consisting of ethyl acetate, vinyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, further preferably selected from the group consisting of ethyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, iv) mixing the plant extract provided in step i) with the esterase provided in step ii) and the ester provided in step iii) to obtain a reaction mixture and reacting the fragrance(s) in the reaction mixture under conditions allowing a transesterification of the carboxylic acid moiety of the ester provided in step iii) to the fragrance(s), to obtain a mixture comprising an esterified fragrance,v) optionally: drying the mixture comprising an esterified fragrance obtained in step iv) to obtain the fragrance composition, wherein in step iv), the conditions allowing the transesterification include a water content in the range of from 0.1 to 7.5 wt.-%, preferably of from 0.1 to 5 wt.-%, particularly preferably 0.1 to 2.5 wt.-%, further preferably 0.1 to 1 wt.-%, based on the total weight of the reaction mixture.

2. Method according to claim 1 , wherein the, one, two, three or more or all fragrance(s) in the plant extract 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, triple-unsaturated 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 plant extract provided in step i) is / are selected from the group consisting of benzyl alcohol, bisab- olols, borneols, fenchols, isopulegols, terpineols, verbenols, ambrein, aphidicolin, betulin, cadinol, 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, and / or wherein the, one, two, three or more or all fragrance(s) in the plant extract 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.

3. Method according to any one of the previous claims, wherein the plant extract provided in step i) comprises further fragrance(s),wherein the, one, two, three or more or all further fragrance(s) is / are selected from the group consisting of aldehydes, olefins, and carbonic acids.

4. Method according to any one of the previous claims, wherein in step iv), the conditions allowing the transesterification include a reaction temperature in the range of from 25 to 60 °C, preferably of from 30 to 50 °C, particularly preferably of from 35 to 45 °C, and / or wherein in step iv), the conditions allowing the transesterification include a reaction time in the range of from 8 to 240 hours, preferably of from 10 to 216 hours, particularly preferably of from 12 to 192 hours, and / or wherein in step iv), the conditions allowing the transesterification include stirring at a speed in the range of from 100 to 2,000 rpm.

5. Method according to any one of the previous claims, wherein the drying in step v) is present and consists of or includes adding one or more drying agent(s) to the mixture comprising an esterified fragrance obtained in step iv), preferably wherein the drying agent(s) is / are added as a solution, preferably saturated solution, comprising the, one, two, three or more drying agent(s), preferably wherein the, one, two, three or more drying agent(s) is / are salt(s), particularly preferably wherein the, one, two, three or more drying agent(s) is / are salt(s) selected from the group consisting of lithium fluoride, sodium fluoride, potassium fluoride, magnesium fluoride, calcium fluoride, lithium chloride, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, lithium bromide, sodium bromide, potassium bromide, calcium bromide, magnesium bromide, lithium iodide, sodium iodide, potassium iodide, calcium iodide, magnesium iodide, lithium sulfate, sodium sulfate, potassium sulfate, calcium sulfate, magnesium sulfate, calcium oxide, lithium nitrate, sodium nitrate, potassium nitrate, calcium nitrate, magnesium nitrate, lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, lithium acetate, sodium acetate, potassium acetate,magnesium acetate, calcium acetate, lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, lithium phosphate, sodium phosphate, potassium phosphate, magnesium phosphate, calcium phosphate, lithium chlorate, sodium chlorate, potassium chlorate, calcium chlorate, magnesium chlorate, lithium perchlorate, sodium perchlorate, potassium perchlorate, calcium perchlorate, magnesium perchlorate, lithium thiocyanate, sodium thiocyanate, potassium thiocyanate, calcium thiocyanate, and magnesium thiocyanate.

6. Method according to any one of the previous claims, wherein the, one, two, three or more or all plant extracts) provided in step i) 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, lentisque 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, jonquille extract, lavender extract, lavandin extract, mimosa extract, narcisse extract, orange flower extract, orange leaf extract, orris extract, osman-thus 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, schinus 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, gen- tiane 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) provided in step i) is I are extracts) of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

7. Method according to any one of the previous claims, wherein the method further comprises the stepiv.b) removing esterase, preferably the esterase, and / or acyl donor, preferably the acyl donor, from the mixture comprising an esterified fragrance obtained in step iv), and / or vi) removing esterase, preferably the esterase, and / or acyl donor, preferably the acyl donor, from the mixture obtained after step iv) or the dried mixture obtained in step v), preferably wherein the removing in step iv.b) and / or vi) includes a distillation step.

8. Method according to any one of the previous claims, wherein step v) is present and in step v) the mixture is dried to a water content of at most 5 wt.-%, preferably at most 2.5 wt.-%, further preferably at most 1 wt.-%, even further preferably at most 0.5 wt.%, more preferably at most 0.25 wt.-%, based on the total weight of the dried mixture.

9. Fragrance composition obtained or obtainable by a method according to any one of the claims 1 to 8, wherein the amount(s) of one, two, three or more or all compounds selected from the group consisting of2-Phenylethyl acetate, Citronellyl acetate, Ethyl linoleate, Ethyl palmitate, Ger- macrene D, Citronellol, Benzyl alcohol, Neophytadiene, Geranic acid, Methyl hexadecanoate, Jasmin lactone, Trans-Nerolidol, Trans-Jasmone, 2-Phenylethyl acetate, Phytol, Phytol acetate E, Isophytol, Linalooloxide, 2-Methyl-methyl butyrate, Limonene is / are altered in the fragrance composition, when compared to the plant extract provided in step i) of the method.

10. Fragrance composition according to claim 9, wherein the water content in the fragrance composition is at most 5 wt.-%, preferably at most 2.5 wt.-%, further preferably at most 1 wt.-%, even further preferably at most 0.5 wt.%, more preferably at most 0.25 wt.-%, based on the total weight of the fragrance composition,preferably wherein the water content in the fragrance composition is in a range of from 0.001 to 5 wt.-%, preferably of from 0.01 to 5 wt.-%, particularly preferably of from 0.025 to 2.5 wt.-%, further preferably of from 0.05 to 1 wt.-%, more preferably of from 0.075 to 0.5 wt.-%, based on the total weight of the fragrance composition.11 . Fragrance composition according to claim 9 or 10, wherein the fragrance composition comprises the ester provided in step iii) of the method according to any one of claims 1 to 8, preferably wherein the ester is an acetic acid ester, particularly preferably selected from the group consisting of ethyl acetate, vinyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, further preferably selected from the group consisting of ethyl acetate, isopropenyl acetate, acetonenole acetate, and mixtures thereof, and / or wherein the plant extract provided in step i) of the method according to any one of claims 1 to 8 is an extract of a plant of the genus selected from the group consisting of Jasminum, Rosa, Magnolia, and mixtures thereof.

12. Fragrance composition according to any one of claims 9 to 11 , wherein three odours selected from the group consisting of floral, green, fruity and sweet are changed in their intensity compared to the plant extract provided in step 1 of the method according to any one of claims 1 to 8.

13. Fragrance composition according to any one of claims 9 to 12, wherein one or two odours selected from the group consisting of floral, green, fruity and sweet is increased in its intensity compared to the plant extract provided in step 1 of the method according to any one of claims 1 to 8, preferably at least one but at most two odours selected from the group consisting of floral, green, fruity and sweet are increased in its intensity compared to the plant extract provided in step 1 of the method according to any one of claims 1 to 8.

14. Fragrance composition according to any one of claims 9 to 13, wherein one or both odours selected from fruity and sweet is decreased in its intensity compared to the plant extract provided in step 1 of the method according to any one of claims 1 to 8.

15. Perfumed product, preferably pharmaceutical preparation, cosmetic preparation or preparation serving for nutrition or pleasure comprising a fragrance composition according to any one of claims 9 to 14.