Improved process for the preparation of a mixture comprising cocoamidopropyl betaine

Abstract

The present invention relates to a process for the preparation of mixtures comprising cocoamidopropyl betaine, at least one glycolipid, and at least one aroma compound of coconut. The mixtures are obtained in particular from coconut oil or palm oil and are characterized by a particularly neutral odor. The present invention also relates to mixtures comprising at least one glycolipid, cocoamidopropyl betaine, and at least one aroma compound of coconut. The present invention also relates to the use of glycolipids for neutralizing coconut odor, in particular in mixtures comprising at least one glycolipid, cocoamidopropyl betaine, and at least one aroma compound of coconut.

Description

[0001] 202400161 Foreign Filing 1

[0002] Improved method for producing a mixture comprising cocamidopropyl betaine

[0003] The present invention relates to a process for producing mixtures comprising cocamidopropyl betaine, at least one glucolipid, and at least one coconut flavoring agent. The mixtures are obtained, in particular, from coconut oil or palm oil and are characterized by a particularly neutral odor. The present invention also relates to mixtures comprising at least one glucolipid, cocamidopropyl betaine, and at least one coconut flavoring agent. Furthermore, the present invention relates to the use of glucolipids for neutralizing coconut odor, particularly in mixtures comprising at least one glucolipid, cocamidopropyl betaine, and at least one coconut flavoring agent.

[0004] Field of invention

[0005] Cocoamidopropyl betaine (“CAPB”) is a surfactant used in cosmetics and personal care products. The production of cocamidopropyl betaine typically involves two steps (ANN Fatihah, M. Pratiwi, AN Istyami, R. Ouwadi, D. Lestari, Tenside Surfact. 2023, 60, 419–425; A. Gholami, M. Golestaneh, Z. Andalib, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 192, 122–127).

[0006] In the first stage (“amidation”), 3-aminopropyldimethylamine (“DMAPA”; CAS number: 109-55-7) is reacted with a triglyceride from coconut oil or palm oil. Alternatively, a fatty acid (as described in CN 101219966 A) or a fatty acid methyl ester can be used, which is present in coconut oil and palm oil or is obtained from them beforehand by hydrolysis of the fatty acid triglycerides or by separation. The respective fatty acid amidopropyldimethylamine is obtained as an intermediate [corresponding to the structural formula (II), which is shown below];

[0007] In the second stage (“Carboxymethylation” also described in CN 106631864 A), the fatty acid amidopropyldimethylamine is reacted with sodium monochloroacetate (“SMCA”) to form CAPB, with sodium chloride being obtained as a by-product.

[0008] EP 0560114 A2 discloses aqueous, liquid solutions of betaine that do not contain surfactants, organic solvents, or other impurities, such as the aminoamide as an intermediate. This is achieved by adjusting the content of free fatty acids and a small amount of glycerol.

[0009] EP 3050946 A1 discloses palm kernel oil-based betaines exhibiting a specific fatty acid chain distribution. These betaines show advantageous viscosity properties. 202400161 Foreign Filing 2

[0010] EP 1 659109 A1 describes a process for the production of betaines, wherein thickeners are added during the synthesis. Preferred thickeners are nonionic, highly ethoxylated surfactants.

[0011] KR 10-2019-0023563 A discloses a process for the production of color-stable CAPB using boron catalysts.

[0012] WO 2023 / 030699 A1 discloses mixtures of fatty acid amidoalkyl betaines and dimethylaminoalkylamines characterized by low viscosity.

[0013] Besides a high yield of CAPB, it is desirable to obtain a high-quality, neutral-smelling product. Aromatic compounds, which are commonly found in coconut but also in palm oil, pose a challenge in this regard.

[0014] Coconut scent is a natural fragrance used intentionally in the production of food, cleaning products, and cosmetics, and is appreciated in many kitchens around the world. However, many people find it too intense or even unpleasant. Similarly, coconut-scented coconut oil blends (CAPBs) are undesirable in many applications, such as cleaning products and personal care items that should have a neutral scent. Therefore, there is a need to neutralize or mask coconut scent in many applications. This presents a particular challenge in the production of CAPBs, as they are typically made from coconut oil, which should ideally be used in its most untreated form to simplify the process.A similar problem arises when considering other natural fats or oils that have a similar aroma profile to coconut, such as palm oil.

[0015] The flavor compounds responsible for the typical coconut smell are organic compounds, some of which play a key role in the coconut smell (see FM Lin & WF Wilkens, “VOLATILE FLAVOR COMPONENTS OF COCONUT MEAT”, Food Science 1970, 35, 538-539, hereinafter “Lin & Wilkens”; Z. Li, T. Wang, H. Jiang, W.-T. Wang, T. Lan, L. Xu, Y.-H. Yun, W. Zhang, Food Chemistry: X 2024, 21, 101141; hereinafter “Li et al”).

[0016] When coconut oil or palm oil is used in the first stage of CAPB synthesis, the presence of these flavorings in the starting material is difficult to avoid. They are then carried along through the two synthesis stages and ultimately end up in the CAPB product, from which they are difficult to separate.

[0017] The object of the present invention was therefore to provide a process for the production of CAPB, which starts with a raw product such as raw coconut oil or palm oil, which, in addition to the triglycerides / fatty acids or their methyl esters, contains the flavoring substances typically found in coconuts. The process according to the invention should nevertheless allow for the simple production of an odorless CAPB product. 202400161 Foreign Filing 3

[0018] Another object of the present invention was to provide a mixture of CAPB and coconut flavorings that is as odorless as possible.

[0019]

[0020] Surprisingly, a process for producing mixtures comprising cocamidopropyl betaine was found which solves the problem according to the invention. The process is characterized in that it starts with reactants that exhibit typical coconut aroma compounds, yet leads to an odorless product.

[0021] In a first aspect, the present invention thus relates to a method for producing a mixture M*. The mixture M* comprises at least one compound of structural formula (I):

[0022]

[0023] wherein R is a saturated or unsaturated alkyl group with 3 to 24 carbon atoms, in particular a saturated or unsaturated alkyl group with 5 to 19 carbon atoms, preferably a saturated or unsaturated alkyl group with 5 to 18 carbon atoms, more preferably a saturated or unsaturated alkyl group with 10 to 17 carbon atoms, even more preferably a saturated alkyl group with 11 carbon atoms, wherein it is most preferably an unbranched alkyl group with 11 carbon atoms.

[0024] For the purposes of the invention, an alkylene residue is referred to as an "unsaturated alkyl residue". An alkylene residue has at least one C=C double bond. Preferably, an alkylene residue has one to three, more preferably one or two, and even more preferably one C=C double bond.

[0025] In a preferred embodiment, the residue RC(=O)- is selected from the fatty acid acyl groups of the following acids: caproic acid (R = n-pentyl), caprylic acid (R = n-heptyl), capric acid (R = n-nonyl), lauric acid (R = n-undecyl), myristic acid (R = n-tridecyl), palmitic acid (R = n-pentadecyl), stearic acid (R = n-heptadecyl), oleic acid, linoleic acid, linolenic acid, arachidic acid (R = n-nonadecyl), and gadoleic acid. The residue RC(=O)- is particularly preferred as the fatty acid acyl group of lauric acid.

[0026] For oleic acid, the residue RC(=O)- has the following structure (Ö), for linoleic acid, the residue RC(=O)- has the following structure (L2), for linolenic acid, the residue RC(=O)- has the following structure (L3), for gadoleic acid, the residue RC(=O)- has the following structure (A): 202400161 Foreign Filing 4

[0027]

[0028] Step a.

[0029] In step a. of the process according to the invention, a mixture M is reacted with 3-aminopropyldimethylamine.

[0030] The mixture M includes

[0031] i. at least one triglyceride of structural formula (III) and / or a compound of formula RCOOR 1 with R' = H, Methyl,

[0032]

[0033] where the residues R in structural formula (III) can be the same or different,

[0034] ii. at least one coconut flavouring substance AKOKO, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably at least six, more preferably at least nine, more preferably at least twenty, more preferably at least thirty coconut flavouring substances AKOKO.

[0035] Any mixture comprising the components mentioned under points i. and ii. can be used as a mixture M.

[0036] Preferably, coconut oil and / or palm kernel oil are used as a mixture, preferably coconut oil.

[0037] The terms "coconut oil" and "coconut fat" are used synonymously within the scope of the present invention. 202400161 Foreign Filing 5

[0038] The terms “palm kernel oil” and “palm kernel fat” are used synonymously within the scope of the present invention.

[0039] In an optional embodiment of the present invention, the coconut oil or palm kernel oil used is subjected to a pretreatment step before being used in step a. This pretreatment step is preferably selected from the group consisting of deodorization, bleaching, and other processes.

[0040] Deodorization can be carried out using methods known to those skilled in the art, e.g. by steam distillation, as described in DE 33 16523 A1 or DE 19531 806 C1.

[0041] Even after such pre-purification steps, the pre-purified coconut oil typically still contains flavorings (AKOKO) that could be perceived as unpleasant. Therefore, the inventive method can also be advantageously used in embodiments where pre-purification takes place.

[0042] The mixture M used in step a. comprises at least one coconut flavoring agent AKOKO, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably at least six, more preferably at least nine, more preferably at least twenty, more preferably at least thirty coconut flavoring agents AKOKO. For the purposes of the invention, "coconut flavoring agent" (the synonymous term "coconut flavoring agent" is also used) means a substance that is responsible for or contributes to the typical aroma of coconut oil. These coconut flavoring agents also occur in other fruits or nuts, e.g., in palm kernel oils.

[0043] AKOKO is preferably selected from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic ester, ethyl capric ester, methyl caproic ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-acetyl-1-pyrroline (“2-AP”), 2-methylfuran.

[0044] AKOKO is preferably selected from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanon, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic ester, ethyl capric ester, methyl caproic ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran.

[0045] AKOKO is even more preferably from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic ester, ethyl capric ester, methyl caproic ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 202400161 Foreign Filing 6

[0046] 1-Heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran selected.

[0047] According to Li et al. and Lin & Wilkens, the components that contribute most to the coconut smell are A-Octalactone, A-Decalactone, A-Undecalactone, 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal.

[0048] AKOKO is therefore more preferably selected from the group consisting of A-Octalactone, A-Decalactone, A-Undecalactone, 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal, and even more preferably selected from the group consisting of 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal.

[0049] In a preferred embodiment, the mixture M used in step a. comprises at least one, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably all six coconut flavorings AKOKO selected from the group consisting of 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal, wherein more preferably in each case at least 1-Octanol is included.

[0050] In a more preferred embodiment, the mixture M used in step a. comprises

[0051] A-octalactone, A-decalactone, A-undecalactone, 1-octanol, 2-AP, 2,3-butanedione, ethyl acetate, acetoin and 1-nonanal.

[0052] In a more preferred embodiment, the following comprises the elements described in step a. Mixture used: M Octanal, 2-Heptanol, 1-Hexanol, Nonanal, 2-Nonanon, 2-Octanol, 2-Nonanol, 1-Octanol, 2-Undecanone, ethyl caproic ester, ethyl capric ester, methyl caproic ester, 2-Undecanol, 2-Phenylethanol, Benzothiazole, A-Octalactone, A-Decalactone, A-Undecalactone, 1-Propanol, 2-Methyl-1-propanol, 1-Butanol, 1-Hexanol, 1-Heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, isovaleraldehyde, 2,3-Butanedione, acetoin, 2-AP, 2-Methylfuran, and more preferably additionally acetaldehyde, and more preferably additionally acetaldehyde and ethanol.

[0053] The content of coconut flavoring agent AKOKO in mixture M is subject to natural fluctuations and can therefore vary naturally. Furthermore, it also depends on whether mixture M has undergone pretreatment (which occurs in one embodiment of the invention) or whether unprocessed coconut oil is used directly after isolation from the nut (which occurs in another embodiment of the invention).

[0054] In one embodiment, the content of all coconut flavoring substances AKOKO, which are included in the mixture M used in step a., is in the range of 0.01 ppm to 1 wt%, based on the total weight of the mixture M used in step a. The advantages of the process according to the invention also apply in this concentration range, because neutralization of the coconut odor is achieved even at concentrations above 1000 ppm. 202400161 Foreign Filing 7

[0055] Preferably, the total content of all coconut flavoring substances AKOKO in the mixture M used in step a. is in the range of 250 ppt to 5 ppm, preferably from 500 ppt to 1 ppm, more preferably from 1 ppb to 100 ppb, more preferably from 10 ppb to 50 ppb, in each case based on the total weight of the mixture M used in step a.

[0056] The content of the coconut flavoring substances AKOKO, which are included in mixture M, can be reduced before mixture M is used in step a. of the process according to the invention. This can be done using methods or pretreatment steps known to those skilled in the art.

[0057] It is also preferred that in embodiments in which the mixture M used in step a. comprises the respective coconut flavoring AKOKO mentioned below, the proportion of the respective coconut flavoring AKOKO, based on the total weight of the mixture M used in step a., lies in the following preferred ranges:

[0058] In the context of this invention, the terms “ppm”, “%”, “ppt”, “ppb” refer to mass per mass, thus determining the mass fraction (e.g. “kg / kg”).

[0059] Therefore, 1 ppb = 1000 ppt = 1 pg / kg.

[0060] Ethanol: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0061] 1-Propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0062] 2-Methyl-1-propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0063] 1-Butanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0064] 1-Hexanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0065] 1-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0066] 2-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0067] 1-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0068] 2-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0069] 2-Nonanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0070] 2-Undecanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0071] 2-Phenylethanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0072] Ethyl acetate: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0073] Methylhexanoate (= caproic acid methyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0074] Ethylhexanoate (= caproic acid ethyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0075] Methyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0076] Ethyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0077] Ethyl caprylic acid: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0078] A-Octalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0079] A-Decalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0080] A-Undecalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0081] Acetaldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0082] Isovaleraldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb; 202400161 Foreign Filing

[0083] Octanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0084] 1 -Nonanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0085] 2-Nonanone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0086] 2-Undecanon: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0087] 2,3-Butanedione: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0088] Acetoin: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0089] 2-AP: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0090] 2-Methylfuran: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0091] Benzothiazole: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb.

[0092] The preferred total content of all coconut flavoring substances is AKOKO selected from the group consisting of octanal, 2-heptanol, 1-hexanol, 1-heptanol, 1-nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl caproic acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP,

[0093] 2-Methylfuran, benzothiazole in the mixture M used in step a. in the range of 250 ppt to 5 ppm, preferably 500 ppt to 1 ppm, more preferably 1 ppb to 100 ppb, more preferably 10 ppb to 50 ppb, in each case based on the total weight of the mixture M used in step a.

[0094] The mixture M comprises, in addition to at least one coconut flavoring substance AKOKO, at least one further reaction component. This further reaction component is a triglyceride of structural formula (III) and / or a compound of formula RCOOR" with R' = H, methyl, preferably R' = H. The further reaction component is therefore selected from the group consisting of a triglyceride of structural formula (III), a compound of formula RCOOH, and a compound of formula RCOOCH3. The triglyceride of structural formula (III) has the following structure:

[0095]

[0096] The residue R in structural formula (III) has the same meaning as given for the residue R in structural formula (I). The residues R in structural formula (III) can be the same or different.

[0097] The remainder R in the formula RCOOR 1 has the same meaning as given for the remainder R in the structural formula (I).

[0098] Which of the components mentioned under i. [triglyceride of structural formula (III), RCOOH and / or RCOOCH3] is included in the mixture M used in step a. depends on the mixture used as mixture M in the process according to the invention. 202400161 Foreign Filing 9

[0099] Mixtures M containing at least one triglyceride of structural formula (III) are preferred. This applies, for example, to coconut oil and palm kernel oil.

[0100] However, mixtures M comprising RCOOH can also be used in the process according to the invention, and can be obtained, for example, from the respective triglyceride by at least partial saponification, as described, for example, in EP 0 891 963 A1.

[0101] However, mixtures M comprising RCOOCH3 can also be used in the process according to the invention, and can be obtained, for example, from the respective triglyceride by at least partial transesterification with methanol, as described, for example, in EP 0 127 104 A1.

[0102] Mixture M can be obtained from coconuts, for example, as described by Lin & Wilkens under “Sample preparation”.

[0103] It is preferred that the mixture M used in step a. comprises at least 10 wt.%, more preferably at least 20 wt.%, even more preferably at least 30 wt.%, even more preferably at least 40 wt.%, even more preferably at least 50 wt.%, even more preferably at least 60 wt.%, even more preferably at least 70 wt.%, even more preferably at least 80 wt.%, even more preferably at least 90 wt.%, even more preferably at least 99 wt.%, even more preferably substantially 100 wt.% triglycerides of structural formula (III), in each case based on the total weight of the mixture M used in step a. of the process according to the invention.

[0104] The pH value of the mixture M is preferably in the range of 3 to 9, more preferably in the range of 4 to 8, more preferably in the range of 4.5 to 7.5, even more preferably in the range of 5.0 to 7.0, even more preferably in the range of 5.5 to 6.5, most preferably at 6.0 (each measured at 25 °C).

[0105] The reaction of the mixture M with 3-aminopropyldimethylamine according to step a. of the process according to the invention can be carried out according to a method known to the skilled person (e.g. described in EP 0656346 A1).

[0106] The conversion according to step a. is preferably carried out at a temperature of > 80 °C, more preferably > 100 °C, even more preferably at a temperature in the range of 150 °C to 220 °C, even more preferably at a temperature in the range of 160 °C to 200 °C, and even more preferably at a temperature in the range of 180 °C to 190 °C.

[0107] In a preferred embodiment, a catalyst, in particular an acid, preferably formic acid or para-toluenesulfonic acid, is used in the reaction according to step a., wherein a preferred catalyst is para-toluenesulfonic acid.

[0108] Following step a., a crude product RP1 comprising at least one compound of structural formula (II) and at least one coconut flavoring substance AKOKO is obtained: 202400161 Foreign Filing 10

[0109]

[0110] The residue R in structural formula (II) has the same meaning as that given for residue R in structural formula (I). The crude product RP1 obtained in step a. can then be used directly, i.e., in particular without further purification steps, in the reaction according to step b. The crude product RP1 may also include byproducts, which are preferably selected from the group consisting of glycerol, RCOOH.

[0111] The crude product RP1 is optionally subjected to a purification step, e.g. distillation to remove the excess 3-aminopropyldimethylamine.

[0112] The content of the coconut flavoring substances AKOKO in the crude product RP1 is not further limited. Preferably, these are the coconut flavoring substances AKOKO comprised of the mixture M used in step a., and it is further preferred that the content of the respective coconut flavoring substance AKOKO comprised of the crude product RP1 is lower than the content of the respective coconut flavoring substance AKOKO in the mixture M used in step a.

[0113] Step b.

[0114] In step b. of the process according to the invention, the at least one compound of structural formula (II) obtained in step a. in the crude product RP1 is reacted with sodium monochloroacetate.

[0115] This implementation is also carried out according to methods known to experts, such as in the

[0116] EP 0656346 A1 described.

[0117] The implementation according to step b. preferably takes place at a temperature of > 40 °C, more preferably > 50 °C, even more preferably at a temperature in the range of 50 °C to 99 °C, even more preferably at a temperature in the range of 60 °C to 90 °C, and even more preferably at a temperature in the range of 70 °C to 80 °C.

[0118] Preferably in step b. monochloroacetic acid is neutralized with sodium hydroxide and then the crude product RP1 obtained in step a. comprising the compound of structural formula (II) is added.

[0119] Choline chloride can optionally be added to the reaction mixture.

[0120] Following step b., a crude product RP2 comprising at least one coconut flavoring AKOKO and at least one compound of structural formula (I) is obtained. 202400161 Foreign Filing 11

[0121] In a preferred embodiment, the crude product RP2 comprises at least one, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably all six coconut flavorings AKOKO selected from the group consisting of 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal, wherein more preferably at least 1-Octanol is included.

[0122] In a more preferred embodiment, the crude product RP2 comprises A-Octalactone, A-Decalactone, A-Undecalactone, 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin and 1-Nonanal.

[0123] In a more preferred embodiment, the crude product RP2 comprises octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic ester, ethyl capric ester, methyl caproic ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran, and, even more preferably, additionally acetaldehyde, and, even more preferably, additionally acetaldehyde and Ethanol.

[0124] The content of coconut flavoring agent AKOKO in the raw product RP2 can vary, e.g. depending on whether the raw product RP2 is purified after step b. or whether purification steps were carried out during the process according to the invention.

[0125] In one embodiment, the total concentration of all coconut flavoring substances AKOKO in RP2 is in the range of 0.01 ppt to 1.1 wt%, based on the total weight of the crude product RP2. More preferably, the total concentration of all coconut flavoring substances AKOKO in RP2 is in the range of 1 ppt to 100 ppm, more preferably in the range of 250 ppt to 5 ppm, more preferably in the range of 500 ppt to 1 ppm, more preferably in the range of 1 ppb to 100 ppb, and more preferably in the range of 10 ppb to 50 ppb, in each case based on the total weight of the crude product RP2.

[0126] It is also preferred that in embodiments in which the raw product RP2 comprises the respective coconut flavoring agent AKOKO, the proportion of the respective coconut flavoring agent AKOKO, based on the total weight of the raw product RP2, lies in the following preferred ranges:

[0127] Ethanol: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0128] 1-Propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0129] 2-Methyl-1-propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0130] 1-Butanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0131] 1-Hexanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0132] 1-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0133] 2-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0134] 1-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0135] 2-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0136] 2-Nonanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb; 202400161 Foreign Filing 12

[0137] 2-Undecanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0138] 2-Phenylethanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0139] Ethyl acetate: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0140] Methylhexanoate (= caproic acid methyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0141] Ethylhexanoate (= caproic acid ethyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0142] Methyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0143] Ethyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0144] Ethyl caprylic acid: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0145] A-Octalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0146] A-Decalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0147] A-Undecalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0148] Acetaldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0149] Isovaleraldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0150] Octanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0151] 1 -Nonanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0152] 2-Nonanone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0153] 2-Undecanon: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0154] 2,3-Butanedione: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0155] Acetoin: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0156] 2-AP: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0157] 2-Methylfuran: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0158] Benzothiazole: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb.

[0159] The preferred total content of all coconut flavoring substances is AKOKO selected from the group consisting of octanal, 2-heptanol, 1-hexanol, 1-heptanol, 1-nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl caproic acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP,

[0160] 2-Methylfuran, benzothiazole in crude product RP2 in the range of 250 ppt to 5 ppm, preferably 500 ppt to 1 ppm, more preferably 1 ppb to 100 ppb, more preferably 10 ppb to 50 ppb, each based on the total weight of crude product RP2.

[0161] In a preferred embodiment, the content of the respective coconut flavoring agent AKOKO comprised of the crude product RP2 (based on the total weight of RP2) is at least 1%, preferably at least 10%, and more preferably at least 51% by weight lower than the content of the same coconut flavoring agent AKOKO comprised of the mixture M used in step a. (based on the total weight of the mixture M used in step a.). 202400161 Foreign Filing 13

[0162] Step c.

[0163] In step c. of the process according to the invention, at least one glucolipid G is added to the crude product RP2, whereby a mixture M* comprising at least one glucolipid, at least one coconut flavouring substance AKOKO and at least one compound of structural formula (I) is obtained.

[0164] Glucolipids are biosurfactants and are described, for example, in WO 2019 / 154970 A1.

[0165] The at least one ‘glucolipid’ added in step c. of the process according to the invention is in particular a compound of the following general structural formula (III) or (V), preferably of the general structural formula (III), more preferably of the general structural formula (IV):

[0166]

[0167] In structural formulas (III) and (IV), mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1. In structural formulas (III) and (IV), the following applies:

[0168] The remains R 1GL and R 2GL are the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms,

[0169] where the remainders R 1GL and R 2GL Preferably selected independently of one another from the group consisting of

[0170] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0171] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12 carbon atoms, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups,

[0172] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CH2)oCH3, where o = 1 to 23, preferably 4 to 12, 202400161 Foreign Filing 14

[0173] where the remainders R 1GL and R 2GLeven more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CH2)oCH3, where o = 4 to 8,

[0174] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CH2)oCH3 are, where o = 4 to 8, preferably 4 to 6.

[0175] R are the most preferred 1GL and R 2GL n-heptyl each.

[0176] Different glucolipids with mGL = 0 are abbreviated according to the following nomenclature:

[0177] “GL-CX” means glucolipids of structural formula (III) in which mGL = 0 and in which the residue R 1GL = (CH2)O-CH3 with o = X-4.

[0178] Different glucolipids with mGL = 1 are abbreviated according to the following nomenclature:

[0179] “GL-CXCY” means glucolipids of structural formula (III) in which mGL = 1 and in which one of the residues R 1GL and R 2GL= (CH2)o-CH3 with o = X-4 and the other remainder R 1GL or R 2GL = (CH2)o-CH3 with o = Y-4.

[0180] The described nomenclature therefore does not distinguish between “CXCY” and “CYCX”.

[0181] If one of the indices X or Y is supplemented with the designation “:Z”, this means that the respective remainder R 1GL or R 2GL an unbranched, unsubstituted hydrocarbon residue with X-3 or Y-3 carbon atoms and Z double bonds.

[0182] The serpentine bond in structural formula (III) means that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring.

[0183] Alkyl groups can be branched or unbranched, and are preferably unbranched.

[0184] Alkenyl residues can be branched or unbranched, and are preferably unbranched.

[0185] Preferred alkenyl groups have one to three double bonds, preferably one double bond.

[0186] In embodiments in which compounds of structural formulas (III) or (IV) have more than one residue R 2GL These residues can exhibit R 2GL be the same or different.

[0187] In a particular embodiment, the amount is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, and even more preferably 25 wt.% to

[0188] 65 wt.% of the glucolipids used in step c. are glucolipids of structure GL-C10C10, where “wt.%” (= weight %; content in percent of the total weight) refers to the total weight of the glucolipids used in step c.

[0189] In a particular embodiment, 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids used in step c. are 202400161 Foreign Filing 15

[0190] Glucolipids of structure GL-C8C10, where “wt%” (= weight %; content in percent of the total weight) refers to the total weight of the glucolipids used in step c.

[0191] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, more preferably 5 wt.% to 15 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C10C12:1, wherein “wt.%” refers to the total weight of the glucolipids used in step c.

[0192] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, more preferably 3 wt.% to 12 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C10C12, wherein “wt.%” refers to the total weight of the glucolipids used in step c.

[0193] In a further special embodiment (abbreviated “elaboration Q”), 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C10C10.

[0194] In a more preferred embodiment of embodiment Q, the

[0195] at 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, even more preferably 25 wt.% to 65 wt.%, even more preferably 35 wt.% to 65 wt.%, even more preferably 50 wt.% to 65 wt.% of the glucolipids used in step c. to glucolipids of the structure GL-C10C10, and

[0196] at 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, even more preferably 10 wt.% to 20 wt.% of the glucolipids used in step c. to be glucolipids of the structure GL-C8C10.

[0197] In embodiment Q, it is even more preferred that it be

[0198] where the glucolipids used in step c. are 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, even more preferably 25 wt.% to 65 wt.%, even more preferably 35 wt.% to 65 wt.%, even more preferably 50 wt.% to 65 wt.%, and

[0199] where 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, even more preferably 10 wt.% to 20 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C8C10, and

[0200] where 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, even more preferably 5 wt.% to 15 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C10C12:1, and

[0201] where 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, even more preferably 3 wt.% to 12 wt.% of the glucolipids used in step c. are glucolipids of the structure GL-C10C12. 202400161 Foreign Filing 16

[0202] Optionally, the glucolipids used in embodiment Q in step c. also include glucolipids of structure GL-C10, wherein preferably 0 wt.% to 5 wt.%, more preferably 0.01 wt.% to 4 wt.%, and even more preferably 0.1 wt.% to 3 wt.% of the glucolipids used in step c. are glucolipids of structure GL-C10.

[0203] In embodiment Q, “wt%” refers to the total weight of the glucolipids used in step c.

[0204] In another special embodiment, it is a

[0205] at 10 wt.% to 70 wt.%, preferably 25 wt.% to 65 wt.%, even more preferably 35 wt.% to 65 wt.%, even more preferably 50 wt.% to 65 wt.% of the glucolipids used in step c. to be glucolipids of the structure GL-C10C10, and

[0206] at 10 wt.% to 20 wt.% of the glucolipids used in step c., glucolipids of the structure GL-C8C10, and

[0207] at 5 wt.% to 15 wt.% of the glucolipids used in step c. to glucolipids of the structure GL-C10C12:1 , and

[0208] at 3 wt.% to 12 wt.% of the glucolipids used in step c., glucolipids of the structure GL-C10C12,

[0209] where “wt%” refers to the total weight of the glucolipids used in step c.

[0210] Compounds (so-called “di-glucolipids”) of the general structural formula (V) in the context of the process according to the invention are as follows:

[0211]

[0212] (V) (T)

[0213] In the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1.

[0214] The following applies to the structural formula (V):

[0215] The remains R 1GL and R 2GLare the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms,

[0216] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of 202400161 Foreign Filing 17

[0217] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 7 to 12, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0218] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12 carbon atoms, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups,

[0219] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CH2)oCH3, where o = 1 to 23, preferably 4 to 12,

[0220] where the remainders R 1GL and R 2GL even more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CH2)oCH3, where o = 4 to 8,

[0221] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CH2)oCH3 are, where o = 4 to 8, preferably 4 to 6.

[0222] R are the most preferred1GL and R 2GL n-heptyl each.

[0223] One of the remnants R G2 , R G3 , R G4 and R G6 , preferably R G4 , is a residue of the general structural formula (T), and the three remaining residues are R G2 , R G3 , R G4 and R G6 Each of these are hydrogen.

[0224] In the general structural formula (T), one of T G1 , T G2 , T G3 , T G4 and T G6 , preferably T G1 , a direct connection to the structure (V), while the other four are from T G1 , T G2 , T G3 , T G4 and T G6 each are hydroxy, wherein it is preferred that T G1 a direct connection to the structure (V), while the T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

[0225] The serpentine bond in structural formulas (V) and (T) means that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring.

[0226] In embodiments in which compounds of structural formula (V) have more than one residue R 2GL These residues can exhibit R 2GL be the same or different.

[0227] The amount of glucolipid G used in step c. is not further limited and can be adjusted by a person skilled in the art according to their expertise. In particular, in step c., such a quantity of glucolipid G is added that the proportion of all glucolipids G, based on the total weight of the mixture M* obtained in step c., is in the range of 0.01 wt.% to 30 wt.%, preferably in the range of 0.1 wt.% to 25 wt.%, and even more preferably in the range of 1 wt.% to 20 wt.%.

[0228] preferably in the range of 2 wt.% to 15 wt.%, even more preferably in the range of 5 wt.% to 10 wt.%.

[0229] However, it is preferred to use the amount of glucolipids G as a function of the coconut flavorings AKOKO contained in the crude product RP2. In a preferred embodiment, the ratio (i.e., the weight ratio) of the mass of all components is determined in step c. Glucolipids used G, based on the mass of all coconut flavoring substances AKOKO included in RP2, which consist in particular of the group comprising octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-Acetyl-1-pyrroline, 2-methylfuran are selected, in the range of 1:1 to 10 12 : 1 , preferably in the range of 1 : 1 to 10 9: 1 , preferably in the range of 10 : 1 to 10 7 : 1, even more preferred in the range of 100 : 1 to 10 6 : 1, even more preferred in the range of 1000 : 1 to 10 5 : 1, even more preferred in the range of 5000 : 1 to 10 4 : 1.

[0230] Following step c., a mixture M* is obtained comprising at least one glucolipid, at least one coconut flavoring AKOKO, and at least one compound of structural formula (I). The mixture M* preferably comprises at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably at least six, more preferably at least nine, more preferably at least twenty, and more preferably at least thirty coconut flavorings AKOKO-

[0231] The proportion of the coconut flavoring substances AKOKO in the respective mixtures or compositions can be determined using methods known to those skilled in the art, for example as described by Li et al.

[0232] Following step c., a mixture M* is obtained as described in the following section according to the second aspect of the invention.

[0233] Mixture M*

[0234] In a second aspect, the present invention also relates to a mixture M* comprising

[0235] a. at least one glucolipid G,

[0236] b. at least one coconut flavoring agent AKOKO, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably at least six, even more preferably at least nine, even more preferably at least twenty, even more preferably at least thirty coconut flavoring agents AKOKO, c. at least one compound of structural formula (I),202400161 Foreign Filing 19

[0237]

[0238] where R is a saturated or unsaturated alkyl group with 3 to 24 carbon atoms.

[0239] The at least one “glucolipid” in the mixture M* according to the second aspect of the invention is in particular a compound of the following general structural formulas (III) or (V), preferably of the general structural formula (III), more preferably of the general structural formula (IV):

[0240]

[0241] In structural formulas (III) and (IV), mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1. In structural formulas (III) and (IV), the following applies:

[0242] The remains R 1GL and R 2GL are the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms,

[0243] where the remainders R 1GL and R 2GL Preferably selected independently of one another from the group consisting of

[0244] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0245] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12 carbon atoms, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups,

[0246] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CFhjoCHs), where o = 1 to 23, preferably 4 to 12,

[0247] where the remainders R 1GL and R 2GLeven more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CFhjoCHs, where o = 4 to 8, 202400161 Foreign Filing 20

[0248] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CH2)oCH3 are, where o = 4 to 8, preferably 4 to 6.

[0249] R are the most preferred 1GL and R 2GL n-heptyl each.

[0250] The serpentine bond in structural formula (III) means that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring.

[0251] Alkyl groups can be branched or unbranched, and are preferably unbranched.

[0252] Alkenyl residues can be branched or unbranched, and are preferably unbranched.

[0253] Preferred alkenyl groups have one to three double bonds, preferably one double bond.

[0254] In embodiments in which compounds of structural formulas (III) or (IV) have more than one residue R 2GL These residues can exhibit R 2GL be the same or different.

[0255] In a particular embodiment, the amount is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, and even more preferably 25 wt.% to

[0256] 65 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C10, wherein “wt.%” (= weight %; content in percent of the total weight) refers to the total weight of all glucolipids in the mixture M* according to the second aspect of the invention.

[0257] In a particular embodiment, 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C8C10, wherein “wt.%” refers to the total weight of all glucolipids in the mixture M* according to the second aspect of the invention.

[0258] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, more preferably 5 wt.% to 15 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C12:1, wherein “wt.%” refers to the total weight of all glucolipids in the mixture M* according to the second aspect of the invention.

[0259] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, more preferably 3 wt.% to 12 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C12, wherein “wt.%” refers to the total weight of all glucolipids in the mixture M* according to the second aspect of the invention. 202400161 Foreign Filing 21

[0260] In a further particular embodiment (abbreviated “elaboration Q*”), 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C10.

[0261] In a more preferred embodiment of embodiment Q*, the

[0262] at 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention, comprising glucolipids of structure GL-C10C10, and at 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention, comprising glucolipids of structure GL-C8C10.

[0263] In embodiment Q*, it is even more preferred that it be

[0264] where 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C10, and where 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C8C10, and

[0265] where 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, even more preferably 5 wt.% to 15 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C12:1, and

[0266] where 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, even more preferably 3 wt.% to 12 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of the structure GL-C10C12.

[0267] Optionally, the glucolipids in the mixture M* according to embodiment Q* also include glucolipids of structure GL-C10, wherein preferably 0 wt.% to 5 wt.%, more preferably 0.01 wt.% to 4 wt.%, and even more preferably 0.1 wt.% to 3 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention are glucolipids of structure GL-C10.

[0268] In embodiment Q*, “wt%” refers to the total weight of all glucolipids in the mixture M* according to the second aspect of the invention. 202400161 Foreign Filing 22

[0269] In another special embodiment, it is a

[0270] at 10 wt.% to 70 wt.%, preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention, comprising glucolipids of the structure GL-C10C10, and at 10 wt.% to 20 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention, comprising glucolipids of the structure GL-C8C10,

[0271] at 5 wt.% to 15 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention to glucolipids of the structure GL-C10C12:1 ,

[0272] at 3 wt.% to 12 wt.% of the glucolipids in the mixture M* according to the second aspect of the invention to glucolipids of the structure GL-C10C12,

[0273] where “wt%” refers to the total weight of all glucolipids in the mixture M*.

[0274] Compounds (so-called “di-glucolipids”) of the general structural formula (V) in the context of the mixture M* according to the second aspect of the invention are as follows:

[0275]

[0276] (V) (T)

[0277] In the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1.

[0278] The following applies to the structural formula (V):

[0279] The remains R 1GL and R 2GL are the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms,

[0280] where the remainders R 1GL and R 2GL Preferably selected independently of one another from the group consisting of

[0281] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 7 to 12, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0282] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12 carbon atoms, more preferably 5 to 9, more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups, 202400161 Foreign Filing 23

[0283] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CH2)oCH3, where o = 1 to 23, preferably 4 to 12,

[0284] where the remainders R 1GL and R 2GLeven more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CH2)oCH3, where o = 4 to 8,

[0285] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CH2)oCH3 are, where o = 4 to 8, preferably 4 to 6.

[0286] R are the most preferred 1GL and R 2GL n-heptyl each.

[0287] One of the remnants R G2 , R G3 , R G4 and R G6 , preferably R G4 , is a residue of the general structural formula (T), and the three remaining residues are R G2 , R G3 , R G4 and R G6 Each of these are hydrogen.

[0288] In the general structural formula (T), one of T G1 , T G2 , T G3 , T G4 and T G6 , preferably T G1 , a direct connection to the structure (V), while the other four are from T G1 , T G2, T G3 , T G4 and T G6 each are hydroxy, wherein it is preferred that T G1 a direct connection to the structure (V), while the T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

[0289] The serpentine bond in structural formulas (V) and (T) means that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring.

[0290] In embodiments in which compounds of structural formula (V) have more than one residue R 2GL These residues can exhibit R 2GL be the same or different.

[0291] The amount of glucolipids G comprising mixture M* is not further limited and can be selected by a person skilled in the art according to their expertise. In particular, the total weight of all glucolipids G in mixture M*, based on the total weight of mixture M*, is in the range of 0.01 wt.% to 30 wt.%, more preferably in the range of 0.1 wt.% to 25 wt.%, even more preferably in the range of 1 wt.% to 20 wt.%, even more preferably in the range of 2 wt.% to 15 wt.%, and even more preferably in the range of 5 wt.% to 10 wt.%.

[0292] In a further preferred embodiment, the ratio (i.e., the weight ratio) of the mass of all glucolipids G comprising the mixture M*, based on the mass of all coconut flavorings AKOKO comprising the mixture M*, which in particular consist of the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, Acetaldehyde,202400161 Foreign Filing 24

[0293] Isovaleraldehyde, 2,3-butanedione, acetoin, 2-acetyl-1-pyrroline, and 2-methylfuran are selected in the range of 1:1 to 10. 12 : 1 , preferably in the range of 1 : 1 to 10 9 : 1 , preferably in the range of 10 : 1 to 10 7: 1, even more preferred in the range of 100 : 1 to 10 6 : 1, even more preferred in the range of 1000 : 1 to 10 5 : 1, even more preferred in the range of 5000 : 1 to 10 4 : 1.

[0294] The at least one coconut flavoring substance AKOKO in the mixture M* is preferably selected from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran.

[0295] The at least one coconut flavoring substance AKOKO in the mixture M* is preferably from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran.

[0296] The at least one coconut flavoring substance AKOKO in the mixture M* is preferably from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, 1-propanol,

[0297] 2-Methyl-1-propanol, 1-Butanol, 1-Hexanol, 1-Heptanol, Ethyl acetate, Methyl octanoate, Ethyl octanoate, Acetaldehyde, Isovaleraldehyde, 2,3-Butanedione, Acetoin, 2-AP, 2-Methylfuran selected.

[0298] The at least one coconut flavoring substance AKOKO in the mixture M* is preferably from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, 1-propanol,

[0299] 2-Methyl-1-propanol, 1-Butanol, 1-Hexanol, 1-Heptanol, Ethyl acetate, Methyl octanoate, Ethyl octanoate, Isovaleraldehyde, 2,3-Butanedione, Acetoin, 2-AP, 2-Methylfuran selected.

[0300] The at least one coconut flavouring substance AKOKO in the mixture M* is preferably selected from the group consisting of A-Octalactone, A-Decalactone, A-Undecalactone, 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin, 1-Nonanal.

[0301] In a preferred embodiment, the mixture M* comprises at least one, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably all six coconut flavorings AKOKO selected from group 202400161 Foreign Filing 25

[0302] consisting of 1-octanol, 2-AP, 2,3-butanedione, ethyl acetate, acetoin, 1-nonanal, wherein more preferably at least 1-octanol is included.

[0303] In a more preferred embodiment, the mixture M* comprises A-Octalactone, A-Decalactone, A-Undecalactone, 1-Octanol, 2-AP, 2,3-Butanedione, Ethyl acetate, Acetoin and 1-Nonanal.

[0304] In a more preferred embodiment, the mixture M* comprises octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole,

[0305] A-Octalactone, A-Decalactone, A-Undecalactone, 1-Propanol, 2-Methyl-1-propanol, 1-Butanol, 1-Hexanol, 1-Heptanol, Ethyl acetate, Methyl octanoate, Ethyl octanoate, Isovaleraldehyde, 2,3-Butanedione, Acetoin, 2-AP, 2-Methylfuran, and more preferably additionally Acetaldehyde, and more preferably additionally Acetaldehyde and Ethanol.

[0306] In one embodiment, the total concentration of all coconut flavoring substances AKOKO in the mixture M* is in the range of 0.01 ppt to 1 wt%, based on the total weight of the mixture M*. More preferably, the total concentration of all coconut flavoring substances AKOKO in the mixture M* is in the range of 1 ppt to 100 ppm, more preferably in the range of 250 ppt to 5 ppm, more preferably in the range of 500 ppt to 1 ppm, more preferably in the range of 1 ppb to 100 ppb, and more preferably in the range of 10 ppb to 50 ppb, in each case based on the total weight of the mixture M*.

[0307] It is also preferred that in embodiments in which the mixture M* comprises the respective coconut flavoring AKOKO, the proportion of the respective coconut flavoring AKOKO, based on the total weight of the mixture M*, lies in the following preferred ranges:

[0308] Ethanol: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0309] 1-Propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0310] 2-Methyl-1-propanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0311] 1-Butanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0312] 1-Hexanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0313] 1-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0314] 2-Heptanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0315] 1-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0316] 2-Octanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0317] 2-Nonanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0318] 2-Undecanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0319] 2-Phenylethanol: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0320] Ethyl acetate: 100 ppt to 1000 ppb, preferably 1 ppb to 100 ppb;

[0321] Methylhexanoate (= caproic acid methyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0322] Ethylhexanoate (= caproic acid ethyl ester): 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0323] Methyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0324] Ethyl octanoate: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb; 202400161 Foreign Filing 26

[0325] Ethyl caprylic acid: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0326] A-Octalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0327] A-Decalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0328] A-Undecalactone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0329] Acetaldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0330] Isovaleraldehyde: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0331] Octanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0332] 1 -Nonanal: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0333] 2-Nonanone: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0334] 2-Undecanon: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0335] 2,3-Butanedione: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0336] Acetoin: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0337] 2-AP: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0338] 2-Methylfuran: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb;

[0339] Benzothiazole: 1 ppt to 100 ppb, preferably 10 ppt to 10 ppb.

[0340] The preferred total content of all coconut flavoring substances is AKOKO, selected from the group consisting of octanal, 2-heptanol, 1-hexanol, 1-heptanol, 1-nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran. Benzothiazole in the mixture M* in the range of 250 ppt to 5 ppm, preferably 500 ppt to 1 ppm, more preferably 1 ppb to 100 ppb, more preferably 10 ppb to 50 ppb, each based on the total weight of the mixture M*.

[0341] The mixture M* according to the second aspect of the invention comprises at least one compound of structural formula (I):

[0342]

[0343] wherein R is a saturated or unsaturated alkyl group with 3 to 24 carbon atoms, in particular a saturated or unsaturated alkyl group with 5 to 19 carbon atoms, preferably a saturated or unsaturated alkyl group with 5 to 18 carbon atoms, more preferably a saturated or unsaturated alkyl group with 10 to 17 carbon atoms, even more preferably a saturated alkyl group with 11 carbon atoms, wherein it is most preferably an unbranched alkyl group with 11 carbon atoms.

[0344] In a preferred embodiment, the residue RC(=O)- is selected from the fatty acid acyl residues of the following acids: caproic acid (R = n-pentyl), caprylic acid (R = n-heptyl), capric acid (R = n-nonyl), 202400161 Foreign Filing 27

[0345] Lauric acid (R = n-undecyl), myristic acid (R = n-tridecyl), palmitic acid (R = n-pentadecyl), stearic acid (R = n-heptadecyl), oleic acid, linoleic acid, linolenic acid, arachidic acid (R = n-nonadecyl), gadoleic acid. The residue RC(=O)-, the fatty acid acyl group of lauric acid, is particularly favored.

[0346] The pH value of the mixture M* is preferably in the range of 3 to 9, more preferably in the range of 4 to 8, more preferably in the range of 4.5 to 7.5, even more preferably in the range of 5.0 to 7.0, even more preferably in the range of 5.5 to 6.5, most preferably at 6.0 (each measured at 25 °C).

[0347] In the preferred embodiment, in which the mixture M* according to the second aspect of the invention is obtained by the method according to the first aspect of the invention, it is even more preferred that the content of the respective coconut flavoring agent AKOKO, which is included in the mixture M* obtained in step c. (based on the total weight of the mixture M*), is at least 1%, preferably at least 10%, preferably at least 51% lower than the content of the same coconut flavoring agent AKOKO, which was included in the mixture M used in step a. (based on the total weight of the mixture M used in step a.).

[0348] The mixture M* is characterized by the fact that the glucolipid neutralizes the odor of the coconut aroma particularly well. In a preferred embodiment, the mixture also includes a perfume. This perfume is specifically not a coconut aroma and is distinct from the coconut aroma substance AKOKO.

[0349] Depending on the area of ​​application, further additives commonly used in cleaning agents, detergents or personal care products may be added to the mixture M*, for example additives selected from enzymes, biopolymers, various surfactants of glucolipids (e.g. biosurfactants such as rhamnolipids, sophorolipids or derivatives thereof, such as those described in EP 3 034613 A1 and EP 4 317448 A1), dyes, viscosity regulators, defoamers, preservatives, organic solvents, polymers, wherein the polymers preferably do not contain siloxane.

[0350] Use of mixture M*

[0351] Finally, in a third aspect, the present invention also relates to the use of at least one glucolipid G for neutralizing coconut flavor, wherein the at least one glucolipid G is preferably used in a mixture M* according to the second aspect of the invention.

[0352] In the context of the invention, “neutralizing coconut aroma” means masking the coconut aroma caused by the at least one coconut aroma substance AKOKO, in particular masking the coconut aroma for the human nose.

[0353] “Neutralization of coconut aroma” within the meaning of the invention means in particular that the coconut odor caused by the at least one coconut aroma substance AKOKO is no longer perceptible to the human nose in the absence of the at least one glucolipid G in a given composition X202400161 Foreign Filing 28

[0354] is perceptible, but less strongly or no longer, preferably no longer, perceptible in composition XG. Composition X and composition XG differ only in that composition XG additionally contains at least one glucolipid G.

[0355] Neutralization can be determined by olfactory analysis of the respective composition X or XG, e.g. by an odor test.

[0356] Preferably, in accordance with the invention, the following odor test is performed to determine the "neutralization of coconut aroma":

[0357] A composition X containing at least one coconut flavoring agent (AKOKO) is evaluated by a group of eight test subjects. For this purpose, 100 g of formulation X are placed in a 400 g beaker and left to stand for 30 minutes at approximately 25 °C. The eight test subjects then smell the formulation X, assess the coconut scent, and assign a rating between 1 ("smells most neutral") and 3 ("smells worst"). The average of these eight ratings is abbreviated as "nx".

[0358] Then, a specific amount of a substance Y to be tested, or a mixture MY of substances to be tested, e.g., at least one glucolipid G, is added to composition X, resulting in "composition XY". The same eight test subjects then smell composition XY again, assess the coconut scent, and assign a rating between 1 ("smells most neutral") and 3 ("smells worst"). The average of these eight ratings is abbreviated as the grade "AXY".

[0359] If nxY < nx, preferably nxY at least 0.1, more preferably at least 0.2, even more preferably at least 0.5, even more preferably at least 0.9, is smaller than nx, then, in accordance with the invention, a neutralization of coconut aroma by the substance Y or mixture MY is present.

[0360] The at least one glucolipid G used according to the third aspect of the invention is in particular a compound of the following general structural formula (III) or (V), preferably of the general structural formula (III), more preferably of the general structural formula (IV):

[0361]

[0362] In structural formulas (III) and (IV) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1.202400161 Foreign Filing 29

[0363] The remains R 1GL and R 2GL are the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 7 to 15, and even more preferably 7 carbon atoms.

[0364] where the remainders R 1GL and R 2GL Preferably selected independently of one another from the group consisting of

[0365] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 7 to 15, more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0366] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 7 to 15 carbon atoms, or even more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups.

[0367] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CFhjoCHs), where o = 1 to 23, preferably 4 to 12,

[0368] where the remainders R 1GL and R 2GL even more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CFhjoCHs, where o = 4 to 8,

[0369] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CFhjoCHs are, where o = 4 to 8, preferably 4 to 6, is.

[0370] R are the most preferred 1GL and R 2GL n-heptyl each.

[0371] The serpentine bond in structural formula (III) means that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring.

[0372] Alkyl groups can be branched or unbranched, and are preferably unbranched.

[0373] Alkenyl residues can be branched or unbranched, and are preferably unbranched.

[0374] Preferred alkenyl groups have one to three double bonds, preferably one double bond.

[0375] In embodiments in which compounds of structural formulas (III) or (IV) have more than one residue R 2GL These residues can exhibit R 2GLbe the same or different.

[0376] In a particular embodiment, the amount is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, and even more preferably 25 wt.% to

[0377] 65 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C10, where “wt.%” (= weight %; content in percent of the total weight) refers to the total weight of all glucolipids used according to the third aspect of the invention. 202400161 Foreign Filing 30

[0378] In a particular embodiment, 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C8C10, wherein “wt.%” refers to the total weight of all glucolipids used according to the third aspect of the invention.

[0379] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, more preferably 5 wt.% to 15 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C12:1, wherein “wt.%” refers to the total weight of all glucolipids used according to the third aspect of the invention.

[0380] In another particular embodiment, 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, more preferably 3 wt.% to 12 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C12, wherein “wt.%” refers to the total weight of all glucolipids used according to the third aspect of the invention.

[0381] In a further particular embodiment (abbreviated “elaboration Q**”), 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C10.

[0382] In a more preferred embodiment of embodiment Q**, the

[0383] at 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, even more preferably 10 wt.% to 70 wt.%, even more preferably 25 wt.% to 65 wt.%, even more preferably 35 wt.% to 65 wt.%, even more preferably 50 wt.% to 65 wt.% of the glucolipids used according to the third aspect of the invention to be glucolipids of the structure GL-C10C10, and

[0384] at 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids used according to the third aspect of the invention to be glucolipids of structure GL-C8C10.

[0385] In embodiment Q**, it is even more preferred that it be

[0386] where 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C10, and where 1 wt.% to 30 wt.%, preferably 5 wt.% to 25 wt.%, more preferably 10 wt.% to 20 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C8C10, and

[0387] where 0.5 wt.% to 20 wt.%, preferably 3 wt.% to 17 wt.%, more preferably 5 wt.% to 15 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C12:1, and 202400161 Foreign Filing 31

[0388] where 0.5 wt.% to 20 wt.%, preferably 2 wt.% to 15 wt.%, even more preferably 3 wt.% to 12 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of the structure GL-C10C12.

[0389] Optionally, the glucolipids in the mixture M* according to embodiment Q** also comprise glucolipids of structure GL-C10, wherein preferably 0 wt.% to 5 wt.%, more preferably 0.01 wt.% to 4 wt.%, and even more preferably 0.1 wt.% to 3 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of structure GL-C10.

[0390] In embodiment Q**, “wt%” refers to the total weight of all glucolipids used according to the third aspect of the invention.

[0391] In another preferred embodiment, the

[0392] at 10 wt.% to 70 wt.%, preferably 25 wt.% to 65 wt.%, even more preferably

[0393] 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of structure GL-C10C10, and 10 wt.% to 20 wt.% of the glucolipids used according to the third aspect of the invention are glucolipids of structure GL-C8C10,

[0394] 5 wt.% to 15 wt.% of the glucolipids used according to the third aspect of the invention to form glucolipids of the structure GL-C10C12:1,

[0395] 3 wt.% to 12 wt.% of the glucolipids used according to the third aspect of the invention to form glucolipids of structure GL-C10C12,

[0396] where “wt%” refers to the total weight of all glucolipids used according to the third aspect of the invention.

[0397] Compounds (so-called “di-glucolipids”) of the general structural formula (V) in the context of use according to the third aspect of the invention are as follows:

[0398]

[0399] In the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1.202400161 Foreign Filing 32

[0400] The following applies to the structural formula (V):

[0401] The remains R 1GL and R 2GL are the same or different and each comprises an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms,

[0402] where the remainders R 1GL and R 2GLPreferably selected independently of one another from the group consisting of

[0403] optionally substituted alkyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 7 to 12, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkyl groups are preferred substituted alkyl groups,

[0404] optionally substituted alkenyl groups with 2 to 24, preferably 5 to 20, more preferably 5 to 15, even more preferably 5 to 12 carbon atoms, even more preferably 5 to 9, even more preferably 7 carbon atoms, wherein hydroxy-substituted alkenyl groups are preferred substituted alkenyl groups,

[0405] where the remainders R 1GL and R 2GL Preferably selected independently from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl, tridecenyl and -(CFhjoCHs), where o = 1 to 23, preferably 4 to 12,

[0406] where the remainders R 1GL and R 2GL even more preferably selected independently from the group consisting of heptenyl, nonenyl, and -(CFhjoCHs, where o = 4 to 8,

[0407] where the remainders R 1GL and R 2GL even more preferably independent of each other -(CFhjoCHs are, where o = 4 to 8, preferably 4 to 6, is.

[0408] R are the most preferred 1GL and R 2GL n-heptyl each.

[0409] One of the remnants R G2 , R G3 , R G4 and R G6 , preferably R G4 , is a residue of the general structural formula (T), and the three remaining residues are R G2 , R G3 , R G4 and R G6 Each of these are hydrogen.

[0410] In the general structural formula (T), one of T G1 , T G2 , T G3 , T G4 and T G6 , preferably T G1, a direct connection to the structure (V), while the other four are from T G1 , T G2 , T G3 , T G4 and T G6 each are hydroxy, wherein it is preferred that T G1 a direct connection to the structure (V), while the T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

[0411] The twisted bond in structural formulas (V) and (T) indicates that the respective residue is in an axial or equatorial position, preferably an equatorial position, relative to the sugar ring. 202400161 Foreign Filing 33

[0412] In embodiments in which compounds of structural formula (V) have more than one residue R 2GL These residues can exhibit R 2GL be the same or different.

[0413] Preferably, the coconut aroma is produced by at least one coconut aroma compound AKOKO, preferably at least two coconut aroma compounds AKOKO, wherein the coconut aroma compound AKOKO is from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde. 2,3-Butanedione, Acetoin, 2-Acetyl-1-pyrroline, 2-Methylfuran has been selected.

[0414] The at least one glucolipid G is preferably used according to the third aspect of the invention to neutralize coconut flavor in the inventive mixture M* according to the second aspect of the invention.

[0415] pH values ​​are measured at 25 °C within the scope of the present invention, unless otherwise specified.

[0416] The following examples describe the present invention by way of example, without limiting the invention, the scope of which is evident from the entire description and the claims, to the embodiments mentioned in the examples. 202400161 Foreign Filing 34

[0417] Example 1: Extraction of coconut oil from coconuts

[0418] Coconut oil is isolated from coconuts as described by Lin & Wilkins.

[0419] To produce coconut oil, the flesh is scraped from a coconut, shredded, and mixed with water in a 1:1 (w / v) ratio. The mixture is then squeezed in a kitchen towel to remove the coconut milk. The resulting coconut fat (also known as "coconut oil") is processed further as described in Example 2. Beforehand, the concentration of the coconut aroma compounds (AKOKO) in the coconut fat, which are responsible for the characteristic odor of coconut oil, is determined. This is done as follows:

[0420] 150 g of the crushed and squeezed fruit pulp are finely ground with water in a 1:5 (w / v) ratio. The resulting cloudy mixture is transferred to a 5-liter flask in a water bath. The flask is connected to a rotary evaporator with a Liebig condenser and a Friedrich condenser. The distillate is collected in an ice bath-cooled receiver.

[0421] At a water bath temperature of 97 °C and a vacuum of 50 mbar, approximately 500 ml of distillate are collected.

[0422] The aroma compounds are extracted from this distillate using CS2 and analyzed by GC-MS.

[0423] The following flavor compounds can be detected, with the content of each flavor compound (calculated back to the pulp) ranging from 1 ppt to 100 ppt and the total content of all flavor compounds (calculated back to the pulp) ranging from 50 ppt to 1000 ppt:

[0424] Octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, caproic acid ethyl ester, capric acid ethyl ester, caproic acid methyl ester, 2-undecanol, 2-phenylethanol, benzothiazole, A-octalactone, A-decalactone, A-undecalactone, ethanol, 1-propanol, 2-methyl-1 -propanol, 1 -butanol, 1-hexanol, 1 -heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran.202400161 Foreign Filing 35

[0425] Example 2: Production of the amidoamine of structural formula (II) from the triglyceride

[0426] The coconut oil obtained in Example 1 is reacted with 3-aminopropyldimethylamine (“DMAPA”) as follows:

[0427] In a 500 ml stirred tank with reflux condenser and nitrogen inlet, 230 g of the coconut oil, wrung out according to Example 1, are heated to 110 °C to remove the remaining water. The tank is then inerted with nitrogen for 10 minutes. Optionally, para-toluenesulfonic acid or formic acid can be added as a catalyst.

[0428] Subsequently, 180 ml of DMAPA are added while stirring, and the reaction mixture is heated to 165 °C. Stirring continues for 5 hours, and excess DMAPA is then distilled off.

[0429] Example 3: Production of the amidoamine of structural formula (II) from the fatty acid

[0430] The coconut oil obtained in Example 1 is first saponified and then reacted with DMAPA as follows: In a 500 ml beaker, 230 g of the coconut oil extracted according to Example 1 are saponified with NaOH by dissolving 30 g of NaOH in 30 g of water and adding the resulting basic solution to the coconut oil. The mixture is then stirred for 15 minutes at 80 °C.

[0431] The resulting mixture is transferred to a 500 ml stirring apparatus with a reflux condenser and nitrogen inlet and heated to 110 °C to remove the remaining water. It is then inerted with nitrogen for 10 minutes.

[0432] Subsequently, 180 ml of DMAPA are added while stirring, and the reaction mixture is heated to 165 °C. Stirring continues for 5 hours, and excess DMAPA (down to < 0.1 wt% DMAPA based on the reaction mixture) is then distilled off.

[0433] Example 4: Implementation with SMCA

[0434] 130 g of 98% sodium monochloroacetate are placed in a reaction flask with 500 ml of water, heated to approximately 90 °C, and then the mixture obtained in Examples 2 and 3 is added. The pH is maintained at pH 8 to pH 9 by adding NaOH. The mixture is stirred for 8 hours and then allowed to cool.

[0435] The product has a coconut-like smell.

[0436] The following flavorings can be detected in the product by analyzing a portion of the raw product as described in Example 1. The concentration of each flavoring (based on the weight of the product) ranges from 1 ppt to 100 ppt, and the total concentration of all the following flavorings (based on the weight of the product) ranges from 50 ppt to 1000 ppt: 202400161 Foreign Filing 36

[0437] Octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, caproic acid ethyl ester, capric acid ethyl ester, caproic acid methyl ester, 2-undecanol, 2-phenylethanol, benzothiazole, A-octalactone, A-decalactone, A-undecalactone, ethanol, 1-propanol, 2-methyl-1 -propanol, 1-butanol, 1-hexanol, 1 -heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-AP, 2-methylfuran.

[0438] The following substances have a significantly lower content than in the starting mixture, which is attributed to ester hydrolysis during the process: ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, A-Octalactone, A-Decalactone, A-Undecalactone, methyl octanoate, ethyl octanoate.

[0439] Example 5: Addition of glucolipid

[0440] The following mixtures are produced using the formulations:

[0441] 4.5 g of the CAPB mixture obtained in Example 4 are mixed with 1 g NaCI, 0.3 g phenoxyethanol, 0.1 g NaOH and

[0442] - 10 g Di-rhamnolipid (“REWOFERM RL 100” from Evonik Industries AG); mixture C1, not according to the invention;

[0443] - 10 g mono-rhamnolipid (“REWOFERM RL 300” from Evonik Industries AG); mixture C2, not according to the invention;

[0444] - 10 g SLES [sodium dodecyl poly(oxyethylene) sulfate]; mixture C3, not according to the invention;

[0445] - 10 g glucolipid* (obtained as described in Examples 1 to 3 of WO 2019 / 154970 A1 and used as a 50 wt% solution); mixture 11, according to the invention;

[0446] The mixture was then diluted to 100 g with distilled water. The pH of each mixture was approximately 6.

[0447] * The composition of the mixture of glucolipids obtained in examples 1 to 3 of WO 2019 / 154970 A1 is as follows:

[0448] GL-C10C10: 63.7%

[0449] GL-C8C10: 15.5%

[0450] GL-C10C12:1: 7.9 %,

[0451] GL-C10C12: 6.6%

[0452] GL-C8C8: 1.8%

[0453] GL-C10C10:1: 1.3 %,

[0454] GL-C12C12:1: 1.1 %,

[0455] GL-C12C12: 0.8%

[0456] GL-C10: 1.3%.

[0457] The percentage values ​​refer to the weight fraction of the respective glucolipid, relative to the total weight of all glucolipids in the mixture. All glucolipids therefore correspond to 202400161 Foreign Filing 37

[0458] Structural formula (III) in which the residues R 1GL and R 2GL These are alkyl groups with 5 to 9 carbon atoms, which may be monounsaturated. The main representative is therefore GL-C10C10.

[0459] The smell of the formulations was evaluated by a group of eight experts.

[0460] For this purpose, 100 g of the freshly prepared mixture was placed in a 400 g beaker and left to stand for 30 minutes at approximately 25 °C. The test subjects then smelled the respective formulation, assessed the smell, and assigned a rating between 1 ("smelled most neutral") and 3 ("smelled worst").

[0461] The average results were as follows:

[0462] Mixture 11: Grade 1.0 ("neutral, good smell");

[0463] Mixture C1: Grade 2.5 ("Smell of coconut");

[0464] Mixture C2: Grade 1.9 ("Smell of coconut, but fresher than C1");

[0465] Mixture C3: Grade 2.0. ("chemical smell of soap, pungent").

[0466] It was thus surprisingly found that the addition of glucolipid gave the best smell and most effectively neutralized the coconut note.

[0467] It is also confirmed that glucolipids G exhibit improved foaming properties in the inventive mixtures M*. Furthermore, they also ensure a softer hand feel in the inventive mixtures M*. 202400161 Foreign Filing 38

[0468] Other inventive and non-inventive mixtures:

[0469] Glucolipid (“GL”) is obtained as described in Examples 1 to 3 of WO 2019 / 154970 A1. It is used as a 50 wt% solution.

[0470] CAPB is obtained as described in Example 4.

[0471] SLES [= sodium dodecyl poly(oxyethylene) sulfate; CAS No.: 15826-16-1].

[0472] Table 1 (not according to the invention)

[0473]

[0474] Table 2 (according to the invention)

[0475]

Claims

202400161 Foreign Filing Claims 1. Method for producing a mixture M* comprising at least one glucolipid, at least one coconut flavouring AKOKO and at least one compound of structural formula (I): where R is a saturated or unsaturated alkyl group with 3 to 24 carbon atoms, comprehensively the following steps: a. Implementation of a mixture M encompassing i. at least one triglyceride of structural formula (III) and / or a compound of formula RCOOR 1 with R' = H, Methyl, where the residues R in structural formula (III) can be the same or different, ii. at least one coconut flavouring AKOKO, preferably at least two coconut flavourings AKOKO, with 3-aminopropyldimethylamine, whereby a raw product RP1 comprising at least one compound of structural formula (II) and at least one coconut flavoring substance AKOKO is obtained: b. Reaction of at least one compound of structural formula (II), obtained in step a. in crude product RP1, with sodium monochloroacetate, yielding a crude product RP2 comprising at least one coconut flavoring AKOKO and at least one compound of structural formula (I), 202400161 Foreign Filing 40 c. Addition of at least one glucolipid G to the crude product RP2, resulting in a mixture M* comprising at least one glucolipid, at least one coconut flavouring AKOKO and at least one compound of structural formula (I).

2. Method according to claim 1, wherein the glucolipid G is a compound of the general structural formula (III) or (V), preferably of the general structural formula (III): where in the structural formula (III) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GL are the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, where in the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GL are the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, and wherein in the structural formula (V) one of the residues R G2 , R G3 , R G4 and R G6 one residue of the general structural formula (T) is, and the three remaining residues are RG2 , R G3 , R G4 and R G6 each are hydrogen, 202400161 Foreign Filing 41 and where in the general structural formula (T) one of T G1 , T G2 , T G3 , T G4 and T G6 , preferably T G1 , a direct connection to the structure (V), while the other four are from T G1 , T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

3. The method according to claim 2, wherein the concentration is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 50 wt.% to 65 wt.% of the glucolipids G used in step c. are glucolipids of the structure GL-C10C10, wherein "wt.%" refers in each case to the total weight of the glucolipids G used in step c.

4. Method according to any one of claims 1 to 3, wherein R is a saturated or unsaturated alkyl group having 5 to 19, preferably 5 to 18, carbon atoms.

5. The method of claim 4, wherein the residue RC(=O)- is selected from the fatty acid acyl residues of the following acids: caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid.

6. A method according to any one of claims 1 to 5, wherein the coconut flavoring agent AKOKO is composed of the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl 1-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-acetyl-1 -pyrroline, 2-methylfuran is selected.

7. Method according to any one of claims 1 to 6, wherein the total concentration of all coconut flavoring substances AKOKO in RP2 is in the range of 1 ppt to 1.1 wt%, based on the total weight of RP2.

8. Method according to any one of claims 1 to 7, wherein in step a. a mixture M comprising at least one triglyceride of structural formula (III) and at least one coconut flavouring substance AKOKO is used.

9. A method according to any one of claims 1 to 8, wherein the crude product RP1 obtained in step a. is used in the reaction according to step b. without further purification steps. 202400161 Foreign Filing 42 10. A method according to any one of claims 1 to 9, wherein in step c. such a quantity of glucolipid G is added that the proportion of all glucolipids G, based on the total weight of the mixture M* obtained in step c., is in the range of 0.01 wt.% to 30 wt.%, preferably in the range of 0.1 wt.% to 25 wt.%, more preferably in the range of 1 wt.% to 20 wt.%, more preferably in the range of 2 wt.% to 15 wt.%, more preferably in the range of 5 wt.% to 10 wt.%.

11. Method according to any one of claims 1 to 10, wherein the ratio of the mass of all glucolipids G used in step c., based on the mass of all coconut flavorings AKOKO comprising RP2, is in the range of 1 : 1 to 10 12 : 1, preferably in the range of 1:1 to 10 9 : 1 , preferably in the range of 10 : 1 to 10 7 : 1, even more preferred in the range of 100 : 1 to 10 6 : 1, even more preferred in the range of 1000 : 1 to 10 5 : 1, even more preferred in the range of 5000 : 1 to 10 4 : 1 lies.

12. Mixture M* comprising a. at least one glucolipid G, b. at least one coconut flavoring agent AKOKO, preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five, more preferably at least six, even more preferably at least nine, even more preferably at least twenty, even more preferably at least thirty coconut flavoring agents AKOKO, c. at least one compound of structural formula (I), wherein R is a saturated or unsaturated alkyl group with 3 to 24, in particular 5 to 19, preferably 5 to 18, carbon atoms, and wherein preferably the group RC(=O)- is selected from the fatty acid alkyl groups of the following acids: caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid.

13. Mixture M* according to claim 12, in which the at least one glucolipid G is a compound of the general structural formula (III) or (V), preferably of the general structural formula (III): 202400161 Foreign Filing 43 where in the structural formula (III) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GLare the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, where in the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GL are the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, and wherein in the structural formula (V) one of the residues R G2 , R G3 , R G4 and R G6 one residue of the general structural formula (T) is, and the three remaining residues are R G2 , R G3 , R G4 and R G6 each are hydrogen and where in the general structural formula (T) one of TG1 , T G2 , T G3 , T G4 and T G6 , preferably T G1 , a direct connection to the structure (V), while the other four are from T G1 , T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

14. Mixture M* according to claim 13, wherein the amount is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 202400161 Foreign Filing 44 50 wt.% to 65 wt.% of the glucolipids G in the mixture M* are glucolipids of the structure GL-C10C10, where “wt.%” refers to the total weight of all glucolipids G in the mixture M*.

15. Mixture M* according to any one of claims 12 to 14, wherein the coconut flavoring agent AKOKO is from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl 1-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-Acetyl-1-pyrroline, 2-methylfuran is selected.

16. Mixture M* according to any one of claims 12 to 15, wherein the total concentration of all coconut flavouring substances AKOKO in the mixture M* is in the range of 0.01 ppt to 1 wt%, based on the total weight of the mixture M*.

17. Mixture M* according to one of claims 12 to 16, further comprising at least one perfume different from the coconut flavouring substances AKOKO.

18. Mixture M* according to any one of claims 12 to 17, wherein the total weight of all glucolipids G in the mixture M*, based on the total weight of the mixture M*, is in the range of 0.01 wt.% to 30 wt.%, preferably in the range of 0.1 wt.% to 25 wt.%, more preferably in the range of 1 wt.% to 20 wt.%, more preferably in the range of 2 wt.% to 15 wt.%, more preferably in the range of 5 wt.% to 10 wt.%.

19. Mixture M* according to any one of claims 12 to 18, wherein the ratio of the mass of all glucolipids G comprising the mixture M*, based on the mass of all coconut flavouring substances AKOKO comprising the mixture M*, is in the range of 1 : 1 to 10 12 : 1, preferably in the range of 1:1 to 10 9 : 1 , preferably in the range of 10 : 1 to 10 7 : 1, even more preferred in the range of 100 : 1 to 10 6 : 1, even more preferred in the range of 1000 : 1 to 10 5 : 1, even more preferred in the range of 5000 : 1 to 104 : 1 , lies.

20. Use of at least one glucolipid G to neutralize coconut flavor.

21. Use according to claim 20, wherein the glucolipid G is a compound of the general structural formula (III) or (V), preferably of the general structural formula (III): 202400161 Foreign Filing 45 where in the structural formula (III) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GL are the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, where in the structural formula (V) mGL = 3, 2, 1 or 0, preferably 1 or 0, more preferably mGL = 1 , is, and the remains R 1GL and R 2GLare the same or different and each is an organic residue with 2 to 24 carbon atoms, preferably 5 to 20, more preferably 5 to 15, more preferably 5 to 12, more preferably 5 to 9, more preferably 7 carbon atoms, and wherein in the structural formula (V) one of the residues R G2 , R G3 , R G4 and R G6 one residue of the general structural formula (T) is, and the three remaining residues are R G2 , R G3 , R G4 and R G6 each are hydrogen and where in the general structural formula (T) one of T G1 , T G2 , T G3 , T G4 and T G6 , preferably T G1 , a direct connection to the structure (V), while the other four are from T G1 , T G2 , T G3 , T G4 and T G6 Each is a hydroxyl group.

22. Use according to claim 21, wherein the amount is 1 wt.% to 80 wt.%, preferably 5 wt.% to 75 wt.%, more preferably 10 wt.% to 70 wt.%, more preferably 25 wt.% to 65 wt.%, more preferably 35 wt.% to 65 wt.%, more preferably 202400161 Foreign Filing 46 50 wt.% to 65 wt.% of the glucolipids used are glucolipids of the structure GL-C10C10, and where “wt.%” refers to the total weight of the glucolipids used.

23. Use according to any one of claims 20 to 22, wherein the coconut flavor is produced by at least one coconut flavoring substance AKOKO, preferably at least two coconut flavoring substances AKOKO, wherein the coconut flavoring substance AKOKO is from the group consisting of octanal, 2-heptanol, 1-hexanol, nonanal, 2-nonanone, 2-octanol, 2-nonanol, 1-octanol, 2-undecanone, ethyl caproic acid ester, ethyl capric acid ester, methyl caproic acid ester, 2-undecanol, 2-phenylethanol, benzothiazole, α-octalactone, α-decalactone, α-undecalactone, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 1-hexanol, 1-heptanol, ethyl acetate, methyl octanoate, ethyl octanoate, Acetaldehyde, isovaleraldehyde, 2,3-butanedione, acetoin, 2-acetyl-1-pyrroline, 2-methylfuran is selected.

24. Use according to any one of claims 20 to 23, wherein the at least one glucolipid G is used in a mixture M* according to any one of claims 12 to 19.

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