Aqueous composition comprising 6-undecanol ester

Abstract

This invention relates to aqueous compositions comprising 6-undecaneol esters, methods for producing 6-undecaneol esters, and the use of 6-undecaneol esters in cosmetic applications.

Description

Technical Field

[0001] This invention relates to aqueous compositions comprising 6-undecaneol esters, methods for producing 6-undecaneol esters, and the use of 6-undecaneol esters in cosmetic applications. Background Technology

[0002] No-rinse cosmetic formulations (such as sunscreens) primarily consist of emulsions with both aqueous and oil phases. Various cosmetic oils are used in the oil phase. These can traditionally be, for example, petrochemical-based mineral oils or other low-cost mineral oil-based products. However, in more recent formulations, due to sustainability considerations, there is an attempt to avoid petrochemical sources of formulation components as much as possible. Therefore, fatty acid-fatty alcohol esters or vegetable and animal fats and waxes are frequently used. Suitable oils fall into the medium to heavy oil range and possess fairly typical application properties, such as a viscosity at room temperature in the range of 10-50 mPas, a surface tension in the range of 26-32 mN / m, and associated moderate to good spreading behavior and moderate to low polarity. In addition to the cleansing and nourishing effects that determine the intended application of such cosmetic formulations, emphasis is placed on various parameters such as the highest possible dermatological compatibility, good rerefatting properties, elegant appearance, ease of spreading, optimal sensory impression, and storage stability.

[0003] To provide solutions with further improved CO2 footprints and non-tropical origins, new solutions have been identified. One promising option is to generate cosmetic ingredients directly from CO2 as a starting material. This opens the door to a new level of sustainable ingredients in cosmetic products that match consumer demand for truly sustainable cosmetics.

[0004] The object of this invention is to provide a moisturizer for excellent cosmetic applications. Summary of the Invention

[0005] Surprisingly, 6-undecanoyl esters have been found to have excellent properties for cosmetic applications.

[0006] One advantage of the present invention is that compositions containing at least one 6-undecanoyl ester have excellent sensory properties on surfaces such as skin and hair.

[0007] Another advantage of the present invention is that the composition containing at least one 6-undecanoyl ester is almost colorless.

[0008] Another advantage of the present invention is that the composition containing at least one 6-undecanoyl ester has almost no odor.

[0009] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit very good solubility of the active substance.

[0010] Another advantage of the present invention is that the compositions containing at least one 6-undecanoyl ester exhibit very good spreadability on the skin.

[0011] Another advantage of the present invention is that the compositions containing at least one 6-undecanoyl ester have high hydrolytic stability, especially at low pH and at both high and low temperatures.

[0012] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit good moisturizing properties.

[0013] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit good wetting properties.

[0014] Another advantage of the present invention is that the composition containing at least one 6-undecanoyl ester is based on highly renewable or even fully renewable raw materials.

[0015] Another advantage of the present invention is that the composition containing at least one 6-undecanoyl ester can be carbon (CO2) neutral.

[0016] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit good solubility for organic UV filters.

[0017] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit favorable toxicological properties.

[0018] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit lower spreadability than similar lightweight emollients.

[0019] Another advantage of the present invention is that compositions containing at least one 6-undecanoate exhibit good pigment stability.

[0020] Another advantage of the present invention is that compositions containing at least one 6-undecanoyl ester exhibit good freeze stability.

[0021] This invention provides an aqueous composition containing at least one 6-undecaneol ester, said 6-undecaneol ester being selected from 6-undecaneol esters obtainable by esterification of undecane-6-ol with one selected from:

[0022] A) Monocarboxylic acids having 6-32, preferably 6-22, more preferably 8-22 carbon atoms, and

[0023] B) Polyfunctional carboxylic acids having 2-44, preferably 3-38, more preferably 4-18 carbon atoms, preferably tricarboxylic acids and dicarboxylic acids, more preferably dicarboxylic acids having 2-18, preferably 3-13, more preferably 4-11 carbon atoms.

[0024] The term "6-undecaneol ester" is used in the context of this invention as a synonym for "undecane-6-yl ester".

[0025] In the context of this invention, the term "aqueous" refers to a composition containing at least 2% by weight, preferably at least 10% by weight, more preferably at least 30% by weight of water, wherein the weight percentage refers to the total composition.

[0026] In the context of this invention, the term "polyfunctional carboxylic acid" should be understood to mean a carboxylic acid having more than one carboxyl group.

[0027] In conjunction with this invention, “pH” is defined as the value of the corresponding substance measured at 25°C using a pH electrode calibrated according to ISO 4319 (1977) after stirring for 5 minutes.

[0028] Unless otherwise stated, all percentages (%) given are mass percentages.

[0029] Any kind of monocarboxylic acid can be used in the context of this invention, such as saturated or unsaturated, straight or branched, substituted or unsubstituted monocarboxylic acids, such as hexanoic acid, cyclopentanecarboxylic acid, 2-methylvaleric acid, heptanoic acid, cyclohexanecarboxylic acid, octanoic acid, 2-ethylhexanoic acid, sorbic acid, isononanoic acid, 3,5,5-trimethylhexanoic acid, decanoic acid, nonanoic acid, 2-propylheptanoic acid, isodecanic acid, undecanoic acid, 11-undecenoic acid, 2-butyloctanoic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, ricinoleic acid, stearic acid, oleic acid, isostearic acid, 12-hydroxystearic acid, arachidic acid, or benzanoic acid.

[0030] The preferred aqueous compositions according to the invention are characterized in that the monocarboxylic acid is selected from fatty acids, preferably natural fatty acids. Natural fatty acids can be produced based on naturally occurring plant or animal oils, and preferably have 6-30 carbon atoms, especially 8-22 carbon atoms. Natural fatty acids are generally unbranched and consist of an even number of carbon atoms. Any double bonds have a cis configuration. Examples are: hexanoic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, phellandral acid, transoleic acid, arachidic acid, benzyl acid, erucic acid, codoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, and arachidonic acid.

[0031] A more preferred aqueous composition according to the present invention is characterized in that the monocarboxylic acid is selected from hydroxyacid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, 11-undecenoic acid, myristic acid, palmitic acid, palmitoleic acid, ricinoleic acid, stearic acid, 12-hydroxy-stearic acid, isostearic acid, oleic acid, and benzalkonium chloride.

[0032] Any kind of polyfunctional acid can be used in the context of this invention, such as dicarboxylic acids and tricarboxylic acids, dimer fatty acids as specified in EP1683781, oxalic acid, fumaric acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, malic acid, tartaric acid, malonic acid, maleic acid, citric acid, and aromatic acids (such as phthalic acid, isophthalic acid, or terephthalic acid).

[0033] The preferred aqueous composition according to the invention is characterized in that the polyfunctional carboxylic acid is selected from aliphatic straight-chain dicarboxylic acids, particularly from oxalic acid, malonic acid, propanedioic acid, succinic acid, maleic acid, tartaric acid, maleic acid, fumaric acid, sorbic acid, α-ketoglutaric acid, glutaric acid, adipic acid, pimelic acid, cork acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, dodecanedicarboxylic acid, and tridecanedicarboxylic acid.

[0034] The aqueous composition according to the present invention is preferably a formulation.

[0035] In the context of this invention, the term "formulation" should be understood to mean a composition containing at least one other component besides water and esters, according to its intended use, as will be apparent to those skilled in the art, since the formulation is capable of achieving its intended use. For example, pharmaceutical formulations obviously need to contain at least one therapeutically active ingredient that is considered a "pharmaceutical," while cosmetic formulations typically contain a cosmetically acceptable carrier.

[0036] The formulations according to the present invention can be, for example, pharmaceutical, dermatological, personal care, cosmetic, home care, professional skin care, and pet care formulations.

[0037] The aqueous composition according to the present invention is preferably a cosmetic formulation.

[0038] The preferred formulation according to the invention contains, in addition to water and esters, at least one other component selected from the following:

[0039] Moisturizer

[0040] Emulsifier,

[0041] Thickener / viscosity modifier / stabilizer / consistency enhancer

[0042] UV light protective filter

[0043] Antioxidants

[0044] Moisturizer

[0045] Solids and fillers

[0046] pigment,

[0047] Film-forming agent,

[0048] Pearlescent / Opaque additives

[0049] Deodorant and antiperspirant active ingredients,

[0050] Insect repellent,

[0051] Self-tanning agents,

[0052] spices,

[0053] preservative,

[0054] Propellant

[0055] Conditioner,

[0056] dye,

[0057] Cosmetic active ingredients

[0058] Nursing additives

[0059] Fat enrichment agent,

[0060] solvent,

[0061] The preferred ingredients include moisturizers, emollients, emulsifiers, stabilizers / thickness enhancers, fragrances, preservatives, UV photoprotective filters, pigments, and cosmetic active ingredients, with moisturizers, UV photoprotective filters, and pigments being the most preferred.

[0062] Substances that can be used as exemplary representatives of the various groups are known to those skilled in the art and can be found, for example, in German application DE 102008001788.4. This patent application is incorporated herein by reference and thus forms part of this disclosure.

[0063] For information on other optional components and their dosages, please refer in particular to relevant manuals known to those skilled in the art, such as K. Schrader, "Grundlagen und Rezepturen der Kosmetika [Fundamentals and principles of cosmetics]", 2nd edition, pp. 329-341, Hüthig Buch Verlag Heidelberg.

[0064] The specific amount of additives is determined by the intended use.

[0065] Typical guide formulations for the corresponding applications are known prior art and are contained in the manuals of manufacturers of, for example, specific basic materials and active ingredients. These existing formulations can generally be used without modification. However, if necessary, for adaptation and optimization purposes, the required modifications can be made uncomplicatedly through simple experiments.

[0066] Preferred humectants included in the formulations according to the invention are selected from glycerin, 1,2-propanediol, 1,3-propanediol, diglycerol, dipropylene glycol, xylitol, sorbitol, maltitol, 1,2-butanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, lactic acid, creatine, and urea.

[0067] The 6-undecanoyl ester contained in the composition according to the invention can be prepared according to methods known in the art.

[0068] Advantageously and therefore preferably, according to the invention, the 6-undecanoyl ester contained in the composition according to the invention is prepared by a method for preparing the 6-undecanoyl ester, comprising the following steps:

[0069] (a) Providing ethanol and / or lower alkanes or any salt thereof, and contacting the above substances with at least one microorganism capable of two-carbon chain elongation to produce hexanoic acid and / or its salts and / or its esters;

[0070] (b) Under suitable reaction conditions for the chemical ketation of hexanoic acid and / or its salts and / or its esters to 6-undecane, the hexanoic acid and / or its salts and / or its esters from (a) are contacted with at least one ketation catalyst.

[0071] (c) Contacting 6-undecaneone with at least one hydride metal catalyst for the catalytic hydrogenation of 6-undecaneone to 6-undecaneol;

[0072] (d) Esterifying 6-undecaneol with at least one substance selected from the following:

[0073] A) Providing an acyl donor selected from the following acids: monocarboxylic acids having 6-32, preferably 6-22, more preferably 8-22 carbon atoms, and

[0074] B) Provide an acyl donor selected from the following acids: polyfunctional carboxylic acids having 2-44, preferably 3-38, more preferably 4-18 carbon atoms, preferably tricarboxylic acids and dicarboxylic acids, more preferably dicarboxylic acids having 2-18, preferably 3-13, more preferably 4-11 carbon atoms.

[0075] As used herein, the term "lower alkanonic acid" refers to an alkanonic acid containing fewer than six carbon atoms. Examples of lower alkanonic acids are acetic acid (acetate), propionic acid (propionic ester), butyric acid (butyric ester), or valeric acid (valeric ester).

[0076] As used herein, the term "contact" refers to direct contact between microorganisms and ethanol and / or lower alkanes (e.g., acetates). In one instance, ethanol is the carbon source, and the contact in step (a) involves contacting ethanol with the microorganisms of step (a). The contact can be direct or indirect, and may include membranes that separate cells from ethanol, or situations where cells and ethanol can be held in two separate compartments.

[0077] The source of ethanol and / or lower alkanes or any salt thereof provided in step (a) of the method according to the invention may vary depending on availability.

[0078] For example, ethanol and / or lower alkanes or any salts thereof are fermentation products of syngas or any carbohydrates known in the art. In particular, carbon sources for the microbial production of ethanol and / or lower alkanes or any salts thereof may be selected from alcohols, aldehydes, glucose, sucrose, fructose, dextrose, lactose, xylose, pentose, polyols, hexoses, ethanol, and syngas. Mixtures of sources may be used as carbon sources.

[0079] Preferably, the carbon source is synthesis gas. The synthesis gas is preferably converted into ethanol and / or lower alkanes or any salts thereof by at least one acetic acid-producing microorganism.

[0080] Regarding the source of syngas containing carbon dioxide and / or carbon monoxide, those skilled in the art will understand that numerous possible sources exist for providing syngas containing CO and / or CO2 as a carbon source. Syngas or syngas sources can be derived, for example, from water or CO2 via steam reforming, partial oxidation, or electrochemical synthesis. It can be seen that, in practice, any gas or any mixture of gases capable of supplying sufficient carbon to the microorganisms can be used as the carbon source for the microbial production of ethanol and / or lower alkanes or any salts thereof, as described in this invention.

[0081] Typically, for the acetic acid-producing microorganisms of the present invention, the carbon source comprises at least 50% by weight, at least 70% by weight, and particularly at least 90% by weight of CO2 and / or CO, wherein the weight percentage relates to all carbon sources available to the cells according to any aspect of the present invention.

[0082] Examples of gaseous carbon sources include waste gases, such as syngas, flue gas, and refinery gas produced by yeast or clostridium fermentation. These waste gases are formed by the gasification of cellulose-containing materials or coal gasification. In one instance, these waste gases may not necessarily be produced as byproducts of other processes, but may be specifically produced for use in the mixed cultures of this invention.

[0083] According to any aspect of the invention, the carbon source provided in step (a) of the method according to the invention for the production of ethanol and / or lower alkanes or any salts thereof can be syngas. Syngas can be produced, for example, as a byproduct of coal gasification. Therefore, microorganisms according to any aspect of the invention can be able to transform waste materials into valuable resources.

[0084] In another instance, syngas can be a byproduct of the gasification of widely available, low-cost agricultural feedstocks.

[0085] There are many examples of feedstocks that can be converted into syngas, as almost all forms of plants can be used for this purpose. In particular, feedstocks are selected from perennial grasses (such as miscanthus), corn residues, processing wastes (such as sawdust), etc.

[0086] Syngas is typically obtained in the gasification apparatus of dry biomass, primarily through pyrolysis, partial oxidation, and steam reforming, with the main products being CO, H2, and CO2. Syngas can also be a product of CO2 electrolysis. Those skilled in the art will understand the appropriate conditions for performing CO2 electrolysis to produce syngas containing the desired amount of CO.

[0087] Typically, a portion of the syngas obtained from the gasification process is first treated to optimize product yields and avoid tar formation. Cracking of undesirable tar and CO in the syngas can be carried out using lime and / or dolomite.

[0088] The overall efficiency, ethanol and / or acetate production rate, and / or total carbon capture of the method of the present invention can depend on the stoichiometry of CO2, CO, and H2 in the continuous gas stream. The applied continuous gas stream can be a combination of CO2 and H2. Specifically, in the continuous gas stream, the concentration of CO2 can range from about 10-50%, particularly 3% by weight, and H2 will be between 44% and 84% by weight, particularly 64-66.04% by weight. In another example, the continuous gas stream may also contain an inert gas, such as N2, at a concentration of up to 50% by weight.

[0089] More specifically, a carbon source containing CO and / or CO2 contacts acetic acid-producing microorganisms in a continuous gas stream. Even more specifically, the continuous gas stream contains syngas. These gases can be supplied, for example, using nozzles opening to an aqueous medium, glass frit, membranes within pipes supplying gas to an aqueous medium, etc.

[0090] Those skilled in the art will understand that it may be necessary to monitor the composition and flow rate of the stream at relevant intervals. The composition of the stream can be controlled by changing the proportions of the component streams to achieve a target or desired composition. The composition and flow rate of the blended stream can be monitored by any means known in the art. In one example, the system is adapted to continuously monitor the flow rate and composition of at least two streams and combine them to produce a single blended underflow in a continuous gas stream with an optimal composition, as well as means for delivering the optimized underflow to a fermenter.

[0091] According to any aspect of the invention, a reducing agent (e.g., hydrogen) may be supplied together with a carbon source. Specifically, the hydrogen may be supplied when CO and / or CO2 are supplied and / or used. In one instance, the hydrogen is part of the syngas present according to any aspect of the invention. In another instance, additional hydrogen may be supplied when the hydrogen in the syngas is insufficient for the method of the invention.

[0092] As used herein, the term "acetogenic microorganism" refers to microorganisms capable of performing the Wood-Ljungdahl pathway and thus converting CO, CO2, and / or hydrogen into lower alkanes (e.g., acetates). These microorganisms include those whose wild-type does not possess the Wood-Ljungdahl pathway but acquire this trait through genetic modification. Such microorganisms include, but are not limited to, E. coli cells. These microorganisms may also be referred to as carbon monoxide-producing bacteria. Currently, 21 distinct genera of acetogenic bacteria are known in the art (Drake et al., 2006), and these may also include some Clostridium species (Drake & Kusel, 2005). These bacteria are capable of using carbon dioxide or carbon monoxide as a carbon source and hydrogen as an energy source (Wood, 1991). Furthermore, alcohols, aldehydes, carboxylic acids, and many hexoses can also be used as carbon sources (Drake et al., 2004). The reducing pathway leading to acetate formation is called the acetyl-CoA or Wood-Ljungdahl pathway.

[0093] Specifically, acetic acid-producing microorganisms can be selected from moist anaerobic acetic acid bacteria (Acetoanaerobium notera) (ATCC 35199), *Acetonema longum* (DSM 6540), *Acetobacterium carbinolicum* (DSM 2925), *Acetobacterium malicum* (DSM 4132), *Acetobacterium* species 446 (Morinaga et al., 1990, J. Biotechnol., Vol. 14, pp. 187-194), and *Acetobacterium wieringae* (DSM 4540). 1911), Acetobacterium woodii (DSM 1030), Alkalibaculumbacchi (DSM 22112), Archaeoglobusfulgidus (DSM 4304), Blautia producta (DSM 2950, ​​formerly Ruminococcus productus, formerly Peptostreptococcus productus)), Butyribacterium methylotrophicum (DSM 3468), Clostridium aceticum (DSM 1496), Clostridium autoethanogenum (DSM 10061, DSM 19630 and DSM 23693), Clostridium carboxidivorans (DSM 1911), Acetobacterium woodii (DSM 1030), Alkalibaculumbacchia (DSM 22112), Archaeoglobusfulgidus (DSM 4304), Blautia producta (DSM 2950, ​​formerly Ruminococcus productus, formerly Peptostreptococcus productus)), Butyribacterium methylotrophicum (DSM 3468), Clostridium aceticum (DSM 1496), Clostridium autoethanogenum (DSM 10061, DSM 19630 and DSM 23693), Clostridium carboxidivorans (DSM 1911), Acetobacterium woodii (DSM 1911), Alkalibaculumbacchia (DSM 1911), Archaeoglobusfulgidus (DSM 1911), Acetobacterium carboxidivorans (DSM 1911), Acetobacterium woodii (DSM 1911), Acetobacterium carboxidivorans (DSM 1911), Acetobacterium carboxidivorans (DSM 1911), Acetobact 15243), Clostridium coskatii (ATCC no.).PTA-10522), Clostridium drakei (ATCC BA-623), Clostridium formicoaceticum (DSM92), Clostridium glycolicum (DSM1288), Clostridium ljungdahlii (DSM13528), Clostridium ljungdahlii C-01 (ATCC 55988), Clostridium ljungdahlii ERI-2 (ATCC 55380), Clostridium ljungdahlii O-52 (ATCC 55989), Clostridium mayombei (DSM 6539), Clostridium methoxybenzovorans (DSM 12182), Clostridium lagusdales (DSM 12182). *Clostridium ragsdalei* (DSM 15248), *Clostridium scatologenes* (DSM 757), *Clostridium* species ATCC 29797 (Schmidt et al., 1986, Chem. Eng. Commun., Vol. 45, pp. 61-73), *Desulfotomaculum kuznetsovii* (DSM 6115), *Desulfotomaculum thermobezoicum subsp. thermosyntrophicum* (DSM 14055), *Eubacterium limosum* (DSM 20543), *Methanosarcina acetivorans* C2A C2A)(DSM2834), Moorella sp. HUC22-1 (Sakai et al., 2004, Biotechnol. Let.)Volume 29, pp. 1607-1612), *Moorellathermoacetica* (DSM 521, formerly *Clostridium thermoaceticum*), *Moorella thermoautotrophica* (DSM 1974), *Oxobacter pfennigii* (DSM 322), *Sporomusa aerivorans* (DSM 13326), *Sporomusaovata* (DSM 2662), *Sporomusa silvacetica* (DSM 10669), *Sporomusa sphaeroides* (DSM 2875), *Sporomusa termitida* (DSM 4440), and *Thermoanaerobacter kivui* (DSM 1607-1612). 2030, previously it was Acetogenium kivui (produced by Kaiwu).

[0094] More preferably, the carboxylated Clostridium strain ATCBAA-624 is used. Even more preferably, bacterial strains of carboxylated Clostridium labeled “P7” and “P11” are used, as described, for example, in US2007 / 0275447 and US2008 / 0057554.

[0095] Another particularly suitable bacterium is *Clostridium aerogenes*. Specifically, strains selected from *Clostridium aerogenes* PETC, *Clostridium aerogenes* ERI2, *Clostridium aerogenes* COL, and *Clostridium aerogenes* O-52 can be used to convert syngas into hexanoic acid via the corresponding C2-intermediates. These strains are described, for example, in WO98 / 00558, WO 00 / 68407, ATCC49587, ATCC 55988, and ATCC 55989.

[0096] Preferably, the production of hexanoic acid is derived from ethanol and / or lower alkanes or any salts thereof, which originate from syngas and involve the combined use of acetic acid-producing bacteria with microorganisms capable of carbon chain elongation. For example, *Clostridium jungdahl* can be used concurrently with *Clostridium kluyveri*. In another instance, a single acetic acid-producing cell may be capable of possessing the activities of both organisms. For example, the acetic acid-producing bacteria could be *C. carboxidivorans*, capable of both the Wood-Ljungdahl pathway and the carbon chain elongation pathway.

[0097] Preferably, the lower alkanic acid or any salt thereof provided in step (a) of the method according to the invention is selected from acetic acid and butyric acid.

[0098] Preferably, the ethanol and / or lower alkanes or any salt thereof provided in step (a) of the method according to the invention is ethanol in combination with at least one other carbon source selected from acetate, propionate, butanoate, and valerate. More preferably, the ethanol and / or lower alkanes or any salt thereof provided in step (a) of the method according to the invention is ethanol and acetate. Alternatively, preferably, the ethanol and / or lower alkanes or any salt thereof provided in step (a) of the method according to the invention is a combination of ethanol and butyric acid. However, it is also advantageous to use ethanol or acetate alone as the ethanol and / or lower alkanes or any salt thereof provided in step (a) of the method according to the invention.

[0099] The microorganisms in step (a) of the method according to the invention capable of carbon chain elongation to produce hexanoic acid and / or its salts and / or esters can be any organism capable of carbon chain elongation, as described in Jeon et al., Biotechnol Biofuels (2016) 9:129. The microorganisms present in step (a) of the invention may also include microorganisms whose wild-type form is not capable of carbon chain elongation but has acquired this trait through genetic modification. Preferably, the microorganisms in (a) are selected from Clostridium carboxylate and Clostridium coerulesii, with Clostridium coerulesii being the most preferred.

[0100] The microorganisms capable of carbon chain elongation to produce hexanoic acid and / or its salts and / or esters in step (a) of the method according to the invention can be cultured using any culture medium, substrate, condition, and method commonly known in the art for culturing bacteria. This enables the production of hexanoic acid and / or its salts and / or esters using biotechnological methods. Depending on the microorganisms used to produce hexanoic acid and / or its salts and / or esters, suitable growth media, pH, temperature, stirring rate, inoculation level, and / or aerobic, microaerobic, or anaerobic conditions can be varied. Those skilled in the art will understand that other conditions are necessary to carry out step (a) of the method according to the invention. In particular, the conditions in the vessel (e.g., a fermenter) during step (a) of the method according to the invention can be varied depending on the microorganisms used. Variations of conditions suitable for the optimal functioning of the microorganisms are within the knowledge of those skilled in the art.

[0101] Step (a) of the method according to the invention is preferably carried out in an aqueous medium with a pH between 5 and 8, more preferably between 5.5 and 8, and most preferably between 5.5 and 7. The pressure in step (a) of the method according to the invention is preferably between 1 and 10 bar. In step (a) of the method according to the invention, the microorganisms can be contacted at a temperature range of 20°C to 80°C. Preferably, the microorganisms are contacted at a temperature range of 35°C to about 42°C.

[0102] Preferably, for the growth of microorganisms and for the production of their hexanoic acid and / or its salts and / or esters, the aqueous medium contains any nutrients, components, and / or supplements suitable for the growth of microorganisms or suitable for promoting the production of their hexanoic acid and / or its salts and / or esters. In particular, the aqueous medium may contain at least one of the following: a carbon source, a nitrogen source (e.g., ammonium salts), yeast extract or peptone; minerals; salts; cofactors; buffers; vitamins; and any other components and / or extracts that can promote bacterial growth. The culture medium used must be suitable for the needs of the specific strain. Descriptions of various microbial culture media are given, for example, in the "Manual of Methods for General Bacteriology," such as the use of LB medium in the case of *Escherichia coli*, and the use of ATCC1754 medium in the case of *C. ljungdahlii*.

[0103] During step (a) of the method according to the invention, the microorganisms are incubated with a carbon source for a sufficient time to produce the desired product. For example, at least 1, 2, 4, 5, 10, or 20 hours.

[0104] It may be advantageous to purify hexanoic acid and / or its salts and / or its esters between steps (a) and (b) of the method according to the invention.

[0105] The purification step preferably includes extracting hexanoic acid and / or its salts and / or its esters from (a) using at least one extractant, said extractant preferably selected from alkyl-phosphine oxide and trialkylamine, more preferably the extractant comprising at least one alkyl-phosphine oxide and optionally at least one alkane comprising at least 12 carbon atoms, or at least one trialkylamine and at least one alkane comprising at least 12 carbon atoms;

[0106] At the end of the purification step including extraction, excess water can be removed from the aqueous medium, thus yielding an extract containing the extracted hexanoic acid and / or its salts and / or its esters. Specifically, at the end of the purification step including extraction, where hexanoic acid and / or its salts and / or its esters are extracted and removed, what remains may be a fermentation medium containing cells for the production of hexanoic acid and / or its salts and / or its esters, and these cells, together with the fermentation medium, can then be recycled for step (a).

[0107] Step (b) of the method according to the invention comprises contacting the hexanoic acid and / or its salt and / or its ester from (a) with at least one ketation catalyst under suitable reaction conditions for the chemical ketation of hexanoic acid and / or its salt and / or its ester to 6-undecane.

[0108] In step (b) of the method according to the invention, any metal oxide catalyst or mixture thereof may be used. Ketolation reacts hexanoic acid and / or its salt and / or its ester to a 6-undecanetone, wherein a water and a carbon dioxide are removed. Mechanisms potentially involving the ketation of hexanoic acid, wherein hexanoic anhydride ((CH3(CH2)4)COOCO(CH2)4CH3) can be formed, are disclosed at least in Woo, Y., Ind. Eng. Chem. Res. 2017, 56: 872-880. Ketolation of hexanoic acid in the presence of various metal oxide catalysts is also shown in Wang, SJPhys. Chem. C 2017, 121, 18030-18046.

[0109] The ketation catalyst used in step (b) of the method according to the invention is preferably a heterogeneous catalyst for the efficient production of 6-undecanetone from bio-produced hexanoic acid according to step (a). In particular, the ketation catalyst is preferably any metal oxide catalyst or mixture thereof selected from metal oxide catalysts or mixtures thereof, wherein the metal oxide catalyst is selected from heteropolyacids (H3PW). 12 O 40 Catalysts, including niobium oxide (Nb₂O₅) catalysts, titanium oxide (TiO₂) catalysts, cerium oxide (CeO₂) catalysts, zinc-chromium (Zn-Cr) mixed oxide catalysts, and manganese oxide (MnO₂) catalysts. x Catalysts, including lanthanum oxide (La₂O₃) catalysts, magnesium oxide (MgO) catalysts, iron oxides (FeO, FeO₂, Fe₂O₃, Fe₃O₄, Fe₄O₅, Fe₅O₆, Fe₅O₇), and silicon-aluminum (Si) catalysts. y Al z O) mixed oxide catalyst, alumina (Al2O3) catalyst and zirconium oxide (ZrO2) catalyst. MnO x In this context, 'x' can be 1, 2, or 4. Si y Al z In O, 'y' and 'z' can refer to any number, where the ratio z / y is any number between 0 and 1.

[0110] Exemplary ketation is carried out as disclosed in Pham TN, ACS Catal. 2013, 3:2456-2473, using a suitable heterogeneous hydride metal catalyst and suitable reaction conditions. The disclosed conditions can be varied depending on the catalyst used to efficiently obtain 6-undecanetone.

[0111] In yet another instance, based on the disclosure in Gliński, M et al., Polish J. Chem. 2004, 78:299-302, for the ketation of hexanoic acid to 6-undecanetone, M. Chem. 2004, 78:299-302, MnO2 and / or Al2O3 catalysts can be used.

[0112] In another example, Nb₂O₅ catalysts, such as those disclosed in US 6,265,618 B1, particularly those disclosed in Example 3, can be used for the ketation of hexanoic acid to 6-undecane. Those skilled in the art can identify suitable catalysts and conditions for the production of 6-undecane from hexanoic acid based on existing technology through simple trial and error. Other catalysts that can be used as ketation catalysts in step (b) of the method according to the invention are also disclosed in Orozco, LM et al., ChemSusChem, 2016, 9(17):2430-2442 and Orozco, LM et al., Green Chemistry, 2017, 19(6):1555-1569.

[0113] Metal oxide catalysts or mixtures thereof are preferably selected from heteropoly acids (H3PW). 12 O 40 Catalysts include titanium oxide (TiO2) catalysts, cerium oxide (CeO2) catalysts, zinc-chromium (Zn-Cr) mixed oxide catalysts, manganese oxide (MnO2) catalysts, lanthanum oxide (La2O3) catalysts, magnesium oxide (MgO) catalysts, iron oxides (FeO, FeO2, Fe2O3, Fe3O4, Fe4O5, Fe5O6, Fe5O7), silicon-aluminum (Si-Al) mixed oxide catalysts, and zirconium oxide (ZrO2) catalysts.

[0114] Preferably, the ketation catalyst in step (b) is a zirconia aerogel catalyst. It can be used for the ketation of hexanoic acid and / or its salts and / or its esters, as disclosed in Woo, Y., Ind. Eng. Chem. Res. 2017, 56:872-880. Lee, Y. et al. disclosed different ketation catalysts and their effectiveness in the ketation of hexanoic acid and / or its salts and / or its esters in Applied Catalysis A: General. 2015, 506:288-293. Those skilled in the art can readily use the methods described by Lee, Y. et al. to determine suitable ketation catalysts and / or conditions for the ketation of hexanoic acid and / or its salts and / or its esters.

[0115] Specifically, suitable reaction conditions for step (b) include reaction temperatures of 100°C to 500°C, 100°C to 450°C, 100°C to 400°C, 100°C to 350°C, 100°C to 300°C, 100°C to 250°C, 100°C to 200°C, 150°C to 500°C, 150°C to 450°C, 150°C to 400°C, 150°C to 350°C, and 150°C to 500°C. Temperatures range from ℃ to 300℃, 150℃ to 250℃, 150℃ to 200℃, 200℃ to 500℃, 200℃ to 450℃, 200℃ to 400℃, 200℃ to 350℃, 200℃ to 300℃, 200℃ to 250℃, 250℃ to 500℃, 250℃ to 450℃, 250℃ to 400℃, 250℃ to 350℃, 250℃ to 300℃, etc.

[0116] Preferably, step (b) of the method according to the invention is carried out at a temperature between 150°C and 350°C.

[0117] Preferably, the MgO / SiO2 catalyst is the ketation catalyst in step (b) of the method according to the invention, and step (b) is carried out at a temperature between 150°C and 350°C, preferably between 200°C and 350°C.

[0118] Step (c) of the method according to the invention provides contacting the 6-undecanene obtained in step (b) with at least one hydrogenating metal catalyst for the catalytic hydrogenation of 6-undecanene to 6-undecaneol.

[0119] 6-Undecaneol (C 11 H 24 O) is a secondary alcohol, which is the result of the catalytic hydrogenation of 6-undecaneone, by adding a hydrogen molecule to the carbon-oxygen double bond to finally obtain 6-undecaneol as the final product.

[0120] The hydrogenation metal catalyst used in the method according to the invention can be a homogeneous or heterogeneous catalyst. A homogeneous metal catalyst can be a metal complex known in the art.

[0121] Preferably, the hydride metal catalyst in step (c) of the method according to the invention is a heterogeneous catalyst. Some advantages of using a solid catalyst and a heterogeneous catalytic reaction include ease of catalyst and product separation, ease of recovery and catalyst recycling, and relatively mild operating conditions. There are also clear economic and environmental motivations for using heterogeneous catalysts.

[0122] Preferably, the hydride metal catalyst in step (c) of the method according to the invention is selected from ruthenium (Ru) catalyst, rhenium (Re) catalyst, nickel (Ni) catalyst, iron (Fe) catalyst, cobalt (Co) catalyst, palladium (Pd) catalyst and platinum (Pt) catalyst.

[0123] The hydride metal catalyst in step (c) of the method according to the invention is preferably selected from ruthenium (Ru) catalyst, rhenium (Re) catalyst, nickel (Ni) catalyst, iron (Fe) catalyst, cobalt (Co) catalyst and platinum (Pt) catalyst.

[0124] More preferably, the hydride metal catalyst in step (c) of the method according to the invention is selected from Ni catalysts, Pd catalysts, and Pt catalysts. In one example, the hydride metal catalyst used in step (c) of the method according to the invention is nickel nanoparticles, as described in Alonso, F. Tetrahedron, 2008, 64:1847-52. In another example, iron(II)PNP pincer complexes can be used as the hydride metal catalyst in step (c) of the method according to the invention, as disclosed in Gorgas, N., Organometallics, 2014, 33(23):6905-6914. In yet another embodiment, magnetite nanoparticles of ruthenium (Ru) catalyst, rhenium (Re) catalyst, nickel (Ni) catalyst, iron (Fe), cobalt (Co), palladium (Pd) catalyst or platinum (Pt) catalyst can be used as heterogeneous hydrogenation metal catalysts in step (c) of the method according to the invention, as described in Tariq Shah M. et al., ACS Applied Materials & Interfaces, 2015:7(12), 6480-9.

[0125] In yet another example, in step (c) of the method according to the invention, a copper-phosphine complex is used as a homogeneous hydrogenation metal catalyst, as disclosed in Chen, JX., Tetrahedron, 2000, 56: 2153-2166. In yet another example, in step (c) of the method according to the invention, a heterogeneous Pt catalyst, particularly a Pt / Al₂O₃ catalyst, as disclosed in Journal of Molecular Catalysis A: Chemical, 2014, 388-389: 116-122, can be used. ChemSusChem, 2017: 10(11), 2527-2533 also discloses various heterogeneous catalysts, such as Pt / C, Ru / C, and Pd / C, which can be used in combination with or without an acid catalyst for the hydrogenation of 6-undecanetone to 6-undecaneol. Based on the above, those skilled in the art can determine a suitable hydrogenation catalyst for the production of 6-undecaneol from 6-undecaneone in step (c) of the method according to the invention.

[0126] Technicians can easily identify suitable hydride metal catalysts and modify the conditions accordingly to efficiently produce 6-undecaneol from the hydrogenation of 6-undecaneone.

[0127] In step (d) of the method according to the invention, esterification of 6-undecaneol with at least one acyl donor is performed.

[0128] Acyl donors of any kind can be used for group A) and for group B); these can be, for example, carboxylic acids themselves, their anhydrides or carboxylic esters, such as methyl esters, ethyl esters and / or glycerides.

[0129] Typically, in step (d) of the method according to the invention, the acyl donors for group A) and group B) are preferably supplied with acyl groups contained in 6-undecanoyl esters, which are contained in the compositions according to the invention.

[0130] Preferably, according to the invention, the acyl donor of group A) is selected from triglycerides, especially natural fats and oils, more preferably from coconut oil, palm kernel oil, olive oil, palm oil, argan oil, castor oil, linseed oil, babassu oil, rapeseed oil, seaweed oil, sesame oil, soybean oil, avocado oil, jojoba oil, safflower oil, almond oil, cottonseed oil, shea butter, sunflower oil, guava oil, and oils having a high proportion of polyunsaturated fatty acids (PUFAs), preferably composed of these. Similarly, dehydrated sorbitol esters, monoglycerides, and diglycerides having the above-described chain length distribution and modification can also be preferred.

[0131] In step (d) of the method according to the invention, esterification can be carried out by classical esterification methods. Esterification can be carried out non-catalyzed, enzyme-catalyzed, acid-catalyzed, or base-catalyzed.

[0132] In step (d) of the method according to the invention, esterification can be enzyme-catalyzed esterification, which is the preferred type of esterification.

[0133] This can be done, for example, using at least one lipase.

[0134] Preferably, the lipase used in step (d) of the method according to the invention via enzyme-catalyzed esterification is a lipase that can be isolated from organisms in the fungal field, and those lipases have at least 60%, preferably at least 80%, more preferably at least 90%, and especially preferably at least 95%, 98% or 99% homology at the amino acid level with those lipases that can be isolated from organisms in the fungal field.

[0135] Enzymes homologous at the amino acid level to a reference sequence preferably possess at least 50%, and particularly at least 90%, of enzyme activity, in propyl lauryl units. The measured activity of carboxylate hydrolases in propyl lauryl units is measured at the optimal temperature for a given enzyme, where "optimal temperature" should be understood as the temperature at which the enzyme exhibits its highest activity. For example, for lipases A and B from *Candida antarctica*, accession number P41365, the optimal temperature is 60°C.

[0136] In the context of this invention, "amino acid level homology" should be understood herein and hereinafter as referring to "amino acid identity," which can be determined by known methods. Typically, a dedicated computer program with an algorithm tailored to specific requirements is used. A preferred method for determining identity initially generates the maximum alignment between the sequences to be compared. Computer programs for determining identity include, but are not limited to, the GCG package, including…

[0137] -GAP (Deveroy, J. et al., Nucleic Acid Research 12 (1984), p. 387, Genetics Computer Group University of Wisconsin, Medicine (WI), and

[0138] -BLASTP, BLASTN, and FASTA (Altschul, S. et al., Journal of Molecular Biology 215 (1990), pp. 403-410. The BLAST procedure can be obtained from the National Center for Biotechnology Information (NCBI) and from other sources (BLAST Handbook, Altschul, S. et al., NCBI NLM NIHBethesda ND 22894; Altschul, S. et al., as above).

[0139] Those skilled in the art will know that various computer programs can be used to calculate the similarity or identity between two nucleotide or amino acid sequences. For example, the percentage of identity between two amino acid sequences can be determined by, for instance, an algorithm developed by Needleman and Wunsch (J. Mol. Biol. (48): 444-453 (1970)), which is integrated into the GAP program in the GCG software package (available at http: / / www.gcg.com), using a Blossom 62 matrix or a PAM250 matrix with gap weights of 16, 14, 12, 10, 8, 6, or 4, and length weights of 1, 2, 3, 4, 5, or 6. Those skilled in the art will recognize that using different parameters will lead to slightly different results, but the percentage of identity between two amino acid sequences will not be significantly different overall. Typically, the Blossom 62 matrix uses the default settings (gap weight: 12, length weight: 1).

[0140] In the context of this invention, 60% identity according to the above algorithm refers to 60% homology. This also applies to higher levels of identity.

[0141] In step (d) of the method according to the invention, the lipase used for enzyme-catalyzed esterification is particularly preferred to be an enzyme selected from: lipase from *Thermomyces lanuginosus* (registration number O59952), lipases A and B from *Candida antarcticus* (registration number P41365), lipase from *Mucormiehei* (registration number P19515), lipase from *Humicola* sp. (registration number O59952), lipase from *Rhizomucorjavanicus* (registration number S32492), lipase from *Rhizopus oryzae* (registration number P61872), and lipases from *Candida* (registration numbers P20261, P32946, P32947, P3294, and P32949). The lipases are those derived from *Rhizopus niveus* (registration number P61871), *Penicillium camemberti* (registration number P25234), *Aspergillus niger* (registration numbers ABG73613, ABG73614, and ABG37906), and *Penicillium cyclopium* (registration number P61869), and each is at least 60%, preferably at least 80%, more preferably at least 90%, and especially preferably at least 95%, 98%, or 99% homologous at the amino acid level. For homology, refer to the definitions given above.

[0142] Commercial embodiments and the carboxylic acid ester hydrolysates used in step (d) of the method according to the invention via enzymatic esterification are the following commercial products: Lipozyme TLIM, Novozym 435, Lipozyme IM 20, lipase SP382, lipase SP525, lipase SP523 (all commercial products from Novozymes A / S, Bagsvaerd, Denmark), Chirazyme L2, Chirazyme L5, Chirazyme L8, Chirazyme L9 (all commercial products from Roche Molecular Biochemicals, Mannheim, Germany), CALB Immo Plus™ from Purolite, and lipase M "Amano", lipase F-AP 15 "Amano", lipase AY "Amano", lipase N "Amano", lipase R "Amano", lipase A "Amano", lipase D "Amano", lipase G "Amano" (all commercial products from Amano, Japan).

[0143] In step (d) of the method according to the invention, the enzyme-catalyzed esterification is preferably carried out at a reaction temperature between 20°C and 160°C, more preferably between 25°C and 130°C, and especially between 30°C and 90°C.

[0144] In step (d) of the method according to the invention, the enzyme-catalyzed esterification is preferably carried out at a pressure of less than 1 bar, more preferably less than 0.5 bar, and even more preferably less than 0.05 bar.

[0145] In an alternative preferred embodiment, in step (d) of the method according to the invention, the enzyme-catalyzed esterification is carried out at a pressure greater than 1 bar, preferably in the range of 2 to 10 bar. In this regard, it is preferable to provide an inert gas to the reaction mixture; these inert gases are preferably selected from nitrogen and argon, and preferably consist of nitrogen and argon.

[0146] In step (d) of the method according to the invention, the acid-catalyzed esterification can be carried out, for example, with Brønsted acids or Lewis acids. Examples are hydrochloric acid, sulfonic acids (e.g., methanesulfonic acid, p-toluenesulfonic acid, 10-camphorsulfonic acid), sulfuric acid, phosphoric acid, hypophosphoric acid, phosphorous acid, hypophosphoric acid, tin-(II) salts (e.g., tin oxide), zinc salts (e.g., zinc oxide or zinc acetylacetonate), or zirconium salts. Polymer-based / resin-based or supported catalysts, such as sulfonated polystyrene, can also be used. The above acids can also be used in combination.

[0147] In step (d) of the method according to the invention, the base-catalyzed esterification can be carried out, for example, with an alkali metal, an alkaline earth metal, or an ammonium salt (e.g., its respective hydroxide, oxide, phosphate, or carbonate). Furthermore, a basic salt of an amine, alcohol, or organic acid can be used as the base. In addition, the aforementioned bases can be used in combination.

[0148] In step (d) of the method according to the invention, a temperature of 30-260°C, preferably 100-200°C, is typically used in acid- or base-catalyzed esterification. A vacuum and / or a flow of inert gas (such as nitrogen or argon) may also be applied to support the condensation of water.

[0149] The present invention further provides the use of at least one 6-undecaneol ester in the preparation of cosmetic formulations, said 6-undecaneol ester being selected from 6-undecaneol esters obtainable by esterification of undecane-6-ol with one of the following:

[0150] A) Monocarboxylic acids having 6-32, preferably 6-22, more preferably 8-22 carbon atoms, and

[0151] B) Polyfunctional carboxylic acids having 2-44, preferably 3-38, more preferably 4-18 carbon atoms, preferably tricarboxylic acids and dicarboxylic acids, more preferably dicarboxylic acids having 2-18, preferably 3-13, more preferably 4-11 carbon atoms (equivalent to those 6-undecanoyl esters contained in the aqueous compositions according to the invention) or which can be obtained by the method according to the invention.

[0152] The present invention further provides the use of at least one 6-undecaneol ester contained in an aqueous composition according to the invention or obtainable by the method according to the invention for the prevention of dry skin.

[0153] The present invention further provides the use of at least one 6-undecaneol ester contained in an aqueous composition according to the invention or obtainable by the method according to the invention for the solubilization of active ingredients and UV photoprotective filters (preferably UV photoprotective filters, more preferably organic UV photoprotective filters) in cosmetic formulations.

[0154] The present invention further provides the use of at least one 6-undecaneol ester contained in an aqueous composition according to the invention or obtainable by the method according to the invention for providing a good non-sticky skin feel in cosmetic formulations.

[0155] The present invention further provides the use of at least one 6-undecaneol ester contained in an aqueous composition according to the invention or obtainable by the method according to the invention for reducing the distribution of cosmetic formulations on skin or hair. This is advantageous for use in eye or facial care formulations.

[0156] The present invention further provides the use of at least one 6-undecaneol ester contained in an aqueous composition according to the invention or obtainable by the method according to the invention for stabilizing cosmetic formulations in emulsion form, preferably at a pH value below pH 5 and / or a temperature below 15°C.

[0157] The purpose of this invention is for cosmetic use.

[0158] The embodiments listed below are used to describe the present invention by way of example, and are not intended to limit the present invention to the implementation schemes specified in the embodiments. The scope of this application is obvious from the whole specification and the claims.

[0159] The following figures are part of the embodiments:

[0160] Figure 1 Displays the emulsion after repeated freezing / thawing. Example:

[0161] Example 1: Synthesis of 6-dodecaneol from ethanol and acetate

[0162] Cultivation of Clostridium coccidioides and extraction of hexanoic acid

[0163] Clostridium coccidioides was cultured to bioconvert ethanol and acetate into hexanoic acid. For in-situ extraction of the produced hexanoic acid, a mixture of tetradecane and trioctylphosphine oxide (TOPO) was continuously cultured. All culturing steps were carried out under anaerobic conditions in pressure-resistant glass vials, which were hermetically sealed with butyl rubber stoppers.

[0164] Clostridium coccidioides was pre-cultured in 1000 mL pressure-resistant glass vials in 250 mL EvoDM45 medium (pH 5.5); 0.004 g / L magnesium acetate, 0.164 g / L sodium acetate, 0.016 g / L calcium acetate, 0.25 g / L potassium acetate, 0.107 mL / L H3PO4 (8.5%), 2.92 g / L ammonium acetate, 0.35 mg / L cobalt acetate, 1.245 mg / L nickel acetate, 20 μg / L d-biotin, 20 μg / L folic acid, 10 μg / L pyridoxine-HCl, 50 μg / L thiamine-HCl, 50 μg / L riboflavin, 50 μg / L niacin, 50 μg / L calcium pantothenate, 50 μg / L vitamin B12, 50 μg / L para-aminobenzoate, 50 μg / L lipoic acid, 0.702 mg / L

[0165] The reaction was carried out in an open water bath shaker with a mixture of 25% CO2 and 75% N2 at 37 °C, 150 rpm, and 1 L / h using (NH4)2Fe(SO4)2x4 H2O, 1 mL / L KS-acetate (93.5 mM), 20 mL / L ethanol, and 0.37 g / L acetic acid. The gas was vented into the top space of the reactor. The pH was maintained at 5.5 by automatically adding 2.5 M NH3 solution. Fresh culture medium was added at 2.0 days... -1 The dilution rate is continuously fed into the reactor and passed through a 0.2 μm pore size filter. Hollow fiber polyethersulfone membranes (Spectrumlabs, Rancho Dominguez, USA) continuously remove fermentation broth from the reactor to retain cells in the reactor and maintain OD. 600nm It is ~1.5.

[0166] For the master culture, 150 ml of EvoDM39 medium (pH 5.8; 0.429 g / L magnesium acetate, 0.164 g / L sodium acetate, 0.016 g / L calcium acetate, 2.454 g / L potassium acetate, 0.107 mL / L H3PO4 (8.5%), 1.01 mL / L acetic acid, 0.35 mg / L cobalt acetate, 1.245 mg / L nickel acetate, 20 μg / L d-biotin, 20 μg / L folic acid, 10 μg / L pyridoxine-HCl, 50 μg / L thiamine-HCl, 50 μg / L riboflavin, 50 μg / L niacin, 50 μg / L calcium pantothenate, 50 μg / L vitamin B12, 50 μg / L para-aminobenzoate, 50 μg / L lipoic acid, 0.702 mg / L (NH4)2Fe(SO4)2x A solution of 4H2O, 1 mL / L KS-acetate (93.5 mM), 20 mL / L ethanol, 8.8 mL NH3 solution (2.5 mol / L), and 27.75 mL / L acetic acid (144 g / L) was prepared in a 1000 mL flask and seeded at OD using 100 mL of pre-cultured cell broth. 600nm It is 0.71.

[0167] Cultures were carried out at 37°C, 150 rpm, and 1 L / h aeration rate in an open water bath shaker with a mixture of 25% CO2 and 75% N2 for 65 hours. The gas was vented into the top space of the reactor. The pH was maintained at 5.8 by automatically adding 2.5 M NH3 solution. Fresh culture medium was introduced at 0.5 days... -1 The dilution rate is continuously fed into the reactor, and the OD is maintained. 600nmThe fermentation broth was continuously removed from the reactor at a rate of ~0.5. An additional 120 g of a mixture of 6% (w / w) TOPO in tetradecane was added to the fermentation broth. This organic mixture was then continuously fed into the reactor, also at a rate of 1 day. -1 The organic phase is continuously removed from the reactor at a dilution rate.

[0168] During the incubation period, several 5 mL samples were taken from both the aqueous and organic phases to determine the OD. 600nm pH and product formation. Product concentration was determined by semi-quantitative 1H-NMR spectroscopy. Sodium trimethylsilylpropionate (T(M)SP) was used as an internal quantitative standard.

[0169] During the main culture in the aqueous phase, steady-state concentrations of 8.18 g / L ethanol, 3.20 g / L acetate, 1.81 g / L butyrate, and 0.81 g / L hexanoate were reached. OD 600nm The concentration was maintained at 0.5. Steady-state concentrations of 0.43 g / kg ethanol, 0.08 g / kg acetate, 1.13 g / kg butyrate, and 8.09 g / kg hexanoate were achieved in the organic phase. After the experiment, the cells remained viable and were transferred for further culture.

[0170] The partition coefficients K of the substrate and product in the system's aqueous medium and 6% TOPO in tetradecane were calculated from the concentrations in the two phases. D .

[0171]

[0172] K in steady state D The value is 0.05 for ethanol, 0.03 for acetic acid, 0.62 for butyric acid, and 9.99 for hexanoic acid.

[0173] Ketoconversion of hexanoic acid to 6-undecane

[0174] Ketone formation was carried out in a heated continuous fluidized bed reactor. First, the reactor was charged with magnesium oxide / silica (50 wt%, 14.00 g) and heated at 330 °C for 1 hour under an argon flow (54 mL / min). The temperature was then increased to 360 °C. A mixture of hexanoic acid and tetradecane (v / v: 3 / 1) was then continuously fed into the reactor at a rate of 3.3 mL / h. The gaseous effluent stream was collected through two cooling traps and cooled with a mixture of water and dry ice with isopropanol. The collected fractions were weighed and their composition analyzed by gas chromatography (GC). A total of 370.65 g of hexanoic acid was fed into the reactor, which is equivalent to the maximum theoretical yield of 271.70 g of 6-undecane, 28.75 g of water, and 70.21 g of carbon dioxide as a byproduct. The amount of 6-undecane obtained was 267.67 g, and the amount of water was 28.32 g. This corresponds to a 99% mass recovery upon complete conversion. High productivity and selectivity were confirmed by routine GC measurements, as only trace amounts of hexanoic acid were detected and no byproducts were found.

[0175] 6-Undecaneone hydrogenated to 6-Undecaneol

[0176] The hydrogenation of 6-undecaneone to 6-undecaneol was carried out in a 300 mL autoclave reactor (PARR Instrument Company). The reactor was placed in an aluminum block, and the temperature was controlled by a thermocouple placed inside the reactor. Typically, 30 mg of solid catalyst and 170.3 mg (1.0 mmol) of substrate were added to a 4 mL glass vial equipped with an oven-dried magnetic stirrer. 2.0 mL of dry toluene was used as the solvent. The vial was fitted with a screw cap, and a needle was inserted through the diaphragm. The vial was placed in the reactor. The reactor was purged three times with 10 bar of H₂, and then the pressure was increased to 20 bar. The reactor was heated to the desired temperature of 120 °C for 20 hours. After the reaction, the reactor was cooled to 5 °C using an ice bath, the gas phase was slowly released, and the remaining liquid was carefully separated from the solid catalyst and analyzed separately using an internal standard (100 μL of n-hexadecane).

[0177] Catalyst 3.0Co@γ-Al2O3 showed 99% ketone conversion and 98% alcohol yield.

[0178] The catalyst preparation method is as follows:

[0179] In H2O, using ascorbic acid as a reducing agent and glucose as a capping agent, 3% by weight Co@γ-Al2O3 was pyrolyzed at 800 °C for 2 hours, with the Co salt being cobalt(II) nitrate hexahydrate. In a typical synthesis, 149 mg (0.51 mmol) of Co(NO3)2·6H2O was dissolved in 20 mL of DIH2O, followed by the gradual addition of an aqueous solution of 265 mg (3.0 mmol) ascorbic acid and 92 mg (1 mmol) D-(+)-glucose. The contents were stirred at 90 °C for 2–3 hours. Then, 1.0 g of γ-Al2O3 support was added, and the slurry was stirred overnight at room temperature. Excess water was removed by centrifugation, and the solid was dried in an oven at 120 °C for 10 hours, followed by pyrolysis at 800 °C for 2 hours under an argon atmosphere.

[0180] Example 2: Undecane-6-ylhexanoate

[0181] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and hexanoic acid (at least 98% (from the purified intermediate of Example 1), 116.2 g / mol, 70.9 g, 0.61 mol) was heated under catalytic addition of 0.17 g p-toluenesulfonic acid and stirred at 160 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, washed with water, and distilled under vacuum. A colorless to pale yellow oil was obtained.

[0182] Saponification value: 207 mg KOH / g. Purity (GC): >98%.

[0183] Example 3: Undecane-6-yllaurate

[0184] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and lauric acid (minimum 99% (from Sigma-Aldrich), 200.3 g / mol, 116.2 g, 0.58 mol) was heated under catalytic addition of 1.1 g p-toluenesulfonic acid and stirred to 150 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, washed with water, and distilled under vacuum. A colorless to pale yellow oil was obtained.

[0185] Saponification value: 158 mg KOH / g. Purity (GC): >98%.

[0186] Example 4: Undecane-6-yl stearate

[0187] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and stearic acid (minimum 92%, Palmac 90-18 (from IOI), acid value 199 mg KOH / g, 284 g / mol, 156.2 g, 0.55 mol) was heated under catalytic addition of 0.26 g tin(II) and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, bleached with H₂O₂ solution, and washed with water. Drying yielded a pale yellow waxy substance.

[0188] Acid value: <1 mg KOH / g; Saponification value: 129 mg KOH / g. Purity (GC): >95%.

[0189] Example 5: Undecane-6-yloctanoate / decanoate

[0190] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and octanoic acid / capric acid (Kortacid 0810 (from Oleon), acid value 360 ​​mg KOH / g, 156 g / mol, 95.2 g, 0.61 mol) was heated under catalytic addition of 0.2 g p-toluenesulfonic acid and stirred at 160 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, washed with water, and distilled under vacuum. A pale yellow oil was obtained.

[0191] Saponification value: 181 mg KOH / g. Purity (GC): >97%.

[0192] Example 6: Undecane-6-ylcocoate

[0193] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and distilled coconut oil fatty acids (Wilfarin DC-0818 (from Wilmar), acid value 270 mg KOH / g, 208 g / mol, 114.4 g, 0.55 mol) was heated under catalytic addition of 0.43 g tin(II) and stirred at 160 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, bleached with H₂O₂ solution, and washed with water. Drying yielded a pale yellow oil.

[0194] Acid value: 1 mg KOH / g; Saponification value: 156 mg KOH / g. Purity (GC): >95%.

[0195] Example 7: Undecane-6-yl-12-hydroxystearate

[0196] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and 12-hydroxystearic acid (HCO fatty acid (from Jayant), acid value 182 mg KOH / g, 308 g / mol, 169.4 g, 0.55 mol) was heated under catalytic addition of 0.27 g tin(II) and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, bleached with H₂O₂ solution, and washed with water. Drying yielded a pale yellow waxy substance.

[0197] Acid value: 1 mg KOH / g; Saponification value: 122 mg KOH / g. Purity (GC): >92%.

[0198] Example 8: Undecane-6-yl isostearate

[0199] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and isostearic acid (PRISORINE 3503 (from Croda), acid value 190 mg KOH / g, 295 g / mol, 162.3 g, 0.55 mol) was heated under catalytic addition of 0.13 g tin(II) and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, bleached with H₂O₂ solution, and washed with water. Drying yielded a pale yellow oil.

[0200] Acid value: 2 mg KOH / g; Saponification value: 125 mg KOH / g. Purity (GC): >90%.

[0201] Example 9: Undecane-6-yl oleate

[0202] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and oleic acid (Wilfarin OA 7075 (from Wilmar), acid value 200 mg KOH / g, 281 g / mol, 154.6 g, 0.55 mol) was heated under catalytic addition of 0.25 g tin(II) and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of less than 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered, bleached with H₂O₂ solution, and washed with water. Drying yielded a yellow oily substance.

[0203] Acid value: 1 mg KOH / g; Saponification value: 128 mg KOH / g. Purity (GC): >92%.

[0204] Example 10: bis(undecane-6-yl)malate

[0205] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and D,L-malic acid (minimum 98% (from Sigma-Aldrich), 134.1 g / mol, 37.5 g, 0.28 mol) was heated under catalytic addition of 0.14 g p-toluenesulfonic acid and stirred at 160 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity below 30 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered and washed with water. Drying yielded a pale yellow oil.

[0206] Acid value: 2 mg KOH / g; Saponification value: 255 mg KOH / g. Purity (GC): >90%.

[0207] Example 11: Bis(undecane-6-yl)succinate

[0208] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and succinic acid (minimum 99% (from Sigma-Aldrich), 118.9 g / mol, 33.3 g, 0.28 mol) was heated under catalytic addition of 0.13 g p-toluenesulfonic acid and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity below 30 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered and washed with water. Drying yielded a pale yellow waxy substance.

[0209] Acid value: 2 mg KOH / g; Saponification value: 262 mg KOH / g. Purity (GC): >90%.

[0210] Example 12: bis(undecane-6-yl) sebacate

[0211] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and sebacic acid (minimum 99% (from Sigma-Aldrich), 202.3 g / mol, 56.6 g, 0.28 mol) was heated under catalytic addition of 0.8 g p-toluenesulfonic acid and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity below 30 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered and washed with water. Drying yielded a pale yellow waxy substance.

[0212] Acid value: 1 mg KOH / g; Saponification value: 223 mg KOH / g. Purity (GC): >90%.

[0213] Example 13: Furan-2,5-dicarboxylic acid bis(undecane-6-yl) ester

[0214] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and dimethyl furan-2,5-dicarboxylate (minimum 99% (from Sigma-Aldrich), 184.1 g / mol, 53.4 g, 0.29 mol) was heated under catalytic addition of 0.15 g p-toluenesulfonic acid and stirred at 150 °C. The resulting methanol was continuously distilled off under vacuum until an acidity of approximately 20 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered and washed with water. Drying yielded a pale yellow oil.

[0215] Acid value: 2 mg KOH / g; Saponification value: 260 mg KOH / g. Purity (GC): >85%.

[0216] Example 14: Tris(undecane-6-yl)citrate

[0217] A mixture of undecane-6-ol (172.3 g / mol, 100.0 g, 0.58 mol) and citric acid (minimum 99% (from Sigma-Aldrich), 192.1 g / mol, 34.6 g, 0.18 mol) was heated under catalytic addition of 0.13 g p-toluenesulfonic acid and stirred at 180 °C. The resulting water was continuously distilled off under vacuum and a nitrogen stream until an acidity of approximately 30 mg KOH / g was achieved. The product was neutralized with potassium hydroxide solution, then filtered and washed with water. Drying yielded a pale yellow waxy substance.

[0218] Acid value: 2 mg KOH / g; Saponification value: 260 mg KOH / g. Purity (GC): >85%.

[0219] Example 15: Application Testing

[0220] To demonstrate the advantageous properties of the aqueous composition containing 6-undecanoyl ester, the following W / O emulsion was prepared using a common method. The aqueous phase was slowly added and incorporated into the oil phase. The mixture was then homogenized. In comparative examples outside the scope of this invention, TEGOSOFT DC (decyl cocoate) was used as a reference substrate.

[0221] To evaluate freeze stability, the following body lotion formulations were subjected to two freeze-thaw cycles, from room temperature to -15°C and back to room temperature. After the samples returned to room temperature, the freeze stability of the aqueous compositions was determined by visual inspection. Freeze stability was described using the following terms:

[0222] Freezing stability Excellent (++) No or minimal water separation Good (+) Very weak water separation Medium (0) Weak water separation weak(-) Strong water separation Very weak (--) Very strong oil separation

[0223] The sensory properties of the cosmetic lotion were evaluated by a trained sensory panel. At least five people evaluated the sensory characteristics of the formulation without knowing the composition of the sample being evaluated. Properties described by most panel members are reported in the table below; the figures given are weight percentages.

[0224] Body lotion

[0225]

[0226]

[0227] According to the present invention

[0228] exist Figure 1 In the diagram, after freezing-thawing-cycling, the left side shows formulation B containing Example 3, while the right side shows formulation A containing decyl cocoate.

[0229] Sensory results surprisingly showed that, compared to the reference sample, the system containing the embodiments of the present invention exhibited lower dispensing capacity while displaying high absorption and a smooth texture 5 minutes after absorption. Following a freeze-stability test, the system of the present invention showed no signs of instability, while the comparative sample showed strong water separation, which is unacceptable for cosmetic formulations.

[0230] Example 16: Other exemplary aqueous compositions comprising 6-undecanoyl ester according to the present invention

[0231] The following examples demonstrate the general applicability of 6-undecanoyl esters in various cosmetic formulations and their compatibility with a wide range of other ingredients (e.g., emulsifiers, stabilizers, preservatives, or active compounds such as UV filters or antimicrobial agents) that are typically challenging to formulate. The application of this invention is not limited to the formulations shown. The examples were prepared according to commonly used standard methods.

[0232] Natural body spray

[0233]

[0234]

[0235] W / O Cream

[0236]

[0237] Anti-aging day cream

[0238]

[0239]

[0240] Lightweight Care Cream

[0241]

[0242] serum

[0243]

[0244] Nourishing Natural Cream

[0245]

[0246]

[0247] Aftershave

[0248]

[0249] Lightweight W / O Emulsion

[0250]

[0251] Anti-aging moisturizing cream

[0252]

[0253] Lightweight O / W Sunscreen Moisturizer

[0254]

[0255]

[0256] Sunscreen spray SPF 30

[0257]

[0258] cationic hand cream

[0259]

[0260] AP / Deo roll-on, PEG-free and ACH-free

[0261]

[0262] Oil-control moisturizer

[0263]

[0264] W / O foundation:

[0265]

[0266]

[0267] Transparent Shampoo

[0268]

[0269]

[0270] Pearl Shampoo

[0271]

[0272] Conditioning Shampoo

[0273]

[0274]

[0275] Anti-dandruff shampoo

[0276]

[0277] Shampoo, PEG-free

[0278]

[0279]

[0280] Sulphur-free shampoo

[0281]

[0282]

[0283] Sulphur-free shampoo

[0284]

[0285] Water-wash conditioner

[0286]

[0287] Water-wash conditioner

[0288]

[0289] Wet wipe soaking liquid

[0290]

[0291] Wet wipe soaking liquid

[0292]

[0293]

[0294] Cleaning micelle water

[0295]

[0296] micelle water

[0297]

Claims

1. An aqueous composition containing at least 2% by weight of water and at least one 6-undecanoyl ester, said 6-undecanoyl ester being selected from 6-undecanoyl esters obtainable by esterification of undecane-6-ol with one selected from: (a) Monocarboxylic acids having 6–32 carbon atoms, and (b) Polyfunctional carboxylic acids having 2–44 carbon atoms, The monocarboxylic acid is selected from fatty acids, and the polyfunctional carboxylic acid is selected from aliphatic straight-chain dicarboxylic acids.

2. The aqueous composition according to claim 1, wherein the monocarboxylic acid has 6-22 carbon atoms.

3. The aqueous composition according to claim 1, wherein the monocarboxylic acid has 8-22 carbon atoms.

4. The aqueous composition according to claim 1, wherein the dicarboxylic acid has 3-38 carbon atoms.

5. The aqueous composition according to claim 1, wherein the dicarboxylic acid has 4-18 carbon atoms.

6. The aqueous composition according to claim 1, wherein the dicarboxylic acid has 2-18 carbon atoms.

7. The aqueous composition according to claim 1, wherein the dicarboxylic acid has 3-13 carbon atoms.

8. The aqueous composition according to claim 1, wherein the dicarboxylic acid has 4-11 carbon atoms.

9. The aqueous composition according to claim 1, characterized in that... The monocarboxylic acid is selected from the following: octanoic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, phellic acid, transoleic acid, arachidic acid, benzolic acid, erucic acid, codoleic acid, eicosapentaenoic acid, docosahexaenoic acid, and arachidonic acid.

10. The aqueous composition according to any one of claims 1 to 9, characterized in that... The polyfunctional carboxylic acids are selected from oxalic acid, malonic acid, propanedioic acid, succinic acid, maleic acid, tartaric acid, fumaric acid, sorbic acid, α-ketoglutaric acid, glutaric acid, adipic acid, pimelic acid, cork acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, dodecanedicarboxylic acid, and tridecanedicarboxylic acid.

11. The aqueous composition according to any one of claims 1 to 9, characterized in that... It is a formulation containing at least one other component selected from humectants, UV light-protecting filters, and pigments.

12. The aqueous composition according to claim 11, characterized in that... The preparation is a cosmetic preparation.

13. The aqueous composition according to any one of claims 1 to 9, characterized in that... It contains at least one moisturizer.

14. The aqueous composition according to claim 13, wherein the humectant is glycerin.

15. A method for preparing 6-undecanoyl ester, comprising the following steps: (a) Providing ethanol and / or lower alkanes or any salt thereof, and contacting the above substances with at least one microorganism capable of two-carbon chain elongation to produce hexanoic acid and / or its salts and / or its esters; (b) Under suitable reaction conditions for the chemical ketation of hexanoic acid and / or its salts and / or its esters to 6-undecane, the hexanoic acid and / or its salts and / or its esters from (a) are contacted with at least one ketation catalyst. (c) Contacting 6-undecaneone with at least one hydride metal catalyst for the catalytic hydrogenation of 6-undecaneone to 6-undecaneol; (d) Esterifying 6-undecanool with at least one substance selected from the group consisting of A) Provide an acyl donor selected from the following acids: monocarboxylic acids having 6-32 carbon atoms, and B) Provide an acyl donor selected from the following acids: polyfunctional carboxylic acids having 2-44 carbon atoms.

16. The method of claim 15, wherein the monocarboxylic acid has 6-22 carbon atoms.

17. The method of claim 15, wherein the monocarboxylic acid has 8-22 carbon atoms.

18. The method of claim 15, wherein the polyfunctional carboxylic acid has 3-38 carbon atoms.

19. The method of claim 15, wherein the polyfunctional carboxylic acid has 4-18 carbon atoms.

20. The method of claim 15, wherein the polyfunctional carboxylic acid is a tricarboxylic acid or a dicarboxylic acid.

21. The method of claim 20, wherein the dicarboxylic acid has 2-18 carbon atoms.

22. The method of claim 20, wherein the dicarboxylic acid has 3-13 carbon atoms.

23. The method of claim 20, wherein the dicarboxylic acid has 4-11 carbon atoms.

24. The method according to claim 15, wherein the microorganism in (a) is selected from Clostridium carboxylate and Clostridium coccidioides.

25. The method according to any one of claims 15 to 24, wherein the ketation catalyst in (b) is a metal oxide catalyst or a mixture thereof.

26. The method according to claim 25, wherein the metal oxide catalyst in (b) is selected from the heteropolyacid H3PW. 12 O 40 Catalysts, niobium oxide (Nb₂O₅) catalysts, titanium oxide (TiO₂) catalysts, cerium oxide (CeO₂) catalysts, zinc-chromium mixed oxide catalysts, manganese oxide (MnO₂) x Catalysts, including lanthanum oxide (La2O3) catalysts, magnesium oxide (MgO) catalysts, iron oxides, silicon-aluminum mixed oxide catalysts, aluminum oxide (Al2O3) catalysts, and zirconium oxide (ZrO2) catalysts.

27. The method according to claim 26, wherein the iron oxide is selected from FeO, FeO2, Fe2O3, Fe3O4, Fe4O5, Fe5O6, and Fe5O7.

28. The method according to any one of claims 15 to 24, wherein step (b) is carried out at a temperature between 150°C and 350°C.

29. The method according to any one of claims 15 to 24, wherein the hydride metal catalyst in step (c) is selected from ruthenium (Ru) catalyst, rhenium (Re) catalyst, nickel (Ni) catalyst, iron (Fe) catalyst, cobalt (Co) catalyst, palladium (Pd) catalyst and platinum (Pt) catalyst.

30. The method according to any one of claims 15 to 24, wherein the lower alkanic acid in step (a) is selected from acetic acid and butyric acid.

31. The method according to any one of claims 15 to 24, wherein the provision of ethanol and / or the lower alkanes or any salt thereof in step (a) comprises the synthesis of the above-mentioned substances from syngas.

32. The method of claim 31, wherein the synthesis is carried out by at least one acetic acid-producing microorganism.

33. Use of 6-undecaneol ester contained in an aqueous composition according to any one of claims 1-14 or 6-undecaneol ester obtained by the method according to any one of claims 15-32 for the preparation of cosmetic formulations.

34. 6-Undecaneol ester contained in the aqueous composition according to any one of claims 1-14 or 6-undecaneol ester obtained by the method according to any one of claims 15-32 for non-therapeutic use in preventing dry skin.

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