Use of mono-ester glycolipids in emulsion-based product compositions for cosmetics, food, and pharmaceuticals, and a method for producing such compositions

Abstract

The present invention relates to the use of a mono-ester glycolipid or a mixture of mono- ester glycolipids in an emulsion-based product composition.

Description

[0001] Use of mono-ester glycolipids in emulsion-based product compositions for cosmetics, food, and pharmaceuticals, and a method for producing such compositions

[0002] Technical field of the invention

[0003] The present invention relates to emulsifiers for emulsion-based products.

[0004] Background of the invention

[0005] Emulsion-based products are a mainstay in various industries, with a particularly prominent role in cosmetics and pharmaceuticals. An emulsion is a mixture of two immiscible liquids, where one liquid is dispersed in the other in the form of tiny droplets. The most common types of emulsions in beauty products are oil-in-water (O / W) and water-in-oil (W / O) emulsions. The main component, apart from oil and water, of emulsionbased products are emulsifiers. Additional components may be stabilizers, pH adjusters, preservatives, fillers, and active ingredients. Stabilizers, such as gums, silicones, or waxes, help to maintain the emulsion's stability over time. The preservatives are added to prevent microbial growth, which is a risk in products containing water. Antioxidants prevent oxidation of oils, which can cause rancidity and spoilage. PH adjusters are often used to adjust the pH to an appropriate level for product stability or compatibility with the skin's natural pH. Fillers, such as clays or starches, can adjust the product's feel and viscosity. Finally, active ingredients may be added to provide a desired effect, such as vitamins, minerals, fragrances, or pharmaceuticals.

[0006] Returning to one of the most important components, the emulsifiers are surfactants that stabilize the emulsion by reducing the surface tension between the oil and water phases. Examples include anionic, cationic, and non-ionic emulsifiers. Non-ionic emulsifiers are generally preferred for products designed for sensitive skin due to their mildness. Cationic emulsifiers are preferred for hair conditioners because of their conditioning properties. Anionic emulsifiers are often chosen for their ability to interact with dirt and oils, making them effective in cleansers and scrubs. Hence, emulsion-based products may be designed for many different purposes, such as skin care and hair care. Creams, lotions, serums, sunscreens, and foundations are typical emulsion-based skin care products, while conditioners and some styling products are typical emulsion-based haircare products. One of the mayor concerns when formulating an emulsion-based product is the stability as emulsions can separate over time. There is a consumer demand for stable products with improved overall performance and ingredients from renewable resources that can give multiple value-adds to a product category and therefore lead to more clean label products.

[0007] Summary of the invention

[0008] Thus, an object of the present invention is to provide a high-performing multifunctioning alternative to the currently used emulsifiers.

[0009] The inventors of the present invention have found use of a new subtype of non-ionic surfactants, mono-ester glycolipids, that are high-performing alternatives to conventional non-ionic surfactants for e.g., skin- and haircare products.

[0010] The inventors of the present invention have also found a process for producing mono-ester glycolipids from renewable sources, such as enzymatically cleaved starch (e.g., maltose) and used cooking oils (e.g., sunflower oil, rapeseed oil, corn oil, and olive oil). Furthermore, these mono-ester glycolipids are biodegradable. A part of the by-products (mono- and diglycerides, glycerol) may even be separated as for example valuable food ingredients or food additives.

[0011] Thus, a first aspect relates to the use of a mono-ester glycolipid or a mixture of monoester glycolipids in emulsion-based products. The use is preferably for emulsion-based product compositions in cosmetics, food, and pharmaceuticals.

[0012] A second aspect relates to an emulsion-based product composition comprising a monoester glycolipid or a mixture of mono-ester glycolipids.

[0013] A third aspect relates to an emulsion-based product composition comprising:

[0014] - water;

[0015] - an oil; and

[0016] - a mono-ester glycolipid or a mixture of mono-ester glycolipids.

[0017] Preferably, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

[0018] An unmodified carbohydrate is here defined as a carbohydrate in its closed form, whose functionalities, apart from the anomeric acetal / hemicacetal, only consist of hydroxyl groups and does not have any of these replaced, either naturally or chemically by another functionality such as an amino, alkoxy, carboxylate, or acetyl group.

[0019] The present invention will now be described in more detail in the following.

[0020] Detailed description of the invention

[0021] Glycolipids are amphiphilic, non-ionic molecules that comprises a hydrophilic carbohydrate moiety and one or more fatty acids as lipophilic moiety. Mono-ester glycolipids have a single fatty acid as the lipophilic moiety. The inventors of the present invention have found that mono-ester glycolipids have better properties than conventional anionic and non-ionic surfactants.

[0022] The main component, apart from oil and water, of emulsion-based products are emulsifiers. Additional components may be stabilizers, pH adjusters, preservatives, fillers, and active ingredients. Stabilizers, such as gums, silicones, or waxes, help to maintain the emulsion's stability over time. The preservatives are added to prevent microbial growth, which is a risk in products containing water. Antioxidants prevent oxidation of oils, which can cause rancidity and spoilage. PH adjusters are often used to adjust the pH to an appropriate level for product stability or compatibility with the skin's natural pH. Fillers, such as clays or starches, can adjust the product's feel and viscosity. Finally, active ingredients may be added to provide a desired effect, such as vitamins, minerals, fragrances, or pharmaceuticals.

[0023] A first aspect relates to the use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in emulsion-based products. Preferably the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

[0024] A second aspect relates to an emulsion-based product composition comprising a monoester glycolipid or a mixture of mono-ester glycolipids. Preferably the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

[0025] A third aspect relates to an emulsion-based product composition comprising:

[0026] - water;

[0027] - an oil; and

[0028] - a mono-ester glycolipid or a mixture of mono-ester glycolipids. Preferably the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety. In a preferred embodiment, the emulsion-based product composition is a cream or a lotion.

[0029] The water content in lotions and creams can vary significantly depending on the specific formulation and the intended use of the product. Lotions typically have a relatively higher water content than creams and can range from about 60% w / w to as high as 80% w / w or more. Lotions are usually lighter and less viscous, designed for easy application and absorption into the skin. The relatively high water content helps to hydrate the skin but also means that lotions can be less moisturizing over the long term compared to creams.

[0030] Creams usually have a water content ranging from 45% w / w to 70% w / w. Creams are thicker and more occlusive, providing a barrier that helps to keep moisture in the skin. This makes them particularly suitable for dry skin or for use in harsh weather conditions. The exact water content will depend on the desired consistency and the specific moisturizing properties the product aims to provide.

[0031] The oil content in lotions and creams varies depending on the type of product and its intended use. Generally, the oil content is formulated to achieve a balance with the water content to provide the desired consistency, moisturizing properties, and skin feel.

[0032] Lotions typically have a lower oil content compared to creams. The oil content in lotions can range from approximately 5% w / w to 20% w / w. Creams usually have an oil content ranging from 20% w / w to 50% w / w, or more.

[0033] The concentration of emulsifiers in lotions and creams can vary widely depending on the specific formulation, the nature of the emulsifier(s) used, and the desired properties of the final product. In Lotions, the emulsifier content typically ranges from about 1% w / w to 5% w / w. For creams, the emulsifier content might range from about 2% w / w to 10% w / w. The higher percentage is often needed to stabilize the richer, thicker texture and the higher oil content of creams.

[0034] A fourth aspect relates to an emulsion-based product composition comprising :

[0035] - 40-90% w / w water;

[0036] - 5-50% w / w of an oil; and

[0037] - 1-10% w / w of a mono-ester glycolipid or a mixture of mono-ester glycolipids.

[0038] Preferably, the emulsion-based product composition is selected from the group consisting of a cosmetic, a foodstuff, and a pharmaceutical. In one or more embodiments, the emulsion-based product composition is a sweet emulsion-based foodstuff, such as an ice cream, a custard, a ganache, a frosting, a buttercream, or a caramel sauce.

[0039] A sweet emulsion-based foodstuff can be defined as a culinary preparation in which two immiscible liquids, typically oil or fat and water, are blended into a stable mixture with the aid of an emulsifier, creating a smooth and cohesive texture. These foods are predominantly sweet in flavour and are often used in desserts, confections, or as toppings.

[0040] In one or more embodiments, the emulsion-based product composition is a savoury emulsion-based foodstuff, such as a mayonnaise, a sauce, an aioli, a vinaigrette, or a dressing.

[0041] A savoury emulsion-based foodstuff can be defined as a culinary preparation in which two immiscible liquids, typically oil and water, are blended together into a stable mixture, often with the help of an emulsifier, to create a smooth, cohesive texture and to enhance flavour. These foods are predominantly used in savoury dishes and may e.g., serve as sauces, spreads, dressings, or bases.

[0042] Emulsion-based pharmaceuticals are formulations where two immiscible liquids, typically oil and water, are mixed with the help of an emulsifying agent to create a stable product. These are widely used in dermatology, drug delivery systems, and other pharmaceutical applications. Suitable examples are pharmaceutical creams, such as anti-inflammatory (e.g., hydrocortisone cream), antifungal (e.g., clotrimazole cream), and steroidal creams (e.g., betamethasone valerate cream); parenteral emulsions (e.g., propofol, diazepam, and lipofundin); ophthalmic emulsions (e.g., cyclosporine); oral emulsions (e.g., dronabinol, laxatives, and nutritional supplements); inhalation emulsions; vaccine adjuvants (e.g., MF59, and AS03), emulsions for transdermal drug delivery (e.g., patches or gels for drugs like diclofenac or testosterone); and nanoemulsions (e.g., cannabinoid nanoemulsions or nanoemulsions for anticancer drugs, such as paclitaxel).

[0043] In one or more embodiments, the oil is selected from coconut oil, jojoba oil, olive oil, argan oil, shea butter, sweet almond oil, sunflower seed oil, avocado oil, hemp seed oil, squalene, rosehip oil, marula oil, evening primrose oil, borage oil, mineral oil, caprylic / capric triglyceride and mixtures thereof.

[0044] The inventors of the present invention have also found a process for producing mono-ester glycolipids from renewable sources. The emulsion-based product composition of the present invention can take any of a number of forms. It can take the form of body lotions, creams, hair conditioners, body oils, hair serums, facial moisturizers, body butters, lip balms, facial oils, massage oils, hand creams, hair masks, balms, serums, anti-aging products, sunscreens, makeup products, ointments, baby oils, or any other personal care emulsion-based product composition form known to those skilled in the art.

[0045] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from a disaccharide derived from polysaccharides, such as starch, e.g., by enzymatic cleavage.

[0046] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, sucrose, lactose, cellobiose, trehalose, isomaltulose, lactulose, and isomaltose.

[0047] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetyl glucosamine, N-acetyl neuraminic acid, arabinose, glucuronic acid, guluronic acid, mannuronic acid, and sialic acid.

[0048] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety, preferably unmodified, selected from the group consisting of maltose, cellobiose, and trehalose.

[0049] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety, preferably unmodified, being maltose.

[0050] In one or more embodiments, the mono-ester glycolipid is either a 6-0-(lipid estermaltose, and / or a 6'-0-(lipid ester)-maltose.

[0051] Preferably, the 6-0-(lipid ester)-maltose and 6'-0-(lipid ester)-maltose is present in a molar ratio of 0.1-10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

[0052] The performance of a surfactant depends on the balance between the hydrophilicity of the head group and the hydrophobicity of the tail group. In the case of mono-ester glycolipids, this corresponds to the hydrophilicity of the carbohydrate moity and the hydrophobicity of the hydrocarbon moity. In the case of disaccharides, the solubility in water, and therefore hydrophilicity, varies by up to an order of magnitude (as seen in table below, for example sucrose vs. cellobiose). This makes it non-trivial to predict whether the surfactants made from these different disaccharides would exhibit similar properties and be suitable as surfactants in laundry detergent. Furthermore, the table also shows how the solubility is drastically changed (with a factor of around 8) when comparing glucose and methylglucoside (glucose methylated in the 1 position). This shows that properties of surfactants made from unmodified carbohydrates compared to modified glycosylated carbohydrates would be non-trivial to predict beforehand.

[0053] Apart from the solubility, it is also found that self-assembly giving the micellar structure is highly dependent on the isomeric structure of a particular molecule. See for example the article The underlying order: Isomerism as a blueprint to control the behavior of sugar- based (bio)surfactants (Sanchez-Fernandez, Adrian and Poon, Jia-Fei, Current Opinion in Colloid & Interface Science (69), 2024), which shows that a glycosidic bond in alpha or beta configuration will significantly change the micellar structure. Furthermore, it shows that micellar structure varies drastically between an APG based on maltose and lactose due to the H-bonding pattern between the carbohydrates and between the carbohydrate and water. The latter is correlated with the water solubility. Self-assembly and micellar structure are important for emulsion-based products, as larger elongated micelles will give rise to a thickening effects and smaller spherical micelles will give a free-flowing solution. Macroscopic changes in for example feel, texture, viscosity are highly valuable to the consumer experience of these emulsion-based products such as cosmetics. Due to these complex H-bonding patterns between carbohydrates and between carbohydrates and water in solution, it is non-trivial even to an expert in the field to predict the self-assembly behaviour of two surfactant with identical molecular structure but different isomeric compositions.

[0054] In one or more embodiments, the mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and / or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof. The most common fatty acids present in many of the above oils are oleic acid, linoleic acid, stearic acid, and palmitic acid, why the lipid moiety will predominately be one of these four fatty acids.

[0055] In one or more embodiments, the mono-ester glycolipid comprises a lipid moiety derived from oleic acid and / or linoleic acid.

[0056] In one or more embodiments, the mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, saturated, or unsaturated with 1-6 double bonds. Preferably, the chain length is within the range of C8-C18. More preferably the chain length is within the range of C12-C18. Even more preferably the chain length is within the range of C16-C18.

[0057] Preferably, the lipid moity is derived from oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitelaidic acid and / or palmitoleic acid.

[0058] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose.

[0059] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose, and wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and / or triglyceride selected from a source of sunflower oil.

[0060] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose, and wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and / or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

[0061] As used herein, the term "carbohydrate" refers to monosaccharides and oligosaccharides. It also includes derivatives of these compounds. As the term "carbohydrate" is used herein, it does not include starch, cellulose and guar, or other polysaccharides with high weight average molecular weights. As defined by the present application, "high weight average molecular weights" are those exceeding about 3000 Daltons. As used herein, the term "oligosaccharide" refers chains of two or more saccharides joined by glycosidic bonds with weight average molecular weight less than about 3000 Daltons. Preferably, the carbohydrate is a monosaccharide, or a disaccharide. Preferred disaccharides may e.g., be maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferred monosaccharides may e.g., be glucose, fructose, galactose, mannose, fucose, xylose, glucuronic acid, guluronic acid, mannuronic acid, and ribose. Preferably, the monosaccharide and / or the disaccharide is derived from polysaccharides, such as starch, e.g., by enzymatic cleavage. The inventors of the present invention have found, probably due to steric hindrance, that it is only the C6-alcohol that reacts with the fatty acid when the carbohydrate is glucose, and either the C6-alcohol or the C6'-alcohol that reacts with the fatty acid when the carbohydrate is maltose using the method specific in example 1.

[0062] In one or more embodiments, the carbohydrate is selected from the group consisting of: maltose, sucrose, lactose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

[0063] In one or more embodiments, the carbohydrate is a disaccharide.

[0064] In one or more embodiments, the carbohydrate is selected from the group consisting of: glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetyl glucosamine, N- acetyl neuraminic acid, arabinose, glucuronic acid, guluronic acid, mannuronic acid, sialic acid, and mixtures thereof.

[0065] In one or more embodiments, the carbohydrate is a monosaccharide.

[0066] A process for producing mono-ester glycolipids may be as follows:

[0067] (i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

[0068] (ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;

[0069] (iii) dispersing a lipase in said starting mixture under stirring; (iv) performing a transesterification between said carbohydrate and said diglyceride and / or triglyceride at a temperature between 0-100 degrees Celsius to form a first liquid fraction comprising said polar organic solvent, mono-ester glycolipid, and mono-, di- and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;

[0070] (v) separating the first liquid fraction from the first solid fraction; and

[0071] (vi) separating the mono-ester glycolipid from the first liquid fraction to form a second liquid fraction comprising mono-, di- and / or triglyceride.

[0072] The concept is to use a lipase to catalyse a transesterification between a carbohydrate and a diglyceride and / or triglyceride to form a mono-ester glycolipid and a glyceride with one less fatty acid bound thereto (i.e., a monoglyceride or a diglyceride, respectively). Depending on the type of lipase, the diglyceride (diacylglycerol) may serve as a substrate for a new reaction with another carbohydrate molecule to form a mono-ester glycolipid and a monoglyceride. Again, depending on the used lipase, the monoglyceride (monoacylglycerol) may serve as a substrate for a new reaction with another carbohydrate molecule to form a mono-ester glycolipid and glycerol. The different reaction products (glycerol and / or monoglyceride and / or a diglyceride) may be kept together with the produced mono-ester glycolipid as the oil component, or a part of the oil component, in a subsequent produced emulsion-based product composition, as exemplified in the following process below.

[0073] A process for producing an emulsion-based product composition comprising :

[0074] (i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

[0075] (ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;

[0076] (iii) dispersing a lipase in said starting mixture under stirring;

[0077] (iv) performing a transesterification between said carbohydrate and said diglyceride and / or triglyceride at a temperature between 0-100 degrees Celsius to form a first liquid fraction comprising said polar organic solvent, mono-ester glycolipid, and mono-, di- and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;

[0078] (v) separating the first liquid fraction from the first solid fraction;

[0079] (vi) removing said polar organic solvent from said first liquid fraction to form a second liquid or solid fraction; and

[0080] (vii) adding water to said second liquid or solid fraction to form an emulsion-based product composition.

[0081] Additional oil may be added either subsequent to step vii and / or prior to step vii.

[0082] In the present context, the term "transesterification" designates the chemical reaction in which the alkoxy group of an ester compound, i.e., the diglyceride and / or triglyceride (and optionally a later formed monoglyceride), is exchanged with another alkoxy group via the reaction of said ester with an alcohol, i.e., the carbohydrate, in presence of a catalyst, i.e., the lipase.

[0083] The term "glyceride" (also known as acylglycerol) as used herein refers to a monoglyceride, diglyceride, triglyceride, or combinations thereof. They are esters formed from glycerol and fatty acids. The glyceride in the oil can comprise a plurality of fatty acids saturated, unsaturated. The term "triglyceride" as used herein refers to an ester derived from glycerol and three fatty acids. The triglycerides of the present disclosure may be saturated or unsaturated. Similarly, the term "diglyceride" refers to an ester derived from glycerol and two fatty acids, and the term "monoglyceride" refers to an ester derived from glycerol and one fatty acid.

[0084] Preferably, the source of triglyceride is selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof.

[0085] The term "fatty acid" as used herein refers to a molecule that is derived from a triglyceride and is comprised of a carboxylic acid with a long aliphatic tail (chain) which is either saturated or unsaturated. When not attached to other molecules, they are known as "free" fatty acids. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Short chain fatty acids (SCFA) are fatty acids with aliphatic tails of fewer than six carbons. Medium chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6-12 carbons, which can form medium chain triglycerides. Long chain fatty acids (LCFA) are fatty acids with aliphatic tails 13 to 21 carbons. Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons. In one example, the fatty acid or the ester thereof can comprise at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In some specific examples, the fatty acid or the ester thereof can contain 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 7 , 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms, where any of the stated values can form an upper or lower endpoint when appropriate. In other examples, the glyceride can comprise a mixture of fatty acids or the esters thereof having different ranges of chain lengths.

[0086] As each lipase shows different fatty acid specificity (both saturated / unsatu rated specificity as well as 1,3 specificity), it is important to select an appropriate lipase according to the fatty acid species of the glyceride. If non-regio specificity is wanted, i.e., all fatty acids may be cleaved / transferred from the glyceride, a lipase with non-regio specificity is selected. Suitable examples may e.g., be Candida antarctica B lipase, Lipase OF (origin from Candida rugosa), Lipase G (origin from Penicillum camembertii), Lipase AYS (origin from Candida rugosa), Lipase PS (origin from Burkholderia cepacia), Lipase AK (origin from Pseudomonas flourescens), Lipase AS (origin from Aspergillus niger), and Lipase M (origin from Mucor javanicus). If regio specificity is wanted, i.e., only some of the fatty acids may be cleaved / transferred from the glyceride, a lipase with regio specificity is selected. Suitable examples for 1,3-regio specificity may e.g., be Lipase F-AP15 (origin from Rhizopus oryzae), Lipase Newlase F3G (origin from Rhizopus niveus), Lipase R (origin from Penicillum roqueforti), Lipozyme RM-IM (origin from Rhizomucor miehei), Lipozyme TL-IM (origin from Thermomyces lanuginosus), and Pancreatic Lipase (origin from Porcine Pancreas).

[0087] In one or more embodiments, the lipase is selective for the 1-position, the 3-position or both positions in a glyceride.

[0088] In one or more embodiments, the lipolytic enzyme selective for the 1-position, the 3- position or both positions is selected from Chromobacterium viscosum, dog gastric lipase, dog pancreatic lipase, Fusarium solani cutinase lipase, guinea pig pancreatic lipase, human gastric lipase, Humicola lanuginosus lipase, human pancreatic lipase, lipoprotein lipase, Mucor miehei lipase, Pseudomonas aeruginosa lipase, Penicillium camemberti lipase, Pseudomonas fluorescens lipase, Pseudomonas glumae lipase, porcine pancreatic lipase, Penicillium simplicissimum lipase, Rhizopus arrhizus lipase, rabbit gastric lipase, Fusarium heterosporum lipase, Candida rugosa lipase, and variants thereof.

[0089] In one or more embodiments, the lipase is non-selective for the positions in a glyceride. In one or more embodiments, the process further comprises the step of separating the mono-, di- and / or triglyceride from the second liquid fraction.

[0090] Monoglycerides are used as emulsifying agents in many food products, such as whipped cream, baked goods, and ice cream. Diglycerides are used as common food additives used to blend together certain ingredients, such as oil and water. Furthermore, both mono- and diglycerides are recommended as aerating agents and shelf-life extenders in bakery margarines and shortenings. They are also used as aerating agents in ice cream and imitation creams. Hence, the different reaction products (glycerol and / or monoglyceride and / or a diglyceride) may be kept together with the produced mono-ester glycolipid as the oil component in a subsequent produced emulsion-based food product composition.

[0091] It is anticipated that the lipolytic enzyme specificities mentioned above (both saturated / unsatu rated specificity as well as 1,3 specificity) will be high at a low degree of conversion which will decrease concurrently with the depletion of the preferred substrate and the simultaneously increase of the less preferred substrate. Hence, it is preferred to run the reaction at low conversion in order to secure the highest possible specificity. It is an advantage in certain embodiments of the invention to make the best utility of all reaction products, even at low conversion rates of transesterification.

[0092] In one or more embodiments, the invention relates to a process, wherein the conversion in transesterification to mono-ester glycolipid and mono- or di-glyceride is below 5%, below 10%, below 15%, below 20%, below 25%, below 30%, below 35%, below 40%, below 45% or below 50%.

[0093] In one or more embodiments, the invention relates to a process, wherein the conversion in transesterification to mono-ester glycolipid and mono- or di-glyceride is at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, or at least 70%.

[0094] In one or more embodiments, the invention relates to a process, wherein the lipase is selective for saturated fatty acids, preferably a lipase selected from Candida antarctica lipase A, Fusarium oxysporum lipase, and variants thereof.

[0095] The separation method for purifying mono- or di-glyceride from the first liquid fraction may be selected from deodorization, distillation, evaporation, or any combination thereof. The presence of fatty acid esters or free fatty acids may be removed as the volatile fraction by deodorization, evaporation, or distillation. This volatile fraction can further be separated into alcohol (optionally for reuse in step (I)) and the unreacted free fatty acid or fatty acid ester, which may be reused in step (VI). Deodorisation is essentially a steam distillation under vacuum and is well known in the art. A deodorizer may be operated at 0.15 mbar, 225° C. with steam dosage of 0.20% to 0.25% w / w per hour. Other modes of operation are known in the art, see e.g., 'Introduction to Fats and Oil Technology', Eds O'Brien, Farrr and Wan, AOCS Press, 2000 chapter 13.

[0096] The methods of distillation and evaporation are also known in the art. Evaporation units for oils are usually vapor distillation units, called deodorizers. For step (VIII) it is an embodiment to use distillation under high vacuum to minimize thermal damage. It is in certain embodiments of the invention preferred to use a system with multiple equilibrium stages to achieve a good separation. Other preferred embodiments include Falling film Molecular Distillators operated at pressures of 0.001 to 10 mmHg and temperatures of 140- 200 degrees Celsius, or Centrifugal Molecular Distillators which can operate at pressures around 0.001-10 mmHg and temperatures of 160- 240 degrees Celsius (both of these modes are described in detail in Batistella et al, Appl. Biotechn., vol. 98, 1149-1159, 2002). It is possible to use direct or indirect heating, and it is possible to operate in batch and / or continuous operation.

[0097] The transesterification may preferably be performed at a temperature within the range of 20-95 degrees Celsius, depending on the optimal conditions for the lipase to work, such as within the range of 30-85 degrees Celsius, e.g., within the range of 40-75 degrees Celsius, such as within the range of 50-65 degrees Celsius, e.g., at about 60 degrees Celsius.

[0098] The transesterification may preferably be performed for a period in the range of a few minutes, such as five minutes, to several hours, such as 120 hours, depending on the reaction times of the used reactants.

[0099] Preferred solvents used in the transesterification reaction are tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0100] Purification of the produced glycolipid may be done by standard methods, such as extraction, filtration through a mesoporous adsorbent or filter, affinity or adsorption based chromatographic methods with various solvents, distillation of possible remaining volatile solvents, and centrifugal isolation of precipitated product, by-products, or reactants. Suitable solvents for chromatographic methods may e.g., be water, methanol, ethyl acetate, ethanol, pentane, hexane, heptane, acetone, methyl ethyl ketone, dichloromethane, tert-amyl alcohol and 1-propanol.

[0101] The disclosed production method for the mono-ester glycolipid is an exemplary, but preferred, method. Other methods are also contemplated by the present invention. It should be noted that embodiments and features described in the context of one of the aspects of the present invention also apply to the other aspects of the invention.

[0102] Examples

[0103] Example 1 - production of mono-ester glycolipids

[0104] Mono- or disaccharide was added to a stirring vessel together with the chosen solvent to make a 10% w / w dispersion. Oil was then added under stirring to achieve a molar ratio of 1 : 1 for oil and saccharide. The lipase was added in a concentration of 10% w / w (compared to saccharide mass). The reaction mixture was heated to 60 degrees Celsius and stirred for 120 hours. Product formation was detected by TLC analysis and afterwards purified using column chromatography by eluting with DCM:MeOH.

[0105] Example of solvents tested and used: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0106] Example of lipases tested and used : Candida antarctica B lipase, Lipozyme RM-IM (origin from Rhizomucor miehei), Lipozyme TL-IM (origin from Thermomyces lanuginosus).

[0107] Mono-ester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, glucose, fructose, and isomaltose. The other reactant was selected from sunflower oil, rapeseed oil, olive oil, frying oil (i.e., a mixture of sunflower oil, rapeseed oil, and corn oil), and shea butter. Experiments were unsuccessful when the used carbohydrate was xylose and lactose. cream without additional emulsifier

[0108] A series of six cream compositions (see Table below) were made where only one component differed from one another. Five (#l-#5) different commercial emulsifiers were chosen to test against a mono-ester glycolipid (#6, SBS1) according to the present invention. SBS1 was prepared as in Example 1 and is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl- maltose). Caprylyl / capryl glucoside is a non-ionic surfactant that is used in cosmetic and personal care formulations, including lotions and creams. It is considered to be a gentle and mild emulsifier suitable for sensitive skin. It is typically found in facial cleansers, shampoos, and body washes, especially in products marketed for sensitive skin or natural cosmetics due to its gentle cleansing and foaming properties. Coco glucoside is another non-ionic surfactant that is widely used in personal care and cosmetic formulations. It is derived from coconut oil and glucose, which means it is a natural and biodegradable ingredient. Coco glucoside is valued for its gentle cleansing properties and compatibility with all skin types, making it a staple in formulations aimed at sensitive or delicate skin. It is typically found in baby shampoos, sensitive skin formulations, and natural products. Lauryl glucoside is another non-ionic surfactant from the alkyl glucoside family. Its properties make it suitable for a variety of personal care and cosmetic products, particularly those marketed as natural or gentle, and is often used for its thickening effect. It can be found in cleansers, and in anti-aging products due to its antimicrobial and possible skin beneficial properties. Rhamnolipids are a class of anionic surfactants (pKa around 5.5), which are surface-active substances produced by microorganisms, particularly bacteria of the Pseudomonas genus. They are composed of rhamnose, a naturally occurring sugar, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid, such as 3- hydroxydecanoic acid. Due to their microbial origin and biodegradability, rhamnolipids are considered eco-friendly and have gained attention for use in a variety of applications, including the cosmetic industry. Laureth-7 is a synthetic non-ionic surfactant derived from lauryl alcohol (Laureth-7 is the polyethylene glycol ether of Lauryl Alcohol), which is in turn often derived from coconut or palm kernel oil, and ethoxylated to contain an average of seven moles of ethylene oxide per mole of lauryl alcohol. This ethoxylation process makes the surfactant more soluble in water and less harsh on the skin. Laureth-7 is commonly used in cosmetic and personal care product formulations. SBS1 has been shown to be nonirritant to the eye as the only surfactant mentioned here, as all the other surfactants are irritant to the eyes or cause serious eye damage. For SBS1, this was investigated by an in vitro study following the guidelines of OECD TG 492B.

[0109] It is essential to test the emulsifying properties of selected emulsifiers in products like lotions, creams, and liquid foundations, where oil and water need to be combined to achieve a smooth and uniform texture.

[0110] Test method and results

[0111] A standard cream is prepared by adding the emulsifier to the water and the mix is heated to 50 degrees Celsius. 50 degrees Celsius hot palm oil is then added to the water / surfactant phase and stirred by hand until fully mixed. The resulting cream is allowed to settle for 1 hour to check if phase separation occurs.

[0112] Samples

[0113] #1 #2 #3 #4 #5 #6

[0114] Ingredient % % % % % %

[0115] Water 65 65 65 65 65 65

[0116] Palm oil 30 30 30 30 30 30 Caprylyl / capryl glucoside

[0117] Coco glucoside - 5 - - - -

[0118] Lauryl glucoside - - 5 - - -

[0119] Rhamnolipid - - - 5 - -

[0120] Laureth-7 - - - - 5 -

[0121] SBS1 - - - - - 5

[0122] Results #1 #2 #3 #4 #5 #6

[0123] Stable emulsion after . , X X X X x

[0124] Ih

[0125] Surprisingly, out of the 6 tested emulsifiers, after one hour only the SBSl-based cream still showed emulsion stability. Although this cream is stripped from other additives that could aid to the emulsion stability, it clearly highlights SBSl's (and other mono-ester glycolipids') capability to assist in maintaining the emulsion in other emulsion-based products.

[0126] Example 3 - Simple lotion without additional emulsifier

[0127] A lotion formulation was tested for its stability when using only a glycolipid (Rhamnolipid, coco-glucoside or SBS1) as an emulsifier. An emulsifier in lotion helps to blend and stabilize oil and water-based ingredients, preventing them from separating. It allows the oils (which provide moisture and nourishment) to be evenly dispersed in the water phase, creating a smooth, consistent texture. Emulsifiers also enhance the spreadability of the lotion, ensuring it is easy to apply and absorbs effectively into the skin. The oil phase is stirred into the water phase and lotion is set to rest for 15 min and observing the phase separation for evaluating stability.

[0128] Formulation

[0129] Results

[0130] After 15 minutes both #2 and #3 were phase separated and only #1 was stable.

[0131] Example 4 - Glycolipids for solubilizing perfumes

[0132] Six different surfactants were tested for their ability to solubilize perfumes. Surfactants help solubilize perfumes in water-based products by allowing the fragrance oils (which are typically insoluble in water) to disperse evenly. The surfactant molecules surround the fragrance oils, reducing their surface tension and making them stable in the formulation. This ensures the perfume is evenly distributed in the product without separating or floating on top. The tested glycolipids were SBS1, Rhamnolipid, Sucrose ester emulsifier, Coco- glucoside, Cetearyl glycoside / cetearyl alcohol and sophorolipid. 10 mL solutions of 1% surfactant concentration were mixed with 1% perfumes to see its ability to solubilize perfumes in. The samples were mixed by shaking and evaluated visually to see if droplets of perfume agglomerated on the surface.

[0133] Results

[0134] Score system

[0135] + = Possible to solubilize / dispense in liquid 0 = Possible to solubilize / dispense some in the liquid - = Not possible to solubilize / dispense in liquid

[0136] SBS1 together with Cetearyl glycoside / cetearyl alcohol were able to solubilize perfumes at only 1% actives. Example 5 - Body cream

[0137] A body crema formulation was tested to see how it performed with the glycolipids SBS1, rhamnolipid or Coco-glucoside. The oil phase was heated to 70 degrees together with the emulsifiers polysorbate 20 and secondary alcohol ethoxylate 31EO. The waterphase was also heated to 70 degrees and the oil phase is mixed in under stirring. The cream is cooled to room temperature under continuous stirring before finally adding preservative and adjusting pH.

[0138] Formulation

[0139] Results

[0140] The creams were set to rest for one week at room temperature and evaluated visually.

[0141] Only #1 yielded the desired creamy consistency whereas #3 had a thinner lotion consistency and #2 had formed a water layer at the bottom of the formulation.

[0142] Example 6 - Foundation

[0143] A foundation was formulated with the glycolipid SBS1. The liquid phase ingredients are mixed and heated to 75 degrees. Mix the ingredients in the powder phase thoroughly with a mortar and pestle and add it to the liquid phase under stirring. Remove the mixture from the heat and pour it into a container to let it cool.

[0144] Formulation

[0145] Example 7 - Shaving cream

[0146] A shaving cream was formulated using SBS1. The water phase was mixed and heated to 75 degrees. The ingredients for the oil phase were combined, excluding the essential oil blend, heated to 75 degrees and added to the water phase under stirring. The shaving cream was cooled to 40 degrees under continuous stirring where then the essential oil blend was mixed in. The cream was further cooled to room temperature before finally the preservative was added and the pH adjusted.

[0147] Formulation

[0148] Example 8 - Comparing maltose monoesters with different isomeric composition Maltose monoester was prepared according to the method described in US5550225A, where the isomeric composition is listed as at least 70 percent of monoesters in the 6' position and the remainder being monoester in position 1 (glycosyl ester). This reaction uses mixed carboxylic-carbonic anhydride in an organic solvent medium. SBS1 presented in this patent is produced by an enzyme (more specifically a lipase) producing a mixture of 6 and 6' monoesters. Both products were purified by flash column chromatography before performing the analysis and application tests.

[0149] The two products showed the same retention factor on silica thin layer chromatography in eluent WIPE (1 :2:9), but showed a different isomer composition on HPLC, where it was possible to separate the isomers. Results

[0150] Visually, the maltose monoester produced by the method described in US5550225A was opaque and the SBS1 clear in a 1 mg / mL solution.

[0151] The capacity to dissolve oil droplets was investigated for both products.

[0152] For this test 4 mL of 0.01% maltose monoester samples were mixed with 4 mL sunflower oil by vortexing for 20 seconds. The emulsion was left a minimum of 10 min and a sample of the water phase was removed with a syringe and measured on UV-vis at 660 nm. The test was performed in triplicates. Turbidity was measured 10-30 min after mixing.

[0153] The blank used was water. As a negative control the water phase of deionized water mixed with sunflower oil was measured.

[0154] This clearly shows that SBS1 is much better at solubilizing oil droplets in the water phase. These measurements were complemented with light microscopy images showing many more emulsions droplets in various sizes for SBS1 compared to maltose monoester from US5550225A. These data clearly show that despite the same molecular formulae, the surfactant properties are highly dependent on the isomeric composition.

[0155] Example 9 - Emulsion capacity of different carbohydrate moieties of SBS1

[0156] The emulsification capacity of different surfactants was tested. For each test 2 mL water with 0.01% surfactant and 2 mL sunflower oil was used. The tests were performed in triplicates. Mixing was done by a vortex mixer for 20 seconds and set to rest. The ratio between the height of the emulsion to the total volume height is measured after respectively 10 minutes and 1 hour. The commercially available surfactants Rhamnolipid, Coco glucoside and Caprylyl / capryl glucoside were used as benchmarks. Apart from SBS1, three other surfactants, SBS2, SBS3 and SBS4 were tested. SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). SBS2 is a mono-ester glycolipid with a carbohydrate moiety being sucrose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-sucrose). SBS3 is a mono-ester glycolipid with a carbohydrate moiety being trehalose and a lipid moiety being oleic acid (6- and / or 6'-oleyl- trehalose). SBS4 is a mono-ester glycolipid with a carbohydrate moiety being cellobiose and a lipid moiety being oleic acid (6- and / or 6'- oleyl- cellobiose).

[0157] The emulsification data shows similar capacities after both 10 minutes and 1 hour for all the surfactants tested except SBS2.

[0158] Hence, SBS1, SBS3, and SBS4 can substitute the commonly used surfactants without loss of emulsion capacity.

[0159] Example 10 - Emulsion capacity of different chain lengths of SBS1

[0160] Emulsion capacity was measured by mixing 1 mL of 1 % surfactant solution in water with 1 mL sunflower oil for 20 seconds to form an emulsion. These were left at room temperature for 17 hours after which the emulsion phase was measured relative to the total volume.

[0161] SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). SBS5 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being palmitic acid (6- and / or 6'-palmityl-maltose). SBS6 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being myristic acid (6- and / or 6'-myristyl-maltose). SBS7 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being lauric acid (6- and / or 6'-lauryl-maltose).

[0162] The data show that SBS1 behaves very similar across the range of C12-C18 chain lengths in terms of emulsion capacity. Example 11 - Lotion formulations with mono-ester glycolipids of different chain lengths

[0163] The following lotion formulations were prepared. SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'- oleyl-maltose). SBS5 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being palmitic acid (6- and / or 6'-palmityl-maltose). SBS6 is a monoester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being myristic acid (6- and / or 6'-myristyl-maltose). SBS7 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being lauric acid (6- and / or 6'-lauryl-maltose). SBS8 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being caprylic acid (6- and / or 6'-caprylyl-maltose).

[0164] Example 12 - Mascara formulation A mascara using SBS1 was made. The water phase was mixed, heated to 85 degrees and further homogenized. The ingredients for oil phase 1 were combined and heated to 85 degrees and added slowly to the water phase under stirring. The emulsion was cooled to room temperature under continuous stirring and the ingredients for oil phase 2 were added below 40 degrees.

[0165] Example 13 - Sunscreen lotion formulation A sunscreen lotion was formulated using SBS1. The oil phase was heated to 55 degrees together with the sunscreen actives Avobenzone and Oxybenzone. The water phase was also heated to 55 degrees and the oil phase is mixed in under stirring. The lotion is cooled to room temperature under continuous stirring before finally adding preservative and adjusting the pH.

[0166] Example 14 - Vegan ice cream recipe

[0167] A recipe for vegan ice cream was tested using SBS1 as an emulsifier. All the ingredients are blended to a smooth homogenised mixture and afterwards churned in an ice cream maker until ready.

[0168] Recipe

[0169] Example 15 - Mayonnaise recipe

[0170] A mayonnaise recipe was tested with SBS1 implemented as a co-emulsifier. All ingredients besides sunflower oil were first mixed in a blender at room temperature. The sunflower oil was then added in a small stream during mixing until fully emulsified.

[0171] Recipe

Claims

Claims1. Use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in an emulsionbased product composition within the fields consisting of cosmetics, food, and pharmaceuticals; wherein said mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

2. The use according to claim 1, wherein said mono-ester glycolipid or mixture of monoester glycolipids comprises an unmodified carbohydrate moiety selected from the group consisting of maltose, cellobiose, and trehalose.

3. The use according to claim 1, wherein said mono-ester glycolipid or mixture of monoester glycolipids comprises an unmodified carbohydrate moiety being maltose.

4. The use according to claim 1, wherein the mono-ester glycolipid is either a 6-0-(lipid ester)-maltose, and / or a 6'-O-(l ipid ester)-maltose.

5. The use according to claim 4, wherein the 6-O-(lipid ester)-maltose and 6'-O-(lipid ester)-maltose is present in a molar ratio of 0.1-10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

6. The use according to any one of the claims 1-5, wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and / or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof.

7. The use according to any one of the claims 1-6, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, saturated, or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitelaidic acid and / or palmitoleic acid.

8. The use according to any one of the claims 1-6, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length is within the range of C8-C18, preferably within the range of C12-C18, most preferably within the range of C16-C18.

9. An emulsion-based product composition selected from the group consisting of a cosmetic, a foodstuff, and a pharmaceutical, the emulsion-based product composition comprising :- water;- an oil; and- a mono-ester glycolipid or a mixture of mono-ester glycolipids; wherein said mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

10. The emulsion-based product composition according to claim 9, wherein said monoester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety selected from the group consisting of maltose, cellobiose, and trehalose.

11. The emulsion-based product composition according to claim 9, wherein said monoester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety being maltose.

12. The emulsion-based product composition according to claim 9, wherein the mono-ester glycolipid is either a 6-0-(lipid ester)-maltose, and / or a 6'-0-(lipid ester)-maltose.

13. The emulsion-based product composition according to claim 12, wherein the 6-0-(lipid ester)-maltose and 6'-0-(lipid ester)-maltose is present in a molar ratio of 0.1-10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

14. The emulsion-based product composition according to any one of the claims 9-13, wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and / or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

15. The emulsion-based product composition according to any one of the claims 9-14, wherein said oil is selected from coconut oil, jojoba oil, olive oil, argan oil, shea butter, sweet almond oil, sunflower seed oil, avocado oil, hemp seed oil, squalene, rosehip oil, marula oil, evening primrose oil, borage oil, mineral oil, caprylic / capric triglyceride and mixtures thereof.

16. The emulsion-based product composition according to any one of the claims 9-15, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, saturated, or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitelaidic acid and / or palmitoleic acid.

17. The emulsion-based product composition according to any one of the claims 9-15, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length is within the range of C8-C18, preferably within the range of C12-C18, most preferably within the range of C16-C18.

18. The emulsion-based product composition according to any one of the claims 9-17, being a sweet emulsion-based foodstuff, such as an ice cream, a custard, a ganache, a frosting, a buttercream, or a caramel sauce.

19. The emulsion-based product composition according to any one of the claims 9-17, being a savoury emulsion-based foodstuff, such as a mayonnaise, a sauce, an aioli, a vinaigrette, or a dressing.

20. A process for producing an emulsion-based product composition selected from the group consisting of a cosmetic, a foodstuff, and a pharmaceutical, the emulsion-based product composition comprising :(i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;(ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;(iii) dispersing a lipase in said starting mixture under stirring;(iv) performing a transesterification between said carbohydrate and said diglyceride and / or triglyceride at a temperature between 0-100 degrees Celsius to form a first liquid fraction comprising said polar organic solvent, mono-ester glycolipid, glycerol, and mono-, di- and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;(v) separating the first liquid fraction from the first solid fraction;(vi) removing said polar organic solvent from said first liquid fraction to form a second liquid or solid fraction; and(vii) adding water to said second liquid or solid fraction to form an emulsion-based product composition.

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