Improved Foaming Biosurfactant

Abstract

The present invention provides modified sophorolipids with taurine for improved foaming performance. The present invention also provides compositions containing modified sophorolipids formulated for cosmetic and personal care products. Additionally, methods are provided for improving the skin condition of a subject, improving and / or maintaining oral hygiene in a subject, and cleaning, improving and / or maintaining the health of a subject's hair.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 63 / 317,583, filed March 8, 2022, which is incorporated by reference in its entirety. [Background technology]

[0002] 2. Background of the Invention Foams are metastable dispersions of gas in a liquid matrix, often stabilized by the adsorption of surfactants at the air-liquid interface. They have applications in a variety of industries, including household and personal care, food, and environmental, oil and mineral processing. In products such as beer, consumers desire a stable foam, while in other applications such as cleaning and processing, foaming may be controlled.

[0003] Biosurfactants are amphiphilic molecules derived from microorganisms that consist of both hydrophobic (e.g. fatty acids) and hydrophilic domains (e.g. sugars). Due to their amphiphilic nature, biosurfactants can partition at interfaces between different fluid phases, such as the oil / water or water / air interface, reducing the surface tension of the fluid and increasing the stability of air bubbles, which allows the formation of very stable foams.

[0004] Due to other excellent properties of biosurfactants such as antibacterial, emulsifying and wetting properties, low toxicity, biodegradability, and producibility from renewable resources, they are widely used as wetting agents, emulsifying agents, and cleaning agents in industrial production, agriculture, and daily life. More specifically, there is a great demand for biosurfactants for use in agriculture, environmental protection, pharmaceutical industry, food processing, oil production, detergent industry, and cosmetics.

[0005] Sophorolipids, one of the most promising and attractive biosurfactants combining lower carbon footprint and green chemistry, are specific glycolipids of interest. Sophorolipids contain sophorose, which consists of two glucose molecules linked to a fatty acid by a glycosidic ether bond. Sophorolipids are classified into two broad forms: lactone form, in which the carboxyl group in the fatty acid side chain and the sophorose moiety form a cyclic ester bond, and acidic or linear form, in which the ester bond is hydrolyzed.

[0006] Fermentation of yeast cells on a culture substrate containing sugars and / or lipids and fatty acids with different carbon chain lengths can be used to produce a variety of sophorolipids. The yeast Starmerella (Candida) bombicola is one of the most widely recognized sophorolipid-producing strains. Typically, this yeast produces both lactonic and linear sophorolipids during fermentation.

[0007] Sophorolipids are often produced as a mixture of related molecules. Differences between related molecules arise primarily from their fatty acid structure (degree of unsaturation, chain length, position of unsaturation, and position of hydroxylation), whether they are produced in linear or lactonic form, acetylation patterns, the presence of stereoisomers, and / or whether the glycosidic bond on the fatty acid is at the ω (e.g., terminal) or ω-1 (subterminal) position.

[0008] While consumers are increasingly seeking cleaning and personal care products that are non-toxic, non-irritating to the skin and / or eyes, and have a low impact on the environment, these safer and more sustainable products are still expected to deliver performance in terms of attributes such as cleaning and foaming power.

[0009] Foaming ability and stability are important properties of surfactants.In some industrial fields, it is often useful to add surfactants that can exhibit a certain type of surface activity with desired foaming properties.Therefore, there is a need for improved foaming biosurfactants that are effective, low-cost, and do not contain harmful chemicals for use in various applications such as personal care products. Summary of the Invention

[0010] The present invention provides compositions that exhibit improved foaming properties. Materials and methods for producing sophorolipids that are amenable to modification, as well as materials and methods for modifying sophorolipids, are also provided.

[0011] In certain aspects, taurine is covalently added to linear acidic sophorolipids via an amide bond or to truncated sophorolipids via amide bond or secondary amine formation. These modified sophorolipids with improved foaming performance may be purified for formulation into, for example, beauty and personal care products.

[0012] In one embodiment, the present invention provides a modified sophorolipid or a salt thereof comprising taurine covalently attached to the sophorolipid via an amide bond or an amine, hi some embodiments, the modified sophorolipid or a salt thereof comprises a truncated fatty acid chain, and taurine is covalently attached to such truncated sophorolipid via an amide bond or an amine.

[0013] In particular embodiments, the compounds of the present invention are: i) Formula (II): TIFF2025509276000001.tif43128ii) Formula (IV) TIFF2025509276000002.tif44128 and iii) Formula (V) TIFF2025509276000003.tif43128, In the formula, R 1 and R 2are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, substituted alkane, alkylene, substituted alkylene, alkenylene, or substituted alkenylene; R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + Preferably, R 1 and R 2 is hydrogen; R 4 is a C5-C15 alkane, a C5-C15 alkylene, or a C5-C15 alkenylene; R 3 is methyl.

[0014] In certain embodiments, the modified sophorolipids of the present invention can be used as active ingredients in environmentally friendly cleaning compositions to effectively increase viscosity and foam for personal care and household cleaning applications.

[0015] In one embodiment, the modified sophorolipids of the present invention may be used as cosmetic cleansers that have excellent foaming and washing behavior, while being pleasant to use and possessing advantageous biodegradable properties.

[0016] In one aspect, the present invention provides personal care or cosmetic compositions used for cleaning, conditioning, grooming, beautifying, or otherwise enhancing the appearance and / or well-being of humans or animals.

[0017] Personal care products include, among many others, skin care products, cosmetics, antiperspirants, deodorants, perfumes, toiletries, soaps, bath oils, feminine care products, hair care products, oral hygiene products, depilatories, shampoos, conditioners, hair straightening products, other hair care products, color cosmetics such as lipsticks, creams, make-up, skin creams, lotions (preferably containing water-in-oil or oil-in-water emulsions), shaving creams and gels, aftershave lotions and shaving conditioning compositions, and sunscreen products. In a preferred embodiment, the personal care compositions according to the present invention include hair care and skin care products, particularly shampoos, conditioners, rinses, detangler products, hair color products, body washes, make-up, lipsticks, skin creams and other skin care products.

[0018] In one aspect, the present invention provides a personal care composition comprising, for example, 1-50%, 1-40%, 1-30%, 5-30%, or 10-30% by weight of the modified sophorolipid of the present invention.

[0019] In one aspect, the present invention provides a cosmetic composition comprising, for example, 1 to 30%, 5 to 30%, 5 to 20%, or 5 to 15% by weight of the modified sophorolipid of the present invention.

[0020] The personal care compositions of the present invention may enhance and / or promote deposition of active compounds on keratinous materials, including at least one step of applying an effective amount of the composition of the present invention to keratinous materials, particularly hair.

[0021] In one aspect, the present invention provides a body wash composition comprising, for example, 1 to 50%, 1 to 40%, 1 to 30%, 5 to 30%, or 10 to 30% by weight of the modified sophorolipid of the present invention.

[0022] In one aspect, the present invention provides a shampoo composition comprising, for example, 1 to 50%, 1 to 40%, 1 to 30%, 5 to 30%, or 5 to 20% by weight of the modified sophorolipid of the present invention.

[0023] In one aspect, the present invention provides a facial cleansing composition comprising, for example, 1 to 30%, 5 to 30%, 5 to 20%, or 5 to 10% by weight of the modified sophorolipid of the present invention.

[0024] In one embodiment, the composition of the present invention further comprises a pharma- ceutically or cosmetically acceptable carrier. In one embodiment, the composition may further comprise one or more ingredients selected from viscosity modifiers, skin conditioners, anti-aging ingredients, exfoliants, antioxidants, fragrances, and preservatives.

[0025] In one embodiment, the present invention provides a method for improving the foaming performance of a sophorolipid, comprising the steps of providing a sophorolipid and functionalizing the sophorolipid by covalently attaching to taurine via an amide or amine bond.

[0026] In one embodiment, the invention provides a method for making a composition of the invention, comprising the steps of providing a sophorolipid, functionalizing the sophorolipid by covalently attaching it to taurine via an amide or amine bond, and combining the functionalized sophorolipid with a solvent.

[0027] In one embodiment, the present invention provides a method for improving the skin condition of a subject, comprising applying a composition of the present invention to an area of ​​skin of a subject, and optionally rinsing the composition off.

[0028] In one aspect, the present invention provides a method for improving and / or maintaining the oral hygiene of a subject comprising applying a composition of the present invention to the mouth, lips or oral cavity surfaces of a subject, and optionally rinsing the composition off.

[0029] In one embodiment, the present invention provides a method for cleansing, enhancing and / or maintaining the health of a subject's hair, comprising applying a composition of the present invention to the subject's hair, and optionally rinsing the composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0030] Detailed Description The present invention provides modified sophorolipids with improved foaming performance. Such sophorolipids can be used, for example, as active ingredients in beauty and personal care products (e.g., bath products, anti-acne products, anti-dandruff products, lip balms, lipsticks, and toothpastes). The present invention also provides compositions comprising modified sophorolipids with improved foaming properties.

[0031] The present invention also provides materials and methods for producing sophorolipids amenable to modification, as well as materials and methods for modifying sophorolipids. In a specific embodiment, taurine is covalently added to linear acidic sophorolipids via an amide bond, or to truncated sophorolipids via amide bond or secondary amine formation. These modified sophorolipids with improved foaming performance may be purified for formulation into beauty and personal care products (e.g., cleansing pads, deodorants, lotions, makeup, hand soaps, facial cleansers, body washes, perfumes, shaving creams, moisturizers, and shampoos).

[0032] Sophorolipids are glycolipid biosurfactants produced, for example, by various yeasts of the Starmerella clade. Sophorolipids consist of the disaccharide sophorose linked to a long-chain hydroxy fatty acid. They may contain partially acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units β-glycosidically linked to 17-L-hydroxyoctadecanoic acid or 17-L-hydroxy-Δ9-octadecenoic acid. The hydroxy fatty acid may have, for example, 11 to 20 carbon atoms and may contain one or more unsaturated bonds. Furthermore, the sophorose residues may be acetylated at the 6 and / or 6′ positions. The fatty acid carboxyl group may be free (acidic or linear form) or internally esterified at the 4″ position (lactone form). In most cases, fermentation of sophorolipids results in a mixture of hydrophobic (water-insoluble) sophorolipids, including, for example, lactone sophorolipids, monoacetylated linear sophorolipids, and diacetylated linear sophorolipids, and hydrophilic (water-soluble) sophorolipids, including, for example, non-acetylated linear sophorolipids.

[0033] As used herein, the terms "sophorolipid" and "sophorolipid molecule" include all forms of sophorolipid molecules and their isomers, including, for example, acidic (linear) sophorolipids and lactonic sophorolipids, as well as monoacetylated sophorolipids, diacetylated sophorolipids, esterified sophorolipids, sophorolipids with different hydrophobic chain lengths, sophorolipids with fatty acid-amino acid complexes attached, and others, including those described and / or not described within this disclosure.

[0034] modified sophorolipids A linear sophorolipid molecule may be represented by the general formula (I): TIFF2025509276000004.tif43128 formula, R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R4 is an alkane, a substituted alkane, an alkylene, a substituted alkylene, an alkenylene, or a substituted alkenylene. 1 and R 2 is hydrogen, and R 3 is methyl.

[0035] Sophorolipid molecules are composed of different fatty acid chain lengths and degrees of unsaturation (R 4 ) and possibly R 1 and / or R 2 can be obtained as a collection of over 30 structural analogs that are acetylated or protonated.

[0036] Examples of the substituent include a halogen atom, a hydroxyl, a lower (C1-6) alkyl group, a halo lower (C1-6) alkyl group, a hydroxy lower (C1-6) alkyl group, a halo lower (C1-6) alkoxy group, and the like. 4 Typically has 11 to 20 carbon atoms. In a preferred embodiment of the invention, R 4 has 18 carbon atoms.

[0037] In one embodiment, the present invention provides a modified sophorolipid of general formula (II) comprising a taurine covalently attached to the sophorolipid via an amide bond.

[0038] In one embodiment, the present invention provides a compound of formula (II) which is a modified sophorolipid containing taurine, TIFF2025509276000005.tif43128 formula, R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, substituted alkane, alkylene, substituted alkylene, alkenylene, or substituted alkenylene; R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb +, Ca 2+ , Mg 2+ and N.H. 4 + Preferably, R 1 and R 2 is hydrogen; R 3 is methyl; R 4 is a C5-C15 alkane, a C5-C15 alkylene, or a C5-C15 alkenylene.

[0039] In one embodiment, the compounds of the invention are modified sophorolipids made from linear acidic sophorolipids covalently attached to taurine via an amide bond. In a specific embodiment, the modified sophorolipid has the structure of formula (III): TIFF2025509276000006.tif42128In the formula, R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + is a cation selected from the group consisting of:

[0040] In a preferred embodiment, the modified sophorolipid has the structure: TIFF2025509276000007.tif41128In the formula, R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + is a cation selected from the group consisting of:

[0041] In one embodiment, the present invention provides a modified sophorolipid of general formula (IV) comprising taurine covalently attached to a linear sophorolipid via an amine bond.

[0042] In one aspect, the present invention provides a compound of formula (IV) which is a modified sophorolipid, TIFF2025509276000008.tif44128 formula, R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, substituted alkane, alkylene, substituted alkylene, alkenylene, or substituted alkenylene; R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + Preferably, R 1 and R 2 is hydrogen; R 3 is methyl; R 4 is a C5-C15 alkane, a C5-C15 alkylene, or a C5-C15 alkenylene.

[0043] In one embodiment, the compound of the invention has the structure of formula (V): TIFF2025509276000009.tif43128 formula, R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, substituted alkane, alkylene, substituted alkylene, alkenylene, or substituted alkenylene; R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 +Preferably, R 1 and R 2 is hydrogen; R 3 is methyl, R 4 is a C5-C15 alkane, a C5-C15 alkylene, or a C5-C15 alkenylene.

[0044] In one embodiment, the compound of the invention is a modified truncated sophorolipid formed from oxidative cleavage of a C18 sophorolipid or a salt thereof. In a specific embodiment, the modified sophorolipid has the structure: TIFF2025509276000010.tif41128In the formula, R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + is a cation selected from the group consisting of:

[0045] In a specific embodiment, the modified sophorolipid comprises taurine, which is derived from a truncated sophorolipid (a sophorolipid having a truncated fatty acid chain) covalently attached to taurine via an amide bond. In a specific embodiment, the modified sophorolipid has the structure: TIFF2025509276000011.tif41128In the formula, R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + is a cation selected from the group consisting of:

[0046] In a specific embodiment, the modified sophorolipid comprises taurine, which is derived from a truncated sophorolipid (a sophorolipid having a truncated fatty acid chain) covalently attached to taurine via an amine. In a specific embodiment, the modified sophorolipid has the structure: TIFF2025509276000012.tif44128In the formula, R is hydrogen or, for example, Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + is a cation selected from the group consisting of:

[0047] Selected Definitions As used herein, the term "foam" refers to a dispersion of gas bubbles in or on a liquid, gel, or semi-solid. The gas bubbles may be dispersed throughout the liquid phase in a heterogeneous or homogeneous manner. Examples of bubbles include gases such as air, nitrogen, oxygen, helium, or hydrogen trapped in a liquid such as water or oil. Bubbles may be transient, unstable, or stable.

[0048] As used herein, "surfactant" refers to a substance or compound that reduces surface tension when dissolved in water or an aqueous solution, or reduces the interfacial tension between two liquids or between a liquid and a solid. Thus, the term "surfactant" includes cationic, anionic, nonionic, zwitterionic, amphoteric agents and / or combinations thereof. "Biosurfactant" refers to a surface active agent produced by living organisms and / or produced using naturally occurring substrates. "Surfactant" and "biosurfactant" also refer to substances that cause foaming.

[0049] As used herein, the term "alkyl" refers to a straight-chain or branched hydrocarbon group. Suitable alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, and octadecyl. The term alkyl may be preceded by a specified number of carbon atoms to indicate the number or range of carbon atoms that may be present in the alkyl group, such as C1-C10 alkyl, C1-C20 alkyl, and C10-C20 alkyl. For example, C1-C3 alkyl refers to methyl, ethyl, propyl, and isopropyl.

[0050] As used herein, the term "alkenyl" refers to a straight or branched hydrocarbon group containing at least one double bond. Suitable alkenyl groups include, but are not limited to, vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-pentenyl, 4-methyl-3-pentenyl, 2,4-pentadiene, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 3-methyl-2-hexenyl, 4-methyl-3-hexenyl, and 5-methyl-4-hexenyl. The term alkenyl may be preceded by a specified number of carbon atoms to indicate the number of carbon atoms or range of carbon atoms that may be present in the alkenyl group, such as C1-C10 alkenyl, C1-C20 alkenyl, and C10-C20 alkenyl.

[0051] As used herein, "alkenylene" refers to a straight or branched divalent carbon chain having one or more carbon-carbon double bonds (-CR=CR'-, where R and R' are each independently hydrogen or further substituents). "Alkenylene" refers to an unsaturated, branched or straight chain group having 2 to 18 carbon atoms and two monovalent radical centers derived by the removal of two hydrogen atoms from the same or two different carbon atoms of a parent alkene. Examples of alkenylene include -CH=CH-, -CH2CH=CHCH2-, -CH2CH2CH=CHCH2CH2-, -CH2CH=CHCH2CH2CH2-, -CH2CH=CHCH2CH2CH2-, -CH2CH=CHCH2CH2CH=CHCH2-, -CH2CH2CH2CH=CHCH2CH2CH2-, -CH2CH2CH2CH=CHCH2CH2CH2-, -CH2CH2CH2CH2CH=CHCH2CH2CH2-, -CH2CH2CH2CH2CH=CHCH2CH2CH2CH2-, -CH2CH2CH2CH2CH=CHCH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2CH=CHCH2CH2CH2CH2-, and the like. The term alkenylene may be preceded by a specified number of carbon atoms to indicate the number of carbon atoms, or range of carbon atoms, that may be present in the alkenylene group, such as C1-C10 alkenylene, C1-C20 alkenylene, and C5-C15 alkenylene.

[0052] As used herein, "alkylene" refers to a divalent saturated, straight or branched aliphatic group (such as ethylene) from an alkane by removal of two hydrogen atoms from different carbon atoms. Examples of alkylene include, but are not limited to, methylene (-CH-), 1,2-ethyl (-CHCH-), 1,3-propyl (-CHCHCH-), 1,4-butyl (-CHCHCHCH-), -CH(CH)CH-, -CHCHCHCHCHCHCHCH-, -CHCHCHCHCHCHCHCHCH-, and the like. The term alkylene may be preceded by a specified number of carbon atoms to indicate the number or range of carbon atoms that may be present in the alkylene group, such as C1-C10 alkylene, C1-C20 alkylene, and C5-C15 alkylene.

[0053] As used herein, an "isolated" or "purified" nucleic acid molecule, polynucleotide, polypeptide, protein, or organic compound, e.g., a small molecule, is substantially free of other compounds with which it is naturally associated, such as cellular material. A purified or isolated polynucleotide (ribonucleic acid (RNA) or deoxyribonucleic acid (DNA)) does not contain the genes or sequences with which it is adjacent in its naturally occurring state. A purified or isolated polypeptide does not contain other molecules, i.e., amino acids, with which it is adjacent in its naturally occurring state. An "isolated" strain refers to a strain that is removed from the environment in which it naturally occurs. Thus, an isolated strain may exist, for example, as a biologically pure culture or as a spore (or other form of the strain).

[0054] In certain embodiments, a purified compound is at least 60% by weight of the compound of interest. Preferably, the preparation is at least 75% by weight of the compound of interest, more preferably at least 90%, and most preferably at least 99% by weight. For example, a purified compound is one that is at least 90%, 91%, 92%, 93%, 94%, 95%, 98%, 99%, or 100% (w / w) of the compound of interest by weight. Purity is measured by any suitable standard method, for example, by column chromatography, thin layer chromatography, or high performance liquid chromatography (HPLC) analysis.

[0055] Ranges provided herein are understood to be shorthand for all values ​​within the range. For example, the range of 1-20 is understood to include any number, combination of numbers, or subrange from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, as well as all intervening decimal values ​​between said integers, such as 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, and 1.9. With respect to subranges, "nested subranges" that extend from either end of the range are specifically contemplated. For example, nested subranges within the exemplary range of 1-50 may include 1-10, 1-20, 1-30, and 1-40 in one direction, or 50-40, 50-30, 50-20, and 50-10 in the other direction.

[0056] As used herein, "fermentation" refers to the growth or cultivation of cells under controlled conditions. Growth can be aerobic or anaerobic. Unless the context requires otherwise, the phrase is intended to encompass both the growth and product biosynthesis stages of the process.

[0057] As used herein, "broth," "culture broth," or "fermentation broth" refers to a culture medium that contains at least nutrients. When the broth is referred to after a fermentation process, the broth may also contain microbial growth by-products and / or microbial cells.

[0058] The microbial growth vessel used according to the present invention may be any fermenter or culture reactor for industrial use. As used herein, the terms "reactor", "bioreactor", "fermentation reactor" or "fermentation vessel" include fermentation equipment consisting of one or more vessels and / or towers or piping configurations. Examples of such reactors include, but are not limited to, continuous stirred tank reactors (CSTRs), immobilized cell reactors (ICRs), trickle bed reactors (TBRs), bubble columns, gas lift fermenters, static mixers, or other vessels or other devices suitable for gas-liquid contact. In some embodiments, a bioreactor may include a first growth reactor and a second fermentation reactor. Thus, reference to the addition of substrate to a bioreactor or fermentation reaction should be understood to include addition to either or both of these reactors, as appropriate.

[0059] As used herein, "decrease" means a negative change and "increase" means a positive change, where the change is at least 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 99%, or 100%, including all values ​​in between.

[0060] The term "subject" or "patient" as used herein refers to an organism, including mammals such as primates. Mammalian species that may benefit from the disclosed therapeutic methods include, but are not limited to, apes, chimpanzees, orangutans, humans, and monkeys; domesticated animals such as dogs and cats; livestock animals such as horses, cows, pigs, sheep, goats, and chickens; and other animals such as mice, rats, guinea pigs, and hamsters.

[0061] The transitional word "comprising," which is synonymous with "including" or "containing," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. In contrast, the transitional phrase "consisting of" excludes any element, step, or material not specified in the claim. The transitional phrase "consisting essentially of" limits the scope of the claim to those substances or steps specified and that do not "materially affect the basic and novel characteristics" of the claimed invention. Use of the term "comprising" contemplates other embodiments that "consist of" or "consist essentially of" the recited components.

[0062] As used herein, the term "or" is understood to be inclusive unless specifically stated or obvious from the context. As used herein, the terms "a," "an," and "the" are understood to be singular or plural, unless specifically stated or obvious from the context.

[0063] Unless specifically stated or obvious from the context, as used herein, the term "about" is understood to be within normal tolerances in the art, for example, within 2 standard deviations of the mean. "About" may be understood to be within 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.1%, 0.05%, or 0.01% of the stated value.

[0064] The recitation of a list of chemical groups in any definition of a variable herein includes that definition of the variable as any single group or combination of the listed groups. The recitation of an embodiment of a variable or aspect herein includes that embodiment as any single embodiment or in combination with any other embodiment or portion thereof. All references cited herein are incorporated by reference.

[0065] Production of sophorolipids The present invention provides materials and methods for producing and modifying sophorolipids. Advantageously, the present invention uses safe and environmentally friendly materials and processes suitable for industrial-scale production of purified SLPs.

[0066] Sophorolipids are generally obtained from microbial fermentation using pure fatty acids, mixtures of fatty acids, pure fatty acid esters, mixtures of fatty acid esters, triglycerides as carbon sources together with carbohydrate sources such as corn syrup, dextrin and glucose, using fermentation processes involving wild-type or genetically engineered microorganisms. The production of sophorolipids by using renewable substrates as well as different microbial species and various cultivation parameters (cultivation time, agitation speed, pH value of the medium, added nutrients) allows the obtaining of compounds with well-defined structural and physical properties. This allows the production of a wide range of compounds that can exhibit different physical, chemical, biochemical and biophysical properties.

[0067] In a preferred embodiment, the method comprises first producing a standardized sophorolipid molecule for producing modified and / or purified sophorolipids, which in a particular embodiment comprises culturing a sophorolipid-producing yeast in a submerged fermentation reactor with adapted oleochemical feedstock to produce a yeast culture product, said yeast culture product comprising a fermentation broth, yeast cells, and sophorolipids having a mixture of two or more molecular structures.

[0068] The mixture of molecular structures can include, for example, lactone sophorolipids, linear sophorolipids, deacetylated sophorolipids, monoacetylated sophorolipids, diacetylated sophorolipids, esterified sophorolipids, sophorolipids with different hydrophobic chain lengths, sophorolipids with attached fatty acid-amino acid complexes, and others including those described and / or not within this disclosure.

[0069] In certain embodiments, the distribution of the mixture of sophorolipid molecules can be modified by adjusting fermentation parameters such as, for example, feedstock, fermentation time, and dissolved oxygen concentration.

[0070] The sophorolipids of the present invention may be derived via fermentation processes from recombinant organisms or by strains that naturally produce sophorolipids. Non-limiting examples of sophorolipid producing organisms include Candida bombicola, Candida apicola, Candida bogoriensis, Yarrowia lipolytica, Starmerella bombicola, Starmerella clade, Rhodotorula bogoriensis, Wickerhamiella domericqiae, and Wickerhamomyces anomalus. Several recombinant sophorolipid producing microorganisms have been reported that allow control of sophorolipid structure. As a non-limiting example, certain recombinant S. bombicola strains can be utilized to produce sophorolipids that are either fully lactonic or fully acidic. Additionally, recombinant Candida bombicola strains with an acetyltransferase gene knocked out can be used to produce sophorolipids without acetylation.

[0071] In a preferred embodiment, the microorganism is a yeast or a fungus. Examples of yeast and fungal species suitable for use in accordance with the present invention include Acaulospora, Aspergillus, Aureobasidium (e.g., A. pullulans), Blakeslea, Candida (e.g., C. albicans, C. apicola), Cryptococcus, and the like. ococcus, Debaryomyces (e.g., D. hansenii), Entomophthora, Fusarium, Hanseniaspora (e.g., H. uvarum), Hansenula, Issatchenkia, Kluyveromyces, Maltophilus spp., and others. Mortierella, Mucor (e.g., M. piriformis), Meyerozyma (e.g., M. guilliermondii), Penicillium, Phythium, Phycomyces, Pichia (e.g., P. anomala, P. guilliermondii), Examples of the genus Pseudozyma include P. guilliermondii, P. occidentalis, P. kudriavzevii, Pseudozyma (e.g., P. aphidis), Rhizopus, Saccharomyces (S. cerevisiae, S. boulardii sequela, S. torula), Starmerella (e.g., S. bombicola), Torulopsis, Thraustochytrium, Trichoderma (e.g., T.Examples of suitable serovars include, but are not limited to, T. reesei, T. harzianum, T. virens, Ustilago (e.g., U. maydis), Vickerhamomyces (e.g., W. anomalus), Williopsis, and Zygosaccharomyces (e.g., Z. baiilii).

[0072] In a preferred embodiment, the microorganism is selected from, for example, Starmerella yeast and / or Candida yeast, such as Starmerella (Candida) bombicola, Candida apicola, Candida batistae, Candida floricola, Candida riodocensis, Candida stellate and Candida kuoi. In a specific embodiment, the microorganism is Starmerella bombicola, for example, strain ATCC22214.

[0073] In one embodiment, the fermentation reactor may have or be connected to functional controllers / sensors for measuring important factors in the cultivation process, such as pH, oxygen, pressure, temperature, stirrer power, humidity, viscosity, and / or microbial density and / or metabolite concentration.

[0074] In further embodiments, the container may also monitor the growth of the microorganisms within the container (e.g., measuring cell count and growth stage). Alternatively, samples may be taken from the container for counting, purity measurement, SLP concentration, and / or visual monitoring of oil content. For example, in one embodiment, sampling may be done every 24 hours.

[0075] The microbial inoculum according to the present method preferably comprises cells and / or propagules of the desired microorganism, which may be prepared using any known fermentation method. The inoculum may be premixed with water and / or liquid growth medium, if desired.

[0076] The microorganisms utilized according to the present invention may be naturally occurring or genetically modified microorganisms. For example, the microorganisms may be transformed with specific genes to exhibit specific characteristics. The microorganisms may also be mutants of the desired strain.

[0077] In one embodiment, a single type of microorganism is cultured in the reactor system. In alternative embodiments, multiple microorganisms may be grown in a single reactor system that can be grown together without adverse effects on the growth or the resulting product. For example, two or more different types of microorganisms may be grown simultaneously in a single reactor. In some embodiments, more than one type of microorganism is grown symbiotically in the reactor.

[0078] In certain embodiments, the culture may be supplemented with a carbon source. The carbon source may be a carbohydrate such as glucose, dextrose, sucrose, lactose, fructose, trehalose, mannose, mannitol, and / or maltose; an organic acid such as acetic acid, fumaric acid, citric acid, propionic acid, malic acid, malonic acid, and / or pyruvic acid; an alcohol such as ethanol, propanol, butanol, pentanol, hexanol, isobutanol, and / or glycerol; an oil such as canola oil, soybean oil, rice bran oil, olive oil, corn oil, sunflower oil, sesame oil, and / or linseed oil; powdered molasses, etc. These carbon sources may be used alone or in combination of two or more.

[0079] In certain embodiments, the cultures may be supplemented with high oleic and / or oleic acid only oleochemical feedstocks, which result in yeast culture products with less variation in sophorolipid molecular structure than feedstocks containing other fatty acid sources, where the predominant sophorolipid molecules produced contain an 18C carbon chain and one unsaturated bond at the 9th carbon.

[0080] In one embodiment, the liquid growth medium comprises a nitrogen source. The nitrogen source can be, for example, yeast extract, potassium nitrate, ammonium nitrate, ammonium sulfate, ammonium phosphate, ammonia, urea, and / or ammonium chloride. These nitrogen sources can be used independently or in combination of two or more.

[0081] In one embodiment, one or more inorganic salts may also be included in the liquid growth medium. The inorganic salts may include, for example, potassium dihydrogen phosphate, monopotassium phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, potassium chloride, magnesium sulfate, magnesium chloride, ferrous sulfate, ferrous chloride, manganese sulfate, manganese chloride, zinc sulfate, lead chloride, copper sulfate, calcium chloride, calcium carbonate, calcium nitrate, magnesium sulfate, sodium phosphate, sodium chloride, and / or sodium carbonate. These inorganic salts may be used alone or in combination of two or more.

[0082] In one embodiment, the medium contains growth factors and micronutrients for each microorganism. Inorganic nutrients, including trace elements such as iron, zinc, copper, manganese, molybdenum and / or cobalt, may also be included in the medium. In addition, sources of vitamins, essential amino acids, proteins and trace elements may be included, for example, in corn flour, peptone, yeast extract, potato extract, beef extract, soybean extract, banana peel extract, etc., or in purified form. Amino acids, such as those useful for protein biosynthesis, may also be included.

[0083] The culture method may further provide oxygen to the growth medium. One embodiment is to slowly move air to remove air with low oxygen content and introduce oxygen-containing air. The oxygen-containing air may be ambient air that is replenished daily via a mechanism that includes an impeller for mechanically stirring the liquid and an air sparger for providing gas bubbles to the liquid to dissolve oxygen in the liquid.

[0084] In one embodiment, the microorganisms may be grown on a solid or semi-solid substrate, such as, for example, corn, wheat, soybeans, chickpeas, beans, oatmeal, pasta, rice, and / or flours or meals of these or other similar substances.

[0085] In one embodiment, inorganic salts may also be included. Usable inorganic salts may be potassium dihydrogen phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, magnesium sulfate, magnesium chloride, ferrous sulfate, ferrous chloride, manganese sulfate, manganese chloride, zinc sulfate, lead chloride, copper sulfate, calcium chloride, calcium carbonate, sodium chloride, and / or sodium carbonate. These inorganic salts may be used alone or in combination of two or more.

[0086] In some embodiments, for example, when the microorganisms used to inoculate the substrate are in the form of spores (e.g., bacterial spores), a germination promoter may be added to the substrate. Examples of germination promoters according to the present invention include, but are not limited to, L-alanine, manganese, L-valine, and L-asparagine, or any other known germination promoter.

[0087] The pH of the culture should be suitable for the microorganism of interest. Buffers and pH adjusters such as carbonates and phosphates may be used to stabilize the pH near a preferred value. In certain embodiments, a base solution, e.g., 15%-30% or 20%-25% NaOH solution, is used to adjust the pH of the culture to a preferred level. The base solution may be included in the growth medium and / or fed to the fermentation reactor during cultivation to adjust the pH as needed. When metal ions are present in high concentrations, it may be necessary to use a chelating agent in the liquid medium.

[0088] The methods and apparatus for culturing microorganisms and producing microbial by-products may be carried out in batch, semi-continuous, or continuous processes.

[0089] In one embodiment, the culture method is carried out at about 5° to about 100° C., about 15° to about 60° C., about 20° to about 45° C., about 22° to about 35° C., or about 24° to about 28° C. In one embodiment, the culture may be carried out continuously at a constant temperature. In another embodiment, the culture may be subjected to temperature changes.

[0090] According to the method, the microorganisms may be cultured in a fermentation system for a period of time sufficient to achieve a desired effect, e.g., production of a desired amount of cellular biomass or a desired amount of sophorolipid.

[0091] In certain embodiments, fermentation of the yeast culture occurs for about 40-150 hours, or about 48-140 hours, or about 72-130 hours, or about 96-120 hours. In certain specific embodiments, the fermentation time is in the range of 48-72 hours or 96-120 hours.

[0092] In some embodiments, the sophorolipids produced by the microorganisms of interest may be retained within the microorganisms or secreted into their growth medium. The sophorolipid content may be, for example, at least 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%.

[0093] The growth medium may contain compounds that stabilize the activity of the sophorolipids. The sophorolipids may be purified or may be used in crude form, meaning that they are not separated from the fermentation broth in which they were produced.

[0094] In certain embodiments, the sophorolipids are isolated and / or purified from the growth medium resulting from the fermentation of the biosurfactant-producing microorganism. Isolation and purification can be readily accomplished using standard methods or techniques described in the literature. If desired, the sophorolipids can be further concentrated.

[0095] Modification of sophorolipids In some embodiments, the modified sophorolipids of the present invention are obtained by chemically modifying sophorolipids obtained from the product of fermentation by a sophorolipid-producing microorganism. The chemically modified sophorolipids may be obtained by the fermentation methods and processes described above and / or other methods known in the art. The sophorolipids may be modified using any suitable technique and chemical reaction known in the art. For example, an amide bond may be formed between taurine and a carboxyl group of the sophorolipid using an amide coupling reaction known in the art.

[0096] Chemical modifications may also be carried out, for example to alter the degree of unsaturation of the fatty acid chains. Commonly known hydrogenation or dehydrogenation reactions, or addition or elimination reactions may be used.

[0097] Sophorolipids containing unsaturated bonds at specific positions allow for site-directed functionalization of SLP molecules. In certain embodiments, linear SLPs are ozonated with ozone gas. Upon ozonolysis of linear SLPs, the olefinic portion of the SLP molecule is converted to an ozonide, which is a reactive five-membered ring. In a preferred embodiment, the sophorolipid containing ozonide is reduced to obtain an aldehyde handle. In certain embodiments, the reducing agent is triphenylphosphine, which is used in equimolar concentration with the SLP-ozonide.

[0098] In a preferred embodiment, the linear sophorolipid aldehyde is further reduced in the presence of taurine and a reducing agent to obtain a modified sophorolipid in which taurine is covalently attached to the sophorolipid via amine formation, hi a particular embodiment, the reducing agent is sodium cyanoborohydride, sodium triacetoxyborohydride, or sodium borohydride.

[0099] In some embodiments, the linear sophorolipid aldehyde is extracted from the aqueous mixture with ethyl acetate and concentrated to dryness under reduced pressure (e.g., about 200-250 mbar, or about 240 mbar) at a temperature of about 35-45° C. The dried crude linear sophorolipid aldehyde can then be dissolved in a reaction medium comprising tetrahydrofuran (THF) and water. The proportion of water used as the reaction medium preferably does not exceed 50%, and is typically between 0-25%.

[0100] In certain embodiments, the sophorolipids undergo an amination reaction in which taurine is introduced to the linear sophorolipid aldehyde mixture along with a reducing agent and, optionally, a weak organic acid, preferably acetic acid, although other organic acids (e.g., formic acid, trifluoroacetic acid) may also be used.

[0101] In some embodiments, methods are provided for producing modified sophorolipid compositions, the methods including the steps of providing one or more sophorolipid molecules; functionalizing the sophorolipid molecules to covalently bond to taurine via an amide or amine bond to form a modified sophorolipid molecule; and, optionally, mixing the modified sophorolipid molecule with a liquid, other sophorolipid molecules, and / or additional components specific to the type of product to be produced.

[0102] One embodiment is directed to a method for producing modified sophorolipids, comprising obtaining linear sophorolipid molecules and functionalizing the linear sophorolipid molecules by converting all or a majority of the linear SLP molecules to modified sophorolipid molecules.

[0103] composition In one embodiment, the present invention provides a composition comprising the modified sophorolipid of the present invention. In certain embodiments, the modified sophorolipid produced according to the present method can be used as an active ingredient in personal care products.

[0104] In some embodiments, the composition comprises modified sophorolipids, e.g., at least 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 25%, 30%, 35%, 40%, 45%, or 50% (wt%). In certain embodiments, the composition contains 0.1 to 50% by weight of modified sophorolipid, for example, 0.1 to 45%, 0.1 to 40%, 0.1 to 35%, 0.1 to 30%, 0.1 to 25%, 0.1 to 20%, 0.1 to 20%, 0.1 to 15%, 0.1 to 10%, 0.1 to 9.0%, 0.1 to 8.0%, 0.1 to 7.0%, 0.1 to 6.0%, 0.1 to 5.0%, 0.1-4.0%, 0.1-3.0%, 0.1-2.0%, 1.0-9.0%, 1.0-5.0%, 1.0-3.0%, 3.0-10%, 3.0-7.0%, 5.0-10%, 5.0-9.0%, 6.0-10%, 7.0-10%, 8.0-10%, 5-40%, 10-40%, 10-30%, or 10-20%, inclusive.

[0105] Optionally, the composition may contain, for example, carriers (e.g., water), other biosurfactants, other surfactants (e.g., polyalkylglucosides such as capryl glucoside and lauryl glucoside), hydrophilic and / or hydrophobic compounds, sequestrants, builders (e.g., potassium carbonate, sodium hydroxide, glycerin, citric acid, lactic acid), solvents (e.g., water, ethanol, methanol, isopropanol), organic and / or inorganic acids (e.g., lactic acid, citric acid, boric acid), essential oils, plant extracts, crosslinkers, The compositions may further include one or more other ingredients including chelating agents (e.g., potassium citrate), fatty acids, alcohols, pH adjusters, reducing agents, calcium salts, carbonates, buffers, enzymes, dyes, colorants, fragrances, preservatives (e.g., octylisothiazolinone, methylisothiazolinone), terpenes (e.g., d-limonene), sesquiterpenoids, terpenoids, emulsifiers, demulsifiers, foaming agents, antifoaming agents, bleaching agents, polymers, thickeners and / or viscosity agents (e.g., xanthan gum, guar gum).

[0106] In some embodiments, the composition comprises an additional biosurfactant, which may include, for example, glycolipids, lipopeptides, flavolipids, phospholipids, fatty acid esters, and high molecular weight biopolymers such as lipoproteins, lipopolysaccharide-protein complexes, and / or polysaccharide-protein-fatty acid complexes.

[0107] In one embodiment, the additional biosurfactant is a glycolipid, such as, for example, a rhamnolipid (RLP), a cellobiose lipid, a trehalose lipid, and / or a mannosylerythritol lipid (MEL). In one embodiment, the biosurfactant is a lipopeptide, such as, for example, a surfactin, an iturin, a fengycin, an altrofactin, an amphicin, a viscocin, a lichenycin, a paenibacterin, a polymyxin, and / or a batacin, and in one embodiment, the biosurfactant is another type of amphiphilic molecule, such as, for example, an esterified fatty acid, a saponin, a cardiolipin, a pullulan, an emulsan, a lipomanan, an alasan, and / or a liposan.

[0108] The composition may further comprise additional active or inactive ingredients appropriate to the mode of administration and intended purpose, provided that such additions do not adversely affect the function of the modified sophorolipid.

[0109] In certain embodiments, acceptable carriers may be included in the compositions of the present invention depending on the form of the composition and / or the mode of administration. Pharmaceutically or cosmetically acceptable carriers include, but are not limited to, pharma-ceutically acceptable excipients such as inert diluents, disintegrants, binders, lubricants, sweeteners, flavorings, colorants and preservatives. Suitable inert diluents include sodium and calcium carbonate, sodium and calcium phosphate, and lactose, while cornstarch and alginic acid are suitable disintegrants. Binders may include starch and gelatin, while lubricants, if present, are generally magnesium stearate, stearic acid, or talc. If desired or suitable, coating materials such as glyceryl monostearate or glyceryl distearate may also be used if appropriate and the pharmaceutical composition is in solid form, for example, to delay absorption in the digestive tract.

[0110] In certain embodiments, the present invention provides topical skin care compositions comprising one or more modified sophorolipids. In some embodiments, the topical compositions may further comprise a dermatologically acceptable carrier and one or more active or inactive cosmetic ingredients, such as, for example, vitamins, moisturizers, dyes, fragrances, sunscreens, exfoliants, essential oils, botanical extracts, and the like.

[0111] Dermatologically acceptable carriers include, for example, water; saline; saline; ointments; creams; oil-in-water emulsions; water-in-oil emulsions; silicone-in-water emulsions; water-in-silicone emulsions; wax-in-water emulsions; water-in-oil triple emulsions; microemulsions; gels; vegetable oils; mineral oils; ester oils such as octal palmitate, isopropyl myristate and isopropyl palmitate; ethers such as dicapryl ether and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, cetearyl alcohol, stearyl alcohol and behenyl alcohol; isooctane, isododecane and isohexadecane. isoparaffins such as cyclomethicone, dimethicone, dimethicone crosspolymer, polysiloxane and their derivatives, preferably organically modified derivatives including PDMS, dimethicone copolyol, dimethiconol, and amodimethiconol; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane, and polyolefins, e.g., (hydrogenated) polyisobutene; polyols such as propylene glycol, glycerin, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol; waxes such as beeswax, carnauba, ozokerite, microcrystalline wax, polyethylene wax, and vegetable wax; or any combination or mixture of the foregoing. The aqueous carrier may include one or more solvents miscible with water, including lower alcohols such as ethanol, isopropanol, and the like. The carrier may comprise about 1% to about 99%, 10% to about 85%, 25% to 75%, or 50% to about 65% of the composition by weight.

[0112] In some embodiments, the composition is in solid form and is suitable for reconstitution in a solvent. In another embodiment, the composition further comprises a solvent. Suitable solvents can be aqueous or non-aqueous, and are preferably suitable for foam formation. In certain embodiments, the solvent is an aqueous solvent. Examples of suitable solvents include water, buffer, acetonitrile, water, and alcohol mixtures such as aqueous methanol, aqueous ethanol, and aqueous isopropanol. In some embodiments, the foam may optionally comprise an emulsion, which is an oil-in-water dispersion.

[0113] Non-biological surfactants may also be added to the formulation.Examples of surfactants include, but are not limited to, alkyl sulfates, alkyl ether sulfates (e.g., sodium / ammonium lauryl sulfate and sodium / ammonium laureth sulfate), amphoterics (e.g., amphoacetates, amphopropionates), sulfosuccinates, alkyl polyglucosides, betaines (e.g., cocamidopropyl betaine), sultaines, sacrosinates, isethionates, taurates, ethoxylated sorbitan esters, alkanolamides, and amino acid surfactants.

[0114] Viscosity modifiers may also be added to the composition, including, for example, cocamide DEA, oleamide DEA, sodium chloride, cellulose polymers, polyacrylates, ethoxylated esters, alcohols, glycols, xylene sulfonates, polysorbate 20, alkanolamides, and cellulose derivatives (e.g., hydroxypropyl methylcellulose and hydroxyethyl cellulose).

[0115] Polymers including, for example, xanthan gum, guar gum, polyquaternium-10, PEG-120 methyl glucose dioleate, PEG-150 distearate, PEG-150 polyglyceryl-2 tristearate, and PEG-150 pentaerythrityl tetrastearate may also be added.

[0116] A sunscreen or combination of sunscreens may be included to protect the skin from both UVA and UVB rays. Sunscreens that may be employed in the composition are avobenzone, cinnamic acid derivatives (such as octyl methoxycinnamate), octyl salicylate, oxybenzone, octocrylene, titanium dioxide, zinc oxide, or any mixture thereof. The sunscreen may be present in an amount of about 1 wt% to about 30 wt% of the total weight of the composition.

[0117] In one embodiment, the composition may contain additional skin actives, including, but not limited to, keratolytic agents, keratinocyte proliferation promoters, collagenase inhibitors, elastase inhibitors, depigmenting agents, anti-inflammatory agents, steroids, anti-acne agents, antioxidants (e.g., ascorbic acid), advanced glycation end products (AGE) inhibitors, exfoliants (e.g., glycolic acid, 3,6,9-trioxaundecanedioic acid, and the like), estrogen synthase stimulating compounds (e.g., caffeine and derivatives), compounds capable of inhibiting 5-alpha reductase activity (e.g., linoleic acid, finasteride, and mixtures thereof), barrier function promoters (e.g., ceramides, glycerides, cholesterol and its esters, alpha-hydroxy and omega-hydroxy fatty acids and their esters), and retinoids.

[0118] The composition may optionally include additives, adjuvants, or other components of topical compositions known to those of skill in the art, including, but not limited to, the following: skin penetration enhancers; emollients (e.g., isopropyl myristate, petrolatum, volatile or non-volatile silicone oils, such as methicone and dimethicone, ester oils, mineral oils, and fatty acid esters); humectants (e.g., glycerin, hexylene glycol, caprylyl glycol); skin plumpers (e.g., palmitoyl oligopeptide, collagen, collagen and / or glycosaminoglycan (GAG) enhancers); anti-inflammatory agents (e.g., aloe vera, bioflavonoids, etc.); , diclofenac, salicylic acid); chelating agents (e.g., EDTA or salts thereof such as disodium EDTA); vitamins (e.g., tocopherol and ascorbic acid); vitamin derivatives (e.g., ascorbyl monopalmitate, tocopheryl acetate, vitamin E palmitate); thickening agents (e.g., hydroxyalkylcellulose, carboxymethylcellulose, carbomer, and vegetable gums such as xanthan gum); gelling agents (e.g., ester-terminated polyesteramides); structuring agents; proteins (e.g., lactoferrin); immunomodulators (e.g., corticosteroids and nonsteroidal immunomodulators). Further examples include, but are not limited to, stabilizers; fragrances; film formers; insect repellents; skin cooling compounds; skin protectants; lubricants; preservatives; pearls; chromalite; mica; conditioners; antiallergic agents; pH adjusters; and antimicrobial agents.

[0119] In some embodiments, the topical composition may further comprise additional adjuvants and additives commonly included in skin care compositions, such as organic solvents, stabilizers, silicones, thickeners, emollients, sunscreens, moisturizers, fragrances, or others described herein. The amount of each component, whether active or inactive, is that amount conventionally used in the cosmetic arts to achieve its intended purpose, typically ranging from about 0.0001% to about 25%, or from about 0.001% to about 20% of the composition, although the amount may be outside these ranges. The nature of these components and their amounts must be compatible with the manufacture and function of the disclosed composition.

[0120] In certain embodiments, the composition may optionally include skin conditioners such as emollients, humectants, occlusives, or other moisturizing agents to provide moisturizing, skin softening, skin barrier maintenance, anti-inflammatory, or other skin hygiene benefits.Some non-limiting examples of emollients include alkyl benzoates, myristyl myristate, cetyl myristate, glyceryl dioleate, methyl laurate, PPG-9 laurate, lauryl lauryl allantoin, octyl palmitate, lanolin, propylene glycol, butylene glycol, ethylene glycol monobutyl ether, glycerin, fatty acids, natural oils such as almond, mineral oil, canola, sesame, soybean, wheat germ, corn, peanut and olive oil, isopropyl myristate, myristyl alcohol, aloe vera, hydrolyzed silk protein, vitamin E, stearyl alcohol, isopropyl palmitate, sorbitol, amino acid complex, hydrolyzed vegetable protein, and polyethylene glycol. Some non-limiting examples of humectants include hydroxyethyl urea, agarose, urea, sodium PCA, arginine PCA, fructose, glucose, glutamic acid, glycerin, honey, lactose, maltose, polyethylene glycol, sorbitol, and mixtures thereof.Some non-limiting examples of occlusive agents include petrolatum, shea butter, avocado oil, balm mint oil, cod liver oil, mineral oil, trimyristin, stearyl stearate, synthetic waxes, or mixtures thereof. Some non-limiting examples of other moisturizing agents include ethylhexylglycerin, cholesterol, cystine, hyaluronic acid, keratin, lecithin, egg yolk, glycine, polyquaternium polymers such as PPG-12, polyquaternium-11, behentrimonium chloride, dihydroxypropyl PEG-5 linoleic ammonium chloride, glycerol oleate, PEG-7 glyceryl cocoate, coco glucoside, hydrogenated PEG-200 glyceryl palmitate, panthenol, retinol, salicylic acid, vegetable oils, methyl gluceth-10, methyl gluceth-20, ethoxylated derivatives of skin conditioners such as glycereth-26 and ethoxylated shea butter, and mixtures thereof.Finally, some non-limiting examples of anti-inflammatory agents include bisabolol and panthenol.

[0121] One of ordinary skill in the art will recognize the different strengths of various skin conditioners and will formulate accordingly. In some embodiments, the skin conditioner is preferably present in the composition in an amount of from about 0.01 to about 20 wt%, from about 0.05 to about 15 wt%, and from about 0.1 to about 10 wt%.

[0122] In some embodiments, the composition may optionally include molecules that improve the "feel" of the composition on the skin or hands of the user. For example, it may be undesirable for the composition to have a scaly or rough texture when applied to the skin of the user or after multiple applications of the composition. Some non-limiting examples include amodimethicone, cyclomethicone, bis-PEG / PPG-20 / 20 dimethicone, and silicone copolymers such as stearoxytrimethylsilane, naturally occurring or synthetic fatty acid esters or ethers, and polyalkylene glycols. When included, they are preferably present in the composition in an amount of about 0.001 to about 5 wt%, about 0.01 to about 3 wt%, and about 0.1 to about 2 wt%.

[0123] In one embodiment, the composition may include anti-aging ingredients including, but not limited to, botanical ingredients (e.g., Butea frondosa extract); phytol; phytonic acid; phospholipids; silicones; petrolatum; triglycerides; omega fatty acids; retinoids; hydroxy acids (including alpha-hydroxy acids and beta-hydroxy acids), salicylic acid and alkyl salicylates; exfoliants (e.g., glycolic acid, 3,6,9-trioxaundecanedioic acid, etc.), estrogen synthase stimulating compounds (e.g., caffeine and derivatives); compounds capable of inhibiting 5-alpha reductase activity (e.g., linoleic acid, linoleic acid, finasteride, and mixtures thereof); and barrier function promoters (e.g., ceramides, glycerides, cholesterol and its esters, alpha hydroxy and omega hydroxy fatty acids and their esters).

[0124] Exemplary retinoids include, but are not limited to, retinoic acid (e.g., all-trans, or 9-cis or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters, such as retinyl palmitate, retinyl acetate, and retinyl propionate, and salts thereof. When present, retinoids will typically be included in an amount of about 0.0001% to about 5% by weight, more typically about 0.01% to about 2.5% by weight, or about 0.1% to about 1.0% by weight.

[0125] In one embodiment, the composition may include an exfoliant. Suitable exfoliants include, for example, alpha hydroxy acids, beta hydroxy acids, oxa acids, oxa diacids, and derivatives thereof, such as esters, anhydrides, and salts. Suitable hydroxy acids include, for example, glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, 2-hydroxyalkanoic acid, mandelic acid, salicylic acid, and derivatives thereof. One exemplary exfoliant is glycolic acid. When present, the exfoliant may comprise about 0.001% to about 20% by weight of the composition.

[0126] In one embodiment, the composition may include one or more antioxidants. Suitable antioxidants include compounds with phenolic hydroxyl functionality, such as, for example, ascorbic acid and its derivatives / esters; beta-carotene; catechin; curcumin; ferulic acid derivatives (e.g., ethyl ferulate, sodium ferulate); gallic acid derivatives (e.g., propyl gallate), lycopene; reductic acid; rosmarinic acid; tannic acid; tetrahydrocurcumin; tocopherol and its derivatives, including tocopheryl acetate; uric acid; or any mixture thereof. Other suitable antioxidants are those with one or more thiol functional groups (-SH) in either reduced or non-reduced form, such as glutathione, lipoic acid, thioglycolic acid, and other sulfhydryl compounds. Antioxidants may be inorganic, such as bisulfite, metabisulfite, sulfite, or other inorganic salts and acids containing sulfur. The antioxidants, individually or collectively, may comprise from about 0.001% to about 10% (w / w), or from about 0.01% to about 5% (w / w) of the total weight of the composition.

[0127] In some embodiments, the compositions may optionally include a fragrance. Examples of possible fragrances include natural oils or naturally derived substances, such as hydrocarbons, alcohols, aldehydes, ketones, esters, lactones, ethers, nitriles, and polyfunctional materials, as well as synthetic fragrances. Non-limiting examples of natural oils include: basil (Ocimum basilicum) oil, bay (Pimento acris) oil, bee balm (Monarda didyma) oil, bergamot (Citrus aurantium bergamia) oil, cardamom (Elettaria cardamomum) oil, cedarwood (Cedrus atlantica) oil, chamomile (Anthemis nobilis) oil, cinnamon (Cinnamomum cassia) oil, citronella (Cymbopogon nardus) oil, oleander (Cymbopogon oleander ... nardus) Oil, Salvia (Salvia sclarea) Oil, Clove (Eugenia caryophyllus) Oil, Clove Leaf (Eufenia caryophyllus) Oil, Cyperus esculentus Oil, Cypress (Cupressus sempervirens) Oil, Lemon Eucalyptus (Eucalyptus citriodora) Oil, Geranium maculatum Oil, Ginger (Zingiber officinale) Oil, Grapefruit (Citrus grandis) Oil, Hazel (Corylus avellana) Oil, avellana) Nut Oil, Jasmine (Jasminum officinale) Oil, Juniperus communis Oil, Juniperus oxycedrus Tar, Juniperusvirginiana) oil, kiwi (Actinidia chinensis) water, lavandin (Lavandula hybrida) oil, lavender (Lavandula angustifolia) oil, lavender (Lavandula angustifolia) water, lemon (Citrus medica limonum) oil, lemongrass (Cymbopogon schoenanthus) oil, lime (Citrus aurantifolia) oil, linden (Tilia cordata) oil, linden (Tilia cordata) water, mandarin orange (Citrus nobilis) oil, nobilis) Oil, Nutmeg (Myristica fragrans) Oil, Orange (Citrus aurantium dulcis) Flower Oil, Orange (Citrus aurantium dulcis) Oil, Orange (Citrus aurantium dulcis) Water, Patchouli (Pogostemon cablin) Oil, Peppermint (Mentha piperita) Oil, Peppermint (Mentha piperita) Water, Rosemary (Rosmarinus officinalis) Oil, Rose Oil, Rose (Rosa damascena) Extract, Rose (Rosa multiflora) Extract, Rosewood (Aniba rosaeodora) rosaeodora) extract, sage (Salvia officinalis) oil, sandalwood (Santalum album) oil, spearmint (Menthe viridis) oil, tea tree (Melaleuca alternifolia) oil, and ylang-ylang (Cananga odorata) oil.odorata) oil. Some non-limiting examples of synthetic hydrocarbon fragrances include caryophyllene, β-namethene, limonene, α-pinene, and β-pinene. Some non-limiting examples of synthetic alcohol fragrances include bacdanol, citronellol, linalool, phenethyl alcohol, and α-terpineol (RαH). Some non-limiting examples of synthetic aldehyde fragrances include 2-methylundecanal, citral, hexylcinnamic aldehyde, isocyclocitral, lilial, and 10-undecenal. Some non-limiting examples of synthetic ketone fragrances include cashmeran, α-ionone, isocyclemon E, coavone, muscone, and tonalide. Some non-limiting examples of synthetic ester fragrances include benzyl acetate, 4-t-butylcyclohexyl acetate (cis and trans), cedryl acetate, cyclacet, isobornyl acetate, and α-terpinyl acetate (R=acetyl). Some non-limiting examples of synthetic lactone fragrances include coumarin, jasmine lactone, muscalactone, and peach aldehyde. Some non-limiting examples of synthetic ether fragrances include ambroxan, ANTHER, and galaxolide. Some non-limiting examples of synthetic nitrile fragrances include cinnamonitrile and germonitrile. Finally, some non-limiting examples of synthetic multifunctional fragrances include amyl salicylate, isoeugenol, hedione, heliotropin, lyral, and vanillin.

[0128] The composition may include a blend of flavorings, including a blend of natural and synthetic flavorings. The flavorings may be present in the composition in an amount up to about 5 wt%, preferably about 0.01 to about 3 wt%, about 0.05 to about 1 wt%, and about 0.1 to about 0.2 wt%.

[0129] In some embodiments, the composition may optionally contain preservatives.Generally, preservatives are classified into specific classes, including phenols, halogen compounds, quaternary ammonium compounds, metal derivatives, amines, alkanolamines, nitro derivatives, biguanides, analides, organic sulfur and sulfur-nitrogen compounds, alkylparabens, and various compounds.Some non-limiting examples of phenolic antibacterial agents include pentachlorophenol, orthophenylphenol, chloroxylenol, p-chloro-m-cresol, p-chlorophenol, chlorothymol, m-cresol, o-cresol, p-cresol, isopropylcresol, mixed cresols, phenoxyethanol, phenoxyethylparaben, phenoxyisopropanol, phenylparaben, resorcinol, and their derivatives. Some non-limiting examples of halogen compounds include trichlorohydroxydiphenyl ether (triclosan), sodium trichloroisocyanurate, sodium dichloroisocyanurate, iodine-poly(vinylpyrrolidine-onene) complex, and bromine compounds such as 2-bromo-2-nitropropane-1,3-diol, and their derivatives. Some non-limiting examples of quaternary ammonium compounds include benzalkonium chloride, benzethonium chloride, behentrimonium chloride, cetrimonium chloride, and their derivatives. Some non-limiting examples of amine and nitro-containing compounds include hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine, dithiocarbamates such as sodium dimethyldithiocarbamate, and their derivatives. Some non-limiting examples of biguanides include polyaminopropyl biguanide and chlorhexidine gluconate. Some non-limiting examples of alkylparabens include methyl, ethyl, propyl, and butylparaben. The preservative is preferably present in the composition in an amount of about 0 to about 3 wt%, about 0.1 to about 2 wt%, and about 0.2 to about 1 wt%.

[0130] Other ingredients that may be included are film formers, moisturizers, minerals, viscosity and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, chromalite, mica, conditioners, antiallergic agents, antimicrobial agents (e.g., antifungal, antiviral, antibacterial), disinfectants, pharmaceuticals, light stabilizers, surface smoothing agents, light diffusing agents, and exfoliation promoters. Details regarding these and other suitable cosmetic ingredients may be found on pages 2177-2299 of the International Cosmetic Ingredient Dictionary and Handbook, 10th Edition (2004), published by the Cosmetic, Toiletry, and Fragrance Association (CTFA), which is incorporated herein by reference in its entirety. The amounts of these various substances are those amounts conventionally used in the cosmetic or pharmaceutical arts and may constitute, for example, from about 0.01% to about 20% of the total weight of the composition.

[0131] The composition may include a pH adjuster (e.g., citric acid, ethanolamine, sodium hydroxide, etc.) to be formulated within a wide range of pH levels. In one embodiment, the pH of the topical composition ranges from 1.0 to 13.0. In some embodiments, the pH of the topical composition ranges from 2.0 to 12.0. Other pH ranges suitable for the present compositions include 3.5 to 7.0 or 7.0 to 10.5. Suitable pH adjusters, such as sodium hydroxide, citric acid, and triethanolamine, may be added to bring the pH within the desired range.

[0132] In certain embodiments, a topical composition may be formulated so that it can be applied via, for example, a pen, tube, bottle, brush, stick, sponge, swab, towel (wipe), sprayer, dropper, hand, or finger.

[0133] Topical compositions may be formulated into a variety of product forms, such as, for example, a lotion, cream, serum, spray, aerosol, liquid cake, ointment, essence, gel, paste, patch, pencil, powder, towelette, soap or other cleanser, shampoo, conditioner, stick, foam, mousse, elixir or concentrate.

[0134] In one embodiment, the composition may be provided in the form of a facial mask. The mask may be a peel-off mask or a wash-off mask comprising the composition of the present invention.

[0135] Topical compositions may be formulated, for example, as suspensions, emulsions, nanoemulsions, hydrogels, multiphase solutions, liposomal dispersions, lotions, creams, gels, foams, ointments, pastes, sprays, conditioners, shampoos, masks, cleansers, micellar waters, tonics, makeup (e.g., lipsticks, foundations, bronzers, rouge, eyeshadows), and / or aftershaves.

[0136] The composition may be contained in a container of an appropriate size, for example, taking into consideration the intended use and the intended application method. Thus, the container containing the composition may be, for example, 0.1 gallon to 1,000 gallons or more. The composition may further be contained in a smaller container, such as a bottle (e.g., 1.5 oz, 500 ml, and 1 liter bottle), for dispensing individual doses of the composition.

[0137] How to use The modified sophorolipids of the present invention may be used, for example, for the controlled formation and collapse of foams used in foods, beverages, pharmaceuticals, personal care products, low foaming medical foams, cosmetics, cleaning products, dental care and biotechnology.

[0138] In one embodiment, the modified sophorolipids of the present invention may be useful for controlling foaming in cleaning products. The modified sophorolipids may be incorporated into personal care products and cosmetics to provide a stable foam. The modified sophorolipids may be removed by rinsing.

[0139] In some embodiments, the compositions may be formulated as, for example, a suspension, emulsion, hydrogel, paste, multi-phase solution, vesicular dispersion, liquid, gel, or powder, for use in, for example, toothpaste, mouthwash, oral and / or throat spray, lozenges, breath mints, pens or tubes with brush, sponge, or nozzle applicators, dissolvable strips, dental adhesive tape, toothpicks, chewing gum, tongue scrapers, lip balms, syringes, nasal inhalers, dental floss, and / or other oral care products known in the art.

[0140] In one embodiment, the modified sophorolipids of the present invention may be useful in applications where it is desirable for foam properties to respond to contact with the human body.For example, it may be desirable to modify the stability of food or beverage foams when exposed to the pH and temperature characteristics of the human mouth to modify the flavor release properties, mouthfeel, viscosity or other properties of the foam.Alternatively, it may be desirable to modify the stability of dental foams when exposed to the pH and temperature characteristics of the human mouth or the mouth of certain non-human species, for example, to convert a stable and less active storage form of a dental care product into a more active form.Alternatively, it may be desirable to modify the stability of personal care or cosmetic foams when exposed to the temperature and pH characteristics of human skin, for example, to improve the appearance of a cosmetic or personal care product.In another embodiment, it may be desirable to modify the stability of pharmaceutical foams when exposed to the temperature and pH characteristics of human skin, for example, to improve skin penetration by pharmaceutical products.

[0141] In some embodiments, the present invention is directed to methods for treating / ameliorating skin conditions with compositions comprising the modified sophorolipids or modified SLPs described herein, where a topical cosmetic composition of the present invention is applied directly to the area of ​​skin where such a condition is present.

[0142] As used herein, the term "skin condition" includes any human and animal condition, disorder, or disease that affects the epidermis, dermis (including connective tissue, sebaceous glands, and hair follicles), and / or subcutaneous tissue (hypoderm). Skin conditions that may be treated and / or prevented in certain embodiments using the compositions, products, and methods described herein include, but are not limited to, wounds (including, for example, burns), scars, acne, pimples, rosacea, folliculitis, carcinoma, melanoma, perioral dermatitis, cellulitis, carbuncles, photodamage, skin aging (e.g., wrinkles and dryness), age spots, psoriasis, ichthyosis, atopic dermatitis, rashes (including, but not limited to, erythematous, macular, papular, and / or bullous disorders), chronic wounds, bedsores, keratosis pilaris, sebaceous cysts, vitiligo, melasma, warts, inflammatory skin disorders, allodynia, ectopic dermatitis, telangiectasias, post-inflammatory hyperpigmentation, keratosis, eczema, xerosis, pruritus, lichen planus, prurigo nodularis, microbial infections, body odor, scalp conditions, and miliaria. Symptoms of a skin condition may include, for example, skin irritation / sensitivity, breakouts and other acne-like symptoms, pigmentation or loss thereof, redness, inflammation, wrinkling, dryness, sagging, thickening, scaling, scarring, flaking, rashes, hives, blisters, ulcers, peeling, hair loss, and other changes in skin hygiene, function, and appearance. In some embodiments, the symptoms of a skin condition may also be the skin condition itself.

[0143] In some embodiments, the present invention is directed to a method for treating or preventing acne or acne vulgaris. Acne results from the action of hormones and other impurities on the sebaceous glands and hair follicles of the skin. Acne is a systemic inflammatory disease resulting from blockage of sebaceous glands and hair follicles, which can be infected by the bacteria Propionibacterium acnes (P. acnes). Acne as used herein also includes comedonal acne (or "comedone"), which causes bumpy skin, blackheads, and non-inflammatory breakouts.

[0144] In certain embodiments, a method for treating acne comprises topically administering to a subject an effective amount of a modified sophorolipid of the present invention or a composition comprising a modified sophorolipid. In other embodiments, the composition further comprises a therapeutic agent selected from, for example, a retinoid (e.g., retinol, adapalene, tretinoin, isotretinoin), and an alpha hydroxy acid.

[0145] In some embodiments, the modified sophorolipids alone may be applied topically to affected areas of the skin or may be formulated into a topical skin care composition containing additional ingredients. As discussed above, compositions containing modified sophorolipids may be provided in a variety of forms, including but not limited to creams, lotions, masks, powders, and cleansers. The compositions of the invention may be used in methods for removing makeup and other impurities from the face and skin.

[0146] In a further embodiment, the present invention is directed to a method for treating or preventing various other skin conditions, including hyperpigmentation, wrinkles, and sagging skin. The method comprises topically administering a composition comprising modified sophorolipids or modified SLPs. In a specific embodiment, the composition further comprises salicylic acid, succinic acid, amino acids, retinol, and / or alpha hydroxy acids.

[0147] In certain embodiments, the topical therapeutic composition is applied, for example, every other day, once a day, up to 10 times a day. In some embodiments, the topical composition is applied indefinitely, for example, for at least 1, 2, 3 weeks or more, once a day, every other day, up to 10 times a day, until the skin condition is healed and / or improved.

[0148] In certain embodiments, the composition is rubbed into the skin and the composition is absorbed into the skin. In some embodiments, the composition can be applied to the skin for a period of time (e.g., in the form of a mask) and then washed off the skin, for example, with water.

[0149] In certain embodiments, the skin of the face and neck of a subject is treated according to the present methods. In some embodiments, any part of the skin of a subject may be treated, including, for example, the ears, chest, shoulders, back, arms, underarms, hands, abdomen, buttocks, legs and feet.

[0150] In some embodiments, the present invention provides methods of improving and / or maintaining oral health in a mammalian subject, wherein a composition of the present invention is applied to one or more surfaces of the subject's mouth, lips, or oral cavity, which may include, for example, the subject's teeth, gums, tongue, palate, floor of the mouth, upper jaw, throat, pharynx, tonsils, cheeks, lips (inner and outer), epiglottis, and any tissues or passageways connected thereto.

[0151] In some embodiments, the method further comprises rinsing the composition from one or more surfaces of the mouth, lips, or oral cavity, which may be accomplished, for example, with water or a mouthwash.

[0152] In preferred embodiments, the method may be used to treat and / or prevent plaque, biofilm and / or tartar formation; bad breath; oral infections / abscesses; mouth sores including ulcers, cold sores and / or canker sores; tooth staining; oral candidiasis; oral cancer; gingivitis; tooth decay; periodontal disease; caries; and / or any other oral health condition caused by the presence of bacteria, fungi and / or viruses, such as, for example, inflammatory conditions, tonsillitis, pharyngitis, laryngitis, glossitis, stomatitis, etc.

[0153] In certain embodiments, the method can be used to reduce the number of undesirable microorganisms present in the oral cavity of a subject, thereby allowing for an increase in beneficial and / or commensal microflora.For example, the method can be used to control plaque and tartar buildup, microorganisms that cause bad breath, and those that cause periodontal disease and / or dental caries.

[0154] In some embodiments, the methods may be used to improve healing (e.g., reduce healing time) of open wounds and wounds in the oral cavity, such as canker sores, cold sores, cuts, bites, burns from hot food or drink, surgical incisions, and others caused by tissue trauma.

[0155] In one embodiment, a method is provided for increasing the penetration and / or bioavailability of dental and / or oral hygiene pharmaceutical compounds, in which the composition of the present invention is applied together with the pharmaceutical compound as an adjuvant.For example, the composition can be administered as an adjuvant for painkillers, or as a gel used to treat canker sores or cold sores.Advantageously, the method can allow the concentration of the pharmaceutical compound administered to the subject in need to be reduced while maintaining therapeutic effect. EXAMPLES

[0156] Below are exemplary compounds of the invention, which are offered by way of illustration and are not intended to limit the invention.

[0157] Foam power and foam stability may be determined, for example, by the Ross-Miles method. Examples of modified SLPs of the present invention include, for example, the compounds in Table 1.

[0158] Table 1: Exemplary compounds TIFF2025509276000013.tif223170TIFF2025509276000014.tif217170TIFF20255092760 00015.tif231170TIFF2025509276000016.tif229170TIFF2025509276000017.tif173170

[0159] All patents, patent applications, provisional applications, and publications mentioned or cited in this specification are incorporated by reference in their entirety, including all figures and tables, to the extent not inconsistent with the explicit teachings of this specification.

[0160] It should be understood that the examples and embodiments described herein are for illustrative purposes only, and that various modifications or changes in light thereof will be suggested to those skilled in the art and are within the spirit and scope of the present application.

Claims

1. below: i) Formula (II) ii) Formula (IV) and iii) Formula (V) A compound having a structure selected from During the ceremony, R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, alkylene, substituted alkylene, alkenylene, or substituted alkenylene; R is hydrogen or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + The compound, wherein the cation is selected from the group consisting of:

2. R 1 and R 2 is hydrogen and R 3 2. The compound of claim 1, wherein is methyl.

3. R 4 The compound of claim 1, wherein is a C5 to C15 alkylene or a C5 to C15 alkenylene.

4. The structure: wherein R is hydrogen, or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + 2. The compound of claim 1, wherein the cation is selected from the group consisting of:

5. The structure: wherein R is hydrogen, or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + 2. The compound of claim 1, wherein the cation is selected from the group consisting of:

6. Structure of formula (III): wherein R is hydrogen, or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + 2. The compound of claim 1, wherein the cation is selected from the group consisting of:

7. The structure: wherein R is hydrogen, or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + 2. The compound of claim 1, wherein the cation is selected from the group consisting of:

8. The structure: wherein R is hydrogen, or Na + , K + , Li + , Cs + , Rb + , Ca 2+ , Mg 2+ and N.H. 4 + 2. The compound of claim 1, wherein the cation is selected from the group consisting of:

9. A composition comprising the compound of claim 1.

10. 10. The composition of claim 9, further comprising a pharma- ceutically or cosmetically acceptable carrier.

11. 10. The composition of claim 9, further comprising one or more ingredients selected from viscosity modifiers, skin conditioners, anti-aging ingredients, exfoliants, antioxidants, fragrances, and preservatives.

12. 10. The composition of claim 9, formulated as a suspension, emulsion, nanoemulsion, hydrogel, multiphase solution, liposomal dispersion, lotion, cream, gel, foam, ointment, paste, spray, conditioner, shampoo, cleanser, micellar water, tonic, toothpaste, mouthwash or makeup.

13. Providing a sophorolipid; and Functionalizing the sophorolipid by covalently linking it to taurine via an amide or amine bond A method for improving the foaming performance of a sophorolipid, comprising:

14. The sophorolipid has the structure of formula (I): wherein R 1 and R 2 are each independently selected from hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, alkenyl, and substituted alkenyl; R 3 is hydrogen or alkyl; R 4 is an alkane, alkylene, substituted alkylene, alkenylene or substituted alkenylene; 14. The method of claim 13.

15. R 1 and R 2 is hydrogen and R 3 14. The method of claim 13, wherein is methyl.

16. R 4 is a C5 to C15 alkane, a C5 to C15 alkylene, or a C5 to C15 alkenylene.

17. Providing a sophorolipid; functionalizing the sophorolipid by covalently linking it to taurine via an amide or amine bond; and Mixing the functionalized sophorolipid with a solvent.

10. A method for producing the composition of claim 9, comprising:

18. applying the composition of claim 9 to an area of ​​the skin of a subject.

4. A method for improving a skin condition in a subject, comprising:

19. applying the composition of claim 9 to the mouth, lips or oral cavity surface of a subject.

4. A method for improving and / or maintaining oral hygiene in a subject, comprising:

20. applying the composition of claim 9 to the hair of a subject.

23. A method for cleaning, enhancing and / or maintaining the health of a subject's hair, comprising:

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