Improved foaming biosurfactants

Abstract

The present invention provides modified sophorolipids comprising taurine for improved foaming performance. The present invention also provides compositions comprising modified sophorolipids formulated for use in cosmetics and personal care products. Further provided are methods for improving the skin condition, enhancing and / or maintaining its oral health, and cleansing, enhancing and / or maintaining its healthy hair in a subject.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Patent Application No. 63 / 317,583, filed on March 8, 2022, the contents of which are incorporated herein by reference in their entirety. Background Art

[0003] Foams are metastable dispersions of gas in a liquid matrix, usually stabilized by the adsorption of surfactants at the air-fluid interface. They have applications in various industries including home care, personal care, food, and environmental, petroleum and mineral processing. In products such as beer, consumers expect stable foam, while in other applications such as cleaning or processing, foam may be controlled.

[0004] Biosurfactants are microbially derived amphiphilic molecules that consist of a hydrophobic domain (such as fatty acids, etc.) and a hydrophilic domain (such as sugars, etc.). Due to their amphiphilic nature, biosurfactants can be distributed at the interface between different fluid phases (such as oil / water or water / air interfaces), reduce the surface tension of the fluid and enhance the stability of the bubbles, thereby producing extremely stable foams.

[0005] Other excellent properties of biosurfactants (such as antibacterial properties, emulsification and wetting properties, low toxicity, biodegradability and generation from renewable resources) enable them to be widely used as wetting agents, emulsifiers and detergents in industrial production, agriculture and daily life. More specifically, there is a great demand for biosurfactants in industries such as agriculture, environmental protection, pharmaceuticals, food processing, petroleum production, detergent manufacturing and cosmetics.

[0006] Sophorolipids, one of the most promising and attractive biosurfactants, are a specific glycolipid of interest that combines green chemistry with a lower carbon footprint. Sophorolipids contain sophorose composed of two glucose molecules linked to fatty acids via glycosidic ether bonds. Sophorolipids are classified into two general forms: a lactone form in which the carboxyl group in the fatty acid side chain and the sophorose moiety form a cyclic ester bond; and an acidic form or linear form in which the ester bond is hydrolyzed.

[0007] The fermentation of yeast cells in a medium containing sugars and / or lipids and fatty acids with different carbon chain lengths can be used to produce various sophorolipids. Bombus stamina (Bombus stamina Candida albicans) is one of the most well-known sophorolipid producers. Typically, yeast produces lactic acid sophorolipids and linear sophorolipids during fermentation.

[0008] Sophorolipids are often produced as mixtures of related molecules. The differences between related molecules mainly stem from the following: their fatty acid structure (degree of unsaturation, chain length, position of unsaturation and position of hydroxylation); whether they are produced in linear form or lactone form; acetylation pattern; the presence of stereoisomers; and / or whether the glycosidic bond on the fatty acid is at the ω-position (e.g., terminal) or the ω-1 position (subterminal).

[0009] Consumers are increasingly seeking cleaning and personal care products that are non-toxic, non-irritating to the skin and / or eyes, and have a lower environmental impact, but these safer, more sustainable products are still expected to deliver performance such as cleansing and foaming power.

[0010] Foaming ability and stability are key properties of surfactants. In certain industrial fields, it is often useful to add surfactants that exhibit certain types of surface activity and have desirable foaming properties. Therefore, there is a need for improved foaming biosurfactants for various applications such as personal care products that are effective, low cost, and free of harmful chemicals. Summary of the invention

[0011] The present invention provides compositions with improved foaming properties. Also provided are materials and methods for producing easily modified sophorolipids; and materials and methods for modifying sophorolipids.

[0012] In certain embodiments, taurine is covalently added to a linear acidic sophorolipid via an amide bond, or covalently added to a truncated sophorolipid via an amide bond or secondary amine formation. These modified sophorolipids with improved foaming properties can be purified to be formulated into beauty and personal care products, etc.

[0013] In one embodiment, the present invention provides a modified sophorolipid or a salt thereof, comprising taurine covalently added to the sophorolipid via an amide bond or an amine. In some embodiments, the modified sophorolipid or a salt thereof comprises a truncated fatty acid chain with taurine covalently added to the truncated sophorolipid via an amide bond or an amine.

[0014] In specific embodiments, the compounds of the present invention have a structure selected from the group consisting of:

[0015] i) Formula II:

[0016]

[0017] ii) Formula IV

[0018] and

[0019] iii) Formula V

[0020]

[0021] Where 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, a substituted alkane, an alkylene, a substituted alkylene, an alkenylene or a substituted alkenylene; and R is hydrogen or selected from the group consisting of Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Preferably, R 1 and R 2 is hydrogen; R 4 is a C5-C15 alkane, a C5-C15 alkylene group or a C5-C15 alkenylene group; and R 3 It's methyl.

[0022] 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.

[0023] In one embodiment, the modified sophorolipid of the present invention can be used as a cosmetic cleanser, which has excellent foaming and washing properties, is comfortable to use, and has good biodegradability.

[0024] In one embodiment, the present invention provides a personal care composition or a cosmetic composition for cleansing, conditioning, modifying, beautifying or otherwise enhancing the appearance and / or health of a human or animal.

[0025] Personal care products include skin care products, cosmetics, antiperspirants, deodorants, perfumes, makeup, soaps, bath oils, feminine care products, hair care products, oral hygiene products, depilatories, shampoos, conditioners, hair straightening products, other hair care products, color cosmetics (e.g., lipsticks), face creams, makeup, skin care creams, emulsions (preferably composed of water-in-oil or oil-in-water emulsions), shaving creams and shaving gels, aftershave lotions, shaving conditioning compositions, and sunscreen products, as well as numerous other products, etc. In a preferred embodiment, the personal care compositions according to the present invention include hair care products and skin care products, in particular shampoos, conditioners, rinses, exfoliating products, hair dyes, shower gels, makeup, lipsticks, skin care creams, and other skin care products.

[0026] In one embodiment, the present invention provides a personal care composition comprising, by weight, 1% to 50%, 1% to 40%, 1% to 30%, 5% to 30%, or 10% to 30% of the modified sophorolipid of the present invention.

[0027] In one embodiment, the present invention provides a cosmetic composition comprising, by weight, 1% to 30%, 5% to 30%, 5% to 20%, or 5% to 15% of the modified sophorolipid of the present invention.

[0028] The personal care composition of the present invention can enhance and / or promote the deposition of active compounds on keratin materials, in particular on the hair, comprising at least one step of applying to the keratin materials an effective amount of a composition of the present invention.

[0029] In one embodiment, the present invention provides a shower gel composition, which comprises, by weight, 1% to 50%, 1% to 40%, 1% to 30%, 5% to 30%, or 10% to 30% of the modified sophorolipid of the present invention.

[0030] In one embodiment, the present invention provides a shampoo composition, comprising, by weight, 1% to 50%, 1% to 40%, 1% to 30%, 5% to 30%, or 5% to 20% of the modified sophorolipid of the present invention.

[0031] In one embodiment, the present invention provides a facial cleanser composition, comprising, by weight, 1% to 30%, 5% to 30%, 5% to 20%, or 5% to 10% of the modified sophorolipid of the present invention.

[0032] In one embodiment, the composition of the present invention further comprises a pharmaceutically or cosmetically acceptable carrier. In one embodiment, the composition may further comprise one or more ingredients selected from viscosity modifiers, skin conditioning agents, anti-aging components, exfoliants, antioxidants, fragrances and preservatives.

[0033] In one embodiment, the present invention provides a method for improving the foaming properties of a sophorolipid, the method comprising providing a sophorolipid, and functionalizing the sophorolipid by covalently linking taurine via an amide bond or an amine bond.

[0034] In one embodiment, the present invention provides a method for producing a composition of the present invention, comprising providing a sophorolipid, functionalizing the sophorolipid by covalently linking it to taurine via an amide bond or an amine bond, and mixing the functionalized sophorolipid with a solvent.

[0035] In one embodiment, the present invention provides a method for improving a subject's skin condition, wherein the method comprises applying a composition of the present invention to an area of ​​the subject's skin, and optionally rinsing off the composition.

[0036] In one embodiment, the present invention provides a method for enhancing and / or maintaining oral health of a subject, wherein the method comprises applying a composition of the present invention to the mouth, lips or oral surfaces of the subject, and optionally rinsing off the composition.

[0037] In one embodiment, the present invention provides a method for cleaning, enhancing and / or maintaining healthy hair in a subject, wherein the method comprises applying a composition of the present invention to the subject's hair, and optionally rinsing off the composition. DETAILED DESCRIPTION

[0038] The present invention provides a modified sophorolipid with improved foaming properties. Such sophorolipids can be used as active ingredients in beauty and personal care products (e.g., bath products, anti-acne products, anti-dandruff products, lipsticks, lipsticks and toothpastes). The present invention also provides a composition comprising a modified sophorolipid with improved foaming properties.

[0039] The present invention also provides materials and methods for producing easily modified sophorolipids; and materials and methods for modified sophorolipids. Specifically, taurine is covalently added to linear acidic sophorolipids through amide bonds, or covalently added to truncated sophorolipids through amide bonds or secondary amine formation. These modified sophorolipids with improved foaming properties can be purified to be formulated into beauty and personal care products (e.g., cleansing floss, deodorant, lotion, beauty makeup, hand soap, cleansing milk, shower gel, perfume, shaving cream, moisturizer and shampoo).

[0040] Sophorolipids are glycolipid biosurfactants produced by various yeasts such as Candida albicans. Sophorolipids consist of disaccharide sophorose connected to long-chain hydroxy fatty acids. They may contain partially acetylated 2-O-β-D-pyranose glucopyranose syl-D-pyranose glucopyranose units, which are connected to 17-L-hydroxyoctadecenoic acid or 17-L-hydroxy-Δ9-octadecenoic acid in a β-glycoside manner. Hydroxy fatty acids may have, for example, 11 to 20 carbon atoms and may contain one or more unsaturated bonds. In addition, the sophorose residue may be acetylated at the 6-position and / or 6'-position. The fatty acid carboxyl group can be free (acidic or linear form) or lactonized at the 4" position (lactone form). In most cases, the 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 non-acetylated linear sophorolipids, etc.).

[0041] As used herein, the terms "sophorolipids" and "sophorolipid molecules" include all forms of sophorolipid molecules and isomers thereof, including acidic (straight chain) sophorolipids and lactone sophorolipids, etc. The terms "sophorolipids" and "sophorolipid molecules" further include monoacetylated sophorolipids, diacetylated sophorolipids, esterified sophorolipids, sophorolipids with different hydrophobic chain lengths, sophorolipids attached with fatty acid-amino acid complexes, and other lipids, including sophorolipids described and / or not described in the present disclosure.

[0042] Modified Sophorolipids

[0043] The linear sophorolipid molecule can be represented by the general formula I:

[0044]

[0045] Where 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; and R 4 is an alkane, a substituted alkane, an alkylene group, a substituted alkylene group, an alkenylene group or a substituted alkenylene group. 1 and R 2 is hydrogen; and R 3 It's methyl.

[0046] Sophorolipids can be used as biosurfactants with different fatty acid chain lengths and unsaturation degrees (R 4 ) and in some cases, in R 1 and / or R 2 Acetylation or protonation occurs at the site.

[0047] Examples of the substituent include a halogen atom, a hydroxyl group, a lower (C1-6) alkyl group, a halogenated lower (C1-6) alkyl group, a hydroxy-lower (C1-6) alkyl group, a halogenated-lower (C1-6) alkoxy group, and the like. 4 Typically, it has 11 to 20 carbon atoms. In a preferred embodiment of the present invention, R 4 It has 18 carbon atoms.

[0048] In one embodiment, the present invention provides a modified sophorolipid of Formula II, which comprises taurine covalently added to the sophorolipid via an amide bond.

[0049] In one embodiment, the present invention provides a compound of formula II, which is a modified sophorolipid comprising taurine:

[0050]

[0051] Where R 1and 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, a substituted alkane, an alkylene, a substituted alkylene, an alkenylene or a substituted alkenylene; and R is hydrogen or selected from the group consisting of Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Preferably, R 1 and R 2 is hydrogen; R 3 is methyl; and R 4 It is a C5-C15 alkane, a C5-C15 alkylene group or a C5-C15 alkenylene group.

[0052] In one embodiment, the compound of the present invention is a modified sophorolipid generated by a linear acidic sophorolipid covalently linked to taurine via an amide bond. In a specific embodiment, the modified sophorolipid has a structure of formula III:

[0053]

[0054] Wherein R is hydrogen or selected from such as Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Etc. cations.

[0055] In a preferred embodiment, the modified sophorolipid has the following structure:

[0056]

[0057] Wherein R is hydrogen or selected from such as Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Etc. cations.

[0058] In one embodiment, the present invention provides a modified sophorolipid of Formula IV, which comprises taurine covalently added to a linear sophorolipid via an amine bond.

[0059] In one embodiment, the present invention provides a compound of formula IV, which is a modified sophorolipid:

[0060]

[0061] Where 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, a substituted alkane, an alkylene, a substituted alkylene, an alkenylene or a substituted alkenylene; and R is hydrogen or selected from the group consisting of Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Preferably, R 1 and R 2 is hydrogen; R 3 is methyl; and R 4 It is a C5-C15 alkane, a C5-C15 alkylene group or a C5-C15 alkenylene group.

[0062] In one embodiment, the compound of the present invention has the structure of Formula V:

[0063]

[0064] Where 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, a substituted alkane, an alkylene, a substituted alkylene, an alkenylene or a substituted alkenylene; and R is hydrogen or selected from the group consisting of Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Preferably, R 1 and R 2 is hydrogen; R 3 is methyl; and R 4 It is a C5-C15 alkane, a C5-C15 alkylene group or a C5-C15 alkenylene group.

[0065] In one embodiment, the compound of the present invention is a modified truncated sophorolipid formed by oxidative cleavage of a C18 sophorolipid or a salt thereof. In a specific embodiment, the modified sophorolipid has the following structure:

[0066]

[0067] Wherein R is hydrogen or selected from such as Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Etc. cations.

[0068] In a specific embodiment, the modified sophorolipid comprises taurine, which is derived from a truncated sophorolipid (a sophorolipid with a truncated fatty acid chain) covalently linked to taurine via an amide bond. In a specific embodiment, the modified sophorolipid has the following structure:

[0069]

[0070] Wherein R is hydrogen or selected from such as Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Etc. cations.

[0071] In a specific embodiment, the modified sophorolipid comprises taurine, which is derived from a truncated sophorolipid (a sophorolipid with a truncated fatty acid chain) covalently linked to taurine via an amine. In a specific embodiment, the modified sophorolipid has the following structure:

[0072]

[0073] Wherein R is hydrogen or selected from such as Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + Etc. cations.

[0074] Selected Definitions

[0075] As used herein, the term "foam" refers to a dispersion of gas bubbles in or on a liquid, in a gel, or in a semisolid. The gas bubbles may be dispersed throughout the liquid phase in a heterogeneous or uniform manner. Illustrative examples of foams include gases such as air, nitrogen, oxygen, helium, or hydrogen trapped in a liquid such as water or oil. Foam may be transient, unstable, or stable.

[0076] As used herein, "surfactant" refers to a substance or compound that reduces surface tension when dissolved in water or an aqueous solution, or reduces interfacial tension between two liquids or between a liquid and a solid. Thus, the term "surfactant" includes cationic agents, anionic agents, nonionic agents, zwitterionic agents, amphoteric agents, and / or combinations thereof. "Biosurfactant" refers to a surfactant produced by an organism and / or generated using a naturally derived matrix. "Surfactant" and "biosurfactant" also apply to substances that cause foaming.

[0077] As used herein, the term "alkyl" refers to a straight or branched hydrocarbon group. Suitable alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, and octadecyl. The term alkyl can be prefixed with a specified number of carbon atoms to represent the number of carbon atoms or the 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.

[0078] 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 can be prefixed with a specified number of carbon atoms to represent the number of carbon atoms or the range of carbon atoms that may be present in the alkenyl, such as C1-C10 alkenyl, C1-C20 alkenyl and C10-C20 alkenyl.

[0079] As used herein, "alkenylene" refers to a straight or branched divalent carbon chain (-CR=CR'-, wherein R and R' are each independently hydrogen or other substituents) having one or more carbon-carbon double bonds. "Alkenylene" refers to an unsaturated, branched or straight chain group of 2 to 18 carbon atoms, and has two monovalent radical centers derived by removing two hydrogen atoms from the same or two different carbon atoms of the parent olefin. Examples of alkenylene include -CH=CH-, -CH2CH=CHCH2-, -CH2CH2CH=CHCH2CH2-, -CH2CH=CHCH2CH2CH2-, -CH2CH=CHCH2CH2CH2-, -CH2CH=CHCH2CH2CH=CHCH2-, -CH2CH2CH2CH=CHCH2CH2CH=CHCH2-, -CH2CH2CH2CH=CHCH2CH2CH2-, -CH2CH2CH2CH2CH=CHCH2CH2CH2CH2-, -CH2CH2CH2CH2CH=CHCH2CH2CH2CH=CHCH2CH2CH2-, and the like. The term alkenylene may be prefixed with a designated number of carbon atoms to indicate the number of carbon atoms or range of carbon atoms that may be present in the alkenylene group, for example, C1-C10 alkenylene, C1-C20 alkenylene, and C5-C15 alkenylene.

[0080] As used herein, "alkylene" refers to a divalent saturated, straight-chain or branched aliphatic hydrocarbon group (e.g., ethylene) derived from an alkane by removing two hydrogen atoms from different carbon atoms. Examples of alkylene groups include, but are not limited to, methylene (-CH2-), 1,2-ethyl (-CH2CH2-), 1,3-propyl (-CH2CH2CH2-), 1,4-butyl (-CH2CH2CH2CH2-), -CH(CH3)CH2-, -CH2CH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2CH2CH2CH2-, and the like. The term alkylene group may be prefixed with a specified number of carbon atoms to indicate the number of carbon atoms or a range of carbon atoms that may be present in the alkylene group, such as C1-C10 alkylene, C1-C20 alkylene, and C5-C15 alkylene.

[0081] As used herein, an "isolated" or "purified" nucleic acid molecule, polynucleotide, polypeptide, protein, or organic compound (e.g., small molecule) is substantially free of other compounds (e.g., cellular material) with which it is associated in nature. A purified or isolated polynucleotide (ribonucleic acid (RNA) or deoxyribonucleic acid (DNA)) is free of flanking genes or sequences in its naturally occurring state. A purified or isolated polypeptide is free of other molecules or flanking amino acids in its naturally occurring state. An "isolated" strain refers to a strain that is removed from its naturally occurring environment. Thus, an isolated strain may exist as a biologically pure culture or spores (or other forms of a strain).

[0082] In certain embodiments, the purified compound is at least 60% by weight of the compound of interest. Preferably, the preparation is at least 75%, more preferably at least 90%, and most preferably at least 99% by weight of the compound of interest. For example, the purified compound is at least 90%, 91%, 92%, 93%, 94%, 95%, 98%, 99% or 100% (w / w) by weight of the desired compound. Purity is measured by any appropriate standard method such as column chromatography, thin layer chromatography or high performance liquid chromatography (HPLC) analytical methods.

[0083] The ranges provided herein are understood to be shorthand expressions of all numerical values ​​within the range. For example, a range of 1 to 20 may be understood to be any number, combination of numbers, or subrange in the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20, as well as all decimal values ​​between the above integers, such as 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, and 1.9. With regard to subranges, "nested subranges" extending from either end of the range are particularly contemplated. For example, a nested subrange of an exemplary range of 1 to 50 may include 1 to 10, 1 to 20, 1 to 30, and 1 to 40 in one direction, or 50 to 40, 50 to 30, 50 to 20, and 50 to 10 in another direction.

[0084] 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 include both the growth phase and the product biosynthesis phase of the process.

[0085] As used herein, "broth", "culture broth" or "fermentation broth" refers to a culture medium containing at least nutrients. If the broth refers to the broth after the fermentation process, the broth may also contain microbial growth byproducts and / or microbial cells.

[0086] The microbial growth vessel used according to the present invention can be any fermentation tank or culture reactor for industrial use. As used herein, the term "reactor", "bioreactor", "fermentation reactor" or "fermenter" includes a fermentation device composed of one or more vessels and / or reaction towers or pipeline arrangements. 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, airlift fermenters, static mixers or other vessels or other devices suitable for gas-liquid contact. In some embodiments, the bioreactor may include a first growth reactor and a second fermentation reactor. Therefore, when referring to adding a substrate to a bioreactor or a fermentation reactor, it should be understood that it includes adding a substrate to any one of these reactors or both reactors, where appropriate.

[0087] As used herein, "decrease" refers to a negative change and "increase" refers to a positive change, wherein the change can be 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 ​​therebetween.

[0088] The term "subject" or "patient" as used herein describes an organism, including mammals such as primates. Mammalian species that may benefit from the disclosed treatment methods include, but are not limited to, apes, chimpanzees, orangutans, humans, and monkeys; domestic animals such as dogs and cats; livestock such as horses, cows, pigs, sheep, goats, and chickens; and other animals such as mice, rats, guinea pigs, and hamsters.

[0089] The transitional term "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 ingredient not specified in the claim. The transitional phrase "consisting essentially of" limits the scope of the claim to the specified materials or steps "and those that do not materially affect the basic, novel characteristic." Use of the term "comprising" refers to other embodiments consisting of "consisting of" or "consisting essentially of" the recited components.

[0090] Unless otherwise specified or obvious from the context, the term "or" as used herein should be understood to be inclusive. Unless otherwise specified or obvious from the context, the terms "a", "an", and "the" as used herein should be understood to be singular or plural.

[0091] Unless otherwise specified or apparent from the context, as used herein, the term "about" should be understood to be within the normal tolerance range in the art, such as within 2 standard deviations of the mean. "About" can 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 specified value.

[0092] The narration of a list of chemical groups in any definition of a variable herein includes the definition of the variable as any single group or combination of the listed groups. The narration of an embodiment for a variable or aspect herein includes the embodiment as any single embodiment or in combination with any other embodiment or part thereof. All references cited herein are hereby incorporated herein by reference.

[0093] Production of Sophorolipids

[0094] The present invention provides materials and methods for producing and modifying sophorolipids. Advantageously, the present invention is suitable for industrial-scale production of purified SLPs and uses safe and environmentally friendly materials and processes.

[0095] Sophorolipids are usually obtained by microbial fermentation, which uses fermentation processes involving wild microorganisms or engineered microorganisms, using pure fatty acids, fatty acid mixtures, pure fatty acid esters, fatty acid ester mixtures, triglycerides and carbohydrate sources (such as corn syrup, dextrin and glucose) as carbon sources. The use of renewable substrates and different microbial species to produce sophorolipids, as well as changes in culture parameters (culture time, stirring speed, medium pH and added nutrients), can obtain compounds with different structures and physical properties. This makes it possible to produce a wide variety of compounds that can induce different physical, chemical, biochemical and biophysical properties.

[0096] In a preferred embodiment, the method of the present invention initially comprises producing a standardized sophorolipid molecule to produce a modified and / or purified sophorolipid. In certain embodiments, this requires culturing a sophorolipid-producing yeast in a submerged fermentation reactor containing a customized oleochemical feedstock to produce a yeast culture product, the yeast culture product comprising a fermentation broth, yeast cells, and a sophorolipid having a mixture of two or more molecular structures.

[0097] The mixture of molecular structures may include, for example, lactone sophorolipids, linear sophorolipids, deacetylated sophorolipids, monoacetyl sophorolipids, diacetyl sophorolipids, esterified sophorolipids, sophorolipids with different hydrophobic chain lengths, sophorolipids with attached fatty acid-amino acid complexes, and the like, including sophorolipids described and / or not described in the present disclosure.

[0098] In certain embodiments, the distribution of the mixture of sophorolipid molecules can be altered by adjusting fermentation parameters (eg, feedstock, fermentation time, and dissolved oxygen levels).

[0099] Sophorolipids according to the present invention can be derived from recombinant organisms or naturally produced sophorolipids by fermentation. Non-limiting examples of organisms that produce sophorolipids include Candida bombus, Candida mellifera, Candida bogorii, Yarrowia lipolytica, Candida bombus, Candida globulin, Pseudomonas bogorii, Pseudomonas spp. and Wickham's yeast. It is reported that some recombinant sophorolipid-producing microorganisms can control the structure of sophorolipids. As a non-limiting example, some recombinant Bombus spp. Starmosaccharomyces strains can be used to produce only lactone sophorolipids or only acidic sophorolipids. In addition, recombinant Candida bombus strains with acetyltransferase gene knockout can be used to produce sophorolipids without acetylation.

[0100] In a preferred embodiment, the microorganism is a yeast or fungus. Examples of yeast and fungi suitable for the present invention include, but are not limited to, aconite, Aspergillus, budding short stalk mold (e.g., black yeast), Blakeslea, Candida (e.g., Candida albicans, Candida albicans), Cryptococcus, Debarysaccharomyces (e.g., Hans Debarysaccharomyces), Entomophthora, Fusarium, Hansenula spores (e.g., Hansenula spores), Hansenula, Issaffron, Kluyveromyces, Mortierella, Mucor (e.g., Mucor piriformis), Meyer's yeast (e.g., Meyer's yeast guillemot), Penicillium, Pythium, Phycomyces, Bisporus, The genus Pichia (e.g., Pichia anomala, Pichia guilliermondii, Pichia occidentalis, Pichia kudriavzevii), Pseudomonas (e.g., Pseudomonas aphidoides), Rhizopus, Saccharomyces (e.g., Saccharomyces cerevisiae, Saccharomyces boulardii successor, Saccharomyces cerevisiae), Starmerella (e.g., Starmerella bombus), Torulopsis, Thraustolytica, Trichoderma (e.g., Trichoderma reesei, Trichoderma harzianum, Trichoderma viride), Ustilago (e.g., Ustilago maydis), Wickham's yeast (e.g., Wickham's yeast anomala), Pseudomonas and Zygosaccharomyces (e.g., Zygosaccharomyces bailii).

[0101] In a preferred embodiment, the microorganism is selected from Candida albicans and / or Candida albicans yeasts, such as Candida albicans or Candida albicans, Candida mellifera, Candida batista, Candida floricola, Candida fluvialis, Candida asteroidea and Candida magna. In a specific embodiment, the microorganism is Candida albicans, such as strain ATCC 22214.

[0102] In one embodiment, the fermentation reactor may have functional controls / sensors or may be connected to functional controls / sensors to measure important factors in the culture process, such as pH, oxygen, pressure, temperature, agitator shaft power, humidity, viscosity and / or metabolite concentration, etc.

[0103] In another embodiment, the vessel can also monitor the growth of microorganisms in the vessel (e.g., measuring cell count and growth stage). In addition, samples can be taken from the vessel for enumeration, purity measurement, SLP concentration and / or visible oil level monitoring. For example, in one embodiment, samples can be taken every 24 hours.

[0104] According to the method of the present invention, the microbial inoculant preferably comprises cells and / or propagules of the desired microorganism which may be prepared using any known fermentation method. If desired, the inoculant may be premixed with water and / or liquid growth medium.

[0105] The microorganism of the present invention can be a natural microorganism or a genetically modified microorganism. For example, the microorganism can be transformed with a specific gene to exhibit specific characteristics. The microorganism can be a mutant of a desired strain.

[0106] In one embodiment, a single type of microorganism is grown in a reactor system. In other embodiments, multiple microorganisms may be grown in a single reactor system, and these microorganisms may be grown together without adversely affecting growth or the resulting products. For example, 2 to 3 or more different microorganisms may be grown simultaneously in a single reactor. In some embodiments, more than one microorganism is grown symbiotically in a reactor.

[0107] 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; a fat and oil, such as rapeseed oil, soybean oil, rice bran oil, olive oil, corn oil, sunflower seed oil, sesame oil and / or linseed oil; molasses powder, etc. These carbon sources may be used alone or in combination of two or more.

[0108] In certain embodiments, the culture may be supplemented with a high oleic acid and / or only oleic acid oil chemical feedstock, resulting in a yeast culture product comprising a smaller range of diversity of sophorolipid molecular structures than feedstocks containing other fatty acid sources, wherein the majority of sophorolipid molecules produced contain an 18C carbon chain and a single unsaturated bond located at the ninth carbon atom.

[0109] In one embodiment, the liquid growth medium includes 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 alone or in combination of two or more.

[0110] In one embodiment, the liquid growth medium may further include one or more inorganic salts. The inorganic salts may include potassium dihydrogen phosphate, monopotassium phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, potassium chloride, magnesium sulfate, magnesium chloride, iron sulfate, iron 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, etc. These inorganic salts may be used alone or in combination of two or more.

[0111] In one embodiment, the culture medium includes growth factors and micronutrients for microorganisms. The culture medium may also include inorganic nutrients, which include trace elements such as iron, zinc, copper, manganese, molybdenum and / or cobalt. In addition, the culture medium may also include sources of vitamins, essential amino acids, proteins and trace elements (e.g., corn flour, peptone, yeast extract, potato extract, beef extract, soybean extract, banana peel extract, etc.) or in a purified form. The culture medium may also include amino acids, such as amino acids useful for the biosynthesis of proteins.

[0112] The culture method can further provide oxygenation for the growing culture. One embodiment utilizes slow movement of air to remove low oxygen air and introduce oxygenated air. The oxygenated air can be ambient air that is replenished daily by a mechanical device including an impeller for mechanically agitating the liquid and an air distributor for supplying gas bubbles to the liquid to dissolve oxygen into the liquid.

[0113] In one embodiment, the microorganisms may be grown on a solid or semisolid substrate, such as flours or meals of corn, wheat, soybeans, chickpeas, soy, oatmeal, pasta, rice, and / or these or other similar substances.

[0114] In one embodiment, the culture medium may also include an inorganic salt. Available inorganic salts may be potassium dihydrogen phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, magnesium sulfate, magnesium chloride, iron sulfate, iron 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.

[0115] In some embodiments, for example, when the microorganism used to inoculate the substrate is in spore form (e.g., bacterial endospores), 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 promoters.

[0116] The pH value of the mixture should be suitable for the microorganism of interest. Buffers and pH regulators (e.g., carbonates and phosphates) can be used to stabilize the pH near the preferred value. In certain embodiments, the pH of the culture is adjusted to a favorable level using a base fluid, such as a 15% to 30% or 20% to 25% NaOH solution. The base fluid may be included in the growth medium and / or may be added to a fermentation reactor during the culture process to adjust the pH value as required. When metal ions are present in high concentrations, it may be necessary to use a chelating agent in the liquid culture medium.

[0117] The methods and apparatus for the cultivation of microorganisms and the production of microbial byproducts may be performed as a batch, quasi-continuous or continuous process.

[0118] In one embodiment, the culturing method is carried out at a temperature of about 5°C to about 100°C, about 15°C to about 60°C, about 20°C to about 45°C, about 22°C to about 35°C, or about 24°C to about 28°C. In one embodiment, the culturing can be carried out continuously at a constant pH value. In another embodiment, the culturing may be affected by temperature changes.

[0119] According to the method of the present invention, the microorganism can be cultured in a fermentation system for a period of time sufficient to achieve a desired effect, such as producing a desired amount of cell biomass or a desired amount of sophorolipid.

[0120] In certain embodiments, the fermentation of the yeast culture lasts from about 40 hours to 150 hours, or from about 48 hours to 140 hours, or from about 72 hours to 130 hours, or from about 96 hours to 120 hours. In certain specific embodiments, the fermentation time is from 48 hours to 72 hours or from 96 hours to 120 hours.

[0121] In some embodiments, the sophorolipids produced by the microorganisms of interest can be retained in the microorganisms or secreted into their growth medium. The content of the sophorolipids can be, for example, at least 20%, 30%, 40%, 50%, 60%, 70%, 80% or 90%, etc.

[0122] The growth medium may contain compounds that stabilize the activity of the sophorolipids.The sophorolipids may be purified or the sophorolipids can be used in crude form, meaning that they are not separated from the fermentation broth in which they are produced.

[0123] In certain embodiments, the sophorolipids are isolated and / or purified from a growth medium produced by a microbial fermentation that produces a biosurfactant. Isolation and purification can be easily achieved using standard methods or techniques described in the literature. If necessary, the sophorolipids can be further concentrated.

[0124] Modification of Sophorolipids

[0125] In some embodiments, the modified sophorolipid according to the present invention is obtained by chemically modifying a sophorolipid obtained from a fermentation product of a microorganism that produces a sophorolipid. The sophorolipid to be chemically modified can be obtained by the fermentation method and process described above and / or any other method known in the art. Any suitable technique and chemical reaction known in the art can be used for modifying the sophorolipid. For example, an amide coupling reaction known in the art can be used to form an amide bond between taurine and the carboxyl group of a sophorolipid.

[0126] For example, chemical modifications can also be performed to change the degree of unsaturation on the fatty acid chain. Well-known hydrogenation reactions, dehydrogenation reactions, addition reactions or elimination reactions can be used.

[0127] Sophorolipids containing unsaturated bonds located at specific positions allow for site-specific functionalization of SLP molecules. In certain embodiments, linear SLPs are ozonated with ozone gas. During the ozonolysis of linear SLPs, the olefin portion of the SLP molecule is converted into an ozonide, i.e., a reactive 5-membered ring. In a preferred embodiment, the sophorolipid containing an ozonide is reduced to provide an aldehyde handle. In a specific embodiment, the reducing agent is triphenylphosphine used in an equimolar concentration with the SLP ozonide.

[0128] 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 added to the sophorolipid through amine formation. In certain embodiments, the reducing agent is sodium cyanoborohydride, sodium triacetoxyborohydride or sodium borohydride.

[0129] In some embodiments, the linear sophorinaldehyde is extracted from the aqueous mixture with ethyl acetate and concentrated and dried at a temperature of about 35° C. to 45° C. under reduced pressure (e.g., about 200 mbar to 250 mbar, or about 240 mbar). The dried crude linear sophorinaldehyde can then be dissolved in a reaction medium comprising tetrahydrofuran (THF) and water. The percentage of water used as the reaction medium is preferably no more than 50% water, and is typically between 0% and 25%.

[0130] In certain embodiments, the sophorolipids are subjected to an amination reaction in which taurine is introduced into a 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 be used.

[0131] In some embodiments, a method for producing a modified sophorolipid composition is provided, the method comprising: providing one or more sophorolipid molecules; functionalizing the sophorolipid molecules to covalently link to taurine via an amide bond or an amine bond, thereby forming a modified sophorolipid molecule; and optionally, mixing the modified sophorolipid molecule with a liquid, other sophorolipid molecules, and / or other components specific to the type of product being produced.

[0132] One embodiment relates to a method for producing a modified sophorolipid, the method comprising: obtaining a linear sophorolipid molecule; and functionalizing the linear sophorolipid molecule by converting all or most of the linear SLP molecules into modified sophorolipid molecules.

[0133] Composition

[0134] 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 method of the present invention can be used as an active ingredient in personal care products.

[0135] In some embodiments, the composition comprises, for example, 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% by weight of a modified sophorolipid. In certain embodiments, the composition comprises 0.1% to 50% by weight of a 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 From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%; From about 1% to about 5%

[0136] Optionally, the composition may further comprise one or more other components, including, for example, carriers (such as water, etc.), other biosurfactants, other surfactants (such as polyalkyl glucosides such as caprylyl glucoside and lauryl glucoside), hydrophilic and / or hydrophobic synthetics, sequestrants, builders (such as potassium carbonate, sodium hydroxide, glycerol, citric acid, lactic acid, etc.), solvents (such as water, ethanol, methanol, isopropanol, etc.), organic acids and / or inorganic acids (such as lactic acid, citric acid, boric acid, etc.) , essential oils, plant extracts, cross-linking agents, chelating agents (such as potassium citrate, etc.), fatty acids, alcohols, pH adjusters, reducing agents, calcium salts, carbonates, buffers, enzymes, dyes, colorants, fragrances, preservatives (such as octylisothiazolinone, methylisothiazolinone, etc.), terpenes (such as d-limonene, etc.), sesquiterpenes, terpenes, emulsifiers, demulsifiers, foaming agents, defoaming agents, bleaching agents, polymers, thickeners and / or viscosity increasing agents (such as xanthan gum, guar gum, etc.).

[0137] In some embodiments, the composition comprises additional biosurfactants. Other biosurfactants according to the present invention may include, for example, glycolipids, lipopeptides, flavonoids, phospholipids, fatty acid esters, and high molecular weight biopolymers (such as lipoproteins, lipopolysaccharide-protein complexes and / or polysaccharide-protein-fatty acid complexes, etc.).

[0138] In one embodiment, the additional biosurfactant is a glycolipid, such as rhamnolipid (RLP), cellobiose lipid, trehalose lipid and / or mannoerythritol lipid (MEL), etc. In one embodiment, the biosurfactant is a lipopeptide, such as surfactin, iturin, fengycin, sphingomyelin, anphixin, mucin, lichenin, bacillus, polymyxin and / or octapeptide. In one embodiment, the biosurfactant is another type of amphiphilic molecule, such as esterified fatty acids, saponins, cardiolipin, pullulan, emulsifier, lipman, alasan and / or lipid emulsifier.

[0139] The composition may also contain additional active or inactive ingredients suitable for the mode of application and intended purpose, provided that such addition does not adversely interfere with the function of the modified sophorolipid.

[0140] In certain embodiments, according to the form and / or application mode of the composition, an acceptable carrier may be included in the composition of the present invention. Pharmaceutically or cosmetically acceptable carriers include but are not limited to pharmaceutically acceptable excipients, such as inert diluents, disintegrants, adhesives, lubricants, sweeteners, flavoring agents, coloring agents and preservatives. Suitable inert diluents include sodium carbonate and calcium carbonate, sodium phosphate and calcium phosphate and lactose, while corn starch and alginic acid are suitable disintegrants. Adhesives may include starch and gelatin, while lubricants (if present) are typically magnesium stearate, stearic acid or talc. If necessary or suitable, coating materials such as glyceryl monostearate or distearic acid glyceride may also be used to delay the absorption of the gastrointestinal tract in appropriate circumstances, and the pharmaceutical composition is a solid form.

[0141] In certain embodiments, the present invention provides a topical skin care composition comprising one or more modified sophorolipids. In some embodiments, the topical composition may further include a dermatologically acceptable carrier, and one or more active or inactive cosmetic ingredients, such as vitamins, moisturizers, dyes, fragrances, sunscreens, exfoliants, essential oils, plant extracts, etc.

[0142] Dermatologically acceptable carriers may include, for example, water; saline; physiological saline solution; ointments; creams; oil-in-water emulsions; water-in-oil emulsions; silicone-in-water emulsions; water-in-silicone emulsions; wax-in-water emulsions; water-oil-water triple emulsions; microemulsions; gels; vegetable oils; mineral oils; ester oils such as octyl palmitate, isopropyl myristate and isopropyl palmitate; ethers such as dioctanoate and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, cetearyl alcohol, stearyl alcohol and behenyl alcohol; isoparaffins such as isooctane, isododecane and isohexadecane; silicone oils such as Such as cyclomethicone, dimethicone, dimethicone crosspolymer, polysiloxane, and their derivatives, preferably organic modified derivatives (including PDMS, dimethicone copolyol, dimethiconol and amino dimethicone); hydrocarbon oils such as mineral oil, petrolatum, isoeicosane and polyolefins, such as (hydrogenated) polyisobutylene; polyols such as propylene glycol, glycerol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, etc.; waxes such as beeswax, carnauba wax, ozokerite, microcrystalline wax, polyethylene wax and vegetable wax; or any combination or mixture of the above. The aqueous carrier may include one or more water-miscible solvents (including lower alcohols such as ethanol and isopropanol). The carrier may account for about 1% to about 99%, 10% to about 85%, 25% to 75%, or 50% to about 65% of the composition by weight.

[0143] In certain embodiments, composition is solid form and is suitable for reconstruction in solvent.In other embodiments, composition further comprises solvent.Suitable solvent can be aqueous solvent or non-aqueous solvent, and is preferably applicable to foam formation.In a particular embodiment, solvent is aqueous solvent.The example of suitable solvent comprises water, buffer, acetonitrile, water and alcohol mixture (such as methanol aqueous solution, ethanol aqueous solution and isopropanol aqueous solution etc.).In certain embodiments, foam can optionally comprise emulsion, and this emulsion is the dispersion system of oil in water.

[0144] Non-biological surfactants can also be added to the formulation. Examples of surfactants include, but are not limited to, alkyl sulfates, alkyl ether sulfates (e.g., sodium lauryl sulfate / ammonium lauryl sulfate and sodium laureth sulfate / ammonium laureth sulfate), amphoteric surfactants (e.g., amphoteric acetals and amphoteric propionates), sulfosuccinates, alkyl polyglucosides, betaines (e.g., cocamidopropyl betaine), sulfobetaines, sarcosinates, isethionates, taurates, ethoxylated sorbitan esters, alkanolamides, and amino acid-based surfactants.

[0145] Viscosity modifiers may also be added to the composition and include, for example, cocamide DEA, oleamide DEA, sodium chloride, cellulosic polymers, polyacrylates, ethoxylated esters, alcohols, glycols, xylene sulfonates, polysorbate 20, alkanolamides, and cellulose derivatives (e.g., hydroxypropyl methylcellulose and hydroxyethyl cellulose).

[0146] Polymers may also be added 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 pentaerythritol tetrastearate.

[0147] A sunscreen or combination of sunscreens may be included to protect the skin from UVA and UVB rays. Sunscreens that can be used in the compositions of the present invention include avobenzone, phenylacrylic acid derivatives (such as ethylhexyl methoxycinnamate), octylsalicylate, oxybenzone, octocrylene, titanium dioxide, zinc oxide, or any mixture thereof. The sunscreen may comprise from about 1 wt % to about 30 wt % of the total weight of the composition.

[0148] In one embodiment, the composition may include additional skin active substances, including but not limited to keratolytic agents, keratolytic agents, keratinocyte proliferation promoters, collagenase inhibitors, elastase inhibitors, skin depigmenting agents, anti-inflammatory agents, steroids, anti-acne agents, antioxidants (such as ascorbic acid, etc.), advanced glycation end products (AGE) inhibitors, exfoliants (such as glycolic acid, 3,6,9-trioxoundecanedioic acid, etc.), estrogen synthase stimulating compounds (such as caffeine and derivatives, etc.), compounds capable of inhibiting 5α-reductase activity (such as linolenic acid, linoleic acid, finasteride, and mixtures thereof, etc.), barrier function enhancers (such as ceramides, glycerides, cholesterol and its esters, α-hydroxy fatty acids and ω-hydroxy fatty acids and their esters, etc.), and retinoic acid.

[0149] The composition may optionally include additives, adjuvants or other components of topical compositions known to those skilled in the art, including but not limited to: transdermal absorption enhancers; emollients (such as isopropyl myristate, petrolatum, volatile or non-volatile silicone oils, such as methicone and polydimethylsiloxane, ester oils, mineral oils and fatty acid esters); humectants (such as glycerol, hexylene glycol, caprylyl glycol, etc.); skin plumpers (such as palmitoyl oligopeptides, collagen, collagen and / or glycosaminoglycan (GAG) enhancers, etc.); anti-inflammatory agents (such as aloe vera, bioflavonoids, etc.); ketone, diclofenac, salicylic acid); chelating agents (such as EDTA or its salts, such as disodium EDTA); vitamins (such as tocopherol and ascorbic acid); vitamin derivatives (such as ascorbyl monopalmitate, tocopheryl acetate, vitamin E palmitate); thickeners (such as hydroxyalkyl cellulose, carboxymethyl cellulose, carbomer and vegetable gums, such as xanthan gum); gelling agents (such as ester-terminated polyesteramides); structuring agents; proteins (such as lactoferrin); immunomodulators (such as corticosteroids and non-steroidal immunomodulators). Other examples include, but are not limited to: stabilizers; fragrances; film formers; insect repellents; skin cooling compounds; skin protectants; lubricants; preservatives; pearls; chromates; mica; conditioning agents; antiallergic drugs; pH adjusters; and antibacterial drugs.

[0150] In some embodiments, the topical composition may also include additional adjuvants and additives commonly included in skin care compositions, such as organic solvents, stabilizers, silicones, thickeners, emollients, sunscreens, moisturizers, fragrances, or other substances described herein. The amount of each active ingredient or inactive ingredient is the amount usually used in the cosmetic field to achieve its intended purpose, usually accounting for about 0.0001% to about 25%, or about 0.001% to about 20% of the composition, although these amounts may exceed these ranges. The nature of these ingredients and their amounts must be consistent with the production and function of the compositions disclosed herein.

[0151] In certain embodiments, the composition may optionally include a skin conditioner, such as an emollient, a moisturizer, an occlusive or other moisturizer to provide moisturizing, skin softening, skin barrier maintenance, anti-irritation or other skin health benefits. Some non-limiting examples of emollients include alkyl benzoates, myristyl myristate, isopropyl cetyl, glyceryl dioleate, methyl laurate, PPG-9 laurate, allantoin laurate lactate, octyl palmitate, lanolin, propylene glycol, butylene glycol, ethylene glycol monobutyl ether, glycerol, fatty acids, natural oils (such as almond oil, mineral oil, rapeseed oil, sesame oil, soybean oil, wheat germ oil, corn oil, peanut oil and olive oil, etc.), isopropyl myristate, myristyl alcohol, aloe, 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, balsammint oil, cod liver oil, mineral oil, trimyristin, stearyl stearate, synthetic wax, or mixtures thereof. Some non-limiting examples of other moisturizers include ethylhexylglycerin, cholesterol, cystine, hyaluronic acid, keratin, lecithin, egg yolk, glycine, PPG-12, polyquaternium polymers (such as polyquaternium-11, behentrimonium chloride, dihydroxypropyl PEG-5 linoleyl ammonium chloride, etc.), oleyl glyceryl, PEG-7 cocoyl glyceryl, coco-glucoside, PEG-200 hydrogenated glyceryl palmitoleate, panthenol, retinol, salicylic acid, vegetable oils, methyl gluceth-10, methyl gluceth-20, ethoxylated derivatives of skin conditioning agents (such as glyceryl-26 and ethoxylated shea butter, etc.), and mixtures thereof. Finally, some non-limiting examples of anti-irritants include bisabolol and panthenol.

[0152] Those skilled in the art will recognize the different strengths of different skin conditioning agents and formulate accordingly. In some embodiments, the skin conditioning agent is preferably present in the composition in an amount of about 0.01 wt.% to about 20 wt.%, about 0.05 wt.% to about 15 wt.%, and about 0.1 wt.% to about 10 wt.%.

[0153] In some embodiments, the composition may optionally include molecules that enhance the "feel" of the composition on the user's skin or hands. For example, it may be undesirable for the composition to have a flaky or gritty texture when the composition is applied to the user's skin or after multiple applications. Some non-limiting examples include silicone copolymers, such as amodimethicone, cyclomethicone, bis-PEG / PPG-20 / 20 dimethicone, and stearoxytrimethylsilane, naturally occurring or synthetic fatty acid esters or ethers, and polyalkylene glycols. If a silicone copolymer is included, it is preferably present in the composition in an amount of about 0.001 wt.% to about 5 wt.%, about 0.01 wt.% to about 3 wt.%, and about 0.1 wt.% to about 2 wt.%.

[0154] In one embodiment, the composition may include anti-aging components, including but not limited to plant extracts (e.g., Butea superba extract); phytol; phytanic acid; phospholipids; silicones; petrolatum; triglycerides; omega fatty acids; retinoic acid; hydroxy acids (including α-hydroxy acids and β-hydroxy acids); salicylic acid and alkyl salicylates; exfoliants (such as glycolic acid, 3,6,9-trioxoundecanedioic acid, etc.), estrogen synthase stimulating compounds (such as caffeine and derivatives, etc.), compounds capable of inhibiting 5α-reductase activity (such as linolenic acid, linoleic acid, finasteride, and mixtures thereof); and barrier function enhancers (such as ceramides, glycerides, cholesterol and esters thereof, α-hydroxy fatty acids and β-hydroxy fatty acids and esters thereof),

[0155] Exemplary retinoic acids include, but are not limited to, retinoic acid (such as all-trans retinoic acid, 9-cis retinoic acid or 13-cis retinoic acid, etc.) and derivatives thereof, retinal, retinol (vitamin A) and esters thereof, such as retinyl palmitate, retinyl acetate and retinyl propionate, and salts thereof. When retinoic acid is present, the retinoic acid content is typically from about 0.0001% to about 5%, more typically from about 0.01% to about 2.5%, or from about 0.1% to about 1.0% by weight.

[0156] In one embodiment, the composition may include an exfoliant. Suitable exfoliants include, for example, alpha hydroxy acids, beta hydroxy acids, oxalic acid, and their derivatives (e.g., esters, anhydrides, and salts). Suitable hydroxy acids include glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, 2-hydroxyalkanoic acid, mandelic acid, salicylic acid, and their derivatives. An exemplary exfoliant is glycolic acid. When an exfoliant is present, the exfoliant may comprise from about 0.001% to about 20% of the composition by weight.

[0157] In one embodiment, the composition may include one or more antioxidants. Suitable antioxidants include, for example, compounds with phenolic hydroxyl functional groups, such as ascorbic acid and its derivatives / esters, etc.; beta-carotene; catechins; curcumin; ferulic acid derivatives (such as ethyl ferulate, sodium ferulate, etc.); gallic acid derivatives (such as propyl gallate, etc.); lycopene; reducing acid; rosmarinic acid; tannic acid; tetrahydrocurcumin; tocopherol and its derivatives (including tocopherol acetate); uric acid; or any mixture thereof. Other suitable antioxidants are antioxidants in reduced or non-reduced form with one or more thiol functional groups (-SH), such as glutathione, lipoic acid, thioglycolic acid and other sulfhydryl compounds. Antioxidants may be inorganic antioxidants, such as bisulfite, metabisulfite, sulfite, or other sulfur-containing inorganic salts and acids. The antioxidants may individually or collectively comprise from about 0.001% to about 10% (w / w), or from about 0.01% to about 5% (w / w), based on the total weight of the composition.

[0158] In some embodiments, the composition may optionally include a fragrance. Examples of possible fragrances include natural oils or naturally derived materials, as well as synthetic fragrances (such as hydrocarbons, etc.), alcohols, aldehydes, ketones, esters, lactones, ethers, nitriles, and polyfunctional groups. The following are non-limiting examples of natural oils: basil oil (Ocimum basilicum), bay oil (Pimento acris), lemon balm (Monarda didyma), bergamot oil (Citrus aurantium bergamia), cardamom (Elettaria cardamomum), cedarwood oil (Cedrus atlantica), chamomile oil (Anthemisnobilis), cinnamon (Cinnamomum cassia), lemongrass oil (Cymbopogon nardus), clary sage oil (Salvia sclarea), clove oil (Eugenia caryophyllus), clove leaf (Eugeniacaryophyllus), cypress oil (Cyperus esculentus), cypress oil (Cupressus sempervirens), lemon eucalyptus (Eucalyptus citriodora), geranium oil (Geranium maculatum oil, ginger (Zingiberofficinale) oil, grapefruit (Citrus grandis) oil, hazelnut (Corylus avellana) nut oil, jasmine (Jasminum officinale) oil, European juniper (Juniperus communis) oil, European juniper (Juniperusoxycedrus) tar, Virginia juniper (Juniperus virginiana) oil, kiwi fruit (Actinidiachinensis) water, hybrid lavender (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, orange (Citrus nobilis oil, nutmeg (Myristica fragrans) oil, orange blossom (Citrus aurantium dulcis) oil, sweet orange (Citrus aurantiumdulcis oil, sweet orange (Citrusaurantium dulcis) water, patchouli (Pogostemon cablin) oil, peppermint (Menthe piperita) oil, peppermint (Menthe peperita) water, rosemary (Rosmarinus officinalis) oil, rose oil, damask rose (Rosadamascena) extract, multiflora rose (Rosa multiflora) extract, rosewood (Aniba 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. Some non-limiting examples of synthetic hydrocarbon fragrances include caryophyllene, β-farnesene, limonene, α-pinene and β-pinene. Some non-limiting examples of synthetic alcohol fragrances include santalol, citronellol, linalool, phenylethyl alcohol and α-terpineol (RαH). Some non-limiting examples of synthetic aldehyde fragrances include 2-methylundecyl aldehyde, citral, hexyl cinnamaldehyde, isocitral, lily of the valley aldehyde and 10-undecenal. Some non-limiting examples of synthetic ketone fragrances include cashmeranone, α-ionone, ambroxanone, koavone, musk ketone and tonafol. Some non-limiting examples of synthetic ester fragrances include benzyl acetate, 4-tert-butyl cyclohexyl acetate (cis and trans), cedryl acetate, tricyclodecenyl acetate, isobornyl acetate and α-terpineol acetate (R=acetyl). Some non-limiting examples of synthetic lactone fragrances include coumarin, jasmine lactone, cyclopentadecalactone and peach aldehyde. Some non-limiting examples of synthetic ether fragrances include ambroxan, anther and galaxol. Some non-limiting examples of synthetic nitrile fragrances include cinnamon nitrile and geranyl nitrile.Finally, some non-limiting examples of synthetic multifunctional fragrances include amyl salicylate, isoeugenol, dimethicone, piperonal, lyral and vanillin.

[0159] The composition may include a mixture of fragrances, including a mixture of natural and synthetic fragrances. The fragrance may be present in the composition in an amount up to about 5 wt.%, preferably from about 0.01 wt.% to about 3 wt.%, from about 0.05 wt.% to about 1 wt.%, and from about 0.1 wt.% to about 0.2 wt.%.

[0160] In certain embodiments, composition can optionally include preservative.In general, preservative is divided into specific categories, including phenolic, halogen compounds, quaternary ammonium compounds, metal derivatives, amines, alkanolamines, nitro derivatives, biguanides, analides, organic sulfur and sulfur nitrogen compounds, alkyl-to-alkylbenzenes and miscellaneous compounds.Some non-limiting examples of phenolic antimicrobial agents include pentachlorophenol, o-phenylphenol, chloroxylenol, parachlorometacresol, parachlorophenol, chlorothymol, metacresol, o-cresol, p-cresol, isopropylcresol, mixed cresols, phenoxyethanol, hydroxybenzophenoxyethyl ester, phenoxyisopropanol, phenyl parahydroxybenzoate, resorcinol, and their derivatives.Some non-limiting examples of halogen compounds include trichlorohydroxydiphenyl ether (triclosan), sodium trichloroisocyanurate, sodium dichloroisocyanurate, iodine-poly (vinyl pyrrolidone) 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, behenyl trimethyl ammonium chloride, cetrimonium chloride, and their derivatives. Some non-limiting examples of amines and nitro-containing compounds include hexahydro-1,3,5-tri-(-2-hydroxyethyl)-s-triazine, dithiocarbamates (such as sodium dimethyl dithiocarbamate, etc.), and their derivatives. Some non-limiting examples of biguanides include polyaminopropyl biguanide and chlorhexidine gluconate. Some non-limiting examples of alkyl-to-alkylbenzenes include methylparaben, ethylparaben, propylparaben and butylparaben. Preservatives are preferably present in the composition in an amount of about 0wt.% to about 3wt.%, about 0.1wt.% to about 2wt.% and about 0.2wt.% to about 1wt.%.

[0161] Other components that may be included include film formers, moisturizers, minerals, viscosity and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, chromite, mica, conditioners, antiallergic agents, antimicrobial agents (such as antifungal agents, antiviral agents, antibacterial drugs, etc.), preservatives, pharmaceutical preparations, light stabilizers, surface smoothing agents, optical diffusers and exfoliating promoters. Detailed information about these and other suitable cosmetic ingredients can be found in the International Cosmetic Raw Materials Dictionary and Handbook (10th Edition) (2004) published by the American Cosmetic, Toiletries and Perfume Association (CTFA), pages 2177 to 2299, the entire contents of which are incorporated herein by reference. The amounts of these various substances are those commonly used in cosmetics or pharmaceutical fields, for example, they can account for about 0.01% to about 20% of the total weight of the composition.

[0162] The composition may include a pH adjusting agent (e.g., citric acid, ethanolamine, sodium hydroxide, etc.) to prepare in a wide range of pH levels. In one embodiment, the pH range of the topical composition is 1.0 to 13.0. In certain embodiments, the pH range of the topical composition is 2.0 to 12.0. Other pH ranges suitable for the test composition include 3.5 to 7.0 or 7.0 to 10.5. Appropriate pH adjusting agents (e.g., sodium hydroxide, citric acid, and triethanolamine) may be added to adjust the pH value to within the desired range.

[0163] In certain embodiments, the topical composition can be formulated so that it can be applied by pen, tube, bottle, brush, stick, sponge, cotton swab, wipes (wipes), sprayer, dropper, hand or fingers, etc.

[0164] The topical composition can be formulated into a variety of product forms, such as lotions, creams, serums, sprays, aerosols, liquid cakes, ointments, essences, gels, pastes, patches, pencils, powders, wipes, soaps or other cleansers, shampoos, conditioners, bars, foams, mousses, elixirs, or concentrates.

[0165] In one embodiment, the composition can be provided in the form of a facial mask. The facial mask can be a peel-off facial mask or a rinse-off facial mask comprising the composition of the present invention.

[0166] The topical composition can be formulated as a suspension, emulsion, nanoemulsion, hydrogel, multiphase solution, liposomal dispersion, lotion, cream, gel, foam, ointment, paste, spray, conditioner, shampoo, mask, cleanser, micellar water, tonic, make-up (e.g., lipstick, foundation, bronzer, rouge, eye shadow), and / or aftershave.

[0167] The composition can be placed in a container of appropriate size, taking into account the intended use and the intended method of application. Thus, the container in which the composition is placed can be, for example, 0.1 gallons to 1000 gallons or more. The composition can also be placed in smaller containers for dispensing individual doses of the composition, such as bottles (such as 1.5 ounces, 500 milliliters, and 1 liter bottles).

[0168] How to use

[0169] The modified sophorolipids of the present invention can be used for the controlled formation and collapse of foams used in, for example, foods, beverages, pharmaceuticals, personal care products, low-layer medical foams, cosmetics, cleaning products, dental care and biotechnology.

[0170] In one embodiment, the modified sophorolipids of the present invention can be used to control foaming in cleaning products. The modified sophorolipids can be incorporated into personal care products and cosmetics to provide stable foam. The modified sophorolipids can be removed by rinsing.

[0171] In some embodiments, the composition can be formulated as a suspension, emulsion, hydrogel, paste, multiphase solution, vesicular dispersion, liquid, gel or powder for use in applications such as toothpaste, mouthwash, mouth and / or throat spray, lozenges, breath fresheners, pens or tubes with brush, sponge or nozzle applicators, dissolvable strips, tape for teeth, toothpicks, chewing gum, tongue scrapers, lip balm, syringes, nasal aspirators, dental floss, and / or any other oral care product known in the art.

[0172] In one embodiment, the modified sophorolipids of the present invention can be used for applications where the properties of the desired foam are responsive to contact with the human body. For example, it is desirable to change the stability of food or beverage foams when exposed to the pH and temperature characteristics of the human oral cavity, thereby changing the flavor release characteristics, mouthfeel, viscosity or other characteristics of the foam. Alternatively, it may be necessary to change the stability of dental foams when exposed to the pH and temperature characteristics of the human oral cavity or the oral cavity of a particular non-human species, such as converting a storage form of a dental care product with low stability and activity into a more active form. Alternatively, it may be necessary to change the stability of personal care or cosmetic foams when exposed to the temperature and pH characteristics of human skin, such as improving the appearance of cosmetics or personal care products. In another embodiment, it may be necessary to change the stability of pharmaceutical foams when exposed to the temperature and pH characteristics of human skin, such as improving the skin permeability of pharmaceutical products.

[0173] In some embodiments, the present invention is directed to a method of treating / improving a skin condition with a modified sophorolipid or a composition comprising a modified SLP as described herein, wherein the topical cosmetic composition of the present invention is applied directly to the area of ​​the skin where the condition exists.

[0174] As used herein, the term "skin condition" includes any human and animal condition, disease or disorder affecting the epidermis, dermis (including connective tissue, sebaceous glands and hair follicles), and / or subcutaneous tissue (subcutaneous tissue). In certain embodiments, skin conditions that can be treated and / or prevented using the compositions, products, and methods described herein include, but are not limited to, wounds (including burns, etc.), scars, acne, blemishes, rosacea, folliculitis, cancer, melanoma, perioral dermatitis, cellulitis, carbuncles, photodamage, skin aging (such as wrinkles and dryness, etc.), age spots, psoriasis, ichthyosis, atopic dermatitis, rashes (including but not limited to erythematous, yellow, papular and / or bullous diseases), chronic wounds, bedsores, keratosis pilaris, sebaceous cysts, vitiligo, melasma, warts, inflammatory skin diseases, allodynia, atopic dermatitis, telangiectasia, post-inflammatory pigmentation, keratosis, eczema, dryness, itching, lichen planus, prurigo nodularis, microbial infections, body odor, scalp conditions, and milia, etc. Symptoms of a skin condition may include, for example, skin irritation / sensitivity, blemishes and other acne-like symptoms, hyperpigmentation or loss, flushing, inflammation, wrinkles, dryness, sagging, thickening, peeling, scarring, flaking, rashes, hives, blisters, ulcers, scaling, hair loss, and other changes in skin health, function, and appearance. In some embodiments, a symptom of a skin condition may also be the skin condition itself.

[0175] In some embodiments, the present invention relates to a method for treating or preventing acne or acne vulgaris. Acne is caused by the action of hormones and other impurities in the sebaceous glands and hair follicles of the skin. Acne is a systemic inflammatory disease caused by blockage of sebaceous glands and hair follicles, which can be infected by Propionibacterium acnes (P. acne). Acne as used herein also includes comedonal acne (or "acne"), which causes uneven skin, blackheads and non-inflammatory blemishes.

[0176] In certain embodiments, the method for treating acne comprises topically applying 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, retinoic acid (e.g., retinol, adapalene, tretinoin, isotretinoin) and α-hydroxy acids.

[0177] In some embodiments, the modified sophorolipids can be topically applied alone to the affected area of ​​the skin, or prepared into a topical skin care composition comprising additional ingredients. As described above, the composition comprising the modified sophorolipids can be provided in a variety of forms, including but not limited to creams, lotions, masks, powders and cleansers. The compositions of the present invention can be used in methods for removing makeup and other impurities from the face and skin.

[0178] In a further embodiment, the present invention relates to a method for treating or preventing various other skin conditions, including hyperpigmentation, wrinkles and skin sagging. The method comprises topically applying a modified sophorolipid or a composition comprising a modified SLP. In a specific embodiment, the composition further comprises salicylic acid, succinic acid, an amino acid, retinol and / or an alpha-hydroxy acid.

[0179] In certain embodiments, the topical therapeutic composition is applied every other day, once a day, up to ten times a day. In some embodiments, the topical composition is applied every other day, once a day, up to ten times a day, for an indefinite period of time (e.g., at least one week, two weeks, three weeks, or longer) until the skin condition heals and / or improves.

[0180] In certain embodiments, the composition is rubbed into the skin to allow the composition to be absorbed by 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 rinsed from the skin using, for example, water.

[0181] In certain embodiments, the face and neck skin of a subject is treated according to the methods of the present invention. In certain embodiments, any part of the subject's skin can be treated, including the ears, chest, shoulders, back, arms, underarms, hands, stomach, buttocks, legs, and feet, etc.

[0182] In some embodiments, the present invention provides a method of enhancing and / or maintaining oral health in a mammalian subject, wherein a composition of the present invention is applied to the subject's mouth, lips, or one or more surfaces of the oral cavity. The one or more surfaces may include, for example, the subject's teeth, gums, tongue, palate, floor of the mouth, roof of the mouth, throat, pharynx, tonsils, cheeks, lips (inside and outside), epiglottis, and any tissues or passages connected thereto.

[0183] In some embodiments, the method further comprises rinsing the composition from the mouth, lips, or one or more surfaces of the mouth. This can be done with, for example, water or a mouthwash.

[0184] In preferred embodiments, the methods can be used to treat and / or prevent the formation of dental plaque, biofilm and / or tartar; bad breath; oral infections / abscesses; oral ulcers, including ulcers, cold sores and / or canker sores; tooth discoloration; thrush; oral cancer; gingivitis; tooth decay; periodontal disease; caries; and / or any other oral health condition caused by bacteria, fungi and / or viruses, such as inflammation, tonsillitis, pharyngitis, laryngitis, glossitis, stomatitis, etc.

[0185] In certain embodiments, the methods can be used to reduce the number of undesirable microorganisms present in the oral cavity of a subject, thereby increasing the population of beneficial and / or commensal microorganisms. For example, the methods can be used to control microorganisms that cause plaque and tartar accumulation on teeth, bad breath, and periodontal disease and / or tooth decay.

[0186] In some embodiments, the methods can be used to enhance healing (e.g., shorten healing time) of open sores and wounds in the oral cavity, such as ulcers, cold sores, cuts, bites, burns from hot food or beverages, surgical incisions, and other wounds caused by tissue trauma.

[0187] In one embodiment, a method for increasing the permeability and / or bioavailability of a dental and / or oral health pharmaceutical compound is provided, wherein the composition of the present invention is applied as an adjuvant with the pharmaceutical compound. For example, the composition can be administered as an adjuvant to an analgesic or as a gel for treating ulcers or cold sores. Advantageously, the method can allow for the administration of a reduced concentration of the pharmaceutical compound to a subject in need thereof while maintaining therapeutic effectiveness.

[0188] Examples

[0189] The following are exemplary compounds of the present invention, which are provided by way of illustration and are not intended to limit the present invention.

[0190] The foaming ability and foam stability can be determined by the Ross-Myers method, etc. Examples of the modified SLP of the present invention include the compounds in Table 1, etc.

[0191] Table 1. Exemplary compounds.

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] All patents, patent applications, provisional applications, and publications (including all figures) referenced or cited herein are hereby incorporated by reference in their entirety to the extent not inconsistent with the explicit teachings of this specification.

[0198] It should be understood that the examples and embodiments described herein are for illustrative purposes only, and that those skilled in the art may make various modifications or changes based on these examples and embodiments, which should be included in the spirit and scope of the present application.

Claims

1. A compound having a structure selected from the following formulae: i) Formula II: ii) Formula IV and iii) Formula V Where 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, an alkylene, a substituted alkylene, an alkenylene or a substituted alkenylene; and R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

2. The compound according to claim 1, wherein R 1 and R 2 is hydrogen; and R 3 It's methyl.

3. The compound according to claim 1, wherein R 4 It is a C5-C15 alkylene group or a C5-C15 alkenylene group.

4. The compound according to claim 1, which has the following structure: Where R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

5. The compound according to claim 1, which has the following structure: Where R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

6. The compound according to claim 1, which has the structure of formula III: Where R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

7. The compound according to claim 1, which has the following structure: Where R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

8. The compound according to claim 1, which has the following structure: Where R is hydrogen or selected from Na + , K + , Li + , Cs + , Rb + , Ca 2+ Mg 2+ and NH4 + of cations.

9. A composition comprising the compound according to claim 1.

10. The composition according to claim 9, further comprising a pharmaceutically or cosmetically acceptable carrier.

11. The composition according to claim 9, further comprising one or more ingredients selected from the group consisting of viscosity modifiers, skin conditioning agents, anti-aging components, exfoliants, antioxidants, fragrances, and preservatives.

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

13. A method for improving the foaming performance of a sophorolipid, the method comprising providing the sophorolipid, and functionalizing the sophorolipid by covalently linking taurine via an amide bond or an amine bond.

14. The method of claim 13, wherein the sophorolipid has the structure of formula I: Where 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; and R 4 It is an alkane, an alkylene group, a substituted alkylene group, an alkenylene group or a substituted alkenylene group.

15. The method according to claim 13, wherein R 1 and R 2 is hydrogen; and R 3 It's methyl.

16. The method according to claim 13, wherein R 4 It is a C5-C15 alkane, a C5-C15 alkylene group or a C5-C15 alkenylene group.

17. A method for producing the composition according to claim 9, comprising providing a sophorolipid, functionalizing the sophorolipid by covalently linking it to taurine via an amide bond or an amine bond, and mixing the functionalized sophorolipid with a solvent.

18. A method for improving a subject's skin condition, wherein the method comprises applying the composition of claim 9 to an area of ​​the subject's skin.

19. A method for enhancing and / or maintaining oral health in a subject, wherein the method comprises applying the composition according to claim 9 to the mouth, lips or oral surfaces of the subject.

20. A method for cleaning, enhancing and / or maintaining healthy hair in a subject, wherein the method comprises applying the composition according to claim 9 to the hair of the subject.

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