Biobased-fatty acid arginates
Inventors
Lew, Helen N • Fan, Xuetong • Huang, Kun • Zhang, Jianwei
Assignees
US Department of Agriculture USDA
Publication Number
US-11840499-B2
Publication Date
2023-12-12
Expiration Date
2041-02-26
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Abstract
A biobased fatty acid arginate may be synthesized according to the disclosed process by combining arginine and a fatty acid. The fatty acid arginate may have certain beneficial properties, such as surfactant properties or acting as an antimicrobial agent.
Core Innovation
The invention discloses biobased fatty acid arginates synthesized by combining arginine and a fatty acid, resulting in compounds with surfactant and antimicrobial properties. The fatty acid arginate compounds may have a linear or branched aliphatic chain of length C6-C24, optionally with alkyl or phenolic group substituents, and include specific examples such as oleic arginate, isooleic arginate, stearic arginate, and isostearic arginate.
The invention addresses problems arising from the need for new, harmless, and environmentally friendly antimicrobial agents that can overcome limitations of current synthetic antimicrobials and antimicrobial resistance. There is concern about sustainability and toxicity especially for use in food and personal care products, and the disclosed fatty acid arginates provide an alternative to petroleum-based materials and existing agents such as ethyl lauroyl arginate (LAE).
The fatty acid arginates are produced by halogenation of fatty acids, with a stepwise process differing for phenolic fatty acids due to hydroxyl group protection. These compounds exhibit effective antimicrobial activity against microbes, including the capability to kill or inhibit microbial growth, and demonstrate strong surfactant properties with lower critical micelle concentration than existing commercial surfactants. Thus, the invention provides a new family of biobased antimicrobials and surfactants with improved performance characteristics.
Claims Coverage
The patent claims include nine claims comprising three independent claims: a chemical composition, antimicrobial methods, and methods of production of fatty acid arginates. The main inventive features cover the chemical structure, antimicrobial applications, and synthesis methods of fatty acid arginates.
A chemical composition of fatty acid arginate compounds
This feature claims a chemical composition comprising a compound with the formula where R is a linear or branched aliphatic chain of length C6-C24 with optional alkyl or phenolic substituents, including specific examples such as oleic arginate, isooleic arginate, stearic arginate, and isostearic arginate.
Methods of killing or inhibiting microbes using effective amounts of the composition
This covers methods of killing microbes or inhibiting their growth on objects or areas by exposing them to an effective amount of the fatty acid arginate composition, emphasizing antimicrobial functionality.
Methods of producing fatty acid arginates from fatty acids
This includes distinct methods for producing fatty acid arginates by first halogenating a non-phenolic fatty acid to form a halogenated fatty acid and reacting it with arginine to produce a fatty acid arginate; and for phenolic fatty acids, protecting hydroxyl groups, halogenating, reacting with arginine to form a protected phenolic fatty acid arginate, and deprotecting to yield the final product.
The claims comprehensively cover the chemical compositions of the biobased fatty acid arginates with varied aliphatic chains and substituents, their antimicrobial uses, and specific methods of their synthesis involving halogenation, argination, and protection/deprotection steps for phenolic fatty acids.
Stated Advantages
The synthesized fatty acid arginates have strong surfactant properties with lower critical micelle concentrations than commercial surfactants, enabling effective surface tension reduction at lower concentrations.
The fatty acid arginates demonstrate significant antimicrobial activity, particularly against Gram-positive bacteria such as Listeria innocua, with some synthesized arginates showing stronger activity than precursors or raw materials.
The invention provides a new family of environmentally friendly, biobased antimicrobial agents that may overcome issues associated with synthetic antimicrobials, including antimicrobial resistance and toxicity concerns.
Documented Applications
Use of fatty acid arginates as surfactants in aqueous solutions to lower surface tension effectively.
Use of fatty acid arginates as antimicrobial agents for killing or inhibiting growth of microbes on surfaces, objects, or in specific areas.
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