Methods of making compositions comprising a UV-Absorbing chromophore

Inventors

Laszlo, Joseph A.Compton, David L.DeFilippi, Louis J.Grall, Steven

Assignees

ISOY TECHNOLOGIES CorpBiotechnology Research and Development CorpUS Department of Agriculture USDA

Publication Number

US-7572610-B2

Publication Date

2009-08-11

Expiration Date

2026-06-19

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Abstract

A method of making a compound having the structural formula:wherein at least two of R1, R2, and R3 are non-fatty acid carboxylates, and the other of R1, R2, and R3 are each either a C2-C24 fatty acid moiety, OH, or a non-fatty acid carboxylate, wherein the first and second non-fatty acid carboxylates, when present, are the same or different, comprising (a) partially deacylating a triacylglycerol so as to provide a mono- or diacylglycerol, (b) reacting in a reaction mixture an acyl ester of the phytochemical with said mono- or diacylglycerol in the presence of a esterase catalyst under conditions that permit transesterification of said ester with said mono- or diacylglycerol, and (c) recovering said compound from said reaction mixture.

Core Innovation

The invention relates to methods of making compounds comprising a UV-absorbing chromophore, specifically phytochemicals, conjugated to glycerol-based molecules such as mono- or diacylglycerols. The disclosed method comprises partially deacylating a triacylglycerol to provide mono- or diacylglycerols, then reacting an acyl ester of a phytochemical with these mono- or diacylglycerols in the presence of an esterase catalyst under conditions permitting transesterification to produce compounds wherein at least two of R1, R2, and R3 are non-fatty acid carboxylates, with the others being either fatty acid moieties, OH, or non-fatty acid carboxylates.

The problem being solved arises from the slow rate of existing transesterification processes for attaching phytochemicals such as ferulic acid to triacylglycerols, which can take days to reach equilibrium at 60° C. This limits the commercial value and efficiency of producing sunscreen and phytochemical-containing products from vegetable oils. Existing UV filters also have limitations in their UV absorptivity ranges. Thus, there remains a need for improved methods to enhance the rate and yield of phytochemical transesterification onto glycerol backbones.

The invention significantly improves this by discovering that prior or concomitant partial deacylation of triacylglycerols to form mono- or diacylglycerols increases the rate of transesterification with phytochemical acyl esters by two- to seven-fold. This method uses lipase catalysts such as Candida antarctica lipase B and can be carried out in substantially water-free conditions, enabling faster, more efficient production of UV-absorbing, phytochemical-containing glycerol-based compositions useful in topical and nutritional formulations.

Claims Coverage

The patent includes two independent claims covering methods of making compounds with specific glycerol structures functionalized with non-fatty acid carboxylates, emphasizing increased transesterification rates using partial deacylation and specific reaction conditions.

Method of making compounds having glycerol structures with at least two non-fatty acid carboxylates

A method comprising (a) partially deacylating a triacylglycerol to provide mono- or diacylglycerols, (b) reacting an acyl ester of a phytochemical with the mono- or diacylglycerols in the presence of an esterase catalyst under conditions permitting transesterification, and (c) recovering the compound. The method may be carried out substantially free of water and involves acyl esters such as ethyl ferulate. The resulting compounds have structures wherein at least two of R1, R2, and R3 are non-fatty acid carboxylates that absorb UV and may have additional properties such as anti-aging or antioxidant activities.

Method of making triacylglycerol esters with at least a first carboxylate via mono- or diacylglycerol intermediates

A method comprising (a) providing a mono- or diacylglycerol formed by partial transesterification of glycerol with free fatty acids, (b) reacting in substantial absence of solvent an acyl ester of the first carboxylate with the mono- or diacylglycerol in presence of an esterase catalyst under conditions permitting transesterification, and (c) recovering the desired compound.

Method of making compounds with vegetable oil and phytochemical moieties

A method of preparing compounds having both C2-C24 fatty acid moieties and phytochemicals bonded to glycerol backbones, where the vegetable oil may be selected from common oils like soybean, corn, sunflower seed, canola, and the phytochemicals include flavonoids, isoflavones, organosulfur compounds, and hydroxy-substituted cinnamic acids.

The claims cover methods for enhanced enzymatic transesterification using partially deacylated glycerols and specific phytochemical esters, improving reaction rates and enabling production of UV-absorbing compounds with desirable properties using defined catalysts and reaction conditions.

Stated Advantages

The method increases the rate of transesterification two- to seven-fold compared to prior art, significantly improving production efficiency.

Partial deacylation prior to transesterification yields higher conversion rates and selectively produces diaryl-substituted glycerols.

The improved reaction rate leads to greater reactor productivity and lowers the cost of producing phytochemical-containing compositions.

The method enables production of compounds with both UVA and UVB absorption and desirable bioactive properties like anti-aging, antioxidant, and anti-neoplastic effects.

The disclosed HPLC methods provide enhanced identification and monitoring of reaction products, improving product quality.

Documented Applications

Incorporation of phytochemical-containing compositions into topical products such as sunscreens that absorb UVA and UVB radiation.

Use in pharmaceutical and nutritional products that leverage the bioactive properties of the phytochemicals like antioxidant and anti-neoplastic activities.

Formulations for consumer products including lotions, food supplements, agrochemicals, and other nutritional products.

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