Long chain glycolipids useful to avoid perishing or microbial contamination of materials

11350,628

17/342085

June 08, 2021

The invention relates to the use of, and methods of use employing, certain glycolipid compounds as defined in detail below and having preservative or antimicrobial properties, novel compounds of the glycolipid class, and related invention embodiments. The compounds have the formula I [chemical expression included] wherein m is 3 to 5, n is 2 to 5, o is 0 or 1 and p is 3 to 17, with the proviso that the sum m+n+o+p is not less than 14; and R is a carbohydrate moiety bound via one of its carbon atoms to the binding oxygen, and/or a physiologically, especially pharmaceutically or nutraceutically or cosmetically, acceptable salt thereof, or an ester thereof, as such or in the form of a composition, where the compound may be present in open chain form and/or in the form of a lactone (FIG. 1).

IMD NATURAL SOLUTIONS GMBH (Dortmund, DE)

IMD Natural Solutions GmbH (Dortmund, DE)

1. Method of preserving a material or imparting antimicrobial properties to said material, said method comprising adding to said material an effective amount therefor of a compound of the formula I, or a mixture of two or more such compounds of the formula I, [chemical expression included] wherein m is 3 to 5, n is 2 to 5, o is 0 or 1 and p is 3 to 17, with the proviso that the sum m+n+o+p is not less than 14; and R is a carbohydrate moiety bound via one of its carbon atoms to the O atom to which R is attached in formula I, where the moiety R carries at least one hydroxyl group esterified with isovaleric acid, where the compound is present in an open chain form or in the form of a lactone formed between [chemical expression included] in formula I and any free OH depicted in formula I or on R, or a physiologically acceptable salt of said compound, and/or an ester of said compound with a C 1-10 -alcohol, and where said material is selected from the group consisting of a cosmetic, a food, a beverage, a pharmaceutical, a medical device, and an active packaging material.

2. Method according to claim 1 , where the material to which the compound is added is a cosmetic, a food or a beverage.

3. Method according to claim 1 , where in the compound of the formula I m is 3 to 5, n is 2 to 5, o is 0 or 1, p is 5 to 15 and R is a moiety of the subformula [chemical expression included] wherein the rings A, B and C are monosaccharide moieties each independently from the others with 5 or 6 ring members, wherein one or more of the hydroxyl groups may be acylated.

4. Method according to claim 1 , wherein the compound or mixture of compounds of the formula I comprises at least one compound selected from the group of compounds with the following formulae: [chemical expression included] [chemical expression included] or a physiologically acceptable salt thereof.

5. Method according to claim 1 , where at least one additional preservative is added.

6. Method according to claim 1 , where the compound or compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, is added in the form of an extract from a natural source or obtained from such an extract.

7. Method according to claim 6 , where the source of the extract is Dacryopinax spathularia strain FU50088 , Ditiola radicata strain MUCL 53180 , Ditiola nuda strain CBS 173.60 or Femsjonia luteo - alba (= Ditiola pezizaeformis) strain MUCL 53500.

8. The method according to claim 1 , where the beverage is selected from the group consisting of water, flavoured water, fortified water, a flavoured beverage, carbonated water, a juice, cola, lemon-lime, ginger ale, root beer beverages which are carbonated in the manner of soft drinks, a syrup, a diet beverages, a carbonated soft drink, a fruit juice, other fruit containing beverages which provide the flavor of fruit juices and contain greater than 0% fruit juice but less than 100% fruit juice, fruit flavored beverages, vegetable juices, vegetable containing beverages, which provide the flavor of any of the aforementioned vegetable juices and contain greater than 0% vegetable juice but less than 100% vegetable juice, isotonic beverages, non-isotonic beverages, soft drinks containing a fruit juice, coffee, tea, tea beverages prepared from tea concentrate, extracts, or powders, drinkable dairy products, hot chocolate, chocolate powders/mixes, drinkable soy products, non-diary milks, alcoholic beverages, fruit smoothies, horchata, sport drinks, energy drinks, health drinks, wellness drinks, shakes, protein drinks, drinkable soy yogurts, low acid beverages, acidified beverages, nectars, tonics, frozen carbonated beverages, frozen uncarbonated beverages, liquid meal replacements, infant formulations, and combinations or mixtures thereof; or the material is a cosmetic selected from a cream, emulsion, lotion, gel or oil for the skin; a face masks, a tinted base, a make-up powder, an after-bath powder, a hygienic powder, a toilet soap, a deodorant soap, a perfumes, a toilet water, an eau de Cologne, a bath or shower preparation; a depilatory; a deodorant, an anti-perspirant, a hair care product; a setting product; a cleansing product; a conditioning product; a hairdressing product; a shaving products; a product for making up and removing make-up from the face and the eyes, a product intended for application to the lips, a products for care of the teeth and/or the mouth; a product for nail care and/or make-up, a product for external intimate hygiene, a sunbathing product, a product for tanning without sun, a skin-whitening product, an anti-wrinkle product, a tampon, a sanitary towel, a diaper and a handkerchief.

9. A method of enhancing microbial stability of a material, comprising adding one or more compounds to a material selected from the group consisting of a cosmetic, a food, a beverage, a pharmaceutical, a medical device, and an active packaging material, wherein the one or more compounds are selected from compounds or a mixture of compounds of the formula I: [chemical expression included] wherein m is 3 to 5, n is 2 to 5, o is 0 or 1 and p is 3 to 17, with the proviso that the sum m+n+o+p is not less than 14; and R is a carbohydrate moiety bound via one of its carbon atoms to the O atom to which R is attached in formula I, where the moiety R carries at least one hydroxyl group esterified with isovaleric acid, where the compound is present in an open chain form or in the form of a lactone formed between [chemical expression included] in formula I and any free OH depicted in formula I or on R, or a physiologically acceptable salt of said compound, and/or an ester of said compound with a C 1-10 -alcohol.

10. The method according to claim 9 , where the beverage is selected from the group consisting of water, flavoured water, fortified water, a flavoured beverage, carbonated water, a juice, cola, lemon-lime, ginger ale, root beer beverages which are carbonated in the manner of soft drinks, a syrup, a diet beverages, a carbonated soft drink, a fruit juice, other fruit containing beverages which provide the flavor of fruit juices and contain greater than 0% fruit juice but less than 100% fruit juice, fruit flavored beverages, vegetable juices, vegetable containing beverages, which provide the flavor of any of the aforementioned vegetable juices and contain greater than 0% vegetable juice but less than 100% vegetable juice, isotonic beverages, non-isotonic beverages, soft drinks containing a fruit juice, coffee, tea, tea beverages prepared from tea concentrate, extracts, or powders, drinkable dairy products, hot chocolate, chocolate powders/mixes, drinkable soy products, non-diary milks, alcoholic beverages, fruit smoothies, horchata, sport drinks, energy drinks, health drinks, wellness drinks, shakes, protein drinks, drinkable soy yogurts, low acid beverages, acidified beverages, nectars, tonics, frozen carbonated beverages, frozen uncarbonated beverages, liquid meal replacements, infant formulations, and combinations or mixtures thereof; or the material is a cosmetic selected from a cream, emulsion, lotion, gel or oil for the skin; a face masks, a tinted base, a make-up powder, an after-bath powder, a hygienic powder, a toilet soap, a deodorant soap, a perfumes, a toilet water, an eau de Cologne, a bath or shower preparation; a depilatory; a deodorant, an anti-perspirant, a hair care product; a setting product; a cleansing product; a conditioning product; a hairdressing product; a shaving products; a product for making up and removing make-up from the face and the eyes, a product intended for application to the lips, a products for care of the teeth and/or the mouth; a product for nail care and/or make-up, a product for external intimate hygiene, a sunbathing product, a product for tanning without sun, a skin-whitening product, an anti-wrinkle product, a tampon, a sanitary towel, a diaper and a handkerchief.

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