# US 4,400,403 A · Preservation with acyloxy-5-hexenoic and acyloxy-4-hexenoic acids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,400,403 A - Document ID: US4400403A - Status: Granted - Kind: A - Application number: 06/256,323 - Filed: 1981-04-22 - Granted: 1983-08-23 - Earliest claimed: 1981-04-22 - Assignees: Monsanto Company - Inventors: Michael C. Robach - Web page: https://patentgrep.com/patent/US4400403A ## CPC - A23B 2/754: containing carboxyl groups - C07C 69/732: of unsaturated hydroxy carboxylic acids - A23B: PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The storage life of foods and feeds is extended by treating same with acyloxyalkenoic acids, especially a mixture of acetoxyhexenoic acids. The acyloxyalkenoic acids are shown to inhibit pathogens and food spoilage organisms in laboratory culture media and foodstuffs. ## Claims ### Claim 1 A method of inhibiting growth of pathogenic or food spoilage microorganisms which comprises contacting same with an effective growth inhibiting amount of acyloxyhexenoic acid selected from acyloxy-5-hexenoic acid and acyloxy-4-hexenoic acid, mixtures thereof, salts thereof and mixtures of said salts, said acyloxyhexenoic acid having up to one R.sub.1 substituent on the alpha carbon atom, said acyloxy being represented by RC00-, and said R and R.sub.1 being alkyl or alkenyl having a total of up to 19 carbon atoms. ### Claim 2 (depends on 1) Method of claim 1 wherein said acid is selected from 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof, mixtures of said acids and mixtures of said salts. ### Claim 3 A method of inhibiting growth of pathogenic or food spoilage microorganism in a food or feed product which comprises treating said product with an effective growth inhibiting amount of acyloxyhexenoic acid selected from acyloxy-5-hexenoic acid and acyloxy-4-hexenoic acid, mixtures thereof, salts thereof and mixtures of said salts, said acyloxyhexenoic acid having up to one R.sub.1 substituent on the alpha carbon atom, said acyloxy being represented by RC00-, and said R and R.sub.1 being alkyl or alkenyl having a total of up to 19 carbon atoms. ### Claim 4 (depends on 1) Method of claim 1 wherein said acid is selected from 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof, mixtures of said acids and mixtures of said salts. ### Claim 5 A composition comprising a food or feed product and an effective pathogenic or food spoilage microorganism growth inhibiting amount of acyloxyhexenoic acid selected from acyloxy-5-hexenoic acid and acyloxy-4-hexenoic acid, mixtures thereof, salts thereof and mixtures of said salts, said acyloxyhexenoic acid having up to one R.sub.1 substituent on the alpha carbon atom, said acyloxy being represented by RC00-, and said R and R.sub.1 being alkyl or alkenyl having a total of up to 19 carbon atoms. ### Claim 6 (depends on 5) Compositon of claim 5 wherein said acid is selected from 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof, mixtures of said acids and mixtures of said salts. ### Claim 7 (depends on 6) Composition of claim 6 wherein said acid is a mixture of 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof. ### Claim 8 A method of inhibiting growth of pathogenic or food spoilage microorganisms which comprises contacting same with an effective growth inhibiting amount of a mixtures of sorbic acid and acyloxyhexenoic acid selected from acyloxy-5-hexenoic acid and acyloxy-4-hexenoic acid, mixtures thereof, salts thereof and mixtures of said salts, said acyloxyhexenoic acid having up to one R.sub.1 substituent on the alpha carbon atom, said acyloxy being represented by RC00-, and said R and R.sub.1 being alkyl or alkenyl having a total of up to 19 carbon atoms and wherein the ratio of acylohexenoic acid to sorbic acid varies from about 2:1 to 1:2. ### Claim 9 (depends on 8) Method of claim 8 wherein said acyloxyhexenoic acid is a mixture of 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof. ### Claim 10 A composition comprising a mixture of sorbic acid and acyloxyhexenoic acid selected from acyloxy-5-hexenoic acid and acyloxy-4-hexenoic acid, mixtures thereof, salts thereof and mixtures of said salts, said acyloxyhexenoic acid having up to one R.sub.1 substituent on the alpha carbon atom, said acyloxy being represented by RC00-, and said R and R.sub.1 being alkyl or alkenyl having a total of up to 19 carbon atoms and wherein the ratio of acylohexenoic acid to sorbic acid varies from about 2:1 to 1:2. ### Claim 11 (depends on 10) Composition of claim 10 wherein said acyloxyhexenoic acid is a mixture of 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid. ### Claim 12 (depends on 10) A composition comprising a food or feed product and a pathogenic or food spoilage microorganism growth inhibiting amount of a composition of claim 10. ### Claim 13 (depends on 12) Composition of claim 12 wherein said acyloxyhexenoic acetoxy acid is a mixture of 6-acetoxy-4-hexenoic acid and 4-acetoxy-5-hexenoic acid and salts thereof.