# US 11,998,034 B2 · Particulate composition containing co-crystal of malic acid and alkali metal hydrogen malate > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,998,034 B2 - Document ID: US11998034B2 - Status: Granted - Kind: B2 - Application number: 17/561,271 - Filed: 2021-12-23 - Published: 2022-04-14 - Granted: 2024-06-04 - Earliest claimed: 2019-06-26 - Assignees: Parac Biochem B.V. - Applicants: Purac Biochem B.V. - Inventors: Marija Orlovic; Jan Van Krieken - Web page: https://patentgrep.com/patent/US11998034B2 ## CPC - A23L 27/72: {Encapsulation} - A23L 29/035: {containing oxygen as heteroatom (gums A23L29/25; sugar or sugar alcohols A23L29/30)} - A23G 3/343: {Products for covering, coating, finishing, decorating} - A23G 3/346: {Finished or semi-finished products in the form of powders, paste or liquids (A23G3/343 takes precedence)} - A23G 3/54: Composite products, e.g. layered, coated, filled - A23P 20/18: by spray-coating, fluidised-bed coating or coating by casting (combined with breading A23P20/12) - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF - A23P: SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS ## Abstract The invention provides a particulate composition comprising at least 1 wt. % of malate particles, said malate particles having a diameter of 50 to 1000 μm and comprising at least 70 wt. % of co-crystal of malic acid and alkali metal hydrogen malate. Co-crystals of malic acid and alkali metal hydrogen malate can be produced in the form of powders that exhibit very low hygroscopicity and that are capable of imparting a sour flavour that is very similar to that of malic acid. The invention also relates to the use of the aforementioned malate particles as a food ingredient. ## Claims ### Claim 1 A particulate composition, comprising at least 1 wt. % of malate particles having a diameter of 50 to 1000 μm and comprising at least 70 wt. % of co-crystal of malic acid and alkali metal hydrogen malate. ### Claim 2 (depends on 1) The particulate composition according to claim 1, wherein the malate particles comprise: (a) 75-100 wt. % of the co-crystal; (b) 0-25 wt. % of one or more organic acids selected from the group of citric acid, malic acid, lactic acid, tartaric acid and fumaric acid, wherein the combination of the co-crystal and the one or more organic acids constitutes at least 90 wt. % of the malate particles. ### Claim 3 (depends on 2) The particulate composition according to claim 2, wherein the malate particles comprise at least 90% of the co-crystal. ### Claim 4 (depends on 3) The particulate composition according to claim 3, wherein the malate particles comprise at least 95 wt. % of the co-crystal. ### Claim 5 (depends on 2) The particle composition according to claim 2, wherein the malate particles comprise: (a) 75-95 wt. % of the co-crystal; and (b) 5-25 wt. % of the one or more organic acids. ### Claim 6 (depends on 5) The particulate composition according to claim 5, wherein the malate particles comprise 5-25 wt. % of malic acid. ### Claim 7 (depends on 1) The particulate composition according to claim 1, wherein the particulate composition comprises at least 50 wt. % of the malate particles. ### Claim 8 (depends on 1) The particulate composition according to claim 1, wherein the particulate composition comprises 1-95 wt. % of the malate particles and 5-99 wt. % of sugar particles. ### Claim 9 (depends on 1) The particulate composition according to claim 1, wherein the co-crystal is a co-crystal of malic acid and sodium hydrogen malate or a co-crystal of malic acid and potassium hydrogen malate. ### Claim 10 (depends on 9) The particulate composition according to claim 9, wherein the co-crystal is sodium trihydrogen dimalate represented by formula Na+(C4H5O5)−·C4H6O5. ### Claim 11 A process of preparing malate particles comprising co-crystal of malic acid and alkali metal hydrogen malate, the process comprising: (a) providing seed crystal particles containing at least 80 wt. % of crystalline material selected from crystalline organic acid, crystalline salt of organic acid and combinations thereof; (b) providing an aqueous malate solution, comprising sodium and malate in a molar ratio of 4:10 to 6:10 or comprising potassium and malate in a molar ratio of 5.5:10 to 7.5:10; (c) spraying the aqueous malate solution onto the seed crystal particles to produce coated particles; (d) removing water from the coated particles. ### Claim 12 A process of preparing malate particles comprising co-crystal of malic acid and alkali metal hydrogen malate, the process comprising: (a) providing malic acid particles comprising at least 80 wt. % of malic acid; (b) providing sodium hydrogen malate particles comprising at least 80 wt. % of sodium hydrogen malate or potassium hydrogen malate particles comprising at least 80 wt. % of potassium hydrogen malate; (c) combining 100 parts by weight of the malic acid particles with either 100-138 parts by weight of the sodium hydrogen malate particles or 200-300 parts by weight of potassium hydrogen malate; and 1-10 parts by weight of water; (d) subjecting the resulting combination to mechanical shear. ### Claim 13 (depends on 1) A method of preparing an edible product, the method comprising combining a particulate composition according to claim 1 with one or more other food ingredients. ### Claim 14 A particulate coating for an edible product wherein the coating comprises a particulate composition comprising at least 1 wt. % of malate particles having a diameter of 50 to 1000 μm and comprising at least 70 wt. % of co-crystal of malic acid and alkali metal hydrogen malate. ### Claim 15 (depends on 14) The particulate coating according to claim 14, wherein the edible product is a confectionery product. ### Claim 16 (depends on 14) The particulate coating according to claim 14, further comprising sugar particles.