# US 2019/0167614 A1 · Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the r-enantiomer and methods of use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0167614 A1 - Document ID: US20190167614A1 - Status: Published application - Kind: A1 - Application number: 16/272,165 - Filed: 2019-02-11 - Published: 2019-06-06 - Earliest claimed: 2017-11-22 - Assignees: Axcess Global Sciences, LLC - Applicants: Axcess Global Sciences, LLC - Inventors: Gary Millet - Web page: https://patentgrep.com/patent/US20190167614A1 ## CPC - A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60) - A23L 2/00: Non-alcoholic beverages; Dry compositions or concentrates therefor (soup concentrates A23L23/10); Preparation or treatment thereof (preparation of non-alcoholic beverages by removal of alcohol C12H3/00) - A23L 2/52: Adding ingredients (adding preservatives A23B70/10) - A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration} - A61K 31/047: having two or more hydroxy groups, e.g. sorbitol - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) ## Abstract Ketogenic compositions including a non-racemic mixture of beta-hydroxybutyrate (BHB) enriched with the R-enantiomer are formulated to increase ketone body level in a subject. The non-racemic mixture of BHB is enriched with the R-enantiomer to elevate ketone bodies and increase the rate at which ketosis is achieved yet contains an amount of the S-enantiomer sufficient to provide alternative benefits as discussed herein. In some aspects a composition for increasing ketone body level in a subject contains a dietetically or pharmaceutically acceptable carrier and a non-racemic mixture of R-beta-hydroxybutyrate and S-beta-hydroxybutyrate, wherein the non-racemic mixture of R-beta-hydroxybutyrate and S-beta-hydroxybutyrate contains from about 55% to 98% by enantiomeric equivalents of the R-beta-hydroxybutyrate and from about 45% to about 2% by enantiomeric equivalents of S-beta-hydroxybutyrate enantiomer. ## Claims ### Claim 1 A composition for administering ketone bodies to a subject, comprising: a non-racemic mixture of R-beta-hydroxybutyrate and S-beta-hydroxybutyrate, wherein the non-racemic mixture contains from 52% to 99% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 48% to 1% by enantiomeric equivalents of the S-beta-hydroxybutyrate, with the proviso that the non-racemic mixture contains no more than 88% by enantiomeric equivalents of mono-ester of R-1,3-butanediol and R-beta-hydroxybutyrate, wherein the composition is provided as or in a tablet, capsule, powder, food product, food additive, flavored beverage, vitamin fortified beverage, non-alcoholic beverage, flavored beverage additive, vitamin fortified beverage additive, non-alcoholic beverage additive, candy, sucker, pastille, food supplement, flavored mouth spray, alcohol-free injectable, or suppository. ### Claim 2 (depends on 1) The composition of claim 1, wherein the non-racemic mixture contains from 53% to 98% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 47% to 2% by enantiomeric equivalents of the S-beta-hydroxybutyrate. ### Claim 3 (depends on 1) The composition of claim 1, wherein the non-racemic mixture contains from 55% to 95% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 45% to 5% by enantiomeric equivalents of the S-beta-hydroxybutyrate. ### Claim 4 (depends on 1) The composition of claim 1, wherein the non-racemic mixture contains from 55% to 89% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 45% to 11% by enantiomeric equivalents of the S-beta-hydroxybutyrate. ### Claim 5 (depends on 1) The composition of claim 1, wherein the non-racemic mixture contains from 57% to 87% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 43% to 13% by enantiomeric equivalents of the S-beta-hydroxybutyrate. ### Claim 6 (depends on 1) The composition of claim 1, wherein the non-racemic mixture contains from 60% to 80% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 40% to 20% by enantiomeric equivalents of the S-beta-hydroxybutyrate. ### Claim 7 (depends on 1) The composition of claim 1, wherein the non-racemic mixture comprises one or more salts of R-beta-hydroxybutyrate and/or one or more salts of S-beta-hydroxybutyrate. ### Claim 8 (depends on 1) The composition of claim 1, wherein the non-racemic mixture comprises one or more esters of R-beta-hydroxybutyrate and/or one or more esters of S-beta-hydroxybutyrate. ### Claim 9 (depends on 1) The composition of claim 1, further comprising at least one medium chain fatty acid having 8 to 10 carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid. ### Claim 10 (depends on 1) The composition of claim 1, further comprising at least one short chain fatty acid having 6 or less carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid. ### Claim 11 (depends on 1) The composition of claim 1, further comprising at least one long chain fatty acid having 12 or more carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid. ### Claim 12 (depends on 1) The composition of claim 1, wherein the non-racemic mixture comprises at least one R-beta-hydroxybutyrate ester selected from the group consisting of mono-ester of ethanol, mono-ester of 1-propanol, mono- or di-ester of 1,3-propanediol, mono- or di-ester of S-1,3-butanediol, mono- or di-ester of R-1,3-butanediol, mono- or di-ester of S-R-1,3-butanediol, and mono-, di-, or tri-ester of glycerin. ### Claim 13 A composition for administering ketone bodies to a subject, comprising: a dietetically or pharmaceutically acceptable carrier selected from the group consisting of tablet, capsule, powder, food product, food additive, flavored beverage, vitamin fortified beverage, non-alcoholic beverage, flavored beverage additive, vitamin fortified beverage additive, non-alcoholic beverage additive, candy, sucker, pastille, food supplement, flavored mouth spray, alcohol-free injectable, and suppository; and a non-racemic mixture of R-beta-hydroxybutyrate and S-beta-hydroxybutyrate, wherein the non-racemic mixture contains from 52% to 99% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 48% to 1% by enantiomeric equivalents of the S-beta-hydroxybutyrate, with the proviso that the non-racemic mixture contains no more than 88% by enantiomeric equivalents of mono-ester of R-1,3-butanediol and R-beta-hydroxybutyrate. ### Claim 14 A kit for administering ketone bodies to a subject, comprising: a composition comprising a non-racemic mixture of R-beta-hydroxybutyrate and S-beta-hydroxybutyrate, wherein the non-racemic mixture contains from 52% to 99% by enantiomeric equivalents of the R-beta-hydroxybutyrate and 48% to 1% by enantiomeric equivalents of the S-beta-hydroxybutyrate, with the proviso that the non-racemic mixture contains no more than 88% by enantiomeric equivalents of mono-ester of R-1,3-butanediol and R-beta-hydroxybutyrate; a container in which the composition is placed; and a measuring device configured to hold therein a unit dose, or fraction thereof, of the composition, wherein a unit dose of the composition contains about 0.5 g to about 25 g of beta-hydroxybutyrate mixed salt. ### Claim 15 (depends on 14) The kit of claim 14, wherein the container is selected from the group consisting of carton, box, can, jar, bag, pouch, bottle, jug, and keg. ### Claim 16 (depends on 14) The kit of claim 14, wherein the measuring device is selected from the group consisting of cup, scoop, syringe, dropper, spoon, and colonic irrigation device. ### Claim 17 (depends on 14) The kit of claim 14, wherein the container includes instructions regarding the size of the unit dose, or fraction thereof, and the manner or frequency of administration. ### Claim 18 (depends on 14) The kit of claim 14, the composition further comprising at least one medium chain fatty acid having 8 to 10 carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid. ### Claim 19 (depends on 14) The kit of claim 14, the composition further comprising at least one short chain fatty acid having 6 or fewer carbons, or a mono-, di- or triglyceride of the at least one short chain fatty acid. ### Claim 20 (depends on 14) The kit of claim 14, the composition further comprising at least one long chain fatty acid having 12 or more carbons, or a mono-, di- or triglyceride of the at least one short chain fatty acid.