Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the S-enantiomer and methods of use
Ketogenic compositions including a non-racemic mixture of beta-hydroxybutyrate (BHB) enriched with the S-enantiomer are formulated to control ketone body levels in a subject. The non-racemic mixture of BHB is enriched with the S-enantiomer to modulate the effect of ketone bodies in the subject and control the rate at which ketosis is achieved. In some aspects a composition for controlling ketone body level in a subject contains a dietetically or pharmaceutically acceptable carrier and a non-racemic mixture of S-beta-hydroxybutyrate and R-beta-hydroxybutyrate, wherein the non-racemic mixture contains from about 52% to 99% by enantiomeric equivalents of S-beta-hydroxybutyrate enantiomer and from about 48% to about 1% by enantiomeric equivalents of R-beta-hydroxybutyrate enantiomer.
1. A composition for administering ketone bodies and/or ketone body precursors to a subject, the ketone body composition comprising:
a non-racemic mixture of S-beta-hydroxybutyrate salt and R-beta-hydroxybutyrate salt enriched with the S-beta-hydroxybutyrate salt relative to the R-beta-hydroxybutyrate salt, with the proviso that the S-beta-hydroxybutyrate salt is not calcium S-beta-hydroxybutyrate
wherein the non-racemic mixture comprises from less than 100% by enantiomeric equivalents of the S-beta-hydroxybutyrate salt and greater than 0% by enantiomeric equivalents of the R-beta-hydroxybutyrate salt.
2. The composition of claim 1 , wherein the non-racemic mixture contains from 52% to 99% by enantiomeric equivalents of the S-beta-hydroxybutyrate salt and 48% to 1% by enantiomeric equivalents of the R-beta-hydroxybutyrate salt.
3. The composition of claim 1 , wherein the non-racemic mixture contains from 53% to 99% by enantiomeric equivalents of the S-beta-hydroxybutyrate salt and 47% to 1% by enantiomeric equivalents of the R-beta-hydroxybutyrate salt.
4. The composition of claim 1 , wherein the non-racemic mixture contains from 55% to 98% by enantiomeric equivalents of the S-beta-hydroxybutyrate salt and 40% to 10% by enantiomeric equivalents of the R-beta-hydroxybutyrate salt.
5. The composition of claim 1 , further comprising one or more esters of S-beta-hydroxybutyrate and/or R-beta-hydroxybutyrate.
6. The composition of claim 5 , wherein the one or more esters of S-beta-hydroxybutyrate and/or R-beta-hydroxybutyrate comprise at least one of mono-ester of ethanol, mono-ester of 1-propanol, mono-ester of 1,3-propanediol, 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, or mono-, di-, or tri-ester of glycerin.
7. The composition of claim 1 , wherein the composition is provided as or in a tablet, capsule, powder, food product, food additive, beverage, beverage additive, candy, sucker, pastille, food supplement, spray, injectable, or suppository.
8. The composition of claim 1 , further comprising at least one medium chain fatty acid having 6 to 12 carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid.
9. The composition of claim 1 , further comprising at least one short chain fatty acid having less than 6 carbons, or a mono-, di- or triglyceride of the at least one short chain fatty acid.
10. The composition of claim 1 , further comprising at least one long chain fatty acid having more than 12 carbons, or a mono-, di- or triglyceride of the at least one long chain fatty acid.
11. A composition for administering ketone bodies and/or ketone body precursors to a subject, the ketone body composition comprising:
S-beta-hydroxybutyrate ester or a non-racemic mixture of S-beta-hydroxybutyrate ester and R-beta-hydroxybutyrate ester enriched with the S-beta-hydroxybutyrate ester relative to the R-beta-hydroxybutyrate ester,
wherein the composition comprises from about 52% to 100% by enantiomeric equivalents of the S-beta-hydroxybutyrate ester and about 48% to 0% by enantiomeric equivalents of the R-beta-hydroxybutyrate ester,
wherein the S-beta-hydroxybutyrate ester comprise at least one of mono-ester of ethanol, mono-ester of 1-propanol, mono-ester of 1,3-propanediol, 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, or mono-, di-, or tri-ester of glycerin.
12. The composition of claim 11 , wherein the composition is provided as or in a tablet, capsule, powder, food product, food additive, beverage, beverage additive, candy, sucker, pastille, food supplement, spray, injectable, or suppository.
13. A kit for administering ketone bodies to a subject, comprising:
a composition comprising a non-racemic mixture of S-beta-hydroxybutyrate and R-beta-hydroxybutyrate enriched with the S-beta-hydroxybutyrate relative to the R-beta-hydroxybutyrate, wherein the non-racemic mixture comprises less than 100% by enantiomeric equivalents of the S-beta-hydroxybutyrate and greater than 0% by enantiomeric equivalents of the 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 the non-racemic mixture of S-beta-hydroxybutyrate and R-beta-hydroxybutyrate.
14. The kit of claim 13 , wherein the container is selected from the group consisting of carton, box, can, jar, bag, pouch, bottle, jug, and keg.
15. The kit of claim 13 , wherein the measuring device is selected from the group consisting of cup, scoop, syringe, dropper, spoon, and colonic irrigation device.
16. The kit of claim 13 , wherein the container includes instructions regarding the size of the unit dose, or fraction thereof, and the manner or frequency of administration.
17. The kit of claim 13 , the composition further comprising at least one medium chain fatty acid having 6 to 12 carbons, or a mono-, di- or triglyceride of the at least one medium chain fatty acid.
18. The kit of claim 13 , the composition further comprising at least one short chain fatty acid having less than 6 carbons, or a mono-, di- or triglyceride of the at least one short chain fatty acid.
19. The composition of claim 11 , wherein the S-beta-hydroxybutyrate ester comprises a mono- or di-ester of S-1,3-butanediol, a mono- or di-ester of R-1,3-butanediol, or a mono- or di-ester of S—R-1,3-butanediol.
20. The kit of claim 13 , wherein the S-beta-hydroxybutyrate includes an S-beta-hydroxybutyrate ester that comprises a mono- or di-ester of S-1,3-butanediol, a mono- or di-ester of R-1,3-butanediol, or a mono- or di-ester of S—R-1,3-butanediol.
21. A composition for administering ketone bodies or ketone body precursors to a subject, the composition comprising:
a dietetically or pharmaceutically acceptable earner selected from the group consisting of tablet, capsule, food product, food additive, beverage, beverage additive, candy, sucker, pastille, food supplement, spray, injectable, and suppository; and
a non-racemic mixture of S-beta-hydroxybutyrate and R-beta-hydroxybutyrate enriched with the S-beta-hydroxybutyrate relative to the R-beta-hydroxybutyrate,
wherein the non-racemic mixture comprises less than 100% by enantiomeric equivalents of the S-beta-hydroxybutyrate and greater than 0% by enantiomeric equivalents of the R-beta-hydroxybutyrate.
22. A composition for administering ketone bodies and/or ketone body precursors to a subject, the ketone body composition comprising:
a non-racemic mixture of S-beta-hydroxybutyrate and R-beta-hydroxybutyrate that is enriched with the S-beta-hydroxybutyrate relative to the R-beta-hydroxybutyrate,
wherein the non-racemic mixture comprises less than 100% by enantiomeric equivalents of the S-beta-hydroxybutyrate and greater than 0% by enantiomeric equivalents of the R-beta-hydroxybutyrate
wherein the non-racemic mixture comprises two or more salts of S-beta-hydroxybutyrate.