Medium chain fatty acid esters of beta-hydroxybutyrate and butanediol and compositions and methods for using same
Aspects of the present disclosure include fatty acid β-hydroxyester compounds (e.g., fatty acid esters of β-hydroxybutyrate), fatty acid esters of butanediol, and pharmaceutically acceptable salts thereof. Also provided are pharmaceutical compositions having one or more fatty acid β-hydroxyester compounds and/or one or more fatty acid esters of butanediol. Methods for treating a subject by administering one or more esters to the subject are also provided. Kits containing one or more of the subject esters are also described.
1. A compound of the formula:
and salts, solvates or hydrates thereof, wherein:
R 1 is C(1-6) alkyl or substituted alkyl; and
R 2 and R 3 are independently unsubstituted or substituted C(4-30) alkyl.
2. The compound of claim 1 , wherein R 1 is an unsubstituted C(1-6) alkyl.
3. The compound of claim 2 , wherein R 1 is methyl.
4. The compound of claim 1 , wherein R 2 and R 3 are independently unsubstituted C(6-18) alkyl.
5. The compound of claim 4 , wherein R 2 and R 3 are independently unsubstituted C6 alkyl or independently unsubstituted C8 alkyl.
6. The compound of claim 1 , wherein the compound is a compound of Formula Ia:
7. The compound of claim 1 , wherein the compound is a compound of Formula Ib:
8. The compound of claim 6 , wherein said compound has the formula:
9. The compound of claim 6 , wherein said compound has the formula:
10. An oral preparation comprising one or more compounds of claim 1 and a preservative and/or a flavoring agent.
11. The oral preparation of claim 10 , wherein said preparation comprises water.
12. The oral preparation of claim 11 , wherein said preparation comprises a syrup or an elixir.
13. The oral preparation of claim 11 , wherein said preparation comprises a suspension.
14. The oral preparation of claim 10 , wherein said preparation comprises a binder.
15. The oral preparation of claim 14 , wherein said preparation comprises a binder selected from the group consisting of cellulose, methylcellulose, hydroxymethylcellulose, polypropylpyrrolidone, polyvinylpyrrolidone, gelatin, gum arabic, poly(ethylene glycol), sucrose, and starch.
16. The oral preparation of claim 10 , wherein said preparation comprises a flavoring agent.
17. The oral preparation of claim 16 , wherein said preparation comprises a flavoring agent selected from the group consisting of citric acid, menthol, glycine, and orange powder.
18. The oral preparation of claim 10 , wherein said preparation comprises a preservative.
19. The oral preparation of claim 18 , wherein said preparation comprises a preservative selected from the group consisting of sodium benzoate, sodium bisulflte, methylparaben, and propylparaben.
20. The oral preparation of claim 10 , wherein said compound comprises a compound having the formula:
21. The oral preparation of claim 10 , wherein said compound comprises a compound having the formula:
22. An ingestible composition comprising one or more compounds of claim 1 .
23. The ingestible composition of claim 22 , wherein said composition comprises a food supplemented with one or more of said.
24. The ingestible composition of claim 22 , wherein said one or more compounds comprises a compound having the formula:
25. The ingestible composition of claim 22 , wherein said one or more compounds comprises a compound having the formula:
26. A food supplement comprising one or more compounds of claim 1 .
27. The food supplement of claim 26 , wherein said food supplement comprises one or more additional components of a ketogenic diet.
28. The compound of claim 27 , wherein:
the compound is present in the composition in an amount of from about 1% w/w to about 25% w/w; and/or
the ketogenic diet comprises a ratio by mass of fat to protein and carbohydrates of from about 2:1 to about 10:1.
29. The food supplement of claim 26 , wherein said compound a compound having the formula:
30. The food supplement of claim 26 , wherein said compound a compound having the formula: