Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same
Monomeric bimetal hydroxycitric acid (HCA) compounds are provided. The subject compounds include a divalent metal (X) bonded to the carboxylic acids of C2 and C3 and a monovalent metal (Y) bonded to the carboxylic acid of C1. Also provided are methods of preparing the subject compounds from a dimeric starting material (e.g., X 3 (HCA) 2 ) which include acidifying the dimer to produce a monomeric intermediate which is subsequently neutralized with YOH base. Methods of alleviating at least one symptom associated with a target disease or condition in a subject are provided. Also provided are compositions including the subject monomeric bimetal HCA compounds which find use in a variety of therapeutic applications.
1. A covalent monomeric hydroxycitric acid (HCA) compound of formula (I):
wherein:
X is a divalent metal selected from Group IIA metals, Group IIB metals or a divalent metal selected from Mn, Tc and Re; and
Y is a monovalent metal;
or a hydrate thereof,
wherein X—O and Y—O comprise covalent bonds.
2. The monomeric HCA compound of claim 1 , wherein X is a Group IIA group metal.
3. The monomeric HCA compound of claim 2 , wherein X is selected from Mg, Ca, Sr, Ba and Ra.
4. The monomeric HCA compound of claim 1 , wherein X is a Group IIB group metal.
5. The monomeric HCA compound of claim 4 , wherein X is Zn.
6. The monomeric HCA compound of claim 1 , wherein X is a divalent metal selected from Mn, Tc and Re.
7. The monomeric HCA compound of claim 6 , wherein X is Mn.
8. The monomeric HCA compound of claim 1 , wherein Y is a Group IA metal.
9. The monomeric HCA compound of claim 8 , wherein Y is selected from Li, Na and K.
10. The monomeric HCA compound of claim 1 , wherein the HCA is (−)-hydroxycitric acid.
11. The monomeric HCA compound of claim 1 , wherein:
X is Mg, Ca, Sr, Ba and Ra; and
Y is K.
12. The monomeric HCA compound of claim 1 , wherein the compound has a melting point of 200° C. or less.
13. The monomeric HCA compound of claim 12 , wherein the compound has a melting of from 160° C. to 200° C.
14. The monomeric HCA compound of claim 1 , wherein:
X is selected from Mg, Ca, Sr, Ba and Ra; and
Y is selected from Li, Na and K,
wherein the compound has a melting point of 200° C. or less.
15. The monomeric HCA compound of claim 1 , wherein:
X is selected from Mg, Ca, Sr, Ba and Ra; and
Y is selected from Li, Na and K,
wherein the compound has a melting point of from 160° C. to 200° C.
16. The monomeric HCA compound of claim 1 , wherein thermogravimetric analysis (TGA) of the monomeric HCA compound is characterized by a weight loss step at about 250° C.
17. The monomeric HCA compound of claim 1 , wherein the X—O bond and the Y—O bond each independently comprise 50% or more covalent character as determined by conductivity of an aqueous solution of the monomeric HCA compound.
18. The monomeric HCA compound of claim 1 , wherein the X—O bond and the Y—O bond each independently comprise 70% or more covalent character as determined by conductivity of an aqueous solution of the monomeric HCA compound.