Terpene-derived acids and esters and methods for preparing and using same

1. A method of producing a compound of formula (I):

or a salt thereof, wherein R 1 is selected from the group consisting of H, unsubstituted or substituted C 1 -C 10 alkyl, and unsubstituted or substituted C 2 -C 10 alkenyl, and R 2 is selected from the group consisting of H, unsubstituted or substituted C 1 -C 10 alkyl, and COR a , in which R a is H or unsubstituted or substituted C 1 -C 10 alkyl, the method comprising:

reacting a compound having the formula IB

with ozone and subsequently with an oxidant different from ozone to obtain the compound of formula (I) wherein R 1 is H; or alternatively

reacting a compound having the formula (IB) with ozone and subsequently with a reductant to obtain a mixture comprising the compound of formula (I) wherein R 1 is H and a compound of formula (IC):

and

separating the compound of formula (I) wherein R 1 is H from the compound of formula (IC).

2. The method of claim 1 , wherein the mixture comprising the compound of formula (I) wherein R 1 is H and the compound of formula (IC) is an aqueous mixture.

3. The method of claim 2 , wherein separating the compound of formula (I) from the compound of formula (IC) is performed by:

adjusting the pH of the aqueous mixture to a first pH value that is between 6 and 10 to obtain a first organic phase that comprises the compound of formula (IC) and a first aqueous phase that comprises a salt of compound of formula (I);

separating the first aqueous phase from the first organic phase;

optionally adding an oxidant to the separated first aqueous phase;

adjusting the pH of the first aqueous solution to a second pH value that is not greater than 5 to obtain a second organic phase that comprises the compound of formula (I) wherein R 1 is H and a second aqueous phase; and

separating the second organic phase from the second aqueous phase to obtain the compound of formula (I) wherein R 1 is H.

4. The method of claim 3 , wherein the second pH value is not greater than 4.

5. The method of claim 1 , further comprising reacting the compound of formula I wherein R 1 is H, with an alcohol R b OH wherein R b is unsubstituted or substituted C 1 -C 10 alkyl or unsubstituted or substituted C 2 -C 10 alkenyl, to produce a compound of formula I wherein R 1 is unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl.

6. The method of claim 1 , wherein the oxidant is a peroxide.

7. The method of claim 6 , wherein the peroxide is hydrogen peroxide.

8. The method of claim 1 , wherein the reaction of the compound having the formula (IB) with ozone is carried out in the presence of a solvent.

9. The method of claim 8 , wherein the solvent comprises water, an organic solvent or a mixture there of.

10. The method of claim 1 , wherein the reaction of the compound having the formula (IB) with ozone is carried out in the absence of a solvent.

11. The method of claim 1 , further comprising performing an elimination reaction on the compound of formula (I) to obtain a compound of formula (II) or formula (III):

or a mixture thereof,

wherein R 1 is H, unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl.

12. The method of claim 11 , wherein the elimination reaction is performed in a solvent comprising an alcohol and an acid.

13. A method of producing a compound of formula I:

or a salt thereof, wherein R 1 is H, unsubstituted or substituted C 1 -C 10 alkyl, or unsubstituted or substituted C 2 -C 10 alkenyl, and R 2 is H, unsubstituted or substituted C 1 -C 10 alkyl, or COR a , in which R a is H or unsubstituted or substituted C 1 -C 10 alkyl, the method comprising:

providing an aqueous mixture comprising the compound of formula (I) wherein R 1 is H and a compound of formula (IC):

adjusting the pH of the aqueous mixture to a first pH value that is between 6 and 10 to obtain a first organic phase that comprises the compound of formula (IC) and a first aqueous phase that comprises a salt of compound of formula (I);

separating the first aqueous phase from the first organic phase;

optionally adding an oxidant to the separated first aqueous phase;

adjusting the pH of the first aqueous solution to a second pH value that is not greater than 5 to obtain a second organic phase that comprises the compound of formula (I) wherein R 1 is H and a second aqueous phase; and

separating the second organic phase from the second aqueous phase to obtain the compound of formula (I) wherein R 1 is H.

14. The method of claim 13 , wherein the aqueous mixture comprising the compound of formula (I) and the compound of formula (IC) is obtained by ozonolysis of a compound having the formula (IB)