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1. (WO1992010107) ORGANOLEPTIC COMPOSITIONS
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Claims

1. Organoleptic compositions, comprising one or more dicarboalkoxy dioxolane derivatives of the formula


wherein
R1 and R2 are, independently, -CO2R3 wherein R3 is -H or lower alkyl,
provided that in at least one of R1 and R2, R3 is lower alkyl;
wherein Z is a direct bond, or -CH__C(R4)-; where R4 is -H or an alkyl group; and
Y is


where R5 and R6 are independently -H, lower alkyl or -OR7
where R7 is -H or lower alkyl,
which are present in an amount such that, when subjected to hydrolysis, pyrolysis or both, provide an organoleptically effective level of flavor or aroma.

2. The composition of claim 1 wherein the dicarboalkoxy compound is:

2-(3-ethoxy-4-hydro__y-phenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(3-methθ-_y-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxo
2-(4-methoxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(4-methylphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(3,4-methylenedioxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-l,3-dioxolane, 2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarbomethoxy-l,3-dioxolane or

2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane.

3. The composition of claim 2, wherein the dicarboalkoxy compound is: (4R,5R)-2-(3-ethoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxolane, (4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy- 1,3-dioxolane,
(4R,5R)-2-(4-methoxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
(4R,5R)-2-(4-methylphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
(4R,5R)-2-(3,4-methylenedioxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,

(4R,5R)-2-(2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane,
(4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-l,3-dioxolane,
(E)-(4R,5R)-2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarbomethoxy-l,3-dioxolane or
(E)-(4R,5R)-2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane.

4. A smoking composition which comprises natural tobacco or a tobacco substitute and an organoleptic composition of claims 1, 2 or 3.

5. The smoking composition of claim 4 wherein the concentration of the organoleptic composition is between about 5 ppm and about 50,000 ppm.

6. A media suitable for enclosing natural tobacco or a tobacco substitute, which contains between about 5 ppm and about 50,000 ppm of an organo-leptic composition of claims 1, 2 or 3.

7. The media according to claim 6 wherein the organoleptic composition is present in an amount of from about 5 ppm to about 50,000 ppm.

8. A flavored food product comprising a foodstuff containing an organoleptic composition of claims 1, 2 or 3.

9. A flavored food product as described in claim 8, wherein the food product is baked.

10. The flavored food product according to claim 9 wherein the foodstuff is cake, cookie, cracker, bread or cereal.

11. A flavored gum comprising a gum base and an organoleptic composition of claims 1, 2 or 3.

12. A flavored beverage comprising an ingestible liquid and an organoleptic composition of claims 1, 2 or 3.

13. The use of the dicarboalkoxy dioxolane derivatives of formula I as given i any one of daims 1 to 3 as flavor or aroma precursors.

14. Dicarboalkoxy dioxolone derivatives of the formula:


wherein
R1 and R2 are, independently, -CO2R3 wherein R3 is -H or lower alkyl,
provided that in at least one of R1 and R2, R3 is lower alkyl;
wherein Z is a direct bond, or -CH=C(R4)-; where R4 is an alkyl group; and
Y is, when Z is a direct bond,


where R5 is lower alkyl; and
Y, when Z is -CH=C(R4)-, is


where R6 is H, lower alkyl or OR7, where R7 is H or lower alkyl.

15. A compound selected from the group of

2-(3-ethoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxolane, 2-(3,4-methylenedioxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,
2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-l,3-dioxolane,

2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarbomethoxy-l,3-dioxolane and 2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane.

16. A compound selected from the group of

(4R,5R)-2-(3-ethoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxolane,

(4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarboethoxy-l,3-dioxolane,
(4R,5R)-2-(3,4-methylenedioxyphenyl)-4,5-dicarboethoxy-l,3-dioxolane,

(4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-l,3-dioxolane,
(E)-(4R,5R)-2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarbomethoxy-l,3-dioxolane and
(E)-(4R,5R)-2-(l-hexyl-2-phenyl-l-ethenyl)-4,5-dicarboethoxy-l,3-dioxolane.

17. Process for the manufacture of the compounds of formula


wherein
R1 and R2 are, independently, -CO2R3 wherein R3 is -H or lower alkyl,
provided that in at least one of R1 and R2, R3 is lower alkyl;
wherein Z is a direct bond, or -CH=C(R4)-; where R4 is an alkyl group; and
Y is, when Z is a direct bond,


where R5 is lower alkyl; and
Y, when Z is -CH=C(R4)-, is


where R6 is H, lower alkyl or OR7, where R7 is H or lower alkyl, comprising condensing an aldehyde YZ-CHO (II) or its di-lower alkyl acetal, with a lower alkyl tartrate
HO-CHRi-CHR^OH (III)
, preferably in an inert solvent in the presence of an acid catalyst.