Cyclic acetals
AssigneeBASF K&F Corporation
InventorsRobert G. Eilerman, Philip A. Christenson, John M. Yurecko, Jr., Frank Mild, Peter E. Kucharski
Life of this patent
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Abstract
This invention provides novel cyclic acetals useful as delayed release flavorants and odorants having the general formula: ##STR1## These compounds possess no detectable flavor or odor themselves at normal temperatures and atmospheric conditions but release an aldehyde flavorant upon heating at higher temperatures. The novel cyclic acetals of the present invention may be used as flavorants in tobacco compositions or tobacco substitutes, as sustained flavorants and odorants to mask or enhance the flavors and odors of burning tobacco products, as flavor additives to microwaveable foods, and in the preparation of chewing gums.
Claims32
A compound represented by the formula:
- ##STR29## where R.sup.1 is H or C.sub.1 to C.sub.6 alkyl;
- R is Ar or Ar.sup.1,
- with Ar equal to 3-ethoxy-4-hydroxyphenyl or 5-methylthiophen-2-yl, and
- Ar.sup.1 is ##STR30## with A representing phenyl, 4-methoxyphenyl or 3-methoxy-4-hydroxyphenyl, such that when A is phenyl, R.sup.2 is C.sub.1 to C.sub.6 alkyl;
- when A is 4-methoxyphenyl, R.sup.2 is H or C.sub.1 to C.sub.6 alkyl;
- and when A is 3-methoxy-4-hydroxyphenyl, R.sup.2 is H.
A smoking composition which comprises natural tobacco or a tobacco substitute in combination with an organoleptically effective amount of a compound represented by the formula Ib:
- ##STR33## where R.sup.1b represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.b is Ar.sup.b or Ar.sup.1b, with
- Ar.sup.b equal to 3-ethoxy-4-hydroxyphenyl,
- 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl,
- 3,4-methylenedioxyphenyl or heteroaryl, and Ar.sup.1b is ##STR34## with A.sup.b equal to phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxphenyl, 3,4-methylenedioxyphenyl, or heteroaryl, and
- R.sup.2b is H or C.sub.1 to C.sub.6 alkyl.
A media suitable for enclosing tobacco or a tobacco substitute, which contains between about 5 ppm and about 50,000 ppm of a compound having the name:
- methyl 4,6-0-(4-hydroxy-3-ethoxybenzylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxyphenyl)prop-2-enylidene glucopyranoside;
- methyl 4,6-0-(5-methylthiophenemethylide) glucopyranoside;
- methyl 4,6-0-[3-(4-methoxyphenyl)prop-2-enylidene]glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-pentylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-hexylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxybenzylidene) glucopyranoside;
- methyl 4,6-0-(4-methoxybenzylidene)glucopyranoside;
- methyl 4,6-0-(3-phenylprop-2-enylidene)glucopyranoside;
- methyl 4,6-0-(3-furanylprop-2-enylidene)glucopyranoside;
- methyl 4,6-0-(3,4-methylenedioxybenzylidene) glucopyranoside, or
- methyl 4,6-0-(3-(3,4-methylenedioxyphenyl)prop-2-enylidene)glucopyranoside.
A food product comprising a foodstuff in combination with an amount of a compound represented by formula Ia:
- ##STR35## where R.sup.1a represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.a is Ar.sup.a or Ar.sup.1a, with
- Ar.sup.a representing 3-ethoxy-4-hydroxyphenyl, 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl or heteroaryl,
- and Ar.sup.1a represents ##STR36## with A.sup.a representing phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxyphenyl or heteroaryl, and R.sup.2a representing H or C.sub.1 to C.sub.6 alkyl.
A chewing gum base composition comprising a gum base in combination with a compound represented by formula Ia:
- ##STR37## where R.sup.1a represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.a is Ar.sup.a or Ar.sup.1a, with
- Ar.sup.a representing 3-ethoxy-4-hydroxyphenyl, 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl or heteroaryl,
- and Ar.sup.1a represents ##STR38## with A.sup.a representing phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxyphenyl or heteroaryl, and R.sup.2a representing H or C.sub.1 to C.sub.6 alkyl.
- said compound being present in an amount effective for imparting flavor to said gum base upon mastication thereof.
A method of flavoring a food comprising treating a food with an organoleptically effective amount of a compound of the formula I:
- ##STR39## where R.sup.1 is H or C.sub.1 to C.sub.6 alkyl;
- R is Ar or Ar.sup.1 ,
- with Ar equal to 3-ethoxy-4-hydroxyphenyl or 5-methylthiophen-2-yl, and Ar.sup.1 is ##STR40## wherein A represents phenyl, 4-methoxyphenyl or 3-methoxy-4-hydroxyphenyl, such that when A is phenyl, R.sup.2 is C.sub.1 to C.sub.6 alkyl;
- when A is 4-methoxyphenyl, R.sup.2 is H or C.sub.1 to C.sub.6 alkyl, and when A is 3-methoxy-4-hydroxyphenyl, R.sup.2 is H.
A method of flavoring a chewing gum base comprising adding to the chewing gum base an organoleptically effective amount of a compound of formula I:
- ##STR41## wherein R.sup.1 is H or C.sub.1 to C.sub.6 alkyl;
- R is Ar or Ar.sup.1,
- with Ar equal to 3-ethoxy-4-hydroxyphenyl or 5-methylthiophen-2-yl, and Ar.sup.1 is ##STR42## with A representing phenyl, 4-methoxyphenyl or 3-methoxy-4-hydroxyphenyl, such that when A is phenyl, R.sup.2 is C.sub.1 to C.sub.6 alkyl:
- when A is 4-methoxyphenyl, R.sup.2 is H or C.sub.1 to C.sub.6 alkyl, and when A is 3-methoxy-4-hydroxyphenyl, R.sup.2 is H.
A method of flavoring tobacco comprising adding to the tobacco an organoleptically effective amount of a compound of formula I:
- ##STR43## wherein R.sup.1 is H or C.sub.1 to C.sub.6 alkyl;
- R is Ar or Ar.sup.1,
- with Ar equal to 3-ethoxy-4-hydroxyphenyl or 5-methylthiophen-2-yl, and Ar.sup.1 is ##STR44## with A representing phenyl, 4-methoxyphenyl or 3-methoxy-4-hydroxyphenyl, such that when A is phenyl, R.sup.2 is C.sub.1 to C.sub.6 alkyl;
- when A is 4-methoxyphenyl, R.sup.2 is H or C.sub.1 to C.sub.6 alkyl, and when A is 3-methoxy-4-hydroxyphenyl, R.sup.2 is H.
A method of flavoring a smoking composition comprising treating tobacco or a tobacco substitute with an organoleptically effective compound having the name:
- methyl 4,6-0-(4-hydroxy-3-ethoxybenzylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxyphenyl)prop-2-enylidene glucopyranoside;
- methyl 4,6-0-(5-methylthiophenemethylide) glucopyranoside;
- methyl 4,6-0-[3-(4-methoxyphenyl)prop-2-enylidene] glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-pentylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-hexylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxybenzylidene) glucopyranoside;
- methyl 4,6-0-(4-methoxybenzylidene) glucopyranoside;
- methyl 4,6-0-(3-phenylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-furanylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3,4-methylenedioxybenzylidene) glucopyranoside, or
- methyl 4,6-0-(3-(3,4-methylenedioxyphenyl)prop-2-enylidene)glucopyranoside.
A method of flavoring a smoking composition which comprises natural tobacco or a tobacco substitute comprising treating the tobacco or tobacco substitute with an organoleptically effective amount of a compound represented by the formula Ib:
- ##STR45## where R.sup.1b represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.b is Ar.sup.b or Ar.sup.1b, with
- Ar.sup.b equal to 3-ethoxy-4-hydroxyphenyl,
- 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl,
- 3,4-methylenedioxyphenyl or heteroaryl, and Ar.sup.1b is ##STR46## with A.sup.b equal to phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxyphenyl, 3,4-methylenedioxyphenyl, or heteroaryl, and
- R.sup.2b is H or C.sub.1 to C.sub.6 alkyl.
A method of flavoring a medium suitable for enclosing tobacco or a tobacco substitute, comprising treating said medium with between about 5 ppm and about 50,000 ppm of a compound having the name:
- methyl 4,6-0-(4-hydroxy-3-ethoxybenzylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxyphenyl)prop-2-enylidene glucopyranoside;
- methyl 4,6-0-(5-methylthiophenemethylide) glucopyranoside;
- methyl 4,6-0-[3-(4-methoxyphenyl)prop-2-enylidene] glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-pentylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-phenyl-2-hexylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-methoxy-4-hydroxybenzylidene) glucopyranoside;
- methyl 4,6-0-(4-methoxybenzylidene) glucopyranoside;
- methyl 4,6-0-(3-phenylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3-furanylprop-2-enylidene) glucopyranoside;
- methyl 4,6-0-(3,4-methylenedioxybenzylidene) glucopyranoside, or
- methyl 4,6-0-(3-(3,4-methylenedioxyphenyl)prop-2-enylidene)glucopyranoside.
A method of flavoring a food product comprising treating a foodstuff with an organoleptically effective amount of a compound represented by formula Ia:
- ##STR47## where R.sup.1a represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.a is Ar.sup.a or Ar.sup.1a, with
- Ar.sup.a representing 3-ethoxy-4-hydroxyphenyl, 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl or heteroaryl,
- and Ar.sup.1a represents ##STR48## with A.sup.a representing phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxyphenyl or heteroaryl, and R.sup.2a representing H or C.sub.1 to C.sub.6 alkyl.
A method of flavoring a chewing gum base composition comprising treating a gum base with an organoleptically effective amount of a compound represented by formula Ia:
- ##STR49## where R.sup.1a represents H or C.sub.1 to C.sub.6 alkyl;
- R.sup.a is Ar.sup.a or Ar.sup.1a, with
- Ar.sup.a representing 3-ethoxy-4-hydroxyphenyl, 3-methoxy-4-hydroxyphenyl, 4-methoxyphenyl or heteroaryl,
- and Ar.sup.1a represents ##STR50## with A.sup.a representing phenyl, 4-methoxyphenyl, 3-methoxy-4-hydroxyphenyl or heteroaryl, and R.sup.2a representing H or C.sub.1 to C.sub.6 alkyl.
- said compound being present in an amount effective for imparting flavor to said gum base upon mastication thereof.
Dependencies are inferred from the claim text.