Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
2000-11-09
2002-04-02
Reamer, James H. (Department: 1614)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
Reexamination Certificate
active
06365215
ABSTRACT:
BACKGROUND OF THE INVENTION
Our invention relates to oral sensory perception-affecting compositions containing dimethyl sulfoxide, complexes thereof and salts thereof, specifically comprising (i) dimethyl sulfoxide and (ii) a second compound or group of compounds:
(a) containing at least one menthyl moiety; and/or
(b) containing at least one vanillyl moiety; and/or
(c) containing at least one carboxamide moiety.
The term “oral sensory perception-affecting compositions” is intended to cover “coolant compositions” as well as “heat compositions.”
Compositions containing compounds producing a cooling sensation, specifically hydroxy methyl or hydroxy ethyl derivatives of paramenthane are disclosed in U.S. Pat. No. 4,029,759. Such compositions are disclosed to be useful, for example, for spearmint flavor used in toothpastes, as well as other ingestible materials such as margarine and the like. Breath freshening edible compositions of menthol and a carboxamide are disclosed in U.S. Pat. No. 5,009,893. “Hot, tingling, burning, numbing” causing sensations by use of 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a derivative thereof is disclosed in U.S. Pat. No. 5,545,424 issued on Aug. 13, 1996. Combinations of coolant compositions comprising a ketal and a secondary coolant which may be menthol are disclosed in PCT Application No. 93/23005 published on Nov. 25, 1993. Production of chewing gum containing controlled release acyclic carboxamides as cooling agents are disclosed in PCT Application No. 99/13870 published on Mar. 25, 1999. Chewing gum production using modified, physiological cooling agents, to wit: menthol, menthone and a carboxamide or a ketal or a diol or a succinate or mixtures of same, are disclosed in PCT Application No. 99/13734 published on Mar. 25, 1999.
However, there exists an ongoing need to provide enhancement of such “hot” sensations or such “cooling” sensations in various edible compositions, including beverages, toothpastes, throat lozenges, mouthwashes, dental floss, chewing gums, edible films such as breath freshener films and chewable pharmaceutical products, particularly wherein such “enhancement” raises the level of the “hot” or “cooling” sensation on ingestion of the edible composition, on a scale of 0-10, from about 2 up to about 10. The provision of such enhancement properties has heretofore been unknown and not implied in any prior art. Accordingly, nothing in the prior art sets forth the use of combinations of dimethyl sulfoxide with compounds containing at least one menthyl moiety, compounds containing at least one vanillyl moiety and/or compounds containing at least one carboxamide moiety in order to enhance oral sensory perception, including “hot” sensations and “cool” sensations.
Indeed, the use of dimethyl sulfoxide in foodstuffs and the presence of dimethyl sulfoxide in foodstuffs is well known. Thus, dimethyl sulfoxide is set forth in the TNO Nutrition and Food Research Institute's
Volatile Compounds in Food/Qualitative and Quantitative Data,
Seventh Edition 1996 (Editors: L. M. Nijssen, et al.) at page 8 under CAS No. 67/68/5. Dimethyl sulfoxide is also on the GRAS list as published in
GRAS Flavoring Substances
18, the 18
th
publication by the Flavor and Extract Manufacturers' Association's Expert Panel on recent progress in the consideration of the flavoring ingredients generally recognized as safe for use in food (reference:
Cooked Food Technology,
September 1998, Volume 52, No. 9 (GRAS No. 3875)) (also called “methyl sulfoxide,” “DMSO” and “methyl sulfinyl methane.” Nothing in the prior art discloses the effect of dimethyl sulfoxide on other sensory affecting agents, particularly oral sensory perception-affecting compositions such as coolant compositions or “hot, burning, bitter” compositions.
THE INVENTION
Our invention is directed to oral sensory perception-affecting compositions containing dimethyl sulfoxide, complexes thereof and salts thereof, specifically comprising:
(i) dimethyl sulfoxide having the structure:
(ii) a second compound or group of compounds:
(a) containing at least one menthyl moiety; and/or
(b) containing at least one vanillyl moiety; and/or
(c) containing at least one carboxamide moiety,
wherein the weight ratio of “second compound(s)”:dimethyl sulfoxide, is in the range of from about 1,000:1 down to about 3:1 and food grade acceptable salts thereof.
Our invention also covers oral sensory perception-affecting compositions (e.g., “coolants”)-imparting consumable articles (e.g., beverages, toothpastes, throat lozenges, mouthwashes, dental floss, chewing gums, edible films and chewable pharmaceutical products). The sensory-affecting consumable articles having intensified and substantive sensory-affecting properties such as oral cooling properties and oral heating properties comprise (i) an ultimate product base and intimately admixed therewith (ii) a composition comprising (a) dimethyl sulfoxide and (b) a second compound or mixture of compounds selecting from the group consisting of compounds:
(a) containing at least one menthyl moiety; and/or
(b) containing at least one vanillyl moiety; and/or
(c) containing at least one carboxamide moiety
wherein the weight ratio of second compound or group of compounds:dimethyl sulfoxide, is in the range of from about 1,000:1 down to about 3:10 and food grade acceptable salts thereof, wherein the concentration of dimethyl sulfoxide based on the weight of ultimate product is from about 0.05 up to about 200 parts per million (ppm) and the concentration of second compound or group of compounds or mixture of compounds is from about 2 ppm up to about 10,000 ppm on a mixed basis.
Examples of the “second compound” to be admixed with the dimethyl sulfoxide forming the mixtures of our invention are as follows:
menthol having the structure:
WS 23® (registered trademark of the Warner Lambert Company) having the structure:
menthyl succinate having the structure:
the monomenthyl ether of glycerin having the structure:
WS 3® (registered trademark of the Warner Lambert Company) having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
the compound having the structure:
When dimethyl sulfoxide having the structure:
is admixed with such “second compound(s),” the resulting mixture as stated, supra, has a highly intensified oral sensory perception effect, for example, a “highly intensified cooling effect” or a “highly intensified hot, burning effect.” Such effects are highly desirable in the use of certain oral care products such as mouthwashes, toothpastes and the like as set forth, supra. Thus, the following Table I sets forth a comparison of a “control” which is a “second compound” taken alone vs. the mixture of dimethyl sulfoxide with the said “second compound”:
TABLE I
Dimethyl
Second
Sulfoxide
Effect of Mixture vs.
Compound
(DMSO)
Control—Comparison
“Second Compounds”
(ppm)
(ppm)
on a Scale 0-10
Menthol
5
0.1
increase in perceived
cooling—8 vs. 1.5
Menthol
10
1
increase in perceived
cooling—9 vs. 1.3
Menthol
30
5
increase in perceived
cooling—9.5 vs. 1.1
Menthol
100
10
increase in perceived
cooling—8.7 vs. 2
Menthyl lactate
30
0.1
increase in perceived
cooling—8.4 vs. 1.7
Menthyl lactate
30
100
increase in perceived
cooling—8.2 vs. 2.1
Monomenthyl
100
0.1
increase in perceived
succinate
cooling—9.1 vs. 3.8
Monomenthyl
100
100
increase in perceived
succinate
cooling—8.7 vs. 2.5
50-50 (weight-weight)
100
0.1
increase in perceived
Mixture of mono- and
cooling—9.6 vs. 3.3
dimenthyl glutarates
50-50 (weight-weight)
100
100
increase in perceived
Mixture of mono- and
cooling—9.4 vs. 3.2
dimenthyl glutarates
WS 3 ®
1
30
0.1
increase in perceived
cooling—9.3 vs. 1.5
WS 3 ®
1
30
100
increase in perceived
cooling —9.0 vs. 1.6
WS 23 ®
2
30
0.1
increase in perceived
cooling—9.6 vs. 2.4
WS 23 ®
2
30
100
in
Christensen Gary W.
Grainger Brian T.
Kleinhenz Robert J.
International Flavors & Fragrances Inc.
Leightner Joseph F.
Reamer James H.
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