Claims
- 1. A tobacco or tobacco-containing manufacture comprising tobacco and an agent capable of stimulating the cold receptors of the nervous system of the nasal or oral mucosa when brought into contact therewith upon use of the manufacture, wherein said agent comprises an effective amount of a cold receptor stimulating N-substituted p-methane carboxamide of the formula: ##STR2## Where R', when taken separately, is hydrogen or an aliphatic radical containing up to 25 carbon atoms and selected from alkyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, alkynyl, hydroxyalkynyl, acyloxyalkyl, alkoxyalkyl, aminoalkyl, acylaminoalkyl, calboxyalkyl and alkylcarbonyalkyl;
- R", when taking separately, is hydroxy, or an aliphatic radical containing up to 25 carbon atoms and selected from alkyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, alkynyl, hydroxyalkynyl, acyloxyalkyl, alkylcarbonyalkyl, with the proviso that when R' is hydrogen R" may also be an aryl radical of up to 10 carbon atoms and selected from the group consisting of benzyl, pyridyl, and substituted phenyl wherein the substituents are selected from C.sub.1 - C.sub.4 alkyl, hydroxy, C.sub.1 - C.sub.4 alkoxy, nitro and halogen; and
- R' and R", when taken together with the nitrogen atom to which they are attached, represent a cyclic or heterocyclic group of up to 25 carbon atoms.
- 2. A manufacture according to claim 1, wherein said N-substituted-p-menthane carboxamide is of the formula defined, where R", when taken separately, is hydrogen, C.sub.1 -C.sub.9 straight or branched chain alkyl, C.sub.1 -C.sub.9 straight or branced chain hydroxyalkyl or aminoalkyl or a C.sub.1 -C.sub.4 acylated derivative thereof, or --C.sub.n H.sub.2n COR'" or --C.sub.n H.sub.2n COOR'" where --C.sub.n H.sub.2n is a straight or branched chain alkylene group in which n is an integer of from 1-6 and R'" is hydrogen or C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 hydroxalkyl; R", when taken separately, is an organic group as defined above for R', R' and R" being the same of different; and R' and R", when taken together represent a alkylene chain optionally interrupted by oxygen and forming, together with the nitrogen atom to which R' and R" are attached, a 5- or 6-membered ring.
- 3. Manufactures according to claim 1, wherein said agent is of the formula defined where R' and R" are both alkyl of 1-3 carbon atoms.
- 4. Manufactures according to claim 1, wherein said agent is of the formula defined where R' is hydrogen and R" is alkyl of 1-3 carbon atoms, hydroxyalkyl of 1-4 carbon atoms or --CH.sub.2 COOR'", where R'" is alkyl of 1-4 carbon atoms.
- 5. A manufacture according to claim 1, wherein said agent is one of the following:
- N-methyl-p-menthane-3-carboxamide;
- N-ethyl-p-menthane-3-carboxamide;
- N-t-butyl-p-menthane-3-carboxamide;
- N-p-menth-3-oylglycine ethyl ester;
- N-(1,1-dimethyl-2-hydroxy ethyl)-p-menthane-3-carboxamide;
- N-p-menth-3-oylglycine-n-propyl ester.
- 6. Tobacco impregnated with an amount of a cold receptor stimulant effective to stimulate the cold receptors of the nervous system of the oral or nasal mucosa when said tobacco, or the smoke therefrom, is in contact therewith, wherein said stimulant is a cold receptor stimulating 3-substituted-p-menthane of the formula defined in claim 1.
- 7. A cigarette containing an amount of a cold receptor stimulant effective to stimulate the cold receptors of the nervous system of the oral or nasal mucosa when the cigarette is smoked, wherein said stimulant is a cold receptor stimulating 3-substituted-p-menthane of the formula defined in claim 1.
- 8. A filter-tipped cigarette comprising a filter tip, a tobacco-containing body, and an amount of a cold receptor stimulant effective to stimulate the cold receptors of the nervous system of the oral or nasal mucosa while the cigarette is smoked, wherein said stimulant is a cold receptor stimulating 3-substituted-p-menthane of the formula defined in claim 1 which is impregnated in said filter tip.
- 9. A method of stimulating the cold receptors of the nervous system of the nasal and oral mucosa which comprises contacting said mucosa with an effective amount of a cold receptor stimulating 3-substituted-p-menthane of the formula defined in claim 1, entrained in a stream of tobacco smoke.
- 10. A method of imparting to tobacco and tobacco-containing manufactures the property of stimulating the cold receptors of the nervous system of oral or nasal mucosa when in contact therewith, or when the smoke therefrom is inhaled, which comprises incorporating therein an effective amount of a cold receptor stimulating 3-substituted-p-menthane of the formula defined in claim 1.
RELATED APPLICATIONS
This application is a continuation-in-part of application Ser. No. 221,755, filed Jan, 28, 1972, now abandoned. It is also related to applications Serial Nos. 486,564 and 486,566 both filed on July 8, 1974.
This invention relates to tobacco and tobacco-containing manufactures containing an ingredient having a physiological cooling effect on the mucous membrances of the mouth, nose and throat when the tobacco is chewed or inhaled (as in the case of snuff) or when the smoke therefrom is inhaled, as during normal smoking.
Menthol is well known for its physiological cooling effect on the skin and mucous membrances of the mouth and has been extensively used as a flavouring agent in tobacco for producing a "cool" sensation in the mouth when smoking.
It is well established that the "cooling" effect of menthol is a physiological effect due to the direct action of menthol on the nerve endings of the human body responsible for the detection of hot or cold and is not due to latent heat of evaporation. It is believed that the menthol acts as a direct stimulus on the cold receptors at the nerve endings which in turn stimulate the central nervous system.
Although menthol is well established as a physiological coolant its use in tobacco is circumscribed by its strong minty odour and its relative volatility. For example, it is well known that "mentholated" cigarettes deteriorate quite rapidly on storage.
A few other compounds have been reported in the technical literature as having an odour or flavour similar to menthol and from time to time have been proposed as flavourants in tobacco. For example, Japanese Patent Publication No. 39-19627 reports that 3-hydroxymethyl p-menthane (menthyl carbinol) has a flavour closely resembling that of 1-menthol and suggests its use as a flavourant in tobacco. In Swiss Pat. No. 484,032 certain saccharide esters of menthol are proposed as additives to tobacco. Other compounds have been reported in the literature as having an odour and physiological cooling effect similar to menthol but without any specific recommendation for their use as additives in tobacco. For example, in French Patent Specification No. 1,572,332 N,N-Dimethyl 2-ethylbutanamide is reported as having a minty odour and refreshing effect, and the minty odour of N,N-diethyl 2,2-dimethylpropanamide is referred to. A similar effect is reported for N,N-diethyl 2-ethylbutanamide in Berichte 39, 1223, (1906). A minty odour has also been reported for 2,4,6-trimethylheptan-4-ol and 2,4,6-trimethyl hept-2-en-4-ol in Parfums-Cosmetiques-Savons, May 1956, pp. 17-20. The cooling effect of menthol and other related terpene alcohols and their derivatives has also been studied and reported in Koryo, 95, (1970), pp. 39-43. 2,3-p-menthane diol has also been reported as having a sharp cooling taste (Beilstein, Handbuch der Organischen Chemie, 4th Ed. (1923) Vol. 6, p. 744).
Desprite this knowledge of other compounds having an odour and flavour similar to that of menthol, menthol is still extensively used in tobacco notwithstanding the disadvantages mentioned above, namely its very strong odour and its relative volatility.
It is an object of the present invention to provide tobacco and tobacco-containing manufactures containing an ingredient which creates a "cool" sensation when the ingredient comes into contact with the nasal and oral mucosa, either in the tobacco smoke, or by direct contact of the tobacco on the nasal or oral mucosa, but which are not subject to the disadvantages of a strong minty flavour and storage instability.
It is a further object of the present invention to provide an improved method of imparting to tobacco and tobacco-containing manufactures a physiological cooling activity.
The present invention is based on the discovery of a group of 3-substituted-p-menthanes which have a pronounced physiological cooling activity, which have little or no odour, which are of relatively low volatility and which are substantially non-toxic. These compounds are 3-substituted-p-menthanes of the formula: ##STR1## where R', when taken separately, is hydrogen or an aliphatic radical containing up to 25 carbon atoms;
In the above definitions "aliphatic" is intended to include any straight-chained, branched-chained or cyclic radical free or aromatic unsaturation, and thus embraces alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyalkyl, acyloxyalkyl, alkoxy, alkoxyalkyl, aminoalkyl, acylaminoalkyl, carboxyalkyl and similar combinations.
Typical values for R' and R" when aliphatic are methyl, ethyl, propyl, butyl, isobutyl, n-decyl, cyclopropyl, cyclohexyl, cyclopentyl, cycloheptylmethyl, 2-hydroxyethyl, 3-hydroxy-n-propyl, 6-hydroxy-n-hexyl, 2-aminoethyl, 2-acetoxyethyl, 2-ethylcarboxyethyl, 4-hydroxybut-2-ynyl, carboxymethyl etc.
When R" is aryl typical values are benzyl, naphthyl, 4-methoxyphenyl, 4-hydroxyphenyl, 4-methylphenyl, 3-hydroxy-4-methylphenyl, 4-fluorophenyl, 4-nitrophenyl, 2-hydroxynaphthyl, pyridyl, etc.
According to the present invention, therefore, there are provided tobacco and tobacco-containing manufactures comprising tobacco and a cold receptor stimulating additive, present in an amount effective to stimulate the cold receptors of the nervous system of mucous membranes of the oral and nasal mucosa when the tobacco or tobacco-containing manufacture is smoked, chewed or inhaled by the human user, said additive being a cold receptor stimulating 3-substituted-p-menthane of the formula hereinbefore defined.
By tobacco and tobacco-containing manufactures we mean any article, such as a cigarette or cigar, or any composition, such as pipe or chewing tobacco or snuff, containing tobacco in a prepared form ready for utilisation by the human person whether by smoking, i.e. burning of the prepared tobacco and inhalation of the tobacco smoke, chewing or direct inhalation of the tobacco.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
3644653 |
Tcheiltcheff |
Feb 1972 |
|
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 1,065,767 |
Sep 1959 |
DT |
Non-Patent Literature Citations (1)
| Entry |
| Chem. Abst. Subject Index, 1947-1956, vols. 41-50, pp. 3848s-3849s. |
Continuation in Parts (1)
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Number |
Date |
Country |
| Parent |
221755 |
Jan 1972 |
|
Patent Grant
4060091
