Use of cubebol as a flavoring ingredient

Details Use of cubebol as a flavoring ingredient Use of cubebol as a flavoring ingredient

2000-03-28

2001-04-10

Reamer, James H. (Department: 1614)

Perfume compositions

Perfume compositions

Ring containing active ingredient

C420S536000

Reexamination Certificate

active

06214788

ABSTRACT:

BRIEF SUMMARY OF THE INVENTION
The present invention relates in particular to the flavor industry. More particularly, it relates to the use of (−)-cubebol, or (−)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol of the formula
as a flavoring, and the foods and various other products flavored with cubebol.
BACKGROUND OF THE INVENTION
Cubebol is a compound found in nature, namely in cubeb oil which is isolated from berries of
Piper cubeba
, or true cubebs. A compound having a similar structure (see discussion below) is found in species of cubebs known as “false cubebs”, which are not well defined and can comprise several species of Piper. The oil of true cubebs has long since been known in the flavor industry, but its use is strictly limited to a number of “exotic” applications, for example the flavoring of spicy sauces and bitter alcohols, or “bitters”. This is due to the characteristic bitter, piquant and pungent flavor of the oil, which, as a result, does not lend itself to large-scale use in the flavor industry.
Cubeb oil is a complex mixture of around fifty compounds (see N. B. Shankaracharya et al, Pafai Journal Jan.-Mar. 1995, pp. 33-39). One constituent amongst these compounds which is well defined is the aforementioned cubebol, which has already been referred to in works dating from the 1950s and relating to the flavor and fragrance industry, for example in Guenther, The Essential Oils, Vol. II (1952). At that time, the structure of cubebol had not yet been clarified, and the name “cubebol” was used for a product extracted from false cubebs, while the oil of true cubebs yielded a product known as “cubeb camphor”. The aforementioned work by Guenther, for example, refers on page 287 to a compound by the name of cubebol isolated from the oil of “false” cubebs and said not to be identical to a compound by the name of “cubeb camphor”, isolated from the oil of true cubebs.
According to more recent work on cubebol, the two compounds are, with a fair amount of probability, the same (see F. Vanasek et al, Coll. Czech. Chem. Comm. 1960 (25), p. 919 and A. Tanaka et al, J. Chem. Soc. Perkin 1., 1972, p. 1721), although the identity of these two compounds has not actually been proved. From this point on, the name cubebol will be used to designate the compound of the formula (I) hereinabove which is isolated from the oil of true cubebs.
It is very surprising that cubebol has never been used in the flavor industry, despite the fact that cubebol and cubeb camphor have long been known, as is reflected in the work by Guenther, which states on page 287: “Cubebol as such is not used in our industry.” This has remained the case until now.
A very current topic in the flavor industry is the search for molecules which have a delayed and prolonged refreshing effect when they come into contact with the mucous membranes of the mouth. This is due to the fact that a large number of compounds, in particular derivatives of (−)-menthol, are already known which have a pronounced refreshing effect developing rapidly in the oral cavity and lasting for around 10 to 15 minutes at the most. However, refreshing agents which have a longer-lasting effect are desired. Despite all the effort invested by chemists in the synthesis of new chemical substances or in structural modifications to compounds with a known refreshing effect (see e.g. applications DE-A-26 08 226, EP-A-507 190 and EP-A-583 651 filed by Haarmann & Reimer GmbH, and application PCT/IB98/01821 filed on 16.11.98 by the applicant), they have not succeeded in developing or finding substances having the desired quality of a long-lasting refreshing effect.
DETAILED DESCRIPTION OF THE INVENTION
The object of the present application is to provide a chemical compound having a refreshing effect which is perceptible for a longer period than the effect achievable with known refreshing compounds. We have found that the use of (−)-cubebol, or (−)-(1R,4S,5R,6R,7S,10R)-7-isopropyl4, 10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol, as a flavoring enables this object to be achieved. When (−)-cubebol is incorporated into suitable foods or beverages as a flavoring, a refreshing effect develops in the mouth after a delay of approximately 1 to 2 minutes and lasts for approximately 30 minutes. To our knowledge, cubebol is the first refreshing agent to have this quality, making it particularly useful in the flavor industry.
Since cubebol itself has only a very weak smell and taste, it lends itself to all applications in the field of flavors. Beverages, iced products such as ice creams or sorbets, sweets, confectionery, dairy products, chewing gums, jams, cigarettes, chewing tobacco, pharmaceutical preparations and dental care products are non-limiting examples of its use.
Preferred applications, in which the prolonged effect is particularly welcome, are emulsion-based drinks, fruit juices, soft drinks, cold teas, chewing gums with and without sugar, sweets with and without sugar, pressed tablets, gelatin-based confectionery, fruit jams and jellies, alcoholic beverages, sorbets, dairy ice creams, tooth gels and toothpastes, mouth-washes and throat-washes. As general preferred applications, flavors with acid notes, flavors based on citrus fruits and the foods containing these flavors may be quoted.
Naturally, cubebol also lends itself to use in the field of perfumery. Non-limiting examples of this are shampoos, shower and bath gels, deodorants and anti-perspirants, aftershave lotions and balms, shaving foams, massage oils and perfumes.
In another preferred embodiment of the invention, cubebol is used in combination with other commercially available refreshing agents known to the skilled person, in particular the compounds derived from (−)-menthol, (−)-menthone and (−)-menthane. Non-limiting examples of these are the compounds described in application DE-A-26 08 226, in particular (−)-menthyl lactate; the compounds described in application EP-A-507 190, in particular (−)-menthone glyceryl ketal; the compounds described in application EP-A-583 651, in particular (−)-menthyl ethylene glycol carbonate and (−)-menthyl 1,2-propylene glycol carbonate; (−)-menthyl monosuccinate; (−)-menthyl 5-oxo-prolinate; the compounds described in U.S. Pat. No. 5,545,424 and 4,459,425, in particular 1-glyceryl(−)-menthyl ether; the compounds described in U.S. Pat. No. 4,060,091, in particular N-ethyl-p-(−)-menthane-3-carboxamide; the compounds described in U.S. Pat. No. 3,644,613, in particular (−)-menthyl levulinate and (−)-menthyl acetylacetate; (−)-menthyl N-acetyl-glycinate, described in application DE-A-24 33 165, and the compounds described in application PCT/IB98/01821 filed by the applicant, in particular (−)-menthyl methoxyacetate and (−)-menthyl 3,6-dioxaheptanoate. Naturally, (−)-menthol as such also lends itself to use in combination with cubebol. Another class of suitable refreshing compounds are those disclosed in DE-A-25 03 555, in particular N,2,3-trimethyl-2-(1-methylethyl)-butanamide.
The use of cubebol in combination with at least one of the “conventional” refreshing compounds, in particular those mentioned hereinabove, provides a very distinctive refreshing effect. When the products containing the said combination of refreshing agents come into contact with the mucous membranes, for example of the mouth, the refreshing effect develops rapidly in the mouth, after approximately 30 to 90 seconds, and lasts for approximately 25 to 30 minutes. Such an effect cannot be achieved with known refreshing agents, the effect of which develops rapidly, but subsides after approximately 20 minutes at the most. In contrast, the use of cubebol alone gives rise to a delayed refreshing effect, only produced after more than 90 seconds, but remaining perceptible for a long time. The use of a combination of cubebol with at least one other known refreshing agent produces a rapid, long-lasting refreshing effect

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