AP707A

AP707A - Aromatic composition based on olibanum combined with a synergic agent (e.g. Eucalyptol, borneol, zinc salt, copper salt) and use thereof.

Info

Publication number: AP707A
Application number: APAP/P/1997/000958A
Authority: AP
Inventors: Aurele Mannarini
Original assignee: Aurele Mannarini; Gombert Bernard
Priority date: 1994-10-13
Filing date: 1995-10-11
Publication date: 1998-12-10
Also published as: CA2202554A1; FR2725621B1; FR2725621A1; OA10414A; CN1160354A; AP9700958A0; JPH11500466A; EP0788369A1; WO1996011694A3; AU3658395A; WO1996011694A2

Abstract

The present invention relates to the general field of the aromatic compounds which are contained particularly in essential oils or plant oils. To meet this and other objectives, the present invention relates to an aromatic composition comprising on the one hand at least one active aromatic system based on olibanum and consisting of at least one essential oil of olibanum and/or one or more components thereof, and on the other hand at least one synergistic agent. selected from the compounds of the formula C10H18O and/or a metal selected from copper and zinc salts.

Description

AROMATIC COMPOSITION BASED ON OLIBANUM COMBINED WITH A SYNERGISTIC AGENT (e.g. EUCALYPTOL, BORNEOL, ZINC SALT, COPPER SALT) AND USE THEREOF

TECHNICAL FIELD

The present invention relates to the general field of the aromatic compounds which are contained particularly in essential oils or plant oils.

The prime function of such compounds is obviously to release pleasant and 10 pronounced odors and tastes, so some of them are very naturally and very commonly employed in the field of food flavoring or perfumery. However, these compounds can also possess therapeutic, antiseptic, disinfecting, deodorizing or even antiparasitic and insecticidal/insect repelling properties, these properties being utilized in industrial and commercial products where appropriate.

More precisely, the present invention relates to an aromatic composition comprising at least one aromatic active principle based on olibanum, which consists of at least one essential oil of olibanum or one or more components thereof.

The present invention further relates to the use of such a composition for the preparation of drugs, health care and hygiene products, disinfecting, deodorizing, antiseptic, insecticidal, insect repelling or antiparasitic products, plant protection products, cosmetic products or perfumes, inter alia.

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PRIOR ART

The essential oil of olibanum - olibanum - (incense) is extracted from plants of the Burseraceae family. These plants, whose countries of origin are mainly those of North-East Africa, Arabia and Iran, produce a gum-resin which contains sugars, alcohols and acids. Conventionally the essential oil is obtained by steam distillation of this gum-resin. The distillate consists of a viscous liquid which can be colorless, pale yellow, yellowish or reddish-yellow, depending on its origin and the purification treatments to which it may be subjected.

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Incense is obviously used for its pleasant odoriferous and aromatic properties, which develop especially under the action of heat. Incense has also been incorporated in opium-containing cynoglossum pills, in mercurial plasters or in preparations active against certain forms of neuralgia. The following therapeutic applications are also known for essential oil of olibanum:

- internal and external use for the treatment of infectious states,

- internal use as an antidepressant,

- use as a basis for the production of stimulants and balsamics.

In addition, of course, it owes its use in perfumery to its pleasant 10 odoriferous character.

However, the industrial and commercial exploitation of essential oil of olibanum or its aromatic components has always remained extremely limited and discreet. Moreover, most of these applications in pharmaceutics, cosmetics or perfumery are no longer in use.

There are several reasons for this obsolescence, which will be examined below.

Firstly, essential oil of olibanum suffers from the disadvantage of having a poor solubility in the conventional organic solvents used in pharmacy or perfumery. This considerably hinders the manipulation of this oil and the convenient incorporation of different forms thereof into various preparations.

Moreover, a direct consequence of this lack of solubility is a poorer diffusion, both external and internal, in therapeutic use. This means that the bioavailability of the active principles of olibanum cannot be maximized and hence that these therapeutic performance characteristics are affected accordingly.

Secondly, olibanum oil has an unfortunate tendency to degrade on ageing, in particular when it is exposed to aggressive environmental factors such as air, light and heat. This results in oxidation and “resinification”, i.e. an increase in viscosity, which merely complicates the handling and use of this oil. This phenomenon of degradation, especially by oxidation, is accompanied by the formation of by30 products which are undesirable in terms of the sought-after effects as therapeutic agents, perfumes, deodorants, disinfectants, etc.

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Thirdly, it is quite obvious that aromatic compositions of the olibanum type would have everything to gain, as regards their industrial and commercial value, from an improvement in their functional, therapeutic, odoriferous, disinfecting and other properties. With this in mind, the ultimate objective, for obvious economic reasons, is to increase the activity while at the same time reducing the dose.

There does exist a state of the art relating to the invention forming the subject of the present disclosure, but it only comprises non-pertinent and distantly related documents which do not consider the same technical problem.

The abstract of Japanese patent application JP-A-04 149 136 of 9 October 10 1990 discloses perfume compositions which possess a synergistic physiological activity and contain at least one physiologically active essential oil and at least one essential oil enhancing said activity. However, said abstract does not specify what activity is involved.

In a long list of so-called active and undifferentiated oils, said document 15 indiscriminately mentions bomeol, although this is not an essential oil. An essential oil is actually defined by its botanic origin. Now, bomeol is not a plant but a terpenic alcohol in the solid and non-volatile state, present in certain essential oils (it is improperly called bomeol oil in some popular works).

There is absolutely no emphasis on bomeol in said document. Moreover, 20 for the enhancing essential oil, reference is also made, in a long list of essential oils, to those originating from Boswellia and Geraniates Burseracea Commiphora. It should be noted that, among the latter, only a few well-defined species of Boswellia contain olibanum gum-resin (incense), and these are not disclosed by the Japanese abstract.

Finally, said document does not recommend any particular combination which is capable of solving the technical problem mentioned above, namely the solubility and storage stability of olibanum oil.

The article in INDIAN J. PHARMACOL., 24(2), discloses double-blind crossover clinical trials, with placebo control, of the Indian medicinal formulation “AZURVEDIC”, which comprises not only essential oils but also a root of the Withania somnifera type, a resin-gum derived from Boswellia serrala, a rhizome

AP/P/ 97/00 9 58

AP. Ο Ο 7 Ο 7 bis derived from Curcuma longa and a complex containing zinc, in the treatment of rheumatoid arthritis. In reality, this formulation is an “infusion” in the pharmaceutical sense of the word, i.e. a mixture of dried and divided plants or parts of plants, to which salts are sometimes added.

Said article makes no reference whatsoever to the problem of the solubilization and stabilization of compositions based on essential oil of olibanum. Finally, it should be noted that it is not this resin which acts as the essential active principle in this clinically tested formulation. The teaching of said document is not likely to help in the search for a solution to the problem of solubilization, stabilization and optimization of the properties of essential oils based on olibanum.

The article in J. ETHNOPHARMACOL., 33 (1-2), 1991, 91-96, relates to the same infusion or medicinal formulation as that studied in the document referred to above. This time, however, the intended therapeutic treatment is osteoarthrosis. Said document therefore has no further contribution to make in assessing the patentability of the invention which will be presented below.

DISCLOSURE OF THE INVENTION

In this situation, one of the essential objectives of the present invention is to 20 provide an aromatic composition based on active compounds of olibanum and having physicochemical properties, particularly solubility and ageing stability, which is improved and more adapted to the industrial demands of simplicity of use and long shelf life.

Another objective of the invention is to provide an aromatic composition 25 based on olibanum or the like which has maximum functional properties, especially in pharmaceutics, cosmetics, perfumery or hygiene, at the lowest possible active doses.

Another objective of the invention is to provide an aromatic composition constituting a starting material which is not only effective and economic but can also be used easily and universally in a multiplicity of applications.

To meet these and other objectives, the Applicant has succeeded in c 0 0 / Z 6 /d/dV

AP. Ο Ο 7 Ο 7 ter demonstrating, totally surprisingly and unexpectedly and after much research and experimentation, that the active compounds of olibanum should be associated with at least one synergistic agent selected from the compounds of the formula CioHigO and/or metal salts.

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Thus the present invention relates to an aromatic composition comprising:

- on the one hand at least one active aromatic system based on olibanum and consisting of:

□ at least one essential oil selected from those extracted from the gum-resin (incense) derived from plants of the Burseraceae family which are capable of producing said gum-resin, these plants preferably being selected from the group comprising Boswellia carterii Birdwood, Boswellia Fereana Birdwood, Boswellia bhau-dajiana Birdwood, Boswellia papyrifera (Del) Hochst, Boswellia sacra Flueckiger, Boswellia serrata Ro and mixtures thereof) □ and/or one or more components of this essential oil;

- and on the other hand at least one synergistic agent selected from the compounds of the formula CioHigO and optionally from salts of the following metals: Cu, Ag, Au, Zn, Cd and Hg, zinc and copper being particularly preferred.

The advantage and value of tnis composition lies in the enhancement of the physicochemical and functional properties of the active aromatic system based on olibanum by this particular chemical class of aromatic and/or metallic synergistic compounds. This is represented especially by:

- a synergy of action,

- a better solubility in organic solvents, especially in ethanol, and in aromatic components,

- a better diffusion

- and a greater ageing stability.

This novel association is of definite industrial and commercial value for all aromatic plant products derived from olibanum.

The essential oil of olibanum - olibanum (incense) which is more particularly selected according to the invention is extracted from small trees of the Burseraceae family, preferably Boswellia carterii - birdw and similar species. These small trees grow mainly in Iran, India, Africa and Arabia, on either side of the Red Sea and Indian Ocean. The African locations are the Horn of Africa, Ethiopia, Somalia, the island of Socotra and Eritrea, where Boswellia carterii birdwood, Boswellia frereana birdwood (or female incense) and Boswellia bhau-dajiana birdwood (or

AP/P/ 97/00958

AP . Ο Ο 7 Ο 7 bis frankincense) are found. Boswellia papyrifera (Del.) Hochst is said to grow in Sudan and Eritrea. Boswellia sacra Flueckiger are found in Arabia. Boswellia serrata Ro is found in India. All the Boswellia which have just been cited above, and which the Applicant has succeeded in isolating and selecting, produce a gum5 resin which contains sugars, oo

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- alcohols: olibanol, bomeol, famesol, octanol, incensol (Eritrea) ...

- ethers: 1,8-cineole

- carbonyl compounds: carvone, verbenone ...

- a- and β-boswellic acids ...

- esters: octyl acetate (predominant constituent: up to 50% or more in

Eritrea).

Native or esterified bomeol, and cineole, are present in small proportions in essential oil of olibanum, being on average more or less 1% in Eritrea and Aden.

There is an olfactory unit for gums-resins-incense and their extraction products.

Several technologies can be used to extract the components of olibanum resins, e.g. steam distillation, volatile solvents, thermolyzates.

These three techniques are preferred according to the invention, but steam distillation of this gum-oleoresin is particularly preferred. The distillate consists of a viscous liquid which can be colorless, pale yellow, yellowish or reddish-yellow according to the origin and the treatments to which it may be subjected. The density of this olibanum oil varies from about 0.850 to 1060. Its density increases the more it resinifies or the more resinous it is.

According to a preferred characteristic of the invention, the synergistic agent is at least partly of an aromatic nature and comprises eucalyptol, bomeol (native or esterified) or a mixture thereof. These two compounds are CioHigO isomers which are widely available and relatively inexpensive.

Eucalyptol, which is also known as 1,8-cineole or 1,8-epoxy-p-menthane, is an internal ether corresponding to terpinol. It can be extracted in liquid form from a variety of plant oils. It is of course eucalyptus oils which contain the greatest amount of eucalyptol, namely up to 85%. Examples which may be mentioned are Eucalyptus globulus, Eucalyptus austrialana, Eucalyptus amygdalina, Eucalyptus polybractea and Eucalyptus smithii, inter alia.

Malaleuca leucadendron and Malaleuca viridiflora, which respectively contain from 60 to 75% and from 35 to 70% of eucalyptol, may also be mentioned. Finally, Artemisa cina and Artemisa vulgaris may be indicated by way of interest.

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AP 00707

Eucalyptol is a colorless mobile liquid with an odor reminiscent of both mint and camphor; its density is 0.921. The known pharmacological activities of eucalyptol are those of a potent expectorant and antiseptic. It is used especially as a means of combating infections of the respiratory system and urogenital system in particular.

Uses as a disinfectant, deodorant, antiparasitic or insecticide/insect repellent have also been recorded.

The eucalyptol useful as a synergistic agent within the framework of the invention can be in the pure form or be introduced via an essential oil which is rich therein, for example one or more of the essential oils mentioned above.

As far as bomeol is concerned, it may be pointed out that this is an alcohol produced by a tree growing in Borneo and Sumatra: Dryobalanops Camphora. Bomeol {dextrorotatory camphol), which is also known as 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, is collected in crystalline form from underneath the bark of

Dryobalanops camphora.

Bomeol is soluble in ethanol and fluid plant oils. Its density is less than that of water. It is present in a variety of plant oils, either in the pure form or in the form of an ester. The following may be mentioned as an illustration of these oils which are sources of bomeol:

- Rosmarinus Officinalis (15% by weight)

- essential oils of pine, and more particularly:

* Abies sibirica (40% by weight of bornyl acetate) * Tsuga canadensis, * Pinus silvestris, * Pinus mariana etc.

- Origanum majorana (85% by weight of a mixture of camphor and bomeol called “Bruylants”)

- Thymus satureoides (35% by weight).

Bomeol is an antiseptic and, for many authors, a general tonic and more 30 specifically a stimulant of the suprarenal cortex. It is used in the treatment of infectious diseases and depressive states or as a desensitizer.

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In the same way as for eucalyptol, a bomeol-based synergistic agent can be introduced into the aromatic composition of the invention via one or more essential oils, including especially those mentioned above which are rich in this active aromatic compound.

Given that the aromatic compositions according to the invention can be obtained especially by using all or some of the essential oils of olibanum as well as essential oils containing eucalyptol and/or bomeol, it is interesting to point out that these plant oils can vary in their composition, said variations depending on several factors. First of all, it is obvious that the living plant from which these oils originate fry 10 determines a variability related to the geographic location, on which the climate and the nature of the soil depend. Furthermore, the composition can change as a function of the time at which the plant is harvested. Finally, it is clear that the distillation and the manner in which it is carried out are other factors with some influence on the essential oil obtained in fine.

Considering these factors, it should be noted that the first is not really crucial and that the other two can be controlled so as to ensure a constancy of the properties, especially the physicochemical, therapeutic and cosmetic properties, of the essential oils.

It should also be considered that said essential oils can be in a rectified or non-rectified form for use in the aromatic compositions according to the invention.

Thus, within the framework of the present invention, the term “rectified” θ refers to one or more purification treatments by means of which one or more of the undesirable components are removed from the essential oils. In particular, terpenes, which are present in practically all essential oils, can be removed by deterpenation.

The aim of such a treatment is to improve the solubility of the oil in ethanol and improve its aromatic power. This relates more specifically to perfumery. It is selfevident that the purification or rectification of the oil can also extend to oil constituents other than terpenes, namely alkaloids or other non-terpene component.

These purification/rectification treatments make it possible to remove the troublesome compounds in accordance with the intended use. These troublesome compounds can be totally or partially removed in this way.

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AP . 00707.

In the case where the active system based on olibanum consists of at least one essential oil of olibanum, and where the synergistic agent comprises eucalyptol, the latter is preferably present in a proportion of 15 to 75% by volume, preferably 25 to 35% by volume, relative to the total composition.

On the other hand, if the active aromatic system based on olibanum consists of at least one essential oil of olibanum, and if the synergistic agent comprises bomeol, the proportion of the latter is 5 to 100% by weight, preferably 20 to 30% by weight and particularly preferably about 25% by weight, relative to the active system based on olibanum.

The composition advantageously contains at least one organic solvent selected from fatty substances, alcohols, ethers and mixtures thereof, preferably from alcohols and/or ethers, ethanol being more particularly preferred.

In an advantageous variant of the invention, the synergistic agent comprises at least one metal salt present in an amount such that the metal cation(s) represents (represent) from 0.1 to 10% by weight, preferably 0.1 to 5%, relative to the total weight of aromatic compounds forming the aromatic substance.

The synergistic agent preferably comprises at least one zinc salt and/or at least one copper salt.

In the case where the cation originates from copper, its concentration, expressed in % by weight relative to the total weight of aromatic compounds (or aromatic substance), is advantageously between 0.3 and 1%, preferably between 0.4 and 0.6%.

In the case where the cation originates from zinc, its concentration, expressed in % by weight relative to the total weight of aromatic compounds (or aromatic substance), is advantageously between 0.1 and 2%, preferably between 0.5 and 2%.

The synergistic combination of the system based on olibanum, on the one hand, and eucalyptol and/or bomeol and possibly Zn and/or Cu salt, on the other, has the advantageous effect of increasing the solubility of the olibanum compounds in organic solvents such as, for example, ethanol. This proves to be the case especially for essential oil of olibanum, whether it be in rectified or non-rectified

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AP . Ο ο 7 Ο 7 form and whatever the extraction procedure may be.

It is also found that the composition diffuses much better, compared with the aromatic composition based on olibanum alone, through various solid substrates such as animal or plant tissues and fibrous materials (when the composition is in the liquid or gaseous state) and through gases such as air (when the composition is in the vapor state).

This excellent diffusion is the basis of better performance characteristics in terms of bioavailability and hence therapeutic efficacy, and also as regards perfumery, cosmetics, disinfection or deodorization of the ambient air.

It has also been possible to observe that the synergistic combination described above confers particularly optimized storage stability properties.

The invention can be carried out according to different embodiments.

- a - According to a first embodiment, rectified or non-rectified essential oil of olibanum is mixed with pure (or substantially pure) synergistic agent such as eucalyptol and/or bomeol. Examples of possible proportions are thus:

- 30% by volume of essential oil of olibanum (rectified or non-rectified)

- and 70% by volume of eucalyptol; or:

- 75% by weight of essential oil of olibanum (rectified or non-rectified)

- and 25% by weight of bomeol;

or finally:

- 30% by volume of essential oil of olibanum (rectified or non-rectified),

- 70% by volume of eucalyptol

- and 25% by weight of bomeol, relative to the essential oil of olibanum.

- b - In a second embodiment, the composition can consist of a mixture of essential oils constituting a vehicle for the essential active principles of the invention, namely the olibanum compounds and the synergistic agent based on eucalyptol and/or bomeol and possibly on at least one metal salt. In this particular case, the essential active principles of the invention (olibanum and synergistic agents) are naturally still present in the same proportions as those referred to above. In practice, said composition can be for example a mixture of rectified or nonAP/P/ 9 7/5 0 9 58

AP. Ο Ο 7 Ο ?

rectified essential oils of olibanum with rectified or non-rectified essential oils rich in eucalyptol and/or bomeol, preferably those mentioned above. The chosen essential oils rich in bomeol can be those which contain bomeol in the native state. Now, the latter possesses particularly valuable solubilizing properties compared with bomeol in the form of esters; by contrast, the performance characteristics of bomeol esters can be exploited for their therapeutic properties.

It is thus possible to adjust the respective proportions of native bomeol and bomeol esters according to the intended final applications:

+ in a first variant, the therapeutic properties (synergy) can be favored by 10 enriching the composition in bomeol esters;

+ in a second variant, the solubilizing properties (perfumery) can be exploited by increasing the amount of native bomeol;

+ and in a third variant, both types of properties can be utilized.

- c - Without implying a limitation, and by way of a third embodiment, it is 15 also possible to consider the alternative whereby one or more components of olibanum oil are selected, including the alcohols, like olibanol, and the acids. This can be achieved by employing fractional distillation as well as other methods of purification which afford deterpenation, the consequences of which are to limit the amount of the components and increase the proportion of acids and alcohols or of a preferred component, for example octanol as the alcohol or in the form of an ester like octyl acetate, in Eritrean olibanum oil.

In said alternative, the component(s) of essential oil of olibanum are advantageously associated either with eucalyptol or with a mixture of eucalyptol and bomeol (in the pure form or in the form of essential oil(s)).

Thus the component(s) preferably represents (represent) between 5 and

60% by weight of a composition comprising the component(s) and eucalyptol, a concentration of 15% by weight being particularly preferred.

Preferentially the associated synergistic agent is eucalyptol, although this does not exclude eucalyptol/bomeol mixtures. In the latter cases, the concentration of bomeol is between 10 and 50% by weight, preferably 25% by weight, relative to the mixture of eucalyptol and chosen olibanum component(s). This corresponds to

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e.g.:

- component(s) originating from essential oil of olibanum (15% by weight),) =x

- eucalyptol (85% by weight), J

- optionally bomeol, 25% by weight of x.

Given that:

the more resinous the total olibanum oil is, the greater is its solubility in organic solvents such as ethanol, and this phenomenon tends to disappear with the rectified oil, it is possible to envisage using resinous, non-rectified, total essential oil of olibanum to determine a maximum solubility. This enables the therapeutic properties of the composition to be improved.

Conversely, a rectified, non-resinous essential oil of olibanum can be employed especially for application in perfumery, and it can be associated with bomeol and/or eucalyptol for enhanced diffusion and stability⁷ and better solubility in organic solvents.

Within the framework of the advantageous variant of the invention referred to above, the activity of the essential oil of olibanum and/or one or more components of said essential oil, and their association with bomeol and (or) eucalyptol, is enhanced with the aid of at least one metal salt, the preferred metals being zinc and copper. They appear in the pharmacopeia as sedatives for-the nervous system (neuralgia, epilepsy, spasm) and antiseptics. They have the same therapeutic purpose as the aromatic components with which it can be associated. Even more preferably, they consequently act in synergy with these aromatic components. The novelty consists in associating for example one (or two) metal via a mineral salt such as zinc chloride or cupric chloride, or an organic salt such as zinc acetate and copper acetate. The percentage of the elemental metal (or metals) is between 0.1 and 10% by weight of the aromatic substance consisting of the essential oil of olibanum or one or more of its components, associated with bomeol and (or) eucalyptol. The percentage of zinc is preferably between 0.5 and 2% and more preferably 1.4% by weight. The percentage of elemental copper is preferably between 0.3 and 1% and more preferably 0.5% by weight.

In practice, in this variant, both metals are associated with the aromatic

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substance. The percentage of the sum of the two metals (elemental metal) is preferably less than or equal to 2% by weight of the aromatic substance.

The essential oil of olibanum can thus act as an excipient or intermediate excipient by diluting the bomeol and the metal salts, which are in the solid state, the whole forming a stable product.

The composition according to the invention, which associates essential oil of olibanum or one or more of its components with eucalyptol and (or) bomeol as well as a zinc salt and (or) a copper salt, can be used pure or together with an aromatic or non-aromatic additive for use in drugs, cosmetics or hygiene products. In this case, the different compositions have a complementary role.

In fact, when carrying out polytherapy for example, it is easier to use a single preparation than several preparations. In this case, several compositions are in one and the same solution or form part of one and the same galenical form. A pharmaceutical manufacturer who is interested in the present invention and wishes to associate it with an existing or future aromatic or non-aromatic drug can incorporate it into one and the same preparation with said drug. The same applies to a manufacturer of cosmetic and hygiene products.

The composition according to the invention, with or without an additive, can be used with excipients, preferably fatty substances and particularly preferably ethers and alcohols, ethanol being preferred, and with various pharmaceutical preparations and forms.

Advantageously, at least one other aromatic or non-aromatic ingredient can be added to the compositions according to the invention.

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INDUSTRIAL APPLICATION

According to another of these features, the invention relates to the use of the above-defined composition especially in the preparation of drugs (e.g. antiinfectious agents, antiseptics, antidepressants, stimulants, desensitizers) for internal and/or external use (as appropriate), health care and hygiene products, disinfectant, deodorants, cosmetic products, perfumes or plant protection products.

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Finally, the present invention relates by way of novel products to e.g.:

+ drugs (e.g. anti-infectious agents, antiseptics, antidepressants, stimulants, desensitizers), + perfumes, + cosmetic products, + health care and hygiene products (deodorants, disinfectants), comprising the aromatic composition as described above.

BEST MODE OF CARRYING OUT THE INVENTION

The following Examples will provide a clearer understanding of the invention and will demonstrate all these advantages and these different non-limiting variants.

EXAMPLES:

Examples 1 to 4: Solubility > In Example 1, preparation no. 1 below:

- a - essential oil of olibanum (originating from Arabia)............100 g

- b - dissolved bomeol.............................................................. 50 g

AP/P/ 9 7 / 0 0 9 58 is made up by stirring for 5 min at room temperature (preferably after the tube has been heated gently).

cm³ of 70° alcohol (ethanol) solubilize 1 cm³ of preparation no. 1, whereas the same amount of essential oil - a - as that contained in 1 cm³ of preparation no. 1 is not solubilized by 20 cm³ of 70° ethanol.

t> In Example 2, preparation no. 2 below:

- c - rectified essential oil of olibanum (originating from Iran).... 100 g

- d - bomeol.............................................................................. 50 g is made up by following the same procedure as in Example 1.

cm³ of 70° alcohol solubilize 1 cm³ of preparation no. 2. The same 30 observation is made as in Example 1, namely that the oil - c - without bomeol is insoluble in ethanol.

_AP.O07°7

In general, bomeol improves the solubility of rectified or non-rectified essential oil of olibanum, irrespective of the origin of the olibanum.

> In Example 3, preparation no. 3 below:

- e - essential oil of olibanum (originating from Arabia)..... 30% by volume

- f - eucalyptol.................................................................. 70% by volume is made up by following the same procedure as in Examples 1 and 2.

This preparation no. 3 is solubilized by ten (10) times its volume of 60° ethanol.

The essential oil employed on its own requires 80 times its volume of 60° 10 ethanol to solubilize it.

Whatever its origin and whether it is rectified or non-rectified, essential oil of olibanum is solubilized remarkably by eucalyptol.

Eucalyptol increases the solubility of essential oil of olibanum in ethanol.

> In Example 4, preparation no. 4 below:

- g - essential oil of olibanum provided by Laboratoire MANE, originating from Ethiopia, lot no. 95/01973 ........................................................ 1 ml

- h - 90% pharmaceutical grade ethanol.................................0.6 ml is made up.

A turbid mixture is obtained after stirring.

4.1 The addition of eucalyptol (Cooperation pharmaceutique fran?aise, lot no.

A25565) in 10 μί aliquots gives a slightly colored, clear solution. The total amount of eucalyptol added is 30 μί, i.e. 3% by volume relative to the olibanum oil used.

4.2 In a variant, borneol (Laboratoire de Combe d’Ase, lot no. HB11) is added to the starting mixture causes clarification of the starting mixture after 5 mg of borneol have been added, and complete solubilization of the oil after 8 mg of bomeol have been added (clear solution).

4.3 According to another protocol, olibanum resin (Laboratoire de Combe d’Ase, lot no. HE02), in the form of chips weighed at room temperature, is added to the starting mixture. The addition of 10 mg of resin does not eliminate the turbidity of the starting mixture. Heating to about 40°C, however, produces complete solubilization. The mixture becomes turbid again after cooling to room

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temperature. On the addition of a further 10 mg of resin, the mixture clears and a solution is obtained by very gentle heating. The solution then remains clear at room temperature. 20 mg of resin have eventually been added in order to solubilize 1 ml of essential oil.

Example 5: Oxidation of the three experimental solubilized mixtures of

Example 4 comprising essential oil of olibanum

During the 48 hours following the three experiments 4.1, 4.2 and 4.3 of Example 4, the solubilized mixtures obtained were brought into contact with air by repeated opening of the flasks containing them. It was possible to observe, in fine, that mixtures containing 1 ml of essential oil of olibanum, 0.6 ml of 90% ethanol and a synergistic agent formed by eucalyptol (experiment 4.1), bomeol (experiment 4.2) and olibanum resin (experiment 4.3) give non-oxidized, clear solutions. It is therefore seen that these mixtures are not perturbed by oxidation, especially as regards solubilization of the essential oil of olibanum. i'he NMR spectra of the mixtures before and after oxidation show slight differences.

Example 6: Preparation of a composition of essential oil of olibanum •with synergistic agents of aromatic and metallic type The following composition is prepared:

The following may be mentioned as an example of this variant:

aromatic substance (aromatic - Essential oil of olibanum.... 30% by volume molecules) of the =- Eucalyptol..........................70% by volume composition representing 1 g - Bomeol..............................25% by weight relative to the essential oil of olibanum

- Zinc chloride..................... 0.030 g

- Cupric chloride..................0.015 g

Example 7: Stability

Stability is understood here as meaning constant homogeneity of the liquid composition (without the formation of precipitates). This is assessed by reacting hydrochloric acid (HCI) with the essential oil of olibanum. This causes hyperoxidation, which results in a coloration of the oil ranging from red to dark brown, as well as a characteristic odor. There is precipitation of the most oxidized

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AP.00707 components and the chlorinated components.

The protocol of the test is as follows:

- 1/20 cm³ of a 1/3 aqueous solution of HCI is poured into 1 cm³ of essential oil of olibanum. The mixture is stirred for a few seconds and left to stand for a few minutes. The aqueous solution is then separated from the supernatant oxidized essential oil. The aqueous solution has the same red color as the oxidized essential oil because it contains oxidation and chlorination products. The oxidized essential oil collected contains a precipitate, the amount of which increases the more resinous the oil is.

In the test .with hydrochloric acid (HCI), associating bomeol or eucalyptol with the olibanum oil results in solubilization of the precipitate.

COMMENTS

Eucalyptol and bomeol seem to stabilize the essential oil of olibanum by solubilizing its components and its oxidation and decomposition products.

The phenomenon whereby the decomposition products of olibanum oil are solubilized in ethanol with the aid of bomeol and eucalyptol is also verified when the composition comprises certain non-rectified oils as well as certain components of essential oils other than olibanum oil (aromatic additives).

Example 8: Diffusibility

A drop of eucalyptol on a sheet of paper produces a spot which spreads rapidly and evaporates without leaving a trace.

A drop of essential oil of olibanum produces a spot which spreads slowly and leaves a trace in the same way as fixed oils. This appears to be a particular feature of the essential oil of olibanum compared with other oils. The spot spreads more slowly the more resinous the essential oil of olibanum is; a deposit then forms, the area of which is smaller than that of the spot.

If the above experiment is repeated in the presence of eucalyptol, it is found that the olibanum oil diffuses more rapidly and the area of the deposit is greater for the same resinous essential oil.

The eucalyptol acts as a vehicle. This is important especially for internal and external use in therapeutics.

Claims

1. An aromatic composition comprising;

- on the one hand at least one active aromatic system based on olibanum and consisting of at least one essential oil of olibanum and/or one or more components

5 thereof,

- and on the other hand at least one synergistic agent selected from the compounds of the formula CioHigO and/or salts of metals of groups IB and IIB of the periodic table of the elements (“La Chimie - Dictionnaire encyclopedique” (“Chemistry An Encyclopedic Dictionary”) - Jacques Angenault - published by DUNOD 10 1991), zinc and copper being particularly preferred.

2. An aromatic composition according to claim 1, characterized in that the synergistic agent is at least partly aromatic and comprises eucalyptol, bomeol or a mixture thereof.

3. An aromatic composition according to claim 1 or claim 2, characterized in 15 that the synergistic agent is introduced via at least one essential oil which is rich therein, said essential oil being in rectified or non-rectified form.

4. A composition according to any one of claims 1 to 3, characterized in that the active aromatic system based on olibanum consists of at least one essential oil of olibanum, and in that the synergistic agent comprising eucalyptol is present in a

20 proportion of 15 to 75% by volume, preferably 25 to 35% by volume, of the total composition.

5. A composition according to any one of claims 1 to 4, characterized in that the active aromatic system based on olibanum consists of at least one essential oil of olibanum, in that the synergistic agent comprises bomeol and in that the latter is in a

25 proportion of 5 to 100% by weight, preferably 20 to 30% by weight and particularly preferably about 25% by weight, relative to the active system based on olibanum.

6. A composition according to any one of claims 1 to 3, characterized in that the active aromatic system based on olibanum is formed by one or more components of essential oil of olibanum, in that said composition contains

30 eucalyptol and possibly bomeol as synergistic agents, and in that said composition is quantitatively defined as follows:

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AP.ο Ο 7 Ο 7

- 1 - about 15% by weight of component(s) originating from essential oil of olibanum,

- 2 - about 85% by weight of eucalyptol, it optionally being possible to add bomeol in a proportion of about 25% by weight

5 relative to the mixture 1 + 2.

7. A composition according to any one of claims 1 to 6, characterized in that the synergistic agent comprises at least one zinc salt and/or at least one copper salt, and in that the metal cations of this (or these) salt(s) represents 0.1 to 10% by weight, preferably 0.1 to 5%, of the total weight of the aromatic substance.

10

8. A composition according to any one of claims 1 to 7, characterized in that it contains at least one organic solvent selected from fatty substances, alcohols, ethers and mixtures thereof, preferably from alcohols and/or ethers, ethanol being more particularly preferred.

9. A composition according to any one of claims 1 to 8, characterized in that at

15 least one other aromatic or non-aromatic ingredient is added.

10. Use of the composition according to any one of claims 1 to 9 in the preparation of drugs, health care and hygiene products, cosmetic products, perfumes, disinfectants, deodorants or plant protection products.