Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-06-10
2001-10-09
Witz, Jean C. (Department: 1651)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S462000, C424S725000, C424S778000
Reexamination Certificate
active
06300370
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to camomile oil having a high content of natural cis- and trans-spiroethers and to a method for its preparation.
2. Background Information
Camomile (
Chamomilla recutita
Rauschert (syn.
Matricaria chamomilla
(L.)) is used as such or in the form of various preparations. The activity of camomile is attributed to hydrophilic active ingredients such as flavones and polysaccharides and to lipophilic active ingredients which are components of essential camomile oil.
Lipophilic camomile active ingredients that are of importance in assessing the quality of camomile and of camomile extracts are, in addition to (−)-&agr;-bisabolol and chamazulene, poly-ynes such as cis- and trans-ene-yne-dicycloether (=spiroether). The spiroethers of camomile have anti-inflammatory and spasmolytic properties. These spiroethers are, however, easily decomposed, especially at slightly elevated temperatures.
Cis-ene-yne-dicycloether (also known as cis-spiroether) has the following structure:
Trans-ene-yne-dicycloether (trans-spiroether) has the following structure:
Essential camomile oil can either be obtained by distillation or by extraction of camomile materials, normally dried camomile heads.
Whereas distillation enables an almost complete extraction of the other components of the essential oil, the therapeutically important thermolabile spiroethers are, however, largely decomposed by this process. The oil obtained by distillation consequently no longer displays the active ingredient profile which is characteristic of camomile. On the other hand, it is not possible to obtain the essential oil of camomile completely by extraction. Thus, for example, in the manufacture of fluid extracts with 45% ethanol, only about half of the bisabolol and chamazulene-containing oils contained in the product are recovered in the extract with the sensitive spiroethers.
SUMMARY OF THE INVENTION
In accordance with the present invention, it has now surprisingly been found that by means of steam distillation of camomile extract residues (residues of extractions, dried or deep frozen, of fresh camomile) or of fresh camomile flowers (fresh camomile), camomile oils are obtained which, despite the heat treatment, display high contents of poly-ynes, i.e. in particular high contents of thermolabile cis- and/or trans-ene-yne-dicycloethers.
For aqueous distillation or steam distillation, preferred parts of the camomile plant are camomile flowers and stalks (see Chamomile Oil, German Type: Food Chemical Codex, Fourth Edition, page 98, National Academic Press, Washington, D.C., 1996). For extraction, preferred parts of camomile plant are camomile flowers (only with stalks residues not exceeding a length of 10 to 200 mm) (see German Pharmacopoia, 9th edition, Frankfurt, Germany, 1986, pages 937-939).
The above-mentioned extraction of fresh, dried or deep-frozen camomile flowers is preferably carried out by using an aqueous organic solvent, such as an aqueous C
1
-C
6
alkanol such as methanol, ethanol, isopropanol or aqueous acetone. The water content is preferably not less than 20% (v/v).
The process of the invention therefore makes it possible for the first time to manufacture camomile oil having a high content of natural spiroethers. Such camomile oil is, for example, suitable as an additive to aqueous-alcoholic camomile extracts in order to standardize these to a high content of essential oil with the lipophilic camomile active ingredients, with the typical active ingredient profile of camomile retained.
In addition, the process of the invention makes it possible to economically utilize residues from camomile extraction since the essential oil still present in the extraction residues of the camomile product or of fresh camomile is recovered with a high content of natural spiroethers. Apart from the improved yield of active ingredient, this leads to considerable savings in the cost of raw materials for the manufacture of extracts.
It is not only the use of expensive drying installations which is rendered superfluous in the distillation of extraction residues of fresh camomile flowers or of unprocessed fresh camomile flowers. The appreciable running costs for the conventional preparation of the material to be distilled through drying are also avoided. In this manner it is possible to considerably reduce the cost of the manufacture of extraction preparations.
The addition of camomile oils obtained according to the invention having a high content of spiroethers also yields extracts having an active ingredient profile typical for camomile when mixed with camomile oils conventionally distilled from camomile produce in the manufacture of camomile extract preparations.
The extraction of the oils according to the invention is carried out by means of steam distillation or aqueous distillation.
In the case of steam distillation, superheated steam is introduced into a distillation vessel. The superheated steam can be under normal pressure or under an overpressure of up to 4-5 bar. For example the superheated steam may be under a pressure of 0-1, preferably 0-0.5 bar. The temperature of the superheated steam is, for example, between 100 to 140° C. (maximum 145° C.), preferably 100 to 130° C., in particular 105 to 115° C.
The duration of distillation is, for example, 2-10 hours, preferably 2-4 hours. No additives are added to the material to be distilled during steam distillation. The distillation may be performed continuously or discontinuously.
Aqueous distillation is carried out by heating a distillation vessel charged with water (temperature for example 100° C.). In so doing, one part by weight of the material to be distilled is added to at least one part by weight of water, preferably to 10-100 parts by weight, in particular to 10-60 parts by weight of water which may contain conventional additives such as reducing agents (for example sodium ascorbate, ascorbic acid) as well as mineral acids (such as hydrochloric acid, sulphuric acid) or alkali hydroxides (such as dilute NaOH) to adjust the pH.
Distillation may be effected at pH values between 4-8; adjustment of the pH is preferably avoided so that distillation takes place at neutral pH. Aqueous distillation is completed after 1-4 hours, preferably after 2-3 hours.
The amount of reducing agents added is, for example, 0.1 to 1 part by weight based on 1 part by weight of plant material.
In order to carry out distillation the material to be distilled may be well crushed. The moisture content of the material to be distilled, for example when using residues from camomile extraction, is on average 60% (water-alcohol) and on average 80% (water) when using fresh camomile.
Distillation may be carried out in conventional mobile or stationary distillation vessels.
The distillate condensed by cooling is for example collected in a device (vessel) which enables a phase separation of the essential camomile oil and water on the basis of the different specific gravities (for example a Florentine receiver, but also other conventional separators may be used).
The essential camomile oil of the upper phase can, for example, be used, after separation of the aqueous phase without further purification, for the manufacture of camomile extract preparations. The phase separation may, for example, be facilitated by addition of salts (for example NaCl) (salting out).
In the case of aqueous distillation the distillation apparatus may optionally be flushed once or several times (2 to 3 times) after completion of the distillation with a low-boiling lipophilic solvent, for example with a saturated liquid aliphatic hydrocarbon having 5 to 7 carbon atoms (for example n-pentane, petroleum ether). This flushing serves to remove the last oil residues from the distillation bridge. 1 to 2 parts by weight of hydrocarbon per 1 part by weight dry weight of the extraction residue used may, for example, be used for flushing purposes. After removal of the hydrocarbon (see below) the residue is combined with the camomile oil of the aqueo
Carle Reinhold
Isaac Otto
Asta Medica Aktiengesellschaft
Hobbs Ann S.
Venable
Witz Jean C.
LandOfFree
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