Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-02-26
2002-05-07
Prats, Francisco (Department: 1651)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C424S770000, C424S774000, C424S775000, C424S773000, C424S778000, C424S779000, C424S725000, C514S460000
Reexamination Certificate
active
06384246
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an improved process for the preparation of maltol useful as a food-flavoring compound. Particularly, this invention relates to a processing technology for the isolation of maltol of formula (1) from a readily available plant of the genus Abies. More particularly, the invention relates to a processing technology for the isolation of maltol from the plant
Abies pindrow
.
BACKGROUND OF THE INVENTION
Maltol (2-methyl-3-hydroxy-4-pyrone) is a heterocyclic aroma chemical of formula (1) used extensively in flavour, fragrance and in some pharmaceutical formulations. It is naturally occurring is many plant species, especially in coniferous trees suck as Larch trees (
Larix decidua
mill), pine trees and pine needles (
Abis alba
mill, pinaceae). Its isolation from the above sources has been reported extensively in the literature (Le Blanc and Akers, “Maltol and ethyl maltol from the Larch trees to successful food additive”, Food Technology, pp78-84 (1989); Fleisher and Fleisher, “Water soluble fractions of the essential oils”, Perfumer and Flavorist, vol.16, p.37-41 (1991; Heinz et al. U.S. Pat. No. 3,501,501(1970; Brennan et al. U.S. Pat. No. 4,082,717 (1978); Weeks et al. U.S. Pat. No. 4,342,697 (1982); Fleisher et al. U.S. Pat. No. 5,221,756(1993); ibid U.S. Pat. No. 5,440,053 (1995); ibid U.S. Pat. No. 5,441,612 (1995); ibid U.S. Pat. No. 5,641,489 (1997); Arsenault et al. U.S. Pat. No. 5,646,312 (1997); Guzek et al. U.S. Pat. No. 5,763,626 (1998). The presence of maltol in various plant sources has been known for many years and considerable efforts have been made to develop a cost-effective process for its commercial production. The existing techniques are, however, rather complex and the use of the resulting maltol is cost prohibitive.
Heintz et al. (U.S. Pat. No. 3,501,501), described the purification of crude maltol by its co-distillation with ethylene glycol. The drawback of the process includes that the solubility of maltol in ethylene glycol at ambient temperature is about 4%. This prohibits economical maltol recovery from dilute mixtures, effectively eliminating virtually all natural sources. Moreover, the crystallization of maltol from ethylene glycol at ambient temperature is very slow. At very low temperature, the viscosity of ethylene glycol also considerably hampers filtration of maltol from ethylene glycol-maltol mixture. Ethylene glycol derived maltol is also unsuitable for food application, since the removal of toxic ethylene glycol contamination from maltol is rather difficult.
Maltol can be obtained in very small amounts from the destructive distillation products of woods, and by a partially synthetic process from kojic acid which is obtained from fermentation media. However, maltol obtained therefrom is still quite expensive. (Goos and Reiter, “New products from wood carbonization”, Industrial and Engineering Chemistry, vol.38, p.132-135 (1946); U.S. Pat. Nos. 3,031,204, 4,082,717, and 4,343,697 refer to the processes for the synthesis of gammapyrones such as maltol, ethyl maltol and pyromeconic acid).
The recovery of maltol and its purification have also been reported from maltol containing mixture by co-distillation with an aliphatic or cyclo aliphatic hydrocarbon or hydrocarbon mixtures in which maltol is substantially insoluble (Fleicher, A. et al, U.S. Pat. No. 5,221,756).
The disadvantages of the above process include that the process of co-distillation needs a rather sophisticated technological setup, application of vacuum, high pressure steam and necessary handing of flammable liquids. Moreover, during co-distillation, maltol crystallizes directly from the aqueous phase in a micro crystalline form. Thus, maltol obtained from co-distillation process retains substantial quantities (30-40%) of the hydrocarbon which complicates further purification.
Also, process has been reported in which pure maltol is recovered from a mixture containing maltol by extraction into an aqueous solution, optionally in the presence of a substantially water immiscible solvent in which the maltol in the mixture is substantially insoluble. (Guzek, D. et al U.S. Pat. No. 5,763,626).
The drawback of the above process includes that, although maltol is soluble in hot water, it can not be efficiently recovered from plant material by hot water extraction.
Maltol is a known molecule, but it has never been isolated from the plant belonging to the genus Abies which is used in this invention. This plant is available is India in abundance.
OBJECTS OF THE INVENTION
The main object of the present invention is to provide a process for the preparation of maltol useful as food flavoring compound from plants belonging to the genus Abies.
Another object of the present invention is to develop a processing technology for the preparation of maltol from the plant
Abies pindrow.
Still another object of the present invention is to develop a processing technology for the preparation of maltol which does not use any aqueous extraction of maltol from plant material.
Yet another object of the present invention is to develop a processing technology which does not use any chromatographic separation for its isolation.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides a process for the preparation of maltol from plants belonging to the genus Abies. Particularly, the present invention provides a process for preparation of maltol from the plant
Abies pindrow.
DESCRIPTION OF THE INVENTION
Accordingly, the present invention provides a process for the preparation of maltol of the formula I shown herebelow from plants belonging to the genus Abies; said process comprising (i) extracting the dried and pulverized parts of the plant with an alcohol at 20-40° C. and concentrating the solvent to obtain an alcoholic extract, (ii) adsorbing the alcoholic extract with an adsorbent and drying the adsorbed material at a temperature ranging from 20-50° C. for 4-12 hours, (iii) extracting the adsorbed material with an aliphatic solvent and then with a chlorinated solvent successively, (iv) concentrating the chlorinated solvent to a residue and crystallizing it from a suitable organic solvent or mixtures of such solvents to get pure maltol.
In an embodiment of the present invention, the plants are selected from the group comprising of
Abies pindrow, Abies spectabilis
and
Abies webbiana.
More particularly, the present invention provides a process for the preparation of maltol of the formula I shown herebelow from the plant
Abies pindrow
; said process comprising (i) extracting the dried and pulverized parts of the plant with an alcohol at 20-40° C. and concentrating the solvent to obtain an alcoholic extract, (ii) adsorbing the alcoholic extract with an adsorbent and drying the adsorbed material at a temperature ranging from 20-50° C. for 4-12 hours, (iii) extracting the adsorbed material with an aliphatic solvent and then with a chlorinated solvent successively, (iv) concentrating the chlorinated solvent to a residue and crystallizing it from a suitable organic solvent or mixtures of such solvents to get pure maltol.
In an embodiment of the present invention, the plant parts are selected from leaves, stems, roots and flowers.
In another embodiment of the invention, the alcohol used is an alkanol selected from the group comprising of methanol and ethanol.
In still another embodiment of the invention, the adsorbent material is selected from the group comprising of celite, cellulose and/or a mixture thereof.
In still another preferred embodiment of the present invention, the adsorbent material is celite.
In yet another embodiment of the invention, the aliphatic solvent is selected from the group comprising of hexane and petroleum ether.
In yet another preferred embodiment of the present invention, the aliphatic solvent is petroleum ether.
In a further embodiment of the present invention, the chlorinated solvent is selected from the group comprising of chloroform and dichloromethane.
In a preferred embodiment of the present invention, the chlorinated
Chattopadhyay Sunil Kumar
Kumar Sushil
Sashidhara Koneni Venkata
Srivastava Sachin
Tripathi Vinayah
Browdy and Neimark , P.L.L.C.
Council of Scientific & Industrial Research
Prats Francisco
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