Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1985-04-05
1988-04-12
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536124, C08B 3718, C07H 1500, C07H 1524, C07H 1700
Patent
active
047375841
DESCRIPTION:
BRIEF SUMMARY
The object of the invention is a process for cyclodehydrating ketoses, the obtained products, and their use as food additives.
More particularly, the invention concerns the field of substitutes for food sugars.
Products substituting for food sugars have already long been sought in order to avoid the vexatious consequences of excessive consumption of these food sugars.
For instance, it has already been suggested to use products which while evincing a more or less pronounced sweetening effect are also characterized by not being metabolized by the human organism. These products also are termed "non-caloric food sugars." The sizeable sweetening effect of a dipeptide, namely the methylester of the alpha-aspartyl phenylanilin (or aspartame), described in particular in French Pat. No. 1,577,545 has already been long known.
One of the problems related to using aspartame as a sweetener is that in the light of its high sweetening effect, this compound can only be used in small amounts. Furthermore, it is present only in the crystalline form. To make it acceptable to the consumer, it must therefore be associated with a neutral excipient.
The purpose of the invention, therefore, is to propose glucide analogues of which some are novel products per se and which due to their features of being not assimilated by the organism are capable of entering either alone or in mixture the composition of a non-caloric food sugar, or which can be used as an excipient for a conventional or synthesized sweetener so as to make possible an association with a sweetening power which is equal or higher, but always non-caloric.
Another purpose of the invention is to propose a process for advantageously synthesizing these products.
The process for cyclo-dehydrating glucides of which the molecule includes at least one ketose-type group is characterized in that without adding water, the glucide is made to react with a hydrogen halide acting as the glucide solvent, and in that the hydrogen halide is eliminated in a dry manner.
The hydrogen halides are selected from the hydrogen iodides, bromides, chlorides, or fluorides. Among these, hydrogen chloride and hydrogen fluoride result in substantially higher yields in dehydrated compounds since the reaction in the presence of hydrogen bromide or iodide results in a high proportion of waste residues.
Advantageously hydrogen chloride or fluoride will be used because these halides allow making products at excellent yields. Hydrogen fluoride is the preferred halide because it results in practically quantitative yields.
The glucides of which the molecule includes at least one ketose-type group can be ketotetroses, ketopentoses, or ketohexoses. They may be in monomeric or polymeric form, the latter expression including the dimers.
Advantageously the glucides with a ketopentose group are selected from xylulose or one of its polymers.
The glucides with a ketohexose group are the preferred glucides for implementing the process of the invention. Among these are illustratively fructose, inulin, and sorbose.
The invention further includes the above-cited glucides of which the molecules comprise one of or more substitutents of ether, ester, acetal or other type, and in a position such as not to hamper the cyclo-dehydration reaction.
Of all of these compounds, those glucides are preferred wherein at least one of the saccharide cycles is fructose is sorbose.
The reaction takes placed without added water. This does not mean it takes place anhydrously because-a dehydration process being involved-water is automatically being formed as the reaction proceeds toward the dehydrated compounds. Additionally, the initial products may be partly hydrated.
However, the proportion of water at the end of the reaction may not exceed 10% by weight of the final reaction mixture in order not to decrease the yield in dehydrated compounds.
However, in a preferred variation, the halide is introduced dry. Similarly, the sugar to be reacted is previously dried so it shall no longer contain any water except the water of crystallization.
Th
REFERENCES:
Chemical Abstracts, vol. 90, No. 21, May 21, 1979, abstract 90: 168,844k.
Chemical Abstracts, vol. 85, No. 6, Aug. 9, 1976, abstract 85: 34,931z.
Defaye Jacques
Gadelle Andree
Pedersen Christian
Beghin-Say S.A.
Breiner A. W.
Griffin Ronald W.
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