Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1997-09-12
1999-01-05
Robinson, Douglas W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 111, 536125, 568863, 568862, 568861, C07H 100, C07C 2900, C07C 2700
Patent
active
058564691
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR96/01798, filed Nov. 14, 1996.
The present invention relates to a new process for producing palatinitol.
More particularly it relates to a production process for palatinitol starting from isomaltose or .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-glucose.
BACKGROUND OF THE INVENTION
Palatinitol is a sweetening agent of low caloric mass and low cariogenicity which up to now is obtained by catalytic Hydrogenation at neutral pH of isomaltulose or .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-fructose.
Isomaltulose is itself obtained by enzymatic isomerization, using a saccharose glysosyl transferase, saccharose or .alpha.-D-glucopyranosyl-(1.fwdarw.2)-.beta.-D-fructofuranoside.
Therefore, it is saccharose which constitutes the raw material for obtaining palatinitol, a mixture in roughly equimolecular proportions, of .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-sorbitol (GPS or isomaltitol) and .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-mannitol (GPM).
Palatinitrol, which is also called isomalt, is in particular marketed by the Company Suddeutsche Zucker AG under the name Palatinit.RTM..
Among other documents which concern the obtaining and properties of palatinitol the following work can be referred to: "Alternative Sweeteners" published in 1986 by LYN O'BRIEN NABORS, chapter 11, pages 217 to 244.
Concerned to develop a process which allows palatinitol to be obtained from a raw material other than saccharose, the Applicant Company has noticed that this goal could be achieved by a process using isomaltose or .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-glucose.
In accordance with the present invention, palatinitol is obtained thanks to a process characterized in that conditions which allow a mixture of .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-mannose and isomaltose to be obtained, to obtain a mixture containing a roughly equimolecular proportion of .alpha.-D-glucopyranosyl-(1.fwdarw.6)-D-mannose and isomaltose,
If it is reasonable to imagine that palatinitol may be obtained from saccharose, the person skilled in the art could in no way expect that this same palatinitol might be obtained from isomaltose which is obtained from glucose and thus from diverse and various starches.
In fact, in the first case, saccharose, the structural formula of which includes a fructose unit, will produce, in a known fashion by enzymatic isomerization, the corresponding ketose i.e. isomaltulose.
And it is known to the person skilled in the art that the hydrogenation of such a ketose leads to the formation of the two corresponding itols in approximately equimolecular proportions. Therefore, the fact that the formula of saccharose is related to that of palatinitol allows the result to be anticipated.
However, the process according to the invention does not implement a starting product whose formula is related to that of the sought palatinitol. In fact, isomaltose as well as glucose and starch have a structure which does not contain a fructose unit and is therefore far from being related to that of palatinitol.
BRIEF SUMMARY OF THE INVENTION
The process according to the invention therefore allows freedom from the requirement to use saccharose as raw material for the production of palatinitol since isomaltose can be easily obtained from glucose and therefore from diverse and varied starches, whether they originate from cereals or tubers.
A process for obtaining isomaltose from glucose or a corn syrup is described, for example, in the French Patent Application 2,515,186.
DETAILED DESCRIPTION OF THE INVENTION
In the process according to the invention, it is preferred to use crystallized isomaltose, although syrups which are very rich in isomaltose are also suitable if one accepts that maltitol or isomaltotriitol may be present in the palatinitol. The two last-named compounds originate from the hydrogenation of maltose or isomaltotriose which represent the main impurities in syrups which are very rich in isomaltose.
In the process according to the invention, the epimerization of isomaltose can be carried out as describ
REFERENCES:
patent: 4684720 (1987-08-01), Darsow et al.
patent: 5644044 (1997-07-01), Darsow et al.
Database WPI, Section Ch, Week 9225 Derwent Publications Ltd., London, GB; Class B03, AN 92-203078 XP002010687 & JP 04 121 198 A, Abstract.
"Alternative Sweeteners" by Lyn O'Brien Nabors, Chap. 11, pp. 217-244, 1986 .
Duflot Pierrick
Fouache Catherine
Robinson Douglas W.
Roquette Freres
White Everett
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