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UNITED STATES PATENT OFFICE 2,585,580 STABLIZING ASCORBC; ACD with THO-SUGARS Jan Opplit, Prague-Nusle, Czechoslovakia, No Drawing

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UNITED STATES PATENT OFFICE 2,585,580 STABLIZING ASCORBC; ACD with THO-SUGARS Jan Opplit, Prague-Nusle, Czechoslovakia, No Drawing Patented Feb. 12, 1952 2,585,580 UNITED STATES PATENT OFFICE 2,585,580 STABLIZING ASCORBC; ACD WITH THO-SUGARS Jan Opplit, Prague-Nusle, Czechoslovakia, No Drawing. Application June 10, 1948, Serial No. 32,258. In Czechoslovakia June 12, 1947 8 Claims. (C. 260-344.5) 2 The present invention relates to stabilizing It is broadly known that the preservation of aScorbic acid with thio-sugars. fruit and vegetables has Such an unfavorable The aScorbic acid represents a necessary influence on the aScorbic acid content that the constituent of human food and therefore it is major part of the acid originally present is de of importance to protect the same in the various stroyed while Subsequent storage under unfavor natural and artificially prepared products against able conditions leads to an almost complete loss decomposition by suitable stabilization. The of the rest of the aScorbic acid content So that aScorbic acid, which occurs in the nature as the the health of perSons Who conSurne Such products So called vitamin C, is a relatively unstable sub in absence of any other sources of vitamin C may Stance easily oxidizable by the atmospheric air 0. be seriously impaired. Still more harm for the into dehydro-aScorbic acid, which also is unstable, health may take place if the vitamin content is and to further products of oxidation whereby the reduced in medicaments for in Such cases the physiological value of aScorbic acid as an physician relies on the patient receiving an exact antiscorbutic agent is lost. The l-aScorbic acid ly measured dose of the active Substance. C6HaO6 has the following constitution: Amongst the unfavorable influences leading to decomposition of the aScorbic acid there may be mentioned an ample contact With the atmos pheric oxygen which is unavoidable under normal H. H. E. O. O. C. conditions, higher temperatures which accelerate The ascorbic acid is a compound allied to the the oxidation, and the presence of certain ma simple Sugars having six carbon atoms in their 20 terials such as enzymes (ferments) and catalysts molecule and is characterized by a lactonic ring Which also lead to accelerated Oxidation. In the and by an endiol group -COHECOH-. This vegetable kingdon the ferments ixino Win as group accounts for the easy oxidation of a scorbic oxidases occur very frequently. These ferments acid to dehydro-aScorbic acid C6H6Os having the attack the aScorbic acid, and the most active of constitution: them is the so called ascorbinase which contains chemically combined copper. Amongst the sin OH. O. C-C-C-C-C-C- ple catalysts which speed up the oxidation of H. H. H. O. O. O. aScorbic acid there are known more particularly The last mentioned acid is also unstable, and 30 the copper compounds, while the compounds of by Splitting of the lactonic ring is converted into manganese and iron are less active. The copper 2,3-diketo-l-gulonic acid: exerts an effect already if it is present in traces of the order of 10-6 g. CH2OH-CHOH-CHOH-CO-CO-COOH On the other hand Substances are also knoWn The dehydro-aScorbic acid still may be reduced , which stabilize more or less the aScorbic acid, into aScorbic acid with relative facility also in protecting the same against oxidation also at living organisms and has antiscorbutic effect, but higher temperatures so that such substances the product of further oxidation cannot be easily represent in fact negative catalysts. Alongst converted into ascorbic acid and in any case such such substances may be mentioned e. g. the a reduction cannot take place in a living 40 sulphurous acid, hydrogen sulphide, certain Organism. So that the product is physiologically mercaptains, the cyanides , and iso-cyanides, inefficient. glutathione, methionine, cysteine, cystine, di ASCOrbic acid is contained in relatively large methyl-mercaptal-glucoses, and also highly con proportions in various natural foods, in fresh centrated Solution of Saccharose. However, these condition of the same, such as fruit, vegetables, 5 substances may not be used in the production of meat, more particularly in the muscles and liver foods or in the preparation of medicaments be of animals and in products made therefrom (such cause they either are poisonous or are unsuitable as fruit, marmalades and preserves of various for other reasons or again are not readily avail kinds, meat or liver extracts and the like). able. Synthetically prepared ascorbic acid forms a 5 In the method of treating natural products as component of various medicaments, preparations hitherto used the loss of aScorbic acid depends and injection liquids. In all the aforementioned first of all on the period of boiling and further products it is desirable to stabilize the aScorbic On other circumstances and On other properties of acid so as to retain the original physiologic value the medium, more particularly on its acidity and of the products for an indefinite period. 5 finally on the period of storing (ageing) of the 2,585,580 3. 4. preserves. With a boiling period of 15 minutes simple sugar components. Examples of Such the content of vitamin C will be reduced in the thio-Sugars are the thio-glucose average to 75% and with a boiling period of 90 minutes it will be reduced down to 15% of the CH2OH (CHOH)4CSH original value. Immediately after the completion is or, according to more recent findings of research of the boiling process a loss of about 50% of the CH2OHCH (CHOH)3CHSH ascorbic acid content in the average is to be expected, but these losses vary within large. limits O in any particular case. ithio-fructose CH2OHCCHOH)3CSCH2OH, thio in highly acid medium (lemon or currant juice) is maltose C12H22O10S. It is also possible to use the oxidation of a scorbic acid proceeds at a rela ...the acetylated derivatives of the thio-SugarS. tively low speed and also the losses due to ageing Such derivatives are obtained by the acetylation are low. The natural acidity of fruit juices, of the CH-groups, that is by substitution of the expressed in pH-units, amounts to 4.5-6.5. Due group COCN3 for hydrogen. to the ageing of the preserves 'Subsequent to By further investigation of the thio-sugars it their preparation in the usual Way, the aScorbic has been found that a particularly Suitable sta acid content continuously decreases further So bilizer is the diglucosyl disulphide . that after 6 to 12 months the aScorbic acid content CH2OH (CHOH)4CS.S.C (CHOH)4CH2OH. is reduced in very favorable cases to 20 Or i0% of the original value, while in some unfavorable cases 24 Or, according to more recent findings of research the ascorbic acid may completely disappear. In O-Hi creased temperature, more ample contact with the air and the presence of catalysts impair the chocolai ageing characteristics of preserves. CHOHCH (CHOH)3CHS In neutral and especially in alkaline medium 25 O the oxidation of the aScorbic acid takes place which is obtained as an intermediate product in very rapidly, and this applies also to the loss due the preparation of thio-glucose and which by to ageing so that within three weeks the aScorbic reduction and splitting may be converted to acid completely disappears from such preserves. thio-glucose. The diglucosyl disulphide is still The decomposition of ascorbic acid is also ac 30 more advantageous than the thio-sugars in the celerated by the presence of copper and iron When stabilization of C-Vitainin. making the preserves in copper or iron vessels, The amount of Sulphur Sugar derivatives re because these two metals act as oxidation cata quired for the stabilization depends, on the one lystS. hand, on the amount of aScorbic acid to be Sta An object of the present invention is to provide 85 bilized and, on the other hand, on the concen a method of stabilizing and -a stabilizer for the tration of the ascorbic acid in the Solution under aScorbic acid (vitamin C) in natural and arti treatinent. A larger amount of aScorbic acid ficially prepared products for human food and requires a correspondingly larger amount of Sta also in medicaments, various preparations, in bilizer. However, with increasing dilution of the jection solutions, etc. The new method and Sta 40 ascorbic acid the required amount of stabilizer bilizer are suitable in the first place for fruit and increases too, so that the more dilute the Solu vegetables preserved and prepared in any desired tions of C-Vitamin are, the larger is the required manner, for fruit juices, jams, marmalades, com proportion of Stabilizer. potes, for the preservation of meat, liver, other If thio-sugars are used for the stabilization, organs of the animal body and for extracts made 45 an amount of the order of at least 1% calculated therefron. on the ascorbic acid present Will be required. In As Stabilizers there may be used in the first connection with diglucosyl disulphide it has been place the Various Sulfur derivatives of Sugars found that a still lower amount is required than Such as e. g. Sulpho-ureides of the SugarS, thio With the use of other thio-Sugars, an amount of acetyl derivatives of the sugars, thio-amino 5) the Order of at east, 0.4% of the amount of aSCOr Sugars, etc. The Sugar Sulpho-ureides are chair bic acid present being Suificient. The above acterized by the group minimum proportions of Stabilizer are valid for N at least 1% concentrations. Of C-Vitamin (1 gram -s-C/ of C-Vitamin in 100 grains of Solution). If the -S S5 C-Vitamin Solutions are more diluted, it may be NE necessary to add relatively larger proportions of stabilizer, so that the addition of stabilizer may or by the group -N-CS-NH2 which are united reach under certain conditions an amount of the ...to a residue (a radical) of Some simple Sugar, Order of the an Ount of C-Vitamin present.
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