GB2118933A - Saccharin derivative - Google Patents
Saccharin derivative Download PDFInfo
- Publication number
- GB2118933A GB2118933A GB08303376A GB8303376A GB2118933A GB 2118933 A GB2118933 A GB 2118933A GB 08303376 A GB08303376 A GB 08303376A GB 8303376 A GB8303376 A GB 8303376A GB 2118933 A GB2118933 A GB 2118933A
- Authority
- GB
- United Kingdom
- Prior art keywords
- saccharin
- calcium
- salt
- tablets
- aqueous suspension
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 title claims abstract description 14
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229940081974 saccharin Drugs 0.000 claims abstract description 10
- 235000019204 saccharin Nutrition 0.000 claims abstract description 10
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims abstract description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 5
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 4
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- MQRKKLAGBPVXCD-UHFFFAOYSA-L calcium;1,1-dioxo-1,2-benzothiazol-2-id-3-one;hydrate Chemical compound O.[Ca+2].C1=CC=C2C([O-])=NS(=O)(=O)C2=C1.C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 MQRKKLAGBPVXCD-UHFFFAOYSA-L 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000011575 calcium Substances 0.000 abstract 1
- GSHUZVSNIBLGMR-UHFFFAOYSA-N calcium;1,1-dioxo-1,2-benzothiazol-3-one Chemical compound [Ca].C1=CC=C2C(=O)NS(=O)(=O)C2=C1 GSHUZVSNIBLGMR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- 229940003871 calcium ion Drugs 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Calcium saccharin (C7H4NO3S)2 Ca is produced by addition of calcium carbonate to an agitated aqueous suspension of free saccharin at 50- 55 DEG C until a pH of 4.5 to 5.75 is reached, filtering, and crystallising the filtrate. It retains the sweetness of sodium saccharin and is pharmacologically more acceptable.
Description
SPECIFICATION
Saccharin derivative and method for its preparation
This invention relates to the preparation of a saccharin derivative.
Saccharin is known to have a sweetening power which is greater than that of sugar by a multiple of about 350. It also has the advantage from the organoleptic point of view of not being toxic to the human organism for example to diabetics.
Due to its pronounced sweetness it is at present generally distributed in small dosages, e.g. as pills or tablets, in which it constitutes part or all of the total composition. Such pills or tablets may also contain other therapeutically active materials, and/or additives which are pharmacologically acceptable but not independently active, and/or one or more inert vehicles.
Nevertheless, in spite of being non-toxic and being usable with other materials in a large range of pharmacological and like applications, saccharin itself presents the inconvenience of not being very soluble in water. It is commonly used in salt form, and the best known formulations on the market are based on the sodium salt. Known tablet compositions are generally made up of saccharin in the form of the crystallised sodium salt. Mixtures of saccharin (with the free iminic acid group) and bicarbonate of soda in an aqueous medium, whereby the components react to form the soluble sodium salt, are also known.
The present invention provides the compound calcium saccharin, of formula:
Preferably the compound is provided in crystalline form.
There are advantages of this compound over the known sodium form salt or saccharin itself.
The sweetening power is the same as that of the sodium salt, but sodium ion is eliminated and calcium ion which does not alter the ionic balance of the blood during the physiological processes of distribution and renal elimination of the sweetener is provided. This calcium ion is beneficial as a structural component in both bone and tissue. Thus, pharmacologically such as calcium-ion-containing materials are preferable to those containing sodium ions.
.In another aspect the invention provides a method for preparing the calcium saccharin material of the formula given above which comprises providing an aqueous suspension of saccharin; adding thereto a calcium salt reactive therewith while maintaining the temperature within the range of 50-550C; discontinuing the reaction when the pH of the combined reactants lies at a value between 4.50 and 5.75; filtering the combined reactants; and crystallizing calcium saccharin from the filtrate.
Preferably the calcium salt is calcium carbonate.
The mechanical preparation of the dosage units (tablets, etc) of calcium saccharin with other components and/or inert acceptable therapeutic vehicles may be carried out in accordance with the usual methods. Such dosage units, e.g.
tablets, also constitute an aspect of the invention.
The following non-limiting example illustrates the method of the invention.
Example
Saccharin was suspended in an aqueous suspension containing 85% by weight of the saccharin. This suspension was constantly agitated throughout the operation. At a constant temperature of between 500 and 55"C, finely divided pure calcium carbonate was slowly added, the continuous agitation assisting the escape of carbon dioxide gas during this slow addition.
After the addition was complete the pH of the mixture was checked. When the pH reached a value between 4.50--5.75, i.e. when the mixture was slightly acid, without excess calcium carbonate, and while maintaining the temperature, the solution was filtered, and evaporated to give solid crystals of calcium saccharin of formula:
Claims (5)
1. Calcium saccharin of formula:
2. Calcium saccharin as claimed in claim 1 in crystalline form.
3. A method of preparing calcium saccharin as claimed in claim 1 which comprises: providing an aqueous suspension of saccharin; adding thereto a calcium salt reactive therewith while
maintaining the temperature within the range of 50-550C; discontinuing the reaction when the
pH of the combined reactants lies at a value
between 4.5 and 5.75; filtering the combined
reactants, and crystallising calcium saccharin
from the filtrate.
4. A method as claimed in claim 3 in which the calcium salt is calcium carbonate.
5. Dosage units, such as tablets or the like, comprising calcium saccharin as claimed in claim
1 or2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES509932A ES509932A0 (en) | 1982-02-26 | 1982-02-26 | "PROCEDURE FOR PREPARING COMPOSITIONS OF CALCICA AND CRYSTALLIZED SACARINE". |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8303376D0 GB8303376D0 (en) | 1983-03-16 |
| GB2118933A true GB2118933A (en) | 1983-11-09 |
| GB2118933B GB2118933B (en) | 1987-05-20 |
Family
ID=8483724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08303376A Expired GB2118933B (en) | 1982-02-26 | 1983-02-08 | Saccharin derivative |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS58157776A (en) |
| BE (1) | BE895741A (en) |
| CH (1) | CH657128A5 (en) |
| ES (1) | ES509932A0 (en) |
| GB (1) | GB2118933B (en) |
| IT (1) | IT1171002B (en) |
| NL (1) | NL8300726A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586381A (en) * | 2018-04-16 | 2018-09-28 | 天津北方食品有限公司 | A kind of preparation method of saccharin sodium |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1274288A (en) * | 1969-10-20 | 1972-05-17 | Lionel Leslie Frederic Deadman | The use of glutamic acid and glutamates for modifying the taste of artificial sweeteners |
| GB1275505A (en) * | 1970-03-02 | 1972-05-24 | Pfizer | Artificially sweetened non-dairy, water-based food compositions |
-
1982
- 1982-02-26 ES ES509932A patent/ES509932A0/en active Granted
-
1983
- 1983-01-28 BE BE0/209999A patent/BE895741A/en not_active IP Right Cessation
- 1983-02-08 CH CH695/83A patent/CH657128A5/en not_active IP Right Cessation
- 1983-02-08 GB GB08303376A patent/GB2118933B/en not_active Expired
- 1983-02-18 JP JP58026120A patent/JPS58157776A/en active Pending
- 1983-02-25 NL NL8300726A patent/NL8300726A/en not_active Application Discontinuation
- 1983-02-25 IT IT67215/83A patent/IT1171002B/en active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1274288A (en) * | 1969-10-20 | 1972-05-17 | Lionel Leslie Frederic Deadman | The use of glutamic acid and glutamates for modifying the taste of artificial sweeteners |
| GB1275505A (en) * | 1970-03-02 | 1972-05-24 | Pfizer | Artificially sweetened non-dairy, water-based food compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CH657128A5 (en) | 1986-08-15 |
| ES8304104A1 (en) | 1983-03-01 |
| JPS58157776A (en) | 1983-09-19 |
| ES509932A0 (en) | 1983-03-01 |
| GB2118933B (en) | 1987-05-20 |
| IT1171002B (en) | 1987-06-10 |
| BE895741A (en) | 1983-05-16 |
| IT8367215A0 (en) | 1983-02-25 |
| GB8303376D0 (en) | 1983-03-16 |
| NL8300726A (en) | 1983-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |