Sodium cyclamate (cyclamate) 139-05-9
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Cyclamate is an artificial sweetener whose content is 30 times that of sucrose. It is widely used in pickles, sauces, cakes, biscuits, bread, ice cream, frozen suckers, popsicles, beverages, etc. The maximum usage amount is 0.65g/kg. Secondly, when used in candies, the maximum usage amount is 1.0g/kg. The third is used for tangerine peel, preserved plums, dried bayberry, etc., with the maximum dosage of 8.0g/kg. It is also used in the cosmetic and pharmaceutical industries.
| chemical properties | White powder |
| chemical properties | Cyclamate comes as white, odorless or almost odorless crystals, or crystalline powder with a strong sweet taste. |
| history | Cyclamate was first synthesized in 1937. Like other sweeteners, its sweetness was discovered by accident (US Patent 2,275,125 (March 3, 1942) to LF Andrieth and M. Sveda (granted to EI du Pont de Nemours & Co., Inc.) ). FDA listed cyclamate as a GRAS sweetener in 1958. In 1969, a 2-year chronic toxicity study of a cyclamate-sodium saccharin (10:1) mixture found bladder tumors in rats. FDA removes cyclamate from GRAS. Cyclamate is included in the list, which is prohibited from being used in food and beverages, but allowed to be sold in pharmacies. In 1970, following a congressional investigation, the FDA banned cyclamate entirely. Abbott Laboratories conducted additional toxicity and carcinogenicity studies on cyclamate, 10:1 A mixture of cyclamate-saccharin and cyclohexylamine, claiming to be unable to confirm the 1969 findings. Abbott then filed a food additive petition against cyclamate in 1973, but the petition was rejected by the FDA in 1980. In 1982, the Calorie Control Council and Abbott Laboratories filed a second food additive petition incorporating the results of other safety studies (Calorie Control Council and Abbott Laboratories). Abbott Laboratories, Food Additive Petition Against Cyclamate 2A3672 (September 22, 1982). The petition remains active. |
| use | Cyclamate is an artificial sweetener with 30 times the content of sucrose. Widely used in pickles, sauces, cakes, biscuits, bread, ice cream, frozen suckers, popsicles, beverages, etc., the maximum usage is 0.65g/kg. Secondly, for candy, the maximum usage is 1.0g/kg. The third is used for tangerine peel, preserved plum, bayberry, etc., with a maximum dosage of 8.0g/kg. It is also used in the cosmetic and pharmaceutical industries. |
| use | Cyclamate (cyclamic acid and its calcium and sodium salts) was discovered in the United States in 1937. They are 30 to 80 times sweeter than sucrose and were widely used until late 1969, when they were banned by the FDA due to safety concerns. Canada and the European Union have not banned it. Cyclohexylamine reacts with a sulfonating agent, and then reacts with sodium hydroxide or calcium hydroxide to generate cyclamate and free cyclohexylamine, as follows to produce cyclamate. Due to its good stability, cyclamate is suitable for all applications of intense sweeteners, does not disturb the taste significantly, and is heat stable. The main application of cyclamate is to mix with saccharin in a weight ratio of 10:1. The blend is more than twice as sweet as either of the individual ingredients, making them an important sweetener in countries where both are approved. |
| use | sweetener. |
| production method | Sulfonation of cyclohexylamine in the presence of base can prepare cyclohexylsulfamate. Commercially, sulfonation can involve sulfamic acid, sulfates, or sulfur trioxide. As the condensation agent, tertiary bases such as triethylamine and trimethylamine can be used. The resulting amine salt of cyclamate is converted to the sodium, calcium, potassium or magnesium salt by treatment with an appropriate metal oxide. |
| definition | ChEBI: Cyclamate is an organic molecular entity. |
| brand | Adocyl;Ampenoline balsamoco;Assugrin;Azucrona;Cyclarin;Glusac super;Ilgon;Sladicin;Sucaryl calcium;Sucaryl sodium;Sucrum 7. |
| World Health Organization (WHO) | Cyclamate is a non-nutritive sweetener that has been used as an additive in food and pharmaceuticals since the 1950s. They have been shown to have carcinogenic potential in experimental animals at extremely high and long-term sustained doses. Therefore, some countries ban their use as food additives, while in others they can still be used for this purpose. However, most countries still allow their use in small quantities in pharmaceutical preparations. (Reference: (WHODI) World Health Organization Drug Information, 77.2, 12, 1977) |
| general instructions | Odorless or almost odorless white crystals or crystalline powder. It has an intensely sweet taste even in dilute solution. pH value (10% aqueous solution): 5.5-7.5. Used as a non-nutritive sweetener. |
| air and water reaction | water soluble. |
| reactive profile | Sodium N-cyclohexylsulfamate is incompatible with strong oxidizing agents, acids and bases. Also incompatible with nitrite in acidic solutions. Limited compatibility with potassium salts. |
| adventure | Some evidence of causing cancer in experimental animals. FDA prohibited for use in food. Suspected carcinogen. |
| fire hazard | There are no flash point data for sodium N-cyclohexylsulfamate; however, sodium N-cyclohexylsulfamate may be flammable. |
| Flammability and explosiveness | uncategorized |
| pharmaceutical application | Cyclamate is used as an intense sweetener in pharmaceutical formulations, foods, beverages, and tabletop sweeteners. In dilute solutions, at concentrations up to about 0.17% w/v, the sweetening power is about 30 times that of sucrose. However, at higher concentrations this decreases, and at a concentration of 0.5% w/va the bitterness becomes apparent. Cyclamate enhances the flavor system and can be used to mask some unpleasant taste characteristics. In most applications, cyclamate is used in combination with saccharin, usually in a ratio of 10:1. |
| Biochemical/Physiological Actions | Human detectable amounts of phenylsulfamate sweeteners. The carcinogenic potential of "first-generation" sweeteners has been studied in animal models. |
| toxicology | Cyclamate is an odorless powder. The sweetness of its dilute solution is about 30 times that of sucrose. The structure of cyclamate is shown in Figure 10.10. Capillary transitional cell tumors were found in the bladders of 8 of 80 rats that received 2600 mg/kg body weight per day of a mixture of cyclamate and sodium saccharin (10:1). Up to 105 weeks. When the test mixture was fed at diet levels of 500, 1120 and 2500 mg/kg bw to groups of 35 and 45 female rats, the only significant finding was the development of bladder papillae in 12 of 70 rats Cancers were fed the mixture at maximum dietary levels (equivalent to approximately 25 g/kg body weight) for 78 to 105 weeks (except for one individual who died early). Conversion from cyclamate to cyclohexylamine was observed in vivo, especially in the higher dose groups. Compared with cyclamate (oral LD50 in rats = 12g/kg), cyclohexylamine is very toxic (oral LD50 in rats = 157mg/dg). |
| Security overview | The intravenous and intraperitoneal routes are moderately toxic. Mildly toxic if swallowed. Experimental reproductive effects. Suspected carcinogens with experimental data on tumorigenicity, oncogenicity and teratogenicity. Human mutation data are reported. When heated and decomposed, highly toxic fumes containing NazO, SOx and NOx are released. |
| Safety | After the FDA decided in 1970 to ban the use of cyclamate in the United States, considerable controversy arose regarding the safety of cyclamate. The decision stems from a feeding study in rats that suggested cyclamate may cause an unusual form of bladder cancer. However, the study was criticized because it involved very high doses of cyclamate and saccharin, which itself is controversial over its safety. See saccharin. Although excreted almost entirely unchanged in the urine, cyclohexylamine, a potentially harmful metabolite of cyclamate, has been detected in humans. In addition, there is evidence that cyclamate is metabolized to cyclohexylamine by microorganisms in the large intestine of some people (approximately 25% of the population, higher in Japanese than in Europeans or North Americans). After absorption of cyclohexylamine, 1-2% is metabolized to cyclohexanol and cyclohexane-1,2-diol. The determined No Observed Effect Level (NOEL) and Acceptable Daily Intake (ADI) values were based on cyclohexylamine levels for high cyclamate converters. (6,7) Extensive long-term animal feeding studies and human epidemiological studies have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, cyclamate is now accepted for use in food and pharmaceutical preparations in many countries. 1-2% is metabolized to cyclohexanol and cyclohexane-1,2-diol. The determined No Observed Effect Level (NOEL) and Acceptable Daily Intake (ADI) values were based on cyclohexylamine levels for high cyclamate converters. (6,7) Extensive long-term animal feeding studies and human epidemiological studies have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, cyclamate is now accepted for use in food and pharmaceutical preparations in many countries. 1-2% is metabolized to cyclohexanol and cyclohexane-1,2-diol. The determined No Observed Effect Level (NOEL) and Acceptable Daily Intake (ADI) values were based on cyclohexylamine levels for high cyclamate converters. (6,7) Extensive long-term animal feeding studies and human epidemiological studies have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, cyclamate is now accepted for use in food and pharmaceutical preparations in many countries. 7) Extensive long-term animal feeding studies and human epidemiological studies have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, cyclamate is now accepted for use in food and pharmaceutical preparations in many countries. 7) Extensive long-term animal feeding studies and human epidemiological studies have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, cyclamate is now accepted for use in food and pharmaceutical preparations in many countries. Although cyclamate use has been associated with photosensitivity dermatitis, there are few reports of adverse reactions to cyclamate. The World Health Organization has estimated the acceptable daily intake of sodium cyclamate and cyclamate (expressed as cyclamate acid) to be 11 mg per kilogram of body weight. In Europe, the provisional acceptable daily intake for cyclamate sodium and cyclamate calcium (expressed as cyclamate acid) has been set at a maximum of 1.5 mg/kg body weight. LD50 (mouse, IP): 1.15 g/kg LD50 (mouse, IV): 4.8 g/kg LD50 (mouse, oral): 17 g/kg LD50 (rat, IP): 1.35 g/kg LD50 ( Rat, IV): 3.5 g/kg LD50 (Rat, Oral): 15.25 g/kg |
| storage | Cyclamate is hydrolyzed by sulfuric acid and cyclohexylamine at a very slow rate that is proportional to the hydrogen ion concentration. Therefore, for all practical considerations it can be considered stable. The solution is also stable to heat, light and air over a wide pH range. Tablet samples containing cyclamate and saccharin showed no loss of sweetening ability after storage for up to 20 years. Bulk materials should be stored in closed containers in a cool, dry place. |
| Regulatory status | The use of cyclamate as an artificial sweetener in food, soft drinks and artificial sweetener tablets was once banned in the UK and some other countries due to concerns about the metabolite cyclohexylamine. However, this is no longer the case and cyclamate is now allowed as a food additive in Europe. Included in FDA's Inactive Ingredients Database (oral powders, solutions, chewable tablets, and suspensions). Included in parenteral medicines licensed in the UK. Listed on Canada's list of acceptable non-medicinal ingredients. |
| Sodium N-cyclohexylsulfamate upstream and downstream product information |
| raw material | Trimethylamine --> Petroleum ether -->Sulfamic acid--> Sulfur trioxide --> Cyclohexylamine -- > Tetrachloroethylene --> Cyclohexylsulfamic acid --> Sulfamic acid monosodium salt-- > Sulfur trioxide trimethylamine complex, 95 |
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