SACCHARINE
Saccharin
CAS: 81-07-2
Molecular Formula: C7H5NO3S
SACCHARINE - Names and Identifiers
SACCHARINE - Physico-chemical Properties
| Molecular Formula | C7H5NO3S |
| Molar Mass | 183.18 |
| Density | 0.828 |
| Melting Point | 226-229 °C (lit.) |
| Boling Point | subl |
| Water Solubility | 3.3 g/L (20 ºC) |
| Solubility | Soluble in alkali carbonate solution, soluble in ethanol, acetone, slightly soluble in chloroform and ether. 1g is soluble in 290ml of water, 25ml of boiling water, 31ml of ethanol, 12ml of acetone and about 50ml of glycerol, slightly soluble in chloroform and ether. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | White crystalline powder |
| Color | White |
| Odor | odorless |
| Merck | 14,8311 |
| BRN | 6888 |
| pKa | 11.68(at 18℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00005866 |
| Physical and Chemical Properties | Colorless to white crystals or white crystalline powder, odorless or slightly aromatic. Taste is very sweet, diluted 10000 times the aqueous solution still has sweet taste. The sweetness of the dilute solution is about 500 times that of sucrose, and the taste is slightly bitter. Melting point 228 °c (decomposition). Saturated aqueous solution 0.25%) was acidic (pH 2.0). Very unstable (decomposition) under acidic conditions (pH below 3.8). In case of alkali or its aqueous solution heating can be decomposed (alkali is more stable than acid). Slightly soluble in water (25 ° C, 1g/290ml; Boiling water, 1g/25 m1) and soluble in alkaline solution (ammonia, hydroxide alkali, carbonate alkali, etc.). Slightly soluble in ethanol (1g/31m1), slightly soluble in chloroform and ether. |
| Use | Mainly used for the production of pesticide intermediates and the production of sodium saccharin |
SACCHARINE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R62 - Possible risk of impaired fertility R63 - Possible risk of harm to the unborn child R68 - Possible risk of irreversible effects |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | DE4200000 |
| TSCA | Yes |
| HS Code | 29251100 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 oral in mouse: 17gm/kg |
SACCHARINE - Reference
| Reference Show more | 1. Yang Ban, Feng Liang, Liu Jun, Zhao Jing, Li Chao, Zhu Fagen, Shao Jianguo, Jia Xiaobin, Sun e. Study on improvement of medication compliance of pudilan antiphlogistic oral liquid for children based on material characterization technology [J]. World Chinese medicine, 2020,15(15):2221-2227. 2. Yin, kai‐jing, et al. "Effect and mechanism of high‐fat diet on the preference for sweeteners on mice." Journal of the Science of Food and Agriculture 101.5 (2021): 1844-1853.https:// doi.org/10.1002/jsfa.10798 3. Ren, Jing-Nan, et al. "Effect of short-term, solution consumption and neurotransmitters release on mice." Journal of Food Science and Technology 58.6 (2021): 2227-2236.https://doi.org/10.1007/s13197-020-04733-7 4. [IF=3.638] Kai-Jing Yin et al."Effect and mechanism of high-fat diet on the preference for sweeteners on mice."J Sci Food Agr. 2021 Mar;101(5):1844-1853 |
SACCHARINE - Reference Information
| LogP | -0.024 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. Sup 7, 73) 1999 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | pure saccharin, is a non-toxic, non-calorie, non-nutritive, not absorbed by the body of the sweetener. The use of its sweet characteristics, as a food additive, instead of sugar. Saccharin as a food additive, in addition to the taste caused by the feeling of sweet, taste sweetness can meet the requirements of consumers, the human body without any nutritional value. Commercially available "Saccharin" is actually its sodium salt, sodium saccharin. After being ingested by people, saccharin is excreted in vitro with urination and bowel movement, but excessive consumption will cause poisoning. FAO/WHO (Food and Agriculture Organization of the United Nations/United Nations World Health Organization (WHO)) in 1994, the daily weight intake of 0~5 mg/kg. On October 27, World Health Organization (WHO), the International Agency for Research on Cancer published a preliminary list of carcinogens for reference, saccharin and its salts in the list of three carcinogens. Saccharin is not a good sweetener. Its "sweet" is not pure, after eating the "Aftertaste" is very poor, high concentration and bitter taste. In 1937, a graduate student at the University of Illinois discovered cyclamate. The sweetness of this substance is 30 to 50 times that of sucrose, and its sweet taste is not pure, but its price is lower than that of saccharin. More importantly, when it is mixed with saccharin, it can mask the defects of each other, so as to obtain a sweet taste closer to sucrose. In 1958, sodium cyclamate was also eligible for GRAS. |
| properties | solubility: solubility in water is very low, soluble in sodium carbonate, soluble in alcohol, acetone glycerol, slightly soluble in chloroform and ether. |
| Use | saccharin, also known as saccharin sodium, is the oldest sweetener. Saccharin was discovered by American scientists in 1878 and was soon accepted by the food industry and consumers. The sweetness of saccharin is 300 times to 500 times that of sucrose. It is not metabolized and absorbed by the human body and is stable in the production of various foods. The disadvantage is poor flavor, after the bitter, which makes its application is limited. For many years, saccharin has been the only synthetic sweetener produced and used in large quantities in the world. Especially during the Second World War, the use of saccharin in the world increased significantly. Non-nutritive sweetener. The sodium or ammonium salts thereof are generally used. But it can dissolve slowly in the mouth, so it is suitable for chewing gum, the highest dosage of 0.05g/kg (Japan, 1998). saccharin, I .e., O-benzoylsulfonimide, is an intermediate of the fungicide allyl benzothiazole and the herbicides metsulfuron-methyl, tribenuron-methyl, tribenuron-methyl and chlorsulfuron-methyl. mainly used in the production of pesticide intermediates and production of saccharin sodium mammalian sweet taste enhancer; Used as phosphotransferase and phosphohydrolase inhibitors; for the determination of thallium |
| health hazard | saccharin is a synthetic sweetener ", there is no nutritional value to the human body except for the feeling of sweet in the sense of taste. On the contrary, when eating more saccharin, will affect the normal secretion of gastrointestinal digestive enzymes, reduce the absorption capacity of the small intestine, so that loss of appetite. In particular, a small number of consumers do not know the harm of saccharin, and consume a large amount of saccharin in a short period of time, causing thrombocytopenia and causing acute hemorrhage, multiple organ damage, etc., causing malignant poisoning events. The situation of saccharin in China seems to be more serious. In May 2015, the country implemented the new "standards for the use of food additives", further narrowing the scope of the use of sodium saccharin (soluble saccharin), bread, cakes, biscuits, beverages the use of saccharin in these four types of food is prohibited. |
| content analysis | a pre-dried sample of 0.5g was accurately weighed and dissolved in 75ml of hot water. Rapid cooling, phenolphthalein solution (TS-167) several drops, with 0.1mol/L sodium hydroxide titration. Each ml of 0.1mol/L sodium hydroxide is equivalent to saccharin (C7H5NO3S)18.32mg. |
| toxicity | ADI 0~5(ADI refers to the sum of saccharin and its calcium, potassium and sodium salts; FAO/WHO,2001). LD50 14200mg/kg (rat, oral). |
| usage limit | FDA,§ 180.37(2000): beverages, fruit juices, solid beverages, 12mg/liquid, sweetness corresponds to an amount of 20mg of a tablespoon; 30mg per serving of processed food of the specified size. USDA,9CFR,§ 318.7(2000): pricking meat (bacon) 0.01%. |
| carcinogenic doubt | in the 60 s of the 20th century, various academic studies suggested that saccharin may be a carcinogen. In 1976, a study reported that when mice were fed high doses of saccharin (the amount of saccharin found in hundreds of cans of cola), the risk of bladder cancer rose dramatically. In that year, Canada banned the use of saccharin, while the U. S. Food and Drug Administration imposed a ban on the use of saccharin in food. At that time, saccharin was the only sugar substitute in the US market, and the ban caused strong public opposition, especially for people with diabetes. Finally, the US Congress suspended the ban on saccharin, stating that all foods containing saccharin must display a warning label stating that 'saccharin may be a carcinogen '. Some studies have shown that it has been found in animal experiments to lead to the possibility of bladder cancer, the animal cancer is positive, a large number of intake will cause thrombocytopenia and cause acute bleeding, can damage the structure of cells and liver, kidney, will induce bladder cancer. But no adverse effects were found in human trials. Many studies have demonstrated no association between saccharin and the risk of cancer, particularly bladder cancer. All the studies point to the clear fact that a normal dose of saccharin consumption does not have much impact on human health. Questions about the safety of saccharin come from a flawed study that pointed to the adverse effects of large amounts of sugar substitutes on bladder tumors in laboratory white rats. Further studies have shown that the carcinogen of saccharin in rats does not apply to humans. The National Institute of Environmental Health Sciences concluded in 2000 that saccharin had been removed from the list of suspected carcinogens. In 1991, 14 years after the ban, the U. S. Food and Drug Administration formally withdrew its proposal to ban saccharin, and in 2000, the U, saccharin products need not be labeled with health warnings. |
| production method | the preparation method is the degradation of phthalic anhydride by amination, diazotization, replacement, oxidation, acid Analysis and other steps. Add phthalic anhydride to the reaction pan, add ammonium hydroxide solution at 0 ℃, raise the temperature to 50 ℃, add sodium hydroxide solution, control the rate of adding alkali, keep the temperature below 70 ℃, the pH was maintained between 8.5 and 8.9. After adding alkali, adjust the pH value to 12~13, keep the temperature at 65~70 ℃ for 0.5h, keep the ammonia off for 35h, and cool to -10 ℃, add pre-cooled methanol at -10 °c and sodium hypochlorite solution at -10 °c, react for 45min below 0 °c, then gradually raise the temperature to 30 °c, with potassium iodide starch test paper test should be colorless reaction, and then add the appropriate amount of sodium bisulfite hydrolysis. After the feed liquid was diluted, it was heated to 50 ° C., then hot water of 80 ° C. Was added, stirred and dissolved, left to stand and filtered, and the oil layer was separated to obtain methyl anthranilate. The O-aminobenzoic acid methyl ester and sodium nitrite solution were stirred and mixed, and then added dropwise to the mixed acid in the diazonium pot for reaction, The temperature at which the dropwise addition is started is about 10 ° C., the reaction temperature is not more than 25 ° C., and the potassium iodide starch solution at the end of the reaction is light green. The diazo reaction solution is cooled to 10 ℃, added with copper sulfate, dissolved, and then passed into SO2 (about 1H through) to precipitate methyl benzoate of O-sulfinic acid. The end point of substitution should be colorless by using H acid test paper, add toluene, at 30~35 ℃ through chlorine gas to 2%, benzidine ethylamine test paper test showed dark green as the end of chlorination, static stratification, take organic layer to get O-sulfonyl chloride methyl benzoate toluene solution, then add water and O-sulfonyl chloride methyl benzoate toluene solution to the reaction pot, cool to 10 °c, add ammonium hydroxide solution and stir, temperature up to 70 °c, the end point of the test (2% benzidine pyrazole test paper, not immediately yellow as the end point) is 15min after the reaction of pH value above 9. Take the lower ammonium salt solution and add toluene and 30% hydrochloric acid in layers to make the pH value below 1, after acid analysis, it was cooled to 20 ° C., and the acid water layer and toluene layer were separated and washed with water to remove ammonium chloride, to obtain insoluble saccharin toluene gel. It is obtained from phthalic anhydride by the steps of amination, degradation, esterification, diazotization, substitution, chlorination, cyclization, acid precipitation, etc. (1) amination, degradation, esterification preparation of methyl anthranilate. (2) diazotization, replacement, chlorination of methyl O-sulfochlorobenzoate. (3) The insoluble saccharin was obtained by cyclization and acid analysis. see "02326, saccharin sodium" and the aforementioned "023.3.1". |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | oral-mouse LD50;17000 mg/kg |
| flammability hazard characteristics | flammability; Toxic nitrogen oxide and sulfur oxide fumes from combustion |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:08
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SACCHARINE
2-Propenoic acid, 1-(1-methylethyl)cyclopentyl ester
氨基甲酸胺
(2R,4R)-4-METHYL-2-PIPERIDINECARBOXYLATE
3,5-Dimethoxy
吡啶 盐酸盐
Amyl Acetate (mixed isomers)
TERT-BUTYL N-(3-AMINOPHENYL)-N-METHYLCARBAMATE
Equipax
2-Propenoic acid, 1-(1-methylethyl)cyclopentyl ester
氨基甲酸胺
(2R,4R)-4-METHYL-2-PIPERIDINECARBOXYLATE
3,5-Dimethoxy
吡啶 盐酸盐
Amyl Acetate (mixed isomers)
TERT-BUTYL N-(3-AMINOPHENYL)-N-METHYLCARBAMATE
Equipax