사카린
사카린 · Benzo[d]isothiazol-3(2H)-one 1,1-dioxide · SACCHARINE · INSOLUBLE SACCHARIN · Sacharin · O-SULFOBENZIMIDE · GLUCID · Sacarina

식별자 및 물리적 특성
| CAS No. | 81-07-2 |
|---|---|
| 분자식 | C7H5NO3S |
| 평균 분자량 | 183.19 g/mol |
| 단동위원소 질량 | 182.99901402 g/mol |
| SMILES | O=C1NS(=O)(=O)c2ccccc21 |
| InChIKey | CVHZOJJKTDOEJC-UHFFFAOYSA-N |
| PubChem CID | 5143 |
| ChEMBL | CHEMBL310671 |
| ChEBI | CHEBI:32111 |
| EC No. | 201-321-0 |
| DTXSID | DTXSID5021251 |
| 현지명 | 사카린 |
화학 및 물리적 성질
| XLogP | 0.9 |
|---|---|
| 극성 표면적 | 71.6 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 12 |
| 형식 전하 | 0 |
| 복잡도 | 303 |
| 물질 분류 | Other Uses -> Food Additives |
| 의약품 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| 화장품 | MaskingOral care |
| pH | pH of 0.35% aqueous solution: 2.0 |
| SpringerMaterials Properties | Crystal structure |
| 향료 | Fragrance Ingredient (Saccharin) -> IFRA transparency List |
| 농약 | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP(분배 계수) | log Kow = 0.91 |
| 냄새 | ODORLESS OR HAS FAINT AROMATIC ODOR.냄새 없는 |
| 맛 | In dilute aqueous solution it is 500 times as sweet as sugarsweet taste detectable in 1:100,000 dilution.Bitter, metallic aftertaste |
| 식품 첨가물 | NON-NUTRITIVE SWEETENER -> FDA Substance added to food |
| 밀도 | 0.828 (NTP, 1992) - Less dense than waterwill float0.828 g/cu cm at 25 °C |
| 녹는점 | 226-229 °C (lit.) |
| 끓는 점 | subl |
| 증기압 | 0Pa at 25℃ |
| 굴절률 | 1.5500 (estimate) |
| 저장 조건 | Store below +30°C. |
| 용해도 | 아세톤: 12mL(lit.)에 1g이 용해됩니다. |
| 물리적 상태 | 결정 또는 결정성 분말 |
| pKa(산도 계수) | 11.68(at 18℃) |
| 색상 | 하얀색 |
| 용해도 | 3.3g/L(20℃) |
| Merck | 14,8311 |
| BRN | 6888 |
| 헨리 상수 | 8.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 안정성 | 안정적인. 강한 산화제와 호환되지 않습니다. |
| 화장품 원료 기능 | 향기구강 관리 |
| InChI | 1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9) |
| InChIKey | CVHZOJJKTDOEJC-UHFFFAOYSA-N |
| SMILES | O=C1NS(=O)(=O)c2ccccc12 |
| LogP(분배 계수) | -0.024 at 25℃ |
| NIST | Saccharin(81-07-2) |
| EPA | Saccharin (81-07-2) |
화학적 성질
Saccharin is a crystalline solid with a sweet taste (500 times sweeter than sugar).
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 97% (549 of 566) of all reports.Not ClassifiedAggregated GHS information provided per 566 reports by companies from 6 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxideCommission Regulation No 844/20121,2-Benzisothiazol-3(2H)-one, 1,1-dioxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 12-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11056Saccharin: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 기타 안전 정보 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 화재 위험 | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| 건강 유해성 | SYMPTOMS: Symptoms of exposure to this compound include anorexia, nausea, vomiting, diarrhea and gastric hyperacidity. Other symptoms include coughing, chest pain and irritation of the eyes, nose and throat. |
| 유해성 요약 | May cause irritation[Sigma-Aldrich MSDS] |
| FDA 요건 | The food additives saccharin, ammonium saccharin, calcium saccharin, and sodium saccharin may be safely used as sweetening agents in food in accordance with the following conditions /in part 180, section 37/, if the substitution for nutritive sweeteners is for a valid special dietary purpose and is in accord with current special dietary food regulations and policies or if the use or intended use is for an authorized technological purpose other than calorie reduction.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Saccharin is included in weight control drugs. |
용도
용도
It is a non-nutritive sweetener; pharmaceutic aid (flavor). Saccharin was formerly listed as reasonably anticipated to be a human carcinogen; delisted because the cancer data are not sufficient to meet the current criteria for this listing.
일반 설명
White crystals. Odorless or faintly aromatic odor. Sweet taste.
제조 및 합성 방법
제조 방법
Saccharin is synthesized using two methods: the Remsen-Fahlberg process and the Maumee or Sherwin-Williams method. The Remsen-Fahlberg synthesis of saccharin starts by reacting toluene with chlorosulfonic acid to give ortho and para forms of toluene-sulfonic acid (Figure 78.1). The acid can be converted to sulfonyl chlorides by treating with phosphorus pentachloride. The ortho form, o-toluene-sulfonyl chloride, is treated with ammonia to give o-toluene-sulfonamide, which is then oxidized with potassium permanganate to produce o-sulfamido-benzoic acid. On heating, the latter yields saccharin. Another synthesis was developed at Maumee Chemical Company in Toledo, Ohio, and it came to be known as the Maumee process. This process starts with phthalic anhydride, which is converted into anthranilic acid. Anthranilic acid is then reacted with nitrous acid, sulfur dioxide, chlorine, and ammonia to give saccharin. The Maumee process was further refi ned by the Sherwin-Williams Company and is therefore now referred to as the Sherwin-Williams process.
생산 방법
Saccharin is prepared from toluene by a series of reactions known as the Remsen–Fahlberg method. Toluene is first reacted with chlorosulfonic acid to form o-toluenesulfonyl chloride, which is reacted with ammonia to form the sulfonamide. The methyl group is then oxidized with dichromate, yielding o-sulfamoylbenzoic acid, which forms the cyclic imide saccharin when heated. An alternative method involves a refined version of the Maumee process. Methyl anthranilate is initially diazotized to form 2- carbomethoxybenzenediazonium chloride; sulfonation followed by oxidation then yields 2-carbomethoxybenzenesulfonyl chloride. Amidation of this material, followed by acidification, forms insoluble acid saccharin.