Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Cyclamate
CYCLOHEXANESULFAMIC ACID · Cyclohexylaminesulphonic acid · Sucaryl · Zyklamat · polycat200 · NSC 220327 · hexamicacid · sucarylacid
식별자 및 물리적 특성
| CAS No. | 100-88-9 |
|---|---|
| 분자식 | C6H13NO3S |
| 평균 분자량 | 179.24 g/mol |
| 단동위원소 질량 | 179.06161428 g/mol |
| SMILES | O=S(=O)(O)NC1CCCCC1 |
| InChIKey | HCAJEUSONLESMK-UHFFFAOYSA-N |
| PubChem CID | 7533 |
| ChEMBL | CHEMBL1206440 |
| ChEBI | CHEBI:15964 |
| EC No. | 202-898-1 |
| DTXSID | DTXSID5041809 |
화학 및 물리적 성질
| XLogP | 0.6 |
|---|---|
| 극성 표면적 | 74.8 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 200 |
| 물질 분류 | Other Uses -> Food Additives |
| pH | pH of 10% aqueous solution: 0.8-1.6 |
| SpringerMaterials Properties | Crystal structure |
| 냄새 | Odorless |
| 맛 | Sweet-sourA bitter taste becomes noticeable when quantity in foods approaches 0.5%. |
| Color/Form | CrystalsWhite crystalline powder |
| 용해도 | 1 G DISSOLVES IN ABOUT 7.5 ML OF WATER, 4 ML OF ALC, 4 ML OF PROPYLENE GLYCOL, OR 6 ML OF ACETONESLIGHTLY SOL IN CHLOROFORM AND INSOL IN HEXANEVery soluble in alkaliSoluble in alcoholinsoluble in oils1000000 mg/L @ 25 °C (exp)디옥산: 용해성1g/10mL, 투명, 무색(뜨거운) |
| Human Drugs | Breast FeedingLactationMilk, HumanArtificial SweetenersSweetening Agents |
| Decomposition | When heated to decomposition it emits toxic fumes of sulfoxides and nitroxides.When heated to decomposition it emits toxic fumes of sulfoxides and nitroxides. /Calcium cyclamate dihydrate/ |
| 녹는점 | 169.5 °C169 - 170 °C~180 °C (dec.) |
| 증기압 | 0.0000027 [mmHg]0Pa at 25℃ |
| Physical Description | Large CrystalsWhite odorless solid[Hawley] Fine white crystals[MSDSonline] |
| 끓는 점 | 332.48℃[at 101 325 Pa] |
| 밀도 | 1.149 (estimate) |
| 굴절률 | 1.5500 (estimate) |
| 저장 조건 | Refrigerator |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | pKa 2.28(H2O t=RT c=0.056) (Uncertain) |
| 색상 | 하얀색 |
| 용해도 | 133g/L |
| Merck | 14,2703 |
| BRN | 2208885 |
| InChI | 1S/C6H13NO3S/c8-11(9,10)7-6-4-2-1-3-5-6/h6-7H,1-5H2,(H,8,9,10) |
| InChIKey | HCAJEUSONLESMK-UHFFFAOYSA-N |
| SMILES | OS(=O)(=O)NC1CCCCC1 |
| LogP(분배 계수) | -1.61 at 25℃ |
| NIST | N-cyclohexylsulfamic acid(100-88-9) |
| EPA | Cyclamic acid (100-88-9) |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 25% (7 of 28) of reports.WarningH315 (71.4%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 28 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Sulfamic acid, N-cyclohexyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Sulfamic acid, N-cyclohexyl- 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: 26-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28203Sulfamic acid, cyclohexyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| 유해성 요약 | In lethal dose studies, mice have seizuresOral LD50 (mouse) = 680 mg/kgOral LD50 (rat) = 12,000 mg/kg[ChemIDplus] No toxic effects found in rats fed high doses for entire life[HSDB] An irritantMay cause skin sensitizationEffects in lethal-dose animal studies include convulsions and injury to liver and kidneys[MSDSonline] See Potassium cyclamate. See Sodium cyclamate. |
| FDA 요건 | Cyclamate and its derivatives. Calcium, sodium, magnesium and potassium salts of cyclohexane sulfamic acid. Cyclamates are synthetic chemicals having a sweet taste 30 to 40 times that of sucrose, are not found in natural products at levels detectable by the official methodology, and have been used as artificial sweeteners. Food containing any added or detectable level of cyclamate is deemed to be adulterated in violation of the act based upon an order published in the Federal Register of October 21, 1969 (34 FR 17063). |
| Hazard Classes and Categories | Skin Irrit. 2 (71.4%) |
| 처리 방법 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 상호 작용 | Cyclamate has been shown to interfere with the intestinal absorption of lincomycin by competing for plasma protein absorption sites.PHENYLBUTAZONE ACCELERATES URINARY EXCRETION OF SODIUM CYCLAMATE IN RABBITS, APPARENTLY OWING TO DISPLACEMENT OF CYCLAMATE FROM PLASMA PROTEINS. /SODIUM SALT/NEOMYCIN & SULFAGUANIDINE CAUSED SIGNIFICANT DEPLETION IN URINARY OUTPUT OF SODIUM CYCLAMATE METABOLITES IN MICE & RATS, BUT NOT IN RABBITS... /NA SALT/The effect of cyclamate on the anticoagulant activity of phenprocoumon was investigated in rats after single oral doses of phenprocoumon, cyclamate, or phenprocoumon/cyclamate. By means of high pressure liquid chromatrography (HPLC) the change of the concentration of phenprocoumon per unit time in sera was determined. The anticoagulant acitivity of phenprocoumon was determined by the extension of the prothromin-time (Quick-test). It was found that cyclamate gives rise to an elevation of phenprocoumon in the blood, and a reduction of the anticoagulating potency.For more Interactions (Complete) data for CYCLAMATE (6 total), please visit the HSDB record page. |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that cyclamate is expected to have very high mobility in soil(SRC). The estimated pKa of cyclamate is 1.71(3), indicating that this compound will almost entirely exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and ions do not volatilize. Cyclamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Incubation experiments with activated sludge resulted in a first order half-life of 20 minutes with 99% removal efficiency after 3 hours(6) suggesting that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that cyclamate is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 1.71(3) indicates cyclamate will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). Bioconcentration of cyclamate in aquatic organisms is low due to its ionic nature. Incubation experiments with activated sludge resulted in a first order half-life of 20 minutes with 99% removal efficiency after 3 hours(4) suggesting that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclamate, which has an estimated vapor pressure of 5.3X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyclamate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 3.7 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cyclamate may be removed from the air by wet or dry deposition(SRC). Cyclamate does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 유해 작용 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Average Daily Intake | Cyclamates are widely used as non-caloric sweeteners, the average daily dietary intake generally being less than 3 mg/kg body weight. |
| Effluent Concentrations | Cyclamate concentrations in untreated and treated wastewater from the Canton of Zurich, Switzerland, collected in 2008(1). [Table#960] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of cyclamate can be estimated to be 12(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyclamate is expected to have very high mobility in soil. The estimated pKa of cyclamate is 1.71(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Four groups of 8 men each were administered sodium cyclamate in hard gelatin capsules at 0 (sucrose placebo), 5, 10 or 16 g/day for 213 days. Capsules were taken with regular meals. Blood, urine and semen were collected twice prior to commencing study. Samples of blood and urine were then collected on days 2 and 8 and weekly thereafter while semen was obtained every 2 weeks. Blood was examined for glucose, BUN, cholesterol, Na+, K+, protein bound iodine (PBI), SGPT, hemoglobin, hematocrit and complete blood count. The concentration and motility of sperm in the semen were estimated. Stool was collected on days 2, 4, 9 and 11 and on 2 non-consecutive days and graded as to consistency. Body weight and blood pressure were monitored weekly. The only untoward effect observed was softening of the stool which occurred in 7/8 men receiving 16 g/day and 2/8 receiving 10 g/day. All subjects receiving cyclamate excreted cyclohexylamine in varying amounts on one or more occasions. The percentage of cyclohexylamine that appeared in the urine as free cyclohexylamine varied between 0.25 and 75.4% with a mean value of 17.2%. A significant increase in the concentration of PBI in the serum was also observed. This was shown to be an artifact arising from iodine in the color used in coloring the gelatin capsules/HUMAN EXPOSURE STUDIES/ To determine whether there was a connection between the complaint of restless legs and the ingestion of artificial sweeteners in a patient with these symptoms after drinking certain 'light' beverages.Randomized, double-blind, placebo-controlled N-of-1 trial with a cross-over design. During a period of 48 days, the patient took 4 capsules per day containing either 150 mg of cyclamate, 22.5 mg of saccharine, both sweeteners, or placebo on two successive days. Between each of these 2-day periods there was a 2-day rest period during which no capsules were taken. The hospital pharmacist had prepared the capsules and determined the sequence of the 2-day periods on a random basis. The patient did not know which capsules he was taking. Every day on arising, starting 3 weeks before the trial period, the patient noted the intensity and duration of the symptoms in the late evening and previous night. For this notation he used an 11-point scale, from 0 (= no restless legs) to 10 (= almost total inability to sleep because of restless legs). A score of 1-3 corresponded to mild symptoms that had no effect on the patient's sleepat a score of 4-6 his sleep was disturbed and at a score of 7-10 the patient hardly slept at all. The patient had symptoms more often while using saccharine or the combination of saccharine and cyclamate than when taking the placebo (4 and 4 versus 2 of the 6 nights)moreover, the average score was then statistically significantly higher (5.2 and 5.8 versus 3.3). There was a connection between the patient's complaints of restless legs and the use of saccharine, but not the use of cyclamate./CASE REPORTS/ SOME SKIN CONDITIONS (EG, PRURITUS, DERMOGRAPHIA, URTICARIA, ANGIONEUROTIC EDEMA) HAVE BEEN ATTRIBUTED TO CYCLAMATES. A WOMAN PT WHO TOOK LARGE AMT OF CALCIUM CYCLAMATE HAD PHOTOSENSITIVE DERMATITIS & RENAL TUBULAR NECROSIS ASSOCIATED WITH HYPOPHOSPHATEMIA. ...A CASE OF PHOTOSENSITIZATION IN A BLACK WOMAN TAKING CALCIUM CYCLAMATE PLUS SACCHARIN. /CA SALT//CASE REPORTS/ An 18-yr old male with bulimia nervosa ingested up to 22.0 g of cyclamate daily. He developed diarrhea, dilatation of the proximal small bowel, and loss of the normal mucosal pattern. These findings reverted to normal after cessation of cyclamate ingestion.For more Human Toxicity Excerpts (Complete) data for CYCLAMATE (13 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Cyclamate's production and use as a non-nutritive sweetener(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Cyclamate was eliminated in wastewater treatment plants with activated sludge processes sampled in Zurich Switzerlanda mean removal efficiency of 99% was observed. Incubation experiments with activated sludge resulted in a first order half-life of 20 minutes with 99% removal efficiency after 3 hours. No loss was observed using sterile controls(1). |
| Environmental Bioconcentration | An estimated pKa of 1.71(1) indicates cyclamate will exist almost entirely in the anion form at pH values of 5 to 9 and therefore bioconcentration of cyclamate in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The estimated pKa of 1.71(1) indicates cyclamate will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. Cyclamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-7 mm Hg(SRC), determined from a fragment constant method(2). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ PROLONGED ADMIN OF 2% SODIUM CYCLAMATE IN DRINKING-WATER TO GUINEA PIGS CAUSED CHANGES IN LIVER, KIDNEY & PANCREATIC CELLS. IN A SUBCHRONIC STUDY, 5 WK OLD MICE WERE GIVEN 0, 1, 2, 4, 8 & 16% CALCIUM CYCLAMATE IN DRINKING WATER FOR 5 WK. LEVELS OF 8 & 16% SIGNIFICANTLY REDUCED SURVIVAL & BODY WTBODY WT WAS SLIGHTLY REDUCED WITH THE 4% LEVEL. MICROSCOPIC VACUOLATED CELLS WERE OBSERVED IN LIVER PARENCHYMA & RENAL TUBULES, ESPECIALLY IN...LOWER LEVELS. DESQUAMATOUS CHANGES & NECROSIS OCCURRED IN TRANSITIONAL EPITHELIUM OF URINARY BLADDER. ...MONKEYS GIVEN SINGLE DOSES OF 4 OR 8 G/KG BODY WT OR RATS GIVEN 5 DAILY DOSES OF 2-8 G/KG BODY WT SODIUM CYCLAMATE ORALLY SHOWED DIFFUSE MILD VESICULATION OF THE ENDOPLASMIC RETICULUM ASSOCIATED WITH VACUOLIZATION OF LIVERS & KIDNEYS. /SODIUM & CALCIUM SALT//LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ADMIN OF 5% CALCIUM CYCLAMATE IN DRINKING-WATER TO RABBITS FOR 150 DAYS DELAYED & SUPPRESSED THE TITRE OF ANTIBODIES AGAINST BOVINE SERUM ALBUMIN. PROLONGED ADMIN OF CALCIUM CYCLAMATE TO RATS REDUCED ACTIVITY OF ENZYMES IN INTESTINAL MUCOSA, INCLUDING ACID AND ALKALINE PHOSPHATASE, ATP-ASE & ENZYMES INVOLVED IN GLYCOLYSIS, KREBS CYCLE & IN PROTEIN & LIPID METABOLISM. /CALCIUM SALT//LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 100 female Swiss mice were fed diets containing 0 and 5% sodium cyclamate for 18 months. At the start of the feeding 50 mice in each group received intragastrically a single dose of 50 ug of 3,4-benzopyrene in 0.2 mL of polyethylene glycol 400 (PEG) the other 50 receiving PEG alone. Results did not indicate that the feeding of cyclamate was associated with an increase in tumors either arising in the G.I. tract or tumors at other sites, nor was there any evidence of carcinogenicity or effects upon mortality. /Sodium cyclamate//LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Implantation of cholesterol pellets containing 20% sodium cyclamate into the urinary bladder have produced an increased number of tumors in mice after 16 months. /Sodium cyclamate/For more Non-Human Toxicity Excerpts (Complete) data for CYCLAMATE (33 total), please visit the HSDB record page. |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GV6950000 |
| 독성 | mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01774, |
| 관세 코드 | 2929909000 |
| 안전 문구(S) | 22-24/25 |
| 기존화학 물질 | KE-09268 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 100-88-9(Hazardous Substances Data) |
용도
용도
A non-nutritive sweetener.The sweetness is approximately 30 times that of cane sugar, while the acidity provided by this material is even greater than that derived from an equal weight of Citric acid.Cyclamic acid is being used on an increasing scale (1966) as a sweet acidifying agent in soft drinks of no nutritional value (diet-soda, lowc.rdorie carbonated beverages, etc.).
일반 설명
The N-cyclohexylsulfamic acid salts of wellknown therapeutic agents were prepared.