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cyclohexylsulfamic acid

Dangerous Goods

CAS number:100-88-9    molecular formula:C6H13NO3S

overview

compound introduction

环己基磺胺酸是磺胺酸类化合物的一员,是带有 N-环己基取代基的磺胺酸。它具有人类异生物质代谢物和环境污染物的作用。它与磺胺酸功能相关。它是环己基磺酸酯的共轭酸。

Specs

Chinese aliasN-环己基氨基磺酸 | 环拉酸 | 环己氨磺酸
English aliasE78799 | Cyclamic acid (USAN) | Cyclohexylamide sulfate | s4015 | Cyclamsaeure | HMS3264K03 | Cyclohexylamine sulfamic acid | N-Cyclohexyl-Sulfuric acid monoamide | AB01563182_02 | CALCIUMLEVULINATE | cyclamic-acid | MFCD00065234 | CYCLAMIC ACID [MI] | Cy
CAS number100-88-9molecular formulaC6H13NO3S
molecular weight179.24Exact mass-
PSA74.8logp0.6

numbering system

CAS100-88-9
UNIIHN3OFO5036
HMDB IDHMDB0031340
KEGG IDD02442
ChEBI ID15964
ChEMBL IDCHEMBL1206440
WikipediaCyclamic_acid
NSC NumberNSC Number: NSC220327
AIDS Number160144
PubChem CID7533
MetaboLightsMTBLC15964
Deprecated CAS45951-45-9
Nikkaji NumberJ4.986G
NCI Thesaurus CodeC76514
DSSTox Substance IDDTXSID5041809
Metabolomics Workbench ID44835
European Community (EC) Number202-898-1
PubChem Reference Collection SID516565237
United States Adopted Name (USAN)CYCLAMIC ACID
MEP ID_25Q1B3AR3

physicochemical properties

pHpH of 10% aqueous solution: 0.8-1.6
OdorOdorless
TasteA bitter taste becomes noticeable when quantity in foods approaches 0.5%.
XLogP3XLogP3-AA: 0.6
Color/FormWhite crystalline powder
Complexity200
Exact Mass179.06161445
Solubility1000000 mg/L @ 25 °C (exp)
Human DrugsBreast Feeding; Lactation; Milk, Human; Artificial Sweeteners; Sweetening Agents
DecompositionWhen heated to decomposition it emits toxic fumes of sulfoxides and nitroxides. /Calcium cyclamate dihydrate/
Formal Charge0
Melting Point169 - 170 °C
Vapor Pressure0.0000027 [mmHg]
Chemical ClassesOther Uses -> Food Additives
Heavy Atom Count11
Molecular Weight179.24
Monoisotopic Mass179.06161445
Isotope Atom Count0
Physical DescriptionSolid
Rotatable Bond Count2
Collision Cross Section139.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5041809]
Hydrogen Bond Donor Count2
Covalently-Bonded Unit Count1
Hydrogen Bond Acceptor Count4
Topological Polar Surface Area74.8 Ų
Defined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Atom Stereocenter Count0
Undefined Bond Stereocenter Count0

Safety information

Adverse Effects:
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.
Hazards Summary:
In lethal dose studies, mice have seizures; Oral LD50 (mouse) = 680 mg/kg; Oral LD50 (rat) = 12,000 mg/kg; [ChemIDplus] No toxic effects found in rats fed high doses for entire life; An irritant; May cause skin sensitization; Effects in lethal-dose animal studies include convulsions and injury to liver and kidneys; [MSDSonline] See Potassium cyclamate. See Sodium cyclamate.
Disposal Methods:
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.
FDA Requirements:
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).
Environmental Fate:
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 abso...
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.
Regulatory Information:
New Zealand EPA Inventory of Chemical Status: Sulfamic 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.
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).
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 Switzerland; a 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).
Evidence for Carcinogenicity:
Evaluation: There is inadequate evidence in humans for the carcinogenicity of cyclamates. There is inadequate evidence in experimental animals for the carcinogenicity of cyclamates. Overall classification: Cyclamates are not classifiable as to their carcinogenicity to humans (Group 3). /Cyclamates/
Hazard Classes and Categories:
Eye Irrit. 2 (71.4%)
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).
Antidote and Emergency Treatment:
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use...
Environmental Abiotic Degradation:
The rate constant for the vapor-phase reaction of cyclamate with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). No loss was observed using sterile controls in an activated sludge system(2). Cyclamate does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human Exposure:
Occupational exposure to cyclamate may occur through inhalation and dermal contact with this compound at workplaces where cyclamate is produced or used. Monitoring and use data indicate that the general population may be exposed to cyclamate via ingestion of contaminated drinking water and consumer products containing cyclamate. (SRC)
Environmental Water Concentrations:
SURFACE WATER: Eight lakes in Switzerland were sampled in February and March 2008, resulting in cyclamate concentrations ranging from below the detection limit in a remote mountain lake to 0.13 ug/L in the Greifensee, which is within a densely populated catchment area(1).
Environmental Fate/Exposure Summary:
Cyclamate's production and use as a non-nutritive sweetener may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 5.3X10-7 mm Hg at 25 °C indicates cyclamate will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase cyclamate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 3.7 hours. Particulate-phase cyclamate will be removed from the atmosphere by wet or dry deposition. Cyclamate does not contain chromophores that absorb at wavelengths >290 nm, and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, cyclamate is expected to have very high...
Effects During Pregnancy and Lactation:
◉ Effects on Lactation and Breastmilk

Production methods and uses

Production method
The starting material for cyclamate production is cyclohexylamine, which is reacted with sulfonating agents. The originally used chlorosulfonic acid has been replaced by other compounds. In high-boiling-point solvents, cyclohexylamine reacts with sulfamic acid to N-cyclohexyl-N-cyclohexylammonium sulfamate. Reaction with sodium or calcium hydroxide yields cyclamates and free cyclohexylamine. In a corresponding way, equimolar amounts of cyclohexylamine and tertiary amines react to trialkylammonium-N-cyclohexyl sulfamates, the respective cyclamates being formed after reaction with sodium or calcium hydroxide.
purpose
Uses:
The main application of cyclamates ... is in blends with saccharin in a 10:1 ratio by weight. In these blends, quantitative and qualitative synergistic effects can be used to advantage, rendering them an important sweetener system in countries approving the use of both sweeteners.
Consumer Uses:
Cleaning agent
Industry Uses:
Cleaning agent
Use Classification:
Food Additives -> SWEETENER; -> JECFA Functional Classes
General Manufacturing Information:
Industry Processing Sectors: Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Related

upstream information
Methods of Manufacturing:
cyclamate (CID:7533); cyclohexylamine (CID:7965); chlorosulfonic acid (CID:24638); sulfamic acid (CID:5987); calcium hydroxide (CID:3266381); N-cyclohexylsulphamate (CID:3372845); chloroform (CID:6212); barium hydroxide (CID:6093286); sulphuric acid (CID:1118); Sodium cyclamate (CID:23665706); sodium hydroxide (CID:14798); nitrocyclohexane (CID:14285); sodium dithionite (CID:24489); trisodium phosphate (CID:24243); calcium sulfamate (CID:22644290); Calcium cyclamate (CID:8752)
downstream information

No downstream information yet

MSDS

Found 1 shareMSDS
100-88-9 | N-Cyclohexylsulfamic acid.pdf