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139-05-9

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139-05-9 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 139-05-9 differently. You can refer to the following data:
1. White powder
2. Sodium cyclamate occurs as white, odorless or almost odorless crystals, or as a crystalline powder with an intensely sweet taste.

History

Cyclamate was first synthesized in 1937. Like the other sweeteners, its sweet taste was accidentally discovered (U.S. Pat. 2,275,125 (Mar. 3, 1942), L. F. Andrieth and M. Sveda (to E. I. du Pont de Nemours & Co., Inc.). The FDA in 1958 classified sodium cyclamate as a GRAS sweetener. In 1969, a 2-year chronic toxicity study with a sodium cyclamate–sodium saccharin (10:1) mixture found bladder tumors in rats. The FDA took cyclamate off the GRAS list, banning it from foods and beverages, but permitting its sale in pharmacies. In 1970, after a congressional investigation, the FDA banned the use of cyclamate entirely. Abbott Laboratories, which has conducted additional toxicity and carcinogenicity studies with cyclamate, a 10:1 mixture of cyclamate–saccharin, and cyclohexylamine, claimed to be unable to confirm the 1969 findings. Abbott then filed a food additive petition for cyclamate in 1973, which was denied by the FDA in 1980. In 1982, the Calorie Control Council and Abbott Laboratories filed a second food additive petition containing the results of additional safety studies (The Calorie Control Council and Abbott Laboratories, Food Additive Petition for cyclamate 2A3672 (Sept. 22, 1982). That petition remains active.

Uses

Different sources of media describe the Uses of 139-05-9 differently. You can refer to the following data:
1. Sodium Cyclamate is an artificial sweetener and is 30 times as saccharose's. It is widely used in pickles, seasoning sauce, cakes, biscuits, bread, ice cream, frozen sucker, popsicles, drinks and so on, with a maximum amount of 0.65g/kg. Secondly, it is used in confect, with a maximum amount of 1.0g/kg. Thirdly, it is used in orange peel, preserved plum, dried arbutus and so on, with the largest amount of 8.0g/kg. It is also used in cosmetics and pharmaceutical industry.
2. Cyclamate (cyclohexylsulfamic acid and its calcium and sodium salts) were discovered in the United States in 1937. They are 30 to 80 times as sweet as sucrose and were widely used until late 1969, when it was banned by the FDA because of questions on safety. It is not banned in Canada and the European Union. Cyclamate is produced by reacting cyclohexylamine with sulfonating agents, followed by reactions with sodium or calcium hydroxides to produce cyclamates and free cyclohexylamine as follows. Owing to their good stability, cyclamates are suitable for all applications of intense sweeteners without a significant interfering taste sensation, and are heat stable. The main application of cyclamates is in blends with saccharin in a 10:1 ratio by weight. The mixture is more than twice as sweet as either component alone, making them an important sweetener in countries approving the use of both sweeteners.
3. Sweetening agent.

Production Methods

Cyclamates are prepared by the sulfonation of cyclohexylamine in the presence of a base. Commercially, the sulfonation can involve sulfamic acid, a sulfate salt, or sulfur trioxide. Tertiary bases such as triethylamine or trimethylamine may be used as the condensing agent. The amine salts of cyclamate that are produced are converted to the sodium, calcium, potassium, or magnesium salt by treatment with the appropriate metal oxide.

Brand name

Adocyl;Ampenoline balsamoco;Assugrin;Azucrona;Cyclarin;Glusac super;Ilgon;Sladicin;Sucaryl calcium;Sucaryl sodium;Sucrum 7.

World Health Organization (WHO)

Cyclamates, non-nutritive sweetening agents, have been used as additives in food and drugs since 1950. They have been demonstrated to have a carcinogenic potential at very high and long-sustained dosage in experimental animals. Some countries have consequently banned their use as food additives, whereas in others they remain available for this purpose. Most countries, however, continue to allow their use in small quantities in pharmaceutical preparations. (Reference: (WHODI) WHO Drug Information, 77.2, 12, 1977)

General Description

Odorless or almost odorless white crystals or crystalline powder. Intensely sweet taste, even in dilute solution. pH (10% solution in water): 5.5-7.5. Used as a non-nutritive sweetener.

Air & Water Reactions

Water soluble.

Reactivity Profile

Sodium N-cyclohexylsulfamate is incompatible with strong oxidizing agents, strong acids and strong bases. Also incompatible with nitrites in acid solution. Has only limited compatibility with potassium salts .

Hazard

Some evidence of causing cancer in lab- oratory animals. Prohibited by FDA for food use. Questionable carcinogen.

Fire Hazard

Flash point data for Sodium N-cyclohexylsulfamate are not available; however, Sodium N-cyclohexylsulfamate is probably combustible.

Flammability and Explosibility

Notclassified

Pharmaceutical Applications

Sodium cyclamate is used as an intense sweetening agent in pharmaceutical formulations, foods, beverages, and table-top sweeteners. In dilute solution, up to about 0.17% w/v, the sweetening power is approximately 30 times that of sucrose. However, at higher concentrations this is reduced and at a concentration of 0.5% w/v a bitter taste becomes noticeable. Sodium cyclamate enhances flavor systems and can be used to mask some unpleasant taste characteristics. In most applications, sodium cyclamate is used in combination with saccharin, often in a ratio of 10 : 1.

Biochem/physiol Actions

Phenylsulfamate sweet tastant detectable by humans. ′First generation′ sweetener studied in animal models for its carcinogenic potential.

Toxicology

Sodium cyclamate is an odorless powder. It is about 30 times as sweet as sucrose in dilute solution. The structure of sodium cyclamate is shown in Figure 10.10 Capillary transitional cell tumors were found in the urinary bladders of 8 out of 80 rats that received 2600 mg/kg body weight per day of a mixture of sodium cyclamate and sodium saccharin (10:1) for up to 105 weeks. When the test mixture was fed at dietary levels designed to furnish 500, 1120, and 2500 mg/ kg body weight to groups of 35 and 45 female rats, the only significant finding was the occurrence of papillar carcinomas in the bladders of 12 of 70 rats fed the maximum dietary level of the mixture (equivalent of about 25 g/kg body weight) for periods ranging from 78 to 105 weeks (except for one earlier death). In vivo conversion from sodium cyclamate to cyclohexylamine was observed particularly in the higher dosage group. Cyclohexylamine is very toxic (LD50 rat oral=157 mg/dg) compared to sodium cyclamate (LD50 oral=12g/kg).

Safety Profile

Moderately toxic by intravenous and intraperitoneal routes. Mildly toxic by ingestion. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic, tumorigenic, and teratogenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NazO, SOx, and NOx.

Safety

There has been considerable controversy concerning the safety of cyclamate following the FDA decision in 1970 to ban its use in the USA. This decision resulted from a feeding study in rats that suggested that cyclamate could cause an unusual form of bladder cancer. However, that study has been criticized because it involved very high doses of cyclamate administered with saccharin, which has itself been the subject of controversy concerning its safety; see Saccharin. Although excreted almost entirely unchanged in the urine, a potentially harmful metabolite of sodium cyclamate, cyclohexylamine, has been detected in humans. In addition, there is evidence to suggest cyclamate is metabolized to cyclohexylamine by the microflora in the large intestine of some individuals (approximately 25% of the population with higher precedence in Japanese than Europeans or North Americans). Cyclohexylamine, following absorption, is metabolized to an extent of 1-2% to cyclohexanol and cyclohexane-1,2-diol. Established no-observedeffect level (NOEL) and acceptable daily intake (ADI) values are based on cyclohexylamine levels of high cyclamate converters.(6,7) Extensive long-term animal feeding studies and epidemiological studies in humans have failed to show any evidence that cyclamate is carcinogenic or mutagenic. As a result, sodium cyclamate is now accepted in many countries for use in foods and pharmaceutical formulations. Few adverse reactions to cyclamate have been reported, although its use has been associated with instances of photosensitive dermatitis. The WHO has set an estimated acceptable daily intake for sodium and calcium cyclamate, expressed as cyclamic acid, at up to 11 mg/kg body-weight. In Europe, a temporary acceptable daily intake for sodium and calcium cyclamate, expressed as cyclamic acid, has been set at up to 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

Sodium 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 regarded as stable. Solutions are also stable to heat, light, and air over a wide pH range. Samples of tablets containing sodium cyclamate and saccharin have shown no loss in sweetening power following storage for up to 20 years. The bulk material should be stored in a well-closed container in a cool, dry place.

Regulatory Status

The use of cyclamates as artificial sweetners in food, soft drinks, and artificial sweetening tablets was at one time prohibited in the UK and some other countries owing to concern about the metabolite cyclohexylamine. However, this is no longer the case, and cyclamates are now permitted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (oral powder, solutions, chewable tablets, and suspensions). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 139-05-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 139-05:
(5*1)+(4*3)+(3*9)+(2*0)+(1*5)=49
49 % 10 = 9
So 139-05-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1

139-05-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A18666)  Sodium cyclamate, 98%   

  • 139-05-9

  • 250g

  • 427.0CNY

  • Detail
  • Alfa Aesar

  • (A18666)  Sodium cyclamate, 98%   

  • 139-05-9

  • 1000g

  • 843.0CNY

  • Detail
  • Alfa Aesar

  • (A18666)  Sodium cyclamate, 98%   

  • 139-05-9

  • 5000g

  • 3421.0CNY

  • Detail
  • Supelco

  • (47827)  SodiumCyclamate  analytical standard

  • 139-05-9

  • 000000000000047827

  • 257.40CNY

  • Detail
  • Sigma-Aldrich

  • (S0760000)  Sodiumcyclamate  European Pharmacopoeia (EP) Reference Standard

  • 139-05-9

  • S0760000

  • 1,880.19CNY

  • Detail
  • Aldrich

  • (71440)  SodiumN-cyclohexylsulfamate  ≥99.0% (T)

  • 139-05-9

  • 71440-250G

  • 829.53CNY

  • Detail

139-05-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Sodium N-cyclohexylsulfamate

1.2 Other means of identification

Product number -
Other names sodium cyclohexylsulphamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:139-05-9 SDS

139-05-9Synthetic route

N-dodecylpyridinium chloride
104-74-5

N-dodecylpyridinium chloride

sodium cyclamate
139-05-9

sodium cyclamate

1-dodecylpyridinium cyclamate
1403558-43-9

1-dodecylpyridinium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;99%
C12H20NO(1+)*Cl(1-)

C12H20NO(1+)*Cl(1-)

sodium cyclamate
139-05-9

sodium cyclamate

1-hexyloxymethylpyridinium cyclamate

1-hexyloxymethylpyridinium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;96%
sodium cyclamate
139-05-9

sodium cyclamate

1-Dodecyloxymethylpyridinium-chlorid
21379-35-1

1-Dodecyloxymethylpyridinium-chlorid

1-dodecyloxymethylpyridinium cyclamate

1-dodecyloxymethylpyridinium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;96%
didecyldimethylammonium chloride
7173-51-5

didecyldimethylammonium chloride

sodium cyclamate
139-05-9

sodium cyclamate

didecyldimethylammonium cyclamate
1403558-45-1

didecyldimethylammonium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;95%
sodium cyclamate
139-05-9

sodium cyclamate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium cyclamate
1403558-48-4

1-butyl-3-methylimidazolium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;95%
1-Undecyloxymethylpyridinium-chlorid
22843-12-5

1-Undecyloxymethylpyridinium-chlorid

sodium cyclamate
139-05-9

sodium cyclamate

C17H30NO(1+)*C6H12NO3S(1-)

C17H30NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;94%
C11H18NO(1+)*Cl(1-)

C11H18NO(1+)*Cl(1-)

sodium cyclamate
139-05-9

sodium cyclamate

C11H18NO(1+)*C6H12NO3S(1-)

C11H18NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;93%
1-methyl-3-tetradecyloxymethylimidazolim chloride

1-methyl-3-tetradecyloxymethylimidazolim chloride

sodium cyclamate
139-05-9

sodium cyclamate

1-methyl-3-tetradecyloxymethylimidazolium cyclamate

1-methyl-3-tetradecyloxymethylimidazolium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;93%
sodium cyclamate
139-05-9

sodium cyclamate

1-Tetradecyloxymethylpyridinium-chlorid
52043-72-8

1-Tetradecyloxymethylpyridinium-chlorid

C20H36NO(1+)*C6H12NO3S(1-)

C20H36NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;92%
sodium cyclamate
139-05-9

sodium cyclamate

1-Nonyloxymethyl-pyridinium; chloride
23693-43-8

1-Nonyloxymethyl-pyridinium; chloride

C15H26NO(1+)*C6H12NO3S(1-)

C15H26NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;90%
sodium cyclamate
139-05-9

sodium cyclamate

1-Decyloxymethylpyridinium-chlorid
13501-48-9

1-Decyloxymethylpyridinium-chlorid

C16H28NO(1+)*C6H12NO3S(1-)
1403558-42-8

C16H28NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;89%
C10H16NO(1+)*Cl(1-)
856958-20-8

C10H16NO(1+)*Cl(1-)

sodium cyclamate
139-05-9

sodium cyclamate

C10H16NO(1+)*C6H12NO3S(1-)

C10H16NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;87%
sodium cyclamate
139-05-9

sodium cyclamate

1-Heptyloxymethyl-pyridinium; chloride

1-Heptyloxymethyl-pyridinium; chloride

C13H22NO(1+)*C6H12NO3S(1-)

C13H22NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;85%
sodium cyclamate
139-05-9

sodium cyclamate

1-Octyloxymethyl-pyridinium; chloride
56049-77-5

1-Octyloxymethyl-pyridinium; chloride

C14H24NO(1+)*C6H12NO3S(1-)

C14H24NO(1+)*C6H12NO3S(1-)

Conditions
ConditionsYield
In water at 20℃; for 24h;84%
cetylpyridinium chloride
123-03-5

cetylpyridinium chloride

sodium cyclamate
139-05-9

sodium cyclamate

1-hexadecylpyridinium cyclamate
1403558-44-0

1-hexadecylpyridinium cyclamate

Conditions
ConditionsYield
In water at 20℃; for 24h;82%
ammonium hydroxide
1336-21-6

ammonium hydroxide

sodium cyclamate
139-05-9

sodium cyclamate

platinum(II) chloride

platinum(II) chloride

Cl(1-)*C6H18N3O3PtS(1+)

Cl(1-)*C6H18N3O3PtS(1+)

Conditions
ConditionsYield
In methanol for 1h; pH=7 - 8;72%
ammonium hydroxide
1336-21-6

ammonium hydroxide

vanadium(III) chloride

vanadium(III) chloride

water
7732-18-5

water

sodium cyclamate
139-05-9

sodium cyclamate

C12H29N3O7S2V(1+)*Cl(1-)

C12H29N3O7S2V(1+)*Cl(1-)

Conditions
ConditionsYield
In methanol for 1h; pH=7 - 8;71%
selenium tetrachloride
10026-03-6

selenium tetrachloride

sodium cyclamate
139-05-9

sodium cyclamate

C12H24Cl2N2O6S2Se

C12H24Cl2N2O6S2Se

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 1h; pH=7 - 8;70%
gold(III) chloride

gold(III) chloride

water
7732-18-5

water

sodium cyclamate
139-05-9

sodium cyclamate

C6H12AuCl2NO3S*H2O

C6H12AuCl2NO3S*H2O

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 1h; pH=7 - 8;69%
ruthenium trichloride

ruthenium trichloride

water
7732-18-5

water

sodium cyclamate
139-05-9

sodium cyclamate

C6H16Cl2NO5RuS

C6H16Cl2NO5RuS

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 1h; pH=7 - 8;67%
sodium cyclamate
139-05-9

sodium cyclamate

A

cyclohexenone
930-68-7

cyclohexenone

B

cyclohexylamine hydrochloride
4998-76-9

cyclohexylamine hydrochloride

C

cyclohexanone
108-94-1

cyclohexanone

D

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
With hydrogenchloride for 3h; pH=3; Hydrolysis; Heating;A n/a
B 10%
C n/a
D n/a
sodium cyclamate
139-05-9

sodium cyclamate

A

cyclohexenone
930-68-7

cyclohexenone

B

cyclohexanone
108-94-1

cyclohexanone

C

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
In water at 20℃; for 96h; Product distribution; Further Variations:; pH-values; without irradiation, time; Elimination; hydrolysis; Irradiation;A 0.0008%
B 0.69%
C 0.0002%
sodium cyclamate
139-05-9

sodium cyclamate

cyclohexylsulfamoyl chloride
10314-35-9

cyclohexylsulfamoyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride In benzene for 2h; Heating;
With trichlorophosphate In 1,2-dichloro-ethane at 80℃; for 18h;
sodium cyclamate
139-05-9

sodium cyclamate

cyclohexanesulfamate*β-cyclodextrin complex

cyclohexanesulfamate*β-cyclodextrin complex

Conditions
ConditionsYield
With β‐cyclodextrin; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid Equilibrium constant; pH=7.0;
sodium cyclamate
139-05-9

sodium cyclamate

cyclohexanesulfamate*C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin*Zn(2+) complex

cyclohexanesulfamate*C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin*Zn(2+) complex

Conditions
ConditionsYield
With C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin*Zn(2+); N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid Equilibrium constant; pH=7.0;
sodium cyclamate
139-05-9

sodium cyclamate

cyclohexanesulfamate*C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin complex

cyclohexanesulfamate*C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin complex

Conditions
ConditionsYield
With C-6,6'-(bisimidazol-1-yl)-β-cyclodextrin; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid Equilibrium constant; pH=7.0;
sodium cyclamate
139-05-9

sodium cyclamate

N-cyclohexyl-N'-[4-[2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]-2-methylpropyl]phenyl]-sulfamide
454219-20-6

N-cyclohexyl-N'-[4-[2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]-2-methylpropyl]phenyl]-sulfamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3 / 1,2-dichloro-ethane / 18 h / 80 °C
2: pyridine / 1,2-dichloro-ethane / -35 - 60 °C
3: tetrabutylammonium fluoride / tetrahydrofuran
View Scheme
sodium cyclamate
139-05-9

sodium cyclamate

N-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-N'-cyclohexyl-sulfamide

N-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-N'-cyclohexyl-sulfamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3 / 1,2-dichloro-ethane / 18 h / 80 °C
2: pyridine / CH2Cl2 / -35 - 60 °C
3: KOH / ethanol / 80 °C
View Scheme

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