Cyclamate

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Structural formula
Structure of sodium cyclamate
General
Surname Sodium cyclamate
other names
  • Cyclamate
  • Sodium cyclohexyl sulfamate
  • Sodium N -cyclohexylamidosulfonate
  • E  952
Molecular formula C 6 H 12 NNaO 3 S
Brief description

sweet-tasting, colorless and odorless crystals

External identifiers / databases
CAS number 139-05-9
EC number 205-348-9
ECHA InfoCard 100,004,863
PubChem 23665706
Wikidata Q407786
properties
Molar mass 201.22 g mol −1
Physical state

firmly

solubility

easy in water (200 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: 301 + 312
Toxicological data

17,000 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyclamate ( E 952 ) is a synthetic sweetener . Chemically, it is cyclohexylsulfamic acid and its sodium and calcium salts . Cyclamate is 35 times sweeter than sucrose ( sugar ), but only a tenth as sweet as saccharin . Cyclamat has been approved in Germany since 1963 and has the lowest sweetness intensity of the sweeteners approved in the EU . Cyclamate has a taste that is particularly close to sugar.

history

When searching for antipyretic substances the chemist Michael Sveda synthesized at the University of Illinois Cyclohexylsulphamic by Chlorosulphonation of cyclohexylamine and placed it randomly determined that this substance tasted sweet. This acid and its sodium, potassium and calcium salts were patented under the name Cyclamat after Sveda's move to the DuPont company . The patent was later taken over by Abbott Laboratories . At first, this sweetener could not prevail over saccharin because saccharin was ten times sweeter and could be produced more cheaply. The advantage, however, was that the taste was more like that of sucrose and did not have a metallic aftertaste as with saccharin. The first calorie-free soft drink No-Cal with cyclamate (calcium salt) was introduced in 1953 for chronically diabetic patients in a sanatorium in Brooklyn . As a result, cyclamate in mixtures with saccharin prevailed. The first calorie-free cola with a cyclamate / saccharin mixture under the name Diet-Rite-Cola was launched in 1958.

properties

Cyclamate is heat-resistant and can therefore also be used for cooking and baking. It is mainly used for low-calorie foods. In order to obtain a higher sweetness without disadvantageous taste, mixtures of cyclamate with saccharin in a ratio of 10: 1 are often produced. Due to its synergistic properties, cyclamate can be combined well with all other sweeteners.

Sodium cyclamate declaration for a drink.

The allowable daily dose (Acceptable Daily Intake (ADI)) is 7 mg / kg body weight. This value is usually not exceeded by consumers with an average high consumption of cyclamate. However, if flavored drinks made from water are consumed, they may contain up to 400 mg / l cyclamate. If other foods sweetened with cyclamate are consumed in addition, then “significant ADI values ​​can be expected to be exceeded, especially among younger consumers”. Cyclamate is not metabolized and leaves most consumers unchanged via the kidneys . In this respect it is comparable to the sweeteners acesulfame and saccharin. Very few people have bacteria in their intestinal flora that can convert a small part of the cyclamate. The possible breakdown product is cyclohexylamine .

Health, possible risk of cancer

Cyclamate is suspected of being carcinogenic after animal experiments with an extremely high dose of 2.5 g / kg body weight per day in the USA showed that bladder cancer was favored . However, recent studies have not been able to confirm this suspicion.

Cyclamate has been banned in the United States since 1970. In Europe, it is permitted for certain foods with maximum quantity restrictions: These include low-energy and sugar-free drinks (max. 250 mg / l), desserts (max. 250 mg / kg), spreads (max. 500 - 1000 mg / kg), jams ( max. 500 - 1000 mg / kg), jams (max. 500 - 1000 mg / kg), jellies (max. 500 - 1000 mg / kg), canned fruit (max. 1,000 mg / kg), food supplements (max. 400 - 1250 mg / kg). It is no longer approved for sweetening ice cream , candies and chewing gum .

Up to a daily intake of 7 mg per kilogram of body weight, cyclamate is also considered safe in the long term, but some consumer advocates advise against frequent consumption.

Individual evidence

  1. ↑ Entry on E 952: Cyclamic acid and its Na and Ca salts in the European database for food additives, accessed on June 27, 2020.
  2. ↑ Entry on sodium cyclamate. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
  3. ↑ a b c d Entry on sodium cyclamate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  4. ^ Entry on cyclamate in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  5. ↑ Klaus Roth , Erich Lück: Calorie-free sweetness from the laboratory and nature . In: Chemistry in Our Time . tape 46 , no. 3 , 2012, p. 172 , doi : 10.1002 / ciuz.201200587 .
  6. ↑ BgVV opinion of May 31, 2001, sweetener cyclamate in food (PDF; 17 kB).
  7. ↑ MR Weihrauch, V. Diehl: "Artificial sweeteners - do they bear a carcinogenic risk?" Annals of Oncology 15 (2004), pp. 1460-1465. PMID 15367404 doi : 10.1093 / annonc / mdh256 PDF .
  8. ↑ FDA Consumer magazine, November - December 1999 - Sugar Substitutes: Americans Opt for Sweetness and Lite ( Memento of August 14, 2009 in the Internet Archive ).
  9. ↑ a b c d e f g h plusatzstoffe-online.de: E952 Cyclamat .
  10. ↑ Ordinance amending the additives approval ordinance and other food law ordinances ( Federal Law Gazette 2005 I p. 128 ).
  11. ↑ das-ist-drin.de: E 952 - Cyclamate .

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