Dulcin

Not to be confused with phyllodulcin.
For the sugar alcohol, see galactitol.
Dulcin
Names
IUPAC name
(4-Ethoxyphenyl)urea
Other names
Sucrol; Valzin; Dulcine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.244 Edit this at Wikidata
EC Number
  • 205-767-7
KEGG
RTECS number
  • YT2275000
UNII
  • InChI=1S/C9H12N2O2/c1-2-13-8-5-3-7(4-6-8)11-9(10)12/h3-6H,2H2,1H3,(H3,10,11,12) ☒N
    Key: GGLIEWRLXDLBBF-UHFFFAOYSA-N ☒N
  • InChI=1/C9H12N2O2/c1-2-13-8-5-3-7(4-6-8)11-9(10)12/h3-6H,2H2,1H3,(H3,10,11,12)
    Key: GGLIEWRLXDLBBF-UHFFFAOYAA
  • CCOC1=CC=C(C=C1)NC(=O)N
Properties
C9H12N2O2
Molar mass 180.207 g·mol−1
Appearance White needles
Melting point 173.5 °C (344.3 °F; 446.6 K)
Boiling point Decomposes
1.25 g/L (25 °C)
Solubility Soluble in alcohol
log P 1.28
Hazards
Lethal dose or concentration (LD, LC):
1900 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dulcin is an artificial sweetener about 250 times sweeter than sugar, discovered in 1883 by the Polish chemist Józef (Joseph) Berlinerblau (27 August 1859 – 1935).[1][2][3][4] It was first mass-produced about seven years later. Although it was discovered only five years after saccharin, it never enjoyed the latter compound's market success. Nevertheless, it was an important sweetener of the early 20th century and had an advantage over saccharin in that it did not possess a bitter aftertaste.

Early medical tests marked the substance as safe for human consumption, and it was considered ideal for diabetics. However, an FDA study in 1951 raised many questions about its safety, resulting in its removal from the market in 1954 after animal testing revealed chronic toxicity.[5] The FDA has also said that "the Federal Security Administrator regards these chemicals as poisonous substances which have no place in any food."[6] In Japan, poisoning accidents by dulcin occurred frequently, and use of dulcin was forbidden in 1969.[7]

Dulcin is also known by the names sucrol and valzin.[8]

Preparation

Dulcin can be produced by the addition of potassium cyanate to p-phenetidine hydrochloride in an aqueous solution at room temperature.[9]

An alternate way to make dulcin is by mixing urea and p-phenetidine hydrochloride to a mixture of hydrochloric acid and glacial acetic acid.[10]

Toxicity

Dulcin is toxic to rats at 0.1% of the diet and above. At 0.1%, it causes a slight slowdown in growth; at 1.0%, the slowdown is evident alongside an increase in mortality and noticeable histological changes in liver, kidney, spleen, and heart.[11]

See also

References

  1. ^ Berlinerblau, Joseph (1884). "Ueber die Einwirkung von Chlorcyan auf Ortho- und auf Para-Amidophenetol" [On the reaction of cyanogen chloride with ortho- and para-ethoxyaniline] (PDF). Journal für praktische Chemie. 2nd series (in German). 30: 97–115. doi:10.1002/prac.18840300110. ; see pp. 103–105. From p. 104: "Der Para-Aethoxyphenylharnstoff hat einen sehr süssen Geschmack." (Para-ethoxyphenylurea has a very sweet taste.)
  2. ^ Hess, Ludwig (1921). Über den Süßstoff Dulcin: seine Darstellung und Eigenschaften [On the sweetener Dulcin: its preparation and properties] (in German) (2nd ed.). Berlin & Heidelberg, Germany: Springer Verlag. pp. 5–6. ISBN 9783642993923.
  3. ^ Goldsmith, R.H. (1987). "A tale of two sweeteners". Journal of Chemical Education. 64 (11): 954–955. Bibcode:1987JChEd..64..954G. doi:10.1021/ed064p954.
  4. ^ For a biography of Joseph Berlinerblau (with photographs), see:
  5. ^ "15FR321 Title 21" (PDF). FDA Federal Register. FDA. January 18, 1950. Retrieved January 11, 2021. ... Notice to manufacturers and distributors of foods and drugs containing artificial sweeteners. Chronic-toxicity studies conducted by the Food and Drug Administration show/ that the artificial sweeteners dulcin (also known as sucrol, or 4-ethoxy-phenylurea, or paraphenetolcarbamide) and P-4000 (also known as l-n-propoxy amino4-nitrobenzene) cause injury to rats when fed at relatively low levels for approximately 2 years ...'
  6. ^ Food and Drug Administration- Title 21 chapter 1 Federal Register Archive
  7. ^ ズルチン標準品-Dulcin Standard (Japanese), Wako Pure Chemical Industries
  8. ^ Bender, David A. (2005). A Dictionary of Food and Nutrition. Oxford University Press.
  9. ^ Youssef, Khairia M.; Al-Abdullah, Ebtihal; El-Khamees, Hamad (2003). "Synthesis of sulofenur analogs as antitumour agents: Part II". Medicinal Chemistry Research. 11 (9): 481–503.
  10. ^ "ARYLUREAS II. UREA METHOD p-ETHOXYPHENYLUREA". Org. Synth. 31 (11): 11. 1951. doi:10.15227/orgsyn.031.0011.
  11. ^ Ikeda, Yoshio; Omori, Yoshihito; Oka, Shigenori; Shinoda, Mitsuo; Tsuzi, Kiyo (1960). "Studies on Chronic Toxicity of Dulcin". Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi). 1 (1): 62–69. doi:10.3358/shokueishi.1.62.

Further reading

  • Hodges L (1973). Environmental pollution: a survey emphasizing physical and chemical principles. New York: Holt, Rinehart and Winston Inc.
  • Nanikawa R, Kotoku S, Yamada T (January 1967). "[Death from dulcin poisoning]" [Death from dulcin poisoning]. Nihon Hoigaku Zasshi = the Japanese Journal of Legal Medicine. 21 (1): 17–24. PMID 6068316.
  • Saito K (1969). "ズルチンによる食中毒事件" [Food poisoning case caused by dulcin]. Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) (in Japanese). 10 (2): 112–113. doi:10.3358/shokueishi.10.112.
  • Media related to Dulcin at Wikimedia Commons