Dulcin
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| Names | |
|---|---|
| IUPAC name
(4-Ethoxyphenyl)urea
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| Other names
Sucrol; Valzin; Dulcine
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| Identifiers | |
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3D model (JSmol)
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| 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): | |
LD50 (median dose)
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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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Template:Chembox Footer/trackingTemplate:Short description
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
- 5-Nitro-2-propoxyaniline (P-4000), banned alongside dulcin by the FDA
References
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- ^ Page Module:Citation/CS1/styles.css has no content.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]. Journal für praktische Chemie. 2nd series (in German). 30: 97–115. doi:10.1002/prac.18840300110.
{{cite journal}}: CS1 maint: unrecognized language (link) ; see pp. 103–105. From p. 104: "Der Para-Aethoxyphenylharnstoff hat einen sehr süssen Geschmack." (Para-ethoxyphenylurea has a very sweet taste.) - ^ Page Module:Citation/CS1/styles.css has no content.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.
{{cite book}}: ISBN / Date incompatibility (help)CS1 maint: unrecognized language (link) - ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ For a biography of Joseph Berlinerblau (with photographs), see:
- Page Module:Citation/CS1/styles.css has no content.Balasiewicz, Michał S. (2013). "Józef Berlinerblau i Jan Prot-Berlinerblau – współtwórcy polskiego przemysłu Polski niepodległej" [Józef Berlinerblau and Jan Prot-Berlinerblau – co-founders of Polish industry in independent Poland [i.e., the Second Polish Republic (1918–1939)]]. Przemysł Chemiczny (Chemical Industry) (in Polish). 92 (9): 1692–1700.
{{cite journal}}: CS1 maint: unrecognized language (link) - Reprinted in: "Józef Berlinerblau" in ewamaria2013 (2014) (in Polish)
- Reprinted in: "Josef Berlinerblau" in Reunion 69 (2014) (in Polish)
- Page Module:Citation/CS1/styles.css has no content.Balasiewicz, Michał S. (2013). "Józef Berlinerblau i Jan Prot-Berlinerblau – współtwórcy polskiego przemysłu Polski niepodległej" [Józef Berlinerblau and Jan Prot-Berlinerblau – co-founders of Polish industry in independent Poland [i.e., the Second Polish Republic (1918–1939)]]. Przemysł Chemiczny (Chemical Industry) (in Polish). 92 (9): 1692–1700.
- ^ Page Module:Citation/CS1/styles.css has no content."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 ...'
- ^ Food and Drug Administration- Title 21 chapter 1 Federal Register Archive
- ^ ズルチン標準品-Dulcin Standard (Japanese), Wako Pure Chemical Industries
- ^ Page Module:Citation/CS1/styles.css has no content.Bender, David A. (2005). A Dictionary of Food and Nutrition. Oxford University Press.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content."ARYLUREAS II. UREA METHOD p-ETHOXYPHENYLUREA". Org. Synth. 31 (11): 11. 1951. doi:10.15227/orgsyn.031.0011.
- ^ Page Module:Citation/CS1/styles.css has no content.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
Page Template:Refbegin/styles.css has no content.
- Page Module:Citation/CS1/styles.css has no content.Hodges L (1973). Environmental pollution: a survey emphasizing physical and chemical principles. New York: Holt, Rinehart and Winston Inc.
- Page Module:Citation/CS1/styles.css has no content.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.
- Page Module:Citation/CS1/styles.css has no content.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.
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External links
- Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons
