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{{Distinguish|phyllodulcin}} |
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{{For|the sugar alcohol|galactitol}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 433987599 |
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| Watchedfields = changed |
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|ImageFile=Dulcin.svg |
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| verifiedrevid = 443714534 |
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|ImageSize=200px |
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| ImageFile = Dulcin.svg |
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|IUPACName=(4-Ethoxyphenyl)urea |
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| ImageSize = 200px |
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|OtherNames=Sucrol; Valzin |
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| IUPACName = (4-Ethoxyphenyl)urea |
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|Section1={{Chembox Identifiers |
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| OtherNames = Sucrol; Valzin; Dulcine |
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| CASNo=150-69-6 |
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| Section1 = {{Chembox Identifiers |
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| PubChem=9013 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=150-69-6 |
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| PubChem=9013 |
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| EINECS = 205-767-7 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8663 |
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| 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) |
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| InChIKey = GGLIEWRLXDLBBF-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C9H12N2O2/c1-2-13-8-5-3-7(4-6-8)11-9(10)12/h3-6H,2H2,1H3,(H3,10,11,12) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = GGLIEWRLXDLBBF-UHFFFAOYSA-N |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19415 |
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| KEGG = C19415 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8U78KF577Z |
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| UNII = 8U78KF577Z |
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| SMILES=CCOC1=CC=C(C=C1)NC(=O)N |
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| SMILES=CCOC1=CC=C(C=C1)NC(=O)N |
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| RTECS = YT2275000 |
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|Section2={{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=9 | H=12 | N=2 | O=2 |
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| Formula=C<sub>9</sub>H<sub>12</sub>N<sub>2</sub>O<sub>2</sub> |
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| Appearance= White needles |
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| MolarMass=180.20 g/mol |
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| Appearance= |
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| MeltingPtC= 173.5 |
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| BoilingPt= Decomposes |
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| Solubility= 1.25 g/L (25 °C) |
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| BoilingPt= |
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| SolubleOther = Soluble in alcohol |
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| Solubility= |
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| LogP = 1.28 |
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|Section3={{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| AutoignitionPt = |
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| LD50 = 1900 mg/kg (rat, oral) |
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'''Dulcin''' is an artificial ] about 250 times sweeter than ], discovered in 1883 by the Polish chemist Józef (Joseph) Berlinerblau (27 August 1859 – 1935).<ref>{{cite journal|last1=Berlinerblau|first1=Joseph|title=Ueber die Einwirkung von Chlorcyan auf Ortho- und auf Para-Amidophenetol|journal=Journal für praktische Chemie|date=1884|volume=30|pages=97–115|series=2nd series|doi=10.1002/prac.18840300110|trans-title=On the reaction of ] with ortho- and para-ethoxyaniline|language=German|url=https://zenodo.org/record/2054475/files/article.pdf}} ; see pp. 103–105. From p. 104: ''"Der Para-Aethoxyphenylharnstoff hat einen sehr süssen Geschmack."'' (Para-ethoxyphenylurea has a very sweet taste.)</ref><ref>{{cite book|last1=Hess|first1=Ludwig|title=Über den Süßstoff Dulcin: seine Darstellung und Eigenschaften|date=1921|publisher=Springer Verlag|location=Berlin & Heidelberg, Germany|pages=5–6|isbn=9783642993923|edition=2nd|url=https://books.google.com/books?id=tmrSBgAAQBAJ&pg=PA5|language=German|trans-title=On the sweetener Dulcin: its preparation and properties}}</ref><ref>{{cite journal| doi = 10.1021/ed064p954| author = Goldsmith, R.H. | year = 1987 | title = A tale of two sweeteners | journal = Journal of Chemical Education | volume = 64| issue = 11 | pages = 954–955| bibcode = 1987JChEd..64..954G }}</ref><ref>For a biography of Joseph Berlinerblau (with photographs), see: |
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'''Dulcin''' is an artificial ] about 250 times sweeter than ] discovered in 1884 by ].<ref>{{cite journal| doi = 10.1021/ed064p954| author = Goldsmith, R.H. | year = 1987 | title = A tale of two sweeteners | journal = J. Chem. Educ. | volume = 64| issue = 11 | pages = 954–955}}</ref> It was first mass produced about seven years later. Despite the fact that it was discovered only five years after ], it never enjoyed the latter compound’s market success. Still, it was an important sweetener of the early 20th century and had an advantage over saccharin in that it did not possess a bitter ]. |
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* {{cite journal|last1=Balasiewicz|first1=Michał S.|title=Józef Berlinerblau i Jan Prot-Berlinerblau – współtwórcy polskiego przemysłu Polski niepodległej|journal=Przemysł Chemiczny (Chemical Industry)|date=2013|volume=92|issue=9|pages=1692–1700|trans-title=Józef Berlinerblau and Jan Prot-Berlinerblau – co-founders of Polish industry in independent Poland ] (1918–1939)]|language=Polish}} |
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* Reprinted in: |
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* Reprinted in: </ref> It was first mass-produced about seven years later. Although it was discovered only five years after ], 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 ]. |
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Early medical tests marked the substance as safe for human consumption, and it was considered ideal for ]. However, an ] study in 1951 raised many questions about its safety, resulting in its removal from the market in 1954 after animal testing revealed ].<ref>{{Cite web |url=https://s3.amazonaws.com/archives.federalregister.gov/issue_slice/1950/1/19/317-324.pdf#page=5 |title=15FR321 Title 21 |date=January 18, 1950|website=FDA Federal Register |publisher=FDA |access-date=January 11, 2021| quote=... 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 ...'}}</ref> The FDA has also said that "the Federal Security Administrator regards these chemicals as poisonous substances which have no place in any food."<ref></ref> In ], poisoning accidents by dulcin occurred frequently, and use of dulcin was forbidden in 1969.<ref> (Japanese), ]</ref> |
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Early medical tests marked the substance as safe for human consumption, and it was considered ideal for ]. However, an ] study in 1951 raised many questions about its safety resulting in its removal from the market in 1954 after animal testing revealed unspecified ]ic properties. |
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Dulcin is also known by the names '''sucrol''' and '''valzin'''.<ref>{{cite book|title=A Dictionary of Food and Nutrition|first=David A.|last=Bender|year=2005|publisher=Oxford University Press}}</ref> |
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Dulcin is also known by the names '''sucrol''' and '''valzin'''.<ref>{{cite book|title=A Dictionary of Food and Nutrition|first=David A.|last=Bender|year=2005|publisher=Oxford University Press}}</ref> |
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==Preparation== |
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Phyllodulcin, a chemically unrelated compound, is naturally produced in the leaves of '']'', a native shrub in Japan and eastern Asia.<ref>Mami Ujihara, Masateru Shinozaki and Makoto Kato. 1995. Accumulation of phyllodulcin in sweet-leaf plants of ''Hydrangea serrata'' and its neutrality in the defense against a specialist leaf mining herbivore. Researches on Population Ecology 37: 249-257.</ref> Its leaves are used to make a herbal tea that is regionally popular. |
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Dulcin can be produced by the addition of ] to ] ] in an ] at room temperature.<ref>{{Cite journal | journal = ] | volume = 11 | issue = 9 | pages = 481–503 | date = 2003 | title = Synthesis of sulofenur analogs as antitumour agents: Part II | author = Youssef, Khairia M. | author2 = Al-Abdullah, Ebtihal | author3 = El-Khamees, Hamad }}</ref> |
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An alternate way to make dulcin is by mixing ] and ''p''-phenetidine hydrochloride to a mixture of ] and glacial ].<ref>{{Cite journal | journal = Org. Synth. | date = 1951 | volume = 31 | issue = 11 | title = ARYLUREAS II. UREA METHOD p-ETHOXYPHENYLUREA | page = 11 | doi = 10.15227/orgsyn.031.0011 }}</ref> |
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==References== |
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{{reflist}} |
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==Additional reading== |
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== Toxicity == |
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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.<ref>{{cite journal |last1=Ikeda |first1=Yoshio |last2=Omori |first2=Yoshihito |last3=Oka |first3=Shigenori |last4=Shinoda |first4=Mitsuo |last5=Tsuzi |first5=Kiyo |title=Studies on Chronic Toxicity of Dulcin |journal=Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) |date=1960 |volume=1 |issue=1 |pages=62–69 |doi=10.3358/shokueishi.1.62 |doi-access=free}}</ref> |
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* Hodges, L. 1973. ''Environmental pollution: a survey emphasizing physical and chemical principles''. Holt, Rinehart and Winston Inc., New York. |
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== See also == |
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] |
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* ] (P-4000), banned alongside dulcin by the FDA |
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] |
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== References == |
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{{Reflist}} |
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== Further reading == |
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{{refbegin}} |
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* {{cite book | vauthors = Hodges L | date = 1973 | title = Environmental pollution: a survey emphasizing physical and chemical principles | publisher = Holt, Rinehart and Winston Inc. | location = New York }} |
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* {{cite journal | vauthors = Nanikawa R, Kotoku S, Yamada T | title = | journal = Nihon Hoigaku Zasshi = the Japanese Journal of Legal Medicine | volume = 21 | issue = 1 | pages = 17–24 | date = January 1967 | pmid = 6068316 | trans-title = Death from dulcin poisoning }} |
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* {{cite journal | vauthors = Saito K |title=ズルチンによる食中毒事件 | trans-title = Food poisoning case caused by dulcin | language = Japanese |journal=Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) |date=1969 |volume=10 |issue=2 |pages=112–113 |doi=10.3358/shokueishi.10.112 |doi-access=free }} |
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{{refend}} |
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== External links == |
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*{{Commons category-inline}} |
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