Suosan

Suosan
Names
	IUPAC name Sodium N-[(4-nitrophenyl)carbamoyl]-β-alaninate
	Systematic IUPAC name Sodium 3-{[(4-nitrophenyl)carbamoyl]amino}propanoate
	Other names N-(((4-Nitrophenyl)amino)carbonyl)-β-alanine monosodium salt
Identifiers
CAS Number	140-46-5 ;
3D model (JSmol)	Interactive image;
PubChem CID	8803;
UNII	6V7T3M79X3 ;
CompTox Dashboard (EPA)	DTXSID30930689 ;
	SMILES C1=CC(=CC=C1NC(=O)NCCC(=O)O)[N+](=O)[O-];
Properties
Chemical formula	C10H10N3NaO5
Molar mass	275.196 g·mol−1
Melting point	240 °C (464 °F; 513 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Suosan is calorie-free artificial sweetener derived from β-alanine, discovered in 1948 by Petersen et Muller.^[1]

Suosan is a sodium salt of p-Nitrophenylcarbamidopropionic acid and is 700 times sweeter than sucrose (table sugar)^[2] with a bitter aftertaste.^[3] It was never commercialized due to its low solubility in water, particularly under acidic pH (which limited its use, particularly in soft drinks)^[4]^[5] and concerns that it might form the toxic compound 4-nitroaniline.^[5]

References

^ Petersen S; Muller E (1948). "Über eine neue Gruppe von Süsstoffen (On a new group of sweet substances)". Chemische Berichte. 81: 31–38. doi:10.1002/cber.19480810105.
^ Santhosh, C.; Mishra, P. C. (1994). "Electrostatic potential and electric field mapping of some sweeteners of the suosan series: A search for the structure-activity relationship". International Journal of Quantum Chemistry. 51 (5): 335. doi:10.1002/qua.560510510.
^ AD Kinghorn & CM Compadre (2001). "Less common high-potency sweeteners". In Marcel Dekker (ed.). Alternative Sweeteners (Third ed.). New York. pp. 208–234. ISBN 0-8247-0437-1.{{cite book}}: CS1 maint: location missing publisher (link)
^ Muller, George W; Culberson, J. Chris; Roy, Glenn; Ziegler, Jeanette; Walters, D. Eric; Kellogg, Michael S.; Schiffman, Susan S.; Warwick, Zoe S (May 1992). "Carboxylic acid replacement structure-activity relationships in suosan type sweeteners. A sweet taste antagonist. 1". J. Med. Chem. 35 (10): 1747–1751. doi:10.1021/jm00088a008. PMID 1588556.
^ ^a ^b Nofre, Claude; Tinti, Jean M; Chatzopoulos, Farroudja O (Mar 5, 1991). "Pyridinyl compounds of N-carbamoyl-N-thiocarbamoyl- or N-amidino-glycine or beta-alanine useful as sweetening agents. US Patent 4997667 A". Retrieved 14 September 2014.

External links

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[Peterson-1948-1] Petersen S; Muller E (1948). "Über eine neue Gruppe von Süsstoffen (On a new group of sweet substances)". Chemische Berichte. 81: 31–38. doi:10.1002/cber.19480810105.

[2] Santhosh, C.; Mishra, P. C. (1994). "Electrostatic potential and electric field mapping of some sweeteners of the suosan series: A search for the structure-activity relationship". International Journal of Quantum Chemistry. 51 (5): 335. doi:10.1002/qua.560510510.

[Kinghorn2001-3] AD Kinghorn & CM Compadre (2001). "Less common high-potency sweeteners". In Marcel Dekker (ed.). Alternative Sweeteners (Third ed.). New York. pp. 208–234. ISBN 0-8247-0437-1.{{cite book}}: CS1 maint: location missing publisher (link)

[Muller1992-4] Muller, George W; Culberson, J. Chris; Roy, Glenn; Ziegler, Jeanette; Walters, D. Eric; Kellogg, Michael S.; Schiffman, Susan S.; Warwick, Zoe S (May 1992). "Carboxylic acid replacement structure-activity relationships in suosan type sweeteners. A sweet taste antagonist. 1". J. Med. Chem. 35 (10): 1747–1751. doi:10.1021/jm00088a008. PMID 1588556.

[Nofre1991-5] Nofre, Claude; Tinti, Jean M; Chatzopoulos, Farroudja O (Mar 5, 1991). "Pyridinyl compounds of N-carbamoyl-N-thiocarbamoyl- or N-amidino-glycine or beta-alanine useful as sweetening agents. US Patent 4997667 A". Retrieved 14 September 2014.

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See also

References

External links