Lugduname

Lugduname

Names
IUPAC name N-(4-Cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidinoacetic acid
Identifiers
CAS Number	180045-75-4
ChemSpider	21106452
Jmol interactive 3D	Image
InChI InChI=1S/C18H16N4O4/c19-8-12-4-6-14(7-5-12)22-18(21-10-16(23)24)20-9-13-2-1-3-15-17(13)26-11-25-15/h1-7H,9-11H2,(H,23,24)(H2,20,21,22) Key: IHKGGKRBWGTNNG-UHFFFAOYSA-N InChI=1/C18H16N4O4/c19-8-12-4-6-14(7-5-12)22-18(21-10-16(23)24)20-9-13-2-1-3-15-17(13)26-11-25-15/h1-7H,9-11H2,(H,23,24)(H2,20,21,22) Key: IHKGGKRBWGTNNG-UHFFFAOYAL
SMILES N#Cc1ccc(cc1)N/C(NCC(O)=O)=N\Cc2cccc3OCOc23
Properties
Chemical formula	C18H16N4O4
Molar mass	352.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lugduname (from lat. Lugdunum for Lyons) is one of the most potent sweetening agents known.^[1] Lugduname has been estimated to be between 220,000 and 300,000 times as sweet as sucrose (table sugar), with estimates varying between studies. It was developed at the University of Lyon in 1996.^[1] Lugduname is part of a family of extremely potent sweeteners which contain acetic acid functional groups attached to guanidine. It has not yet been approved for use in foods. A reference for this substance is found on page 17 of the August 4, 2014 issue of Chemical & Engineering News. The same article is available at http://cen.acs.org/articles/92/i31/Case-Against-Sugar.html.

External links

• "Sci.chem FAQ - Part 5 of 7". faqs.org. Retrieved 2008-07-13.

References

1. Hürter, T. (2004). "Wie wir schmecken". Technology Review (Heise.de) 2004 (4).

• Chen, J.; Pattarawarapan, M.; Zhang, A. J.; Burgess, K. (2000). "Solution- and Solid-Phase Syntheses of Substituted Guanidinocarboxylic Acids". Journal of Combinatorial Chemistry 2 (3): 276–281. doi:10.1021/cc990084b.Contains a synthetic method for Lugduname, see Scheme 2
• Nofre, C.; Glaser, D.; Tinti, J.-M.; Wanner, M. (2002). "Gustatory responses of pigs to sixty compounds tasting sweet to humans". Journal of Animal Physiology and Animal Nutrition 86 (3–4): 90–96. doi:10.1046/j.1439-0396.2002.00361.x.