Lugduname

Lugduname
Names


IUPAC name N′-(4-Cyanophenyl)-N′′-(2,3-methylenedioxybenzyl)guanidinoacetic acid
Identifiers
CAS Number	180045-75-4^Y
3D model (JSmol)	Interactive image
ChemSpider	21106452^Y
PubChem CID	57459281
UNII	832G2PE2QQ^Y
CompTox Dashboard (EPA)	DTXSID20726659
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)^Y Key: IHKGGKRBWGTNNG-UHFFFAOYSA-N^Y 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	352.350 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Lugduname (from lat. Lugdunum for Lyon) 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, France in 1996.^[1] Lugduname is part of a family of potent sweeteners which contain acetic acid functional groups attached to guanidine.^[2]^[3]

References

^ ^a ^b Hürter, T. (2004). "Wie wir schmecken". Technology Review. 2004 (4). Heise.de.
^ 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. PMID 10827936. 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. PMID 11972677.