Lugduname

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]

Lugduname
Ball-and-stick model
Names
IUPAC name
N′-(4-Cyanophenyl)-N′′-(2,3-methylenedioxybenzyl)guanidinoacetic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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) checkY
    Key: IHKGGKRBWGTNNG-UHFFFAOYSA-N checkY
  • 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
  • N#Cc1ccc(cc1)N/C(NCC(O)=O)=N\Cc2cccc3OCOc23
Properties
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).
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Infobox references

See also

References
  1. Hürter, T. (2004). "Wie wir schmecken". Technology Review. Heise.de. 2004 (4).
  2. 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
  3. 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.
  • Media related to Lugduname at Wikimedia Commons


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