lugduname

{{chembox

| verifiedrevid = 445885888

| ImageFile = Lugduname.svg

| ImageSize = 220px

| ImageFile1 = Lugduname molecule ball.png

| ImageSize1 = 240

| ImageAlt1 = Ball-and-stick model

| IUPACName = N′-(4-Cyanophenyl)-N′′-(2,3-methylenedioxybenzyl)guanidinoacetic acid

| OtherNames =

|Section1={{Chembox Identifiers

| 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)

| InChIKey = IHKGGKRBWGTNNG-UHFFFAOYAL

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IHKGGKRBWGTNNG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 180045-75-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 832G2PE2QQ

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID=21106452

| PubChem = 57459281

| SMILES = N#Cc1ccc(cc1)N/C(NCC(O)=O)=N\Cc2cccc3OCOc23

}}

|Section2={{Chembox Properties

| C=18 | H=16 | N=4 | O=4

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Lugduname (from lat. Lugdunum for Lyon) is one of the most potent sweetening agents known.{{ cite journal | author = Hürter, T. | title = Wie wir schmecken | journal = Technology Review | year = 2004 | volume = 2004 | issue = 4 | publisher = Heise.de | url = http://heise.de/-280853 }} 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. Lugduname is part of a family of potent sweeteners which contain acetic acid functional groups attached to guanidine.{{ cite journal |author1=Chen, J. |author2=Pattarawarapan, M. |author3=Zhang, A. J. |author4=Burgess, K. | title = Solution- and Solid-Phase Syntheses of Substituted Guanidinocarboxylic Acids | journal = Journal of Combinatorial Chemistry | year = 2000 | volume = 2 | issue = 3 | pages = 276–281 | doi = 10.1021/cc990084b |pmid=10827936 }} Contains a synthetic method for Lugduname, see Scheme 2{{ cite journal |author1=Nofre, C. |author2=Glaser, D. |author3=Tinti, J.-M. |author4=Wanner, M. | title = Gustatory responses of pigs to sixty compounds tasting sweet to humans | journal = Journal of Animal Physiology and Animal Nutrition | year = 2002 | volume = 86 | issue = 3–4 | pages = 90–96 | doi = 10.1046/j.1439-0396.2002.00361.x |pmid=11972677 }}