Monatin

Monatin
Names
	IUPAC name (4S)-4-Hydroxy-4-[(1H-indol-3-yl)methyl]-L-glutamic acid
	Systematic IUPAC name (2S,4S)-4-Amino-2-hydroxy-2-[(1H-indol-3-yl)methyl]pentanedioic acid
	Other names 2-Hydroxy-2-(indol-3-ylmethyl)-4-aminoglutaric acid; (S)-4-Hydroxy-4-(1H-indol-3-ylmethyl)-L-glutamic acid
Identifiers
CAS Number	146142-94-1 Y;
3D model (JSmol)	Interactive image;
ChemSpider	8036546 N;
PubChem CID	9860847;
CompTox Dashboard (EPA)	DTXSID60432020 ;
	InChI InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1 N Key: RMLYXMMBIZLGAQ-HZMBPMFUSA-N N; InChI=1/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1 Key: RMLYXMMBIZLGAQ-HZMBPMFUBZ;
	SMILES O[C@]([C@](O)=O)(C[C@H](N)C(O)=O)CC2=CNC1=CC=CC=C12;
Properties
Chemical formula	C14H16N2O5
Molar mass	292.291 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Monatin, commonly known as arruva, is a naturally occurring, high intensity sweetener isolated from the plant Sclerochiton ilicifolius, found in the Transvaal region of South Africa. Monatin contains no carbohydrate or sugar, and nearly no food energy, unlike sucrose or other nutritive sweeteners.^[1]

The name "monatin" is derived from the indigenous word for it, "molomo monate," which literally means "mouth nice."^[2]

Monatin is an indole derivative and, upon degradation, smells like feces.^[3]

It is 3000 times sweeter than sugar.^[4]

References

^ US application 20,050,106,305 , Timothy W. Abraham, Cargill
^ "Sweeteners and Sugar Alternatives in Food Technology," Kay O'Donnell and Malcolm Kearsley, 2012
^ "The Quest For a Natural Sugar Substitute," Daniel Engber, The New York Times, 01 January 2014[1]
^ "Monatin".

External links

Media related to Monatin at Wikimedia Commons

[1] US application 20,050,106,305 , Timothy W. Abraham, Cargill

[2] "Sweeteners and Sugar Alternatives in Food Technology," Kay O'Donnell and Malcolm Kearsley, 2012

[3] "The Quest For a Natural Sugar Substitute," Daniel Engber, The New York Times, 01 January 2014[1]

[4] "Monatin".

Names

IUPAC name (4S)-4-Hydroxy-4-[(1H-indol-3-yl)methyl]-L-glutamic acid
Systematic IUPAC name (2S,4S)-4-Amino-2-hydroxy-2-[(1H-indol-3-yl)methyl]pentanedioic acid
Other names 2-Hydroxy-2-(indol-3-ylmethyl)-4-aminoglutaric acid (S)-4-Hydroxy-4-(1H-indol-3-ylmethyl)-L-glutamic acid
Identifiers
CAS Number	146142-94-1^Y
3D model (JSmol)	Interactive image
ChemSpider	8036546^N
PubChem CID	9860847
CompTox Dashboard (EPA)	DTXSID60432020
InChI InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1^N Key: RMLYXMMBIZLGAQ-HZMBPMFUSA-N^N InChI=1/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1 Key: RMLYXMMBIZLGAQ-HZMBPMFUBZ
SMILES O[C@]([C@](O)=O)(C[C@H](N)C(O)=O)CC2=CNC1=CC=CC=C12
Properties
Chemical formula	C₁₄H₁₆N₂O₅
Molar mass	292.291 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Monatin

See also

References

External links