Monatin

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]

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
3D model (JSmol)
ChemSpider
  • 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
  • O[C@]([C@](O)=O)(C[C@H](N)C(O)=O)CC2=CNC1=CC=CC=C12
Properties
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).
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Infobox references

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]

See also

References
  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
  4. "Monatin".
  • Media related to Monatin at Wikimedia Commons
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