400769-81-5

Basic information

• Product Name: D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-
• Synonyms: (2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid;4-hydroxy-4-(3-indolylmethyl)glutamic acid;(2R,4R)-monatin;(2R,4R)monatin;R,R-monatin;3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl)indole
• CAS NO: 400769-81-5
• Molecular Formula: C14H16N2O5
• Molecular Weight: 292.291
• Mol File: 400769-81-5.mol

Chemical Properties

• Boiling Point: 656.4±55.0 °C(Predicted)
• Density: 1.525±0.06 g/cm3(Predicted)
• CAS DataBase Reference: D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-(400769-81-5)
• EPA Substance Registry System: D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-(400769-81-5)

Safety Data

• Hazardous Substances Data: 400769-81-5(Hazardous Substances Data)

Upstream product

• 400769-77-9 (2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid 
• 400769-79-1 (2S,4R)-monatin 

Relevant articles and documents

PRODUCTION OF MONATIN ENANTIOMERS

Methods for the preparation of the high intensity sweetener, monatin, 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl)indole, its salts and internal condensation products thereof, including methods applicable to the large-scale production of monatin are described.

PROCESS FOR PRODUCING MONATIN OR SALT THEREOF

[Problems] To provide a process for producing monatin where steric configuration of 2-position is in an R configuration or a salt thereof by isomerization of 2-position of monatin where steric configuration of 2-position is in an S configuration. [Means for Resolution] A process for producing monatin where steric configuration of 2-position is in an R configuration or a salt thereof, characterized in that, the process contains a step where isomerization reaction of 2-position of monatin in which steric configuration of 2-position is in an S configuration is carried out in a mixed solvent of water and organic solvent in the presence of an aldehyde and, after that, a step where monatin in which steric configuration of 2-position is in an R configuration or a salt is crystallized.

PROCESS FOR PRODUCING MONATIN

By simultaneously carrying out an isomerization reaction at position 2 of monatin in different configurations at positions 2 and 4 in the presence of an aldehyde under a condition of pH 4 to 11 in a mixture solvent of water and an organic solvent, and the crystallization of monatin in the same configurations at positions 2 and 4 or a salt thereof, monatin useful as a sweetener, particularly optically active monatin can efficiently be produced.