Glufosinate, (R)-
Basic information
- CAS
51276-47-2- Standard SMILES
CP(=O)(O)CC[C@@H](N)C(=O)O- InChIKey
IAJOBQBIJHVGMQ-SCSAIBSYSA-N- Molecular formula
- C5H12NO4P
- Average molar mass
- 181.13 g/mol
- Monoisotopic mass
- 181.05039486
Overview
(2R)-glufosinate is a 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has R configuration at position 2. The enantiomer of glufosinate-P. It is an enantiomer of a glufosinate-P. It is a tautomer of a (2R)-glufosinate zwitterion.
Names & identifiers
- Preferred name
- Glufosinate, (R)-
- IUPAC
- (2R)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
- English name
- Phosphinothricin
- Molecular formula
- C5H12NO4P
- Molecular weight
- 181.13
Names & synonyms
d-glufosinateD-Phosphinothricin73679-07-9Glufosinate, (d)-(R)-PhosphinothricinGlufosinate, (R)-M758GI0FEXD-2-amino-4-(hydroxymethylphosphinyl)butanoic acidButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (R)-Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2R)-Phosphinothricin D-RefChem:1085866
Show more names
C05042HOE-866HOE-35956GlufositePhosphinothricin2'-Anhydrouridine13C,2H3]-GlufosinateIAJOBQBIJHVGMQ-UHFFFAOYSA-NPhosphinothricin ammonium salt2-amino-4-(hydroxymethylphosphinyl)butyric acid
(R)-glufosinate(2R)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acidPhosphinothricin D-form [MI]UNII-M758GI0FEX(2R)-2-amino-4-(hydroxy(methyl)phosphoryl)butanoic acid(S)-(+)-phosphinothricin(-)-glufosinate(2R)-glufosinate
Database identifiers
- CAS
51276-47-2、73679-07-9
Properties
Computed structural properties
- XLogP
- -5
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 193
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 229 · 229-231° (dec)
- Boiling point
- 519.1 · 519.1±45.0 °C(Predicted)
- Density
- 1.378 · 1.378±0.06 g/cm3(Predicted)
- solubility
- Aqueous Acid (Slightly), Methanol (Very Slightly, Sonicated), Water (Slightly)
- pka
- 2.22 · 2.22±0.10(Predicted)
- form
- Solid
- color
- White to Light Beige
- Stability
- Hygroscopic
- LogP
- -0.75 · -0.750 (est)
- FDA UNII
- 8 W4FP6BTY · C8W4FP6BTY
- EPA Substance Registry System
- 2 · Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)- (51276-47-2)
- Symbol(GHS)
- 7 · GHS07,GHS08
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- Hazard statements
- H360-H302-H312-H373
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P260-P314-P501-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Applications
UsesGlufosinate, a phosphinic acid analogue of glutamic acid, is a herbicide which is converted by plant cells into PT (L-phosphinothricin). Glufosinate exerts neurotoxic activity[1][2].
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid is a non-proteinogenic alpha-amino acid that is 2-aminobutanoic acid which is substituted at position 4 by a hydroxy(methyl)phosphoryl group. It is a member of phosphinic acids and a non-proteinogenic alpha-amino acid.
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