Phosphinothricin

HCID 91619
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Basic information

CAS
35597-44-5
Standard SMILES
CP(=O)(O)CC[C@H](N)C(=O)O
InChIKey
IAJOBQBIJHVGMQ-BYPYZUCNSA-N
Molecular formula
C5H12NO4P
Average molar mass
181.13 g/mol
Monoisotopic mass
181.05039449

Overview

Glufosinate-P is a 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses. It has a role as an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor, a herbicide and an agrochemical. It is an enantiomer of a (2R)-glufosinate. It is a tautomer of a glufosinate-P zwitterion.

Names & identifiers

Preferred name
Phosphinothricin
IUPAC
(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
English name
Glufosinate-P
Molecular formula
C5H12NO4P
Molecular weight
181.13

Names & synonyms

phosphinothricin35597-44-5RefChem:6631642-amino-4-methylphosphinobutyric acidGlufosinate-PL-GlufosinateL-PHOSPHINOTHRICIN(S)-Phosphinothricin(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acidButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-CHEMBL145114(S)-Glufosinate
Show more names
L-Glufosinate ammoniumGlufosinate Impurity 5L-GlufositePhosphinothricine(S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid(S)-4-[Hydroxy(methyl)phosphinyl]-2-aminobutyric acid
DTXSID401020544(2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid(2S)-2-Amino-4-(hydroxy(methyl)phosphoryl)butanoic acidGlufosinate-P [ISO](2S)-2-amino-4-(hydroxy(methyl)phosphinoyl)butyric acidCHEMBL53515315766-01-5(2S)-2-azaniumyl-4-[hydroxy(methyl)phosphoryl]butanoate

Database identifiers

CAS
35597-44-5、51276-47-2
PubChem CID
91619
DTXSID
DTXSID401020544
ChEMBL
CHEMBL145114、CHEMBL535153
ChEBI
CHEBI:142852
UNII
72P470U27C
EC Number
690-077-2
Nikkaji
J391.973K

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

Physicochemical properties

Melting point
209 · 209-210 °C
Boiling point
519.1 · 519.1±45.0 °C(Predicted)
alpha
25 · D25 +13.4° (c = 1 in water)
Density
1.378 · 1.378±0.06 g/cm3(Predicted)
pka
2.22 · 2.22±0.10(Predicted)
InChI
InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P316, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 28 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Health EffectsSeizures; muscle weakness (post-status epileptic myopathy); convulsions; and even death. (T10)
Toxicity SummaryGlufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants. (T10)
Signs and SymptomsNausea, vomiting, and diarrhea that is followed in 24h by impaired respiration. (T10)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

Signal word
Danger
Symbol(GHS)
GHS06
Hazard statements
H302-H331
Precautionary statements
P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

Applications

UsesL-Glufosinate is a highly effective, broad-spectrum, low-toxicity, non-selective herbicide.

Upstream & downstream products

Suppliers25 total

武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Glufosinate-P is a 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses. It has a role as a herbicide, an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor and an agrochemical. It is an enantiomer of a (2R)-glufosinate. It is a tautomer of a glufosinate-P zwitterion.

Related reactions

3 records
New reaction record

Compound notes

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