Basic information
- CAS
35597-44-5- Standard SMILES
CP(=O)(O)CCC(N)C(=O)O- InChIKey
IAJOBQBIJHVGMQ-UHFFFAOYSA-N- Molecular formula
- C5H12NO4P
- Average molar mass
- 181.13 g/mol
- Monoisotopic mass
- 181.05039449
Overview
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.
Names & identifiers
- Preferred name
- Glufosinate
- IUPAC
- 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
- English name
- Glufosinate-P
- Molecular formula
- C5H12NO4P
- Molecular weight
- 181.13
Names & synonyms
GLUFOSINATE51276-47-2DL-Phosphinothricin3-Amino-3-carboxypropylmethylphosphinic acidDL-2-Amino-4-(methylphosphino)butanoic acid(+-)-PhosphinothricinC8W4FP6BTYButanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-HOE-35956DTXSID0043973HOE 359562-Amino-4-(hydroxymethylphosphinyl)butanoic acid
Show more names
L-GlufosinateL-Glufosinate ammoniumL-PhosphinothricinGlufosinate Impurity 5L-GlufositeGlufosinate-PPhosphinothricine(S)-Phosphinothricin(S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid(S)-4-[Hydroxy(methyl)phosphinyl]-2-aminobutyric acid
(2RS)-2-AMINO-4-(HYDROXY(METHYL)PHOSPHINOYL)BUTYRIC ACID(3-azaniumyl-3-carboxypropyl)-methylphosphinate2-azaniumyl-4-(hydroxy(methyl)phosphoryl)butanoate4-(Hydroxy(methyl)phosphinoyl)-DL-homoalanineRefChem:663162DTXCID8023973CHEBI:52136257-102-5
Database identifiers
- CAS
35597-44-5、51276-47-2- PubChem CID
- 4794
- DTXSID
DTXSID0043973- ChEMBL
CHEMBL450298- ChEBI
CHEBI:142851- UNII
- C8W4FP6BTY
- EC Number
- 257-102-5
- Nikkaji
- J8.581B
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
Pesticides
Herbicides
Active substance -> EU Pesticides database: Not approved
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Herbicides
Pesticide
Collision Cross Section
142.7 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
139.3 Ų [M+H]+
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
- InChIKey
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N
- SMILES
- C(CP(O)(=O)C)[C@H](N)C(=O)O
- FDA UNII
- 72 P470U27C · 72P470U27C
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H331
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
Safety & regulation
GHS classification
GHS Classification
Danger
H302+H312+H332 (61.7%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P308+P316, P317, P318, P319, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H360: May damage fertility or the unborn child [Danger Reproductive toxicity]
Hazard information
Regulatory Information
Chemical: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-
07/25/EC, Reg (EU) 2015/408, Reg. (EU) 2015/404, Reg. (EU) 2022/801, Reg. (EU) No 365/2013, Reg. (EU) No 540/2011
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and Categories
Acute Tox. 4 (95.7%)
Acute toxicity (Oral) - Category 4
Reproductive toxicity - Category 1B
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).
USGS Health-Based Screening Levels for Evaluating Water-Quality
Glufosinate
62721
Pesticide
30
Data are for glufosinate-ammonium CASRN 77182822
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
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
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.
Uses & manufacturing
Use Classification
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Herbicides
Applications
UsesL-Glufosinate is a highly effective, broad-spectrum, low-toxicity, non-selective herbicide.
Upstream & downstream products
Upstream raw materials
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]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
南兴化工（江苏）有限公司0512-66387035 18662433356 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
山东朴石新材料有限公司13105464419 13105464419 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
上海万千化工有限公司18796480002 18796480002 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
河北独领国际贸易有限公司18032116176 · [email protected]
上海亿万化工有限公司00-18662433356 18662433356 · [email protected]
北京勤诚亦信科技开发有限公司010-67787816; 13811243025 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
南京枫景晴生物科技有限公司15062262630 · [email protected]
榆林润天畅化工有限责任公司15890142075 15890142075 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
泰兴市海川生物科技有限公司19353112242 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]
Additional notes
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
4 records
Compound notes
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