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Sigma-Aldrich

N-(Phosphonomethyl)glycine

96%, for peptide synthesis

Synonym(s):

Glyphosate

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About This Item

Linear Formula:
(HO)2P(O)CH2NHCH2CO2H
CAS Number:
Molecular Weight:
169.07
Beilstein/REAXYS Number:
2045054
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

product name

N-(Phosphonomethyl)glycine, 96%

assay

96%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

230 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)CNCP(O)(O)=O

InChI

1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)

InChI key

XDDAORKBJWWYJS-UHFFFAOYSA-N

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General description

N-(Phosphonomethyl)glycine (Glyphosate) is a broad spectrum, non-selective systemic herbicide. It plays an important role in inhibiting the activity of 5-enolpyruvylshikimic acid-3-phosphate synthase, which is involved in aromatic amino acid biosynthesis. Due to its chelation property, glyphosate can form coordinate complexes with a wide range of metal ions.

Application

  • Water Pollution Analysis: Campanale et al. assessed glyphosate and AMPA pesticides in river waters and sediments, providing crucial data on the environmental distribution and persistence of N-(Phosphonomethyl)glycine derivatives. This research supports efforts to monitor and regulate environmental pollutants effectively (Campanale et al., 2024).
  • Public Health Studies: Urinary biomonitoring of glyphosate exposure was conducted among farmers, utilizing N-(Phosphonomethyl)glycine as a marker. This study contributes to our understanding of occupational exposure risks and supports the development of health safety guidelines (Chang et al., 2024).

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Aquatic Chronic 2 - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Glyphosate: a once?in?a?century herbicide.
Duke S O and Powles S B
Pest Management Science, 64(4), 319-325 (2008)
Hui Gao et al.
Journal of applied toxicology : JAT, 39(8), 1096-1107 (2019-03-26)
Glyphosate-based herbicides have been used worldwide for decades and have been suggested to induce nephrotoxicity, but the underlying mechanism is not yet clear. In this study, we treated a human renal proximal tubule cell line (HK-2) with glyphosate for 24 hours
The herbicide glyphosate is a potent inhibitor of 5-enolpyruvylshikimic acid-3-phosphate synthase.
Steinrucken H C and Amrhein N
Biochemical and Biophysical Research Communications, 94(4), 1207-1212 (1980)
Biochemical effects of glyphosate (N-(phosphonomethyl) glycine)[Lemna, higher plants, phenylalanine ammonialyase].
Hoagland R E and Duke S O
ACS Symp. Ser. (1982)
Metal complexes with N-(phosphonomethyl) glycine (glyphosate): The preparation and characterization of the group 2 metal complexes with glyphosate and the crystal structure of barium glyphosate dihydrate.
Sagatys D S, et al.
Australian Journal of Chemistry, 53(2), 77-81 (2000)

Protocols

EPA Method 547 outlines the analysis of glyphosate in drinking water by direct aqueous injection HPLC, post column derivatization, and fluorescence detection

LC/MS Analysis of Glyphosate and Metabolites on apHera™ NH2, 2 mm I.D. Column

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