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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:
1071-83-6
Molecular Weight:
169.07
Beilstein:
2045054
EC Number:
213-997-4
MDL number:
MFCD00055350
UNSPSC Code:
12352209
PubChem Substance ID:
24860496
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).

Signal Word

Danger

Hazard Statements

H312,H318,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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)
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
Biochemical effects of glyphosate (N-(phosphonomethyl) glycine)[Lemna, higher plants, phenylalanine ammonialyase].
Hoagland R E and Duke S O
ACS Symp. Ser. (1982)
Glyphosate: a once?in?a?century herbicide.
Duke S O and Powles S B
Pest Management Science, 64(4), 319-325 (2008)
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)
View All Related Papers

Protocols

EPA Method 547: HPLC Analysis of Glyphosate and Glyphosate Degradation Product (Aminomethyl)phosphonic Acid (AMPA)

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

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

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