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P9556

Sigma-Aldrich

N-(Phosphonomethyl)glycine

BioReagent, suitable for plant cell culture

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:
10171502
PubChem Substance ID:
24899043
NACRES:
NA.71

product line

BioReagent

Quality Level

200

form

powder

technique(s)

cell culture | plant: suitable

mp

230 °C (dec.) (lit.)

application(s)

agriculture

shipped in

ambient

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

Glyphosate (N-(phosphonomethyl)glycine) (sold commercially as Roundup) is the most widely used broad-spectrum systemic herbicide in the world. Consequently, the environmental effects of glyphosphate and its mechanism of action are an important area of active research.

Biochem/physiol Actions

Glyphosate (N-[phosphonomethyl] glycine) is the herbicide form of the isopropylamine salt of glyphosate.
Glyphosphate inhibits the shikimate pathway-dependent synthesis of the aromatic amino acids tyrosine, tryptophan and phenylalanine at the growing points of plants.

Preparation Note

Preparation and Use

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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Apoorva Ravishankar et al.
Environmental pollution (Barking, Essex : 1987), 262, 114359-114359 (2020-05-24)
Glyphosate-based herbicides, the most extensively used herbicides in the world, are available in an enormous number of commercial formulations with varying additives and adjuvants. Here, we study the effects of one such formulation, Credit41, in two genetically diverse yeast strains.
Influence of glyphosate (N-(phosphonomethyl) glycine) on performance and selected parameters in broilers
Kubena L F, et al.
Poultry Science, 60(1), 132-136 (1981)
Stephen O Duke
Journal of agricultural and food chemistry, 59(11), 5835-5841 (2010-10-06)
High levels of aminomethylphosphonic acid (AMPA), the main glyphosate metabolite, have been found in glyphosate-treated, glyphosate-resistant (GR) soybean, apparently due to plant glyphosate oxidoreductase (GOX)-like activity. AMPA is mildly phytotoxic, and under some conditions the AMPA accumulating in GR soybean
C Lanctôt et al.
Aquatic toxicology (Amsterdam, Netherlands), 140-141, 48-57 (2013-06-12)
Amphibian tadpoles develop in aquatic environments where they are susceptible to the effects of pesticides and other environmental contaminants. Glyphosate-based herbicides are currently the most commonly used herbicide in the world and have been shown to affect survival and development
Ming-Xue Chen et al.
Journal of chromatography. A, 1272, 90-99 (2012-12-25)
A novel method was developed for the direct, sensitive, and rapid determination of glyphosate and its major metabolite, aminomethylphosphonic acid (AMPA), in fruit and vegetable samples by mixed-mode hydrophilic interaction/weak anion-exchange liquid chromatography (HILIC/WAX) coupled with electrospray tandem mass spectrometry
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