2-[(phosphonomethyl)amino]acetic acid

• ChemBase ID: 4108
• Molecular Formular: C3H8NO5P
• Molecular Mass: 169.073081
• Monoisotopic Mass: 169.01400899
• SMILES: OC(=O)CNCP(=O)(O)O
• Canonical SMILES: OC(=O)CNCP(=O)(O)O
• InChI: InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
• InChIKey: XDDAORKBJWWYJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(phosphonomethyl)amino]acetic acid
• IUPAC Traditional name: roundup
• Synonyms: N-(Phosphonomethyl)glycine; N-(Phosphonomethyl)glycine; Glyphosate; Glyphosate; Glyphosate; 2-[(phosphonomethyl)amino]acetic acid; N-(PHOSPHONOMETHYL) GLYCINE; (Carboxymethylamino)methylphosphonic Acid; GlyGran; Glyfos; Glyphodin A; Glyphomax; Glyphosate CT; Herbatop; Hockey; Kickdown; Klinik; Lancer; Phosphonomethyliminoacetic Acid; Roundup Max, NSC 151063; 草甘膦; N-(磷酰基甲基)甘氨酸; N-(磷酰基甲基)甘氨酸; 甘草膦

Database IDs

• CAS Number: 1071-83-6
• EC Number: 213-997-4
• MDL Number: MFCD00055350
• Beilstein Number: 2045054
• PubChem SID: 24887470; 24899043; 24869040; 46506916; 160967540; 24860496
• PubChem CID: 5288464; 3496
• CHEBI ID: 27744
• CHEMBL: 95764
• Chemspider ID: 3376
• KEGG ID: C01705
• Unique Ingredient Identifier: 4632WW1X5A
• Wikipedia Title: Glyphosate

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.58336174
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.5950933
• LogD (pH = 7.4): -7.237245
• Log P: -3.0976436
• Molar Refractivity: 31.3547 cm^3
• Polarizability: 12.89791 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.04
• LOG S: -1.29
• Solubility (Water): 1.07e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.01 g/100 mL (20 °C) in water; Water
• Apperance: Off-White Solid; white crystalline powder
• Melting Point: >220°C (dec.); 184.5 °C; 230 °C (dec.)(lit.)
• Boiling Point: decomp. at 187 °C
• Flash Point: non-flammable
• Density: 1.704 (20 °C)
• Partition Coefficient: -2.8
• pKa: <2, 2.6, 5.6, 10.6

Safety Information

• Storage Condition: Refrigerator
• RTECS: MC1075000
• European Hazard Symbols: Dangerous for the environment (N); Irritant (Xi); Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 41-51/53; R41, R51/53
• Safety Statements: 26-39-61; S2, S26, S39, S61
• EU Index: 607-315-00-8
• GHS Pictograms: GHS05; : Eye Dam. 1; GHS09; : Aquatic Chronic 2
• GHS Signal Word: DANGER; Danger
• GHS Hazard statements: 318, 411; H318-H411
• GHS Precautionary statements: 273, 280, 305+351+338, 310, 501; P273-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥95.0% (T); 95%; 96%
• Grade: PESTANAL®, analytical standard
• Suitability: plant cell culture tested
• Linear Formula: (HO)2P(O)CH2NHCH2CO2H

DETAILS

MP Biomedicals - 02156237

Purity: 95%

DrugBank - DB04539

Drug information: experimental

Sigma Aldrich - P9556

Biochem/physiol Actions
Glyphosphate inhibits the shikimate pathway-dependent synthesis of the aromatic amino acids tyrosine, tryptophan and phenylalanine at the growing points of plants.
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.

Sigma Aldrich - 337757

Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 79533

Other Notes
Enhancement of glutathione metabolism in plants exposed to glyphosate1

Sigma Aldrich - 45521

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - G765000

Used as a herbicide

REFERENCES

• Davis, V., et al.: Weed Sci., 57, 494 (2009)
• Bellaloui, N., et al.: J. Agric. Food Chem., 57, 9050 (2009)