| Identification | More | [Name]
Glyphosine | [CAS]
2439-99-8 | [Synonyms]
GLYCINE-N,N-BIS(METHYLENEPHOSPHONIC ACID)
GLYPHOSINE
N-(CARBOXYMETHYL)IMINODI(METHYLPHOSPHINIC ACID)
N,N-BIS(PHOSPHONOMETHYL)GLYCINE
cp41845
n,n-bis(phosphonomethyl)-glycin
Polaris(monsanto)
Glyphosphine
polaris
N,N-bis phophonomethyl glycine
glyphosine (ISO) N,N-bis(phosphonomethyl)glycine
2-(Bis(phosphonomethyl)amino)acetic acid
N,N-Di(phosphonomethyl)glycine
Nitrilomonomethylcarbonyldimethylphosphonic acid | [EINECS(EC#)]
219-468-4 | [Molecular Formula]
C4H11NO8P2 | [MDL Number]
MFCD00056670 | [Molecular Weight]
263.08 | [MOL File]
2439-99-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
263°C | [Boiling point ]
668.4±65.0 °C(Predicted) | [density ]
1.952±0.06 g/cm3(Predicted) | [storage temp. ]
+2C to +8C | [solubility ]
PBS (pH: 7.2):5.0(Max Conc. mg/mL);19.01(Max Conc. mM) | [form ]
Solid | [pka]
pK1 1.42; pK2 2.10; pK3 5.02; pK4 6.40; pK5 11.19(at 25℃) | [color ]
White | [Water Solubility ]
248g/L(20 ºC) | [Merck ]
13,4526 | [BRN ]
1884944 | [InChI]
InChI=1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13) | [InChIKey]
OXHDYFKENBXUEM-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O | [CAS DataBase Reference]
2439-99-8(CAS DataBase Reference) | [EPA Substance Registry System]
2439-99-8(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H318 | [Precautionary statements ]
P280-P305+P351+P338+P310 | [Hazard Codes ]
Xi | [Risk Statements ]
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S2:Keep out of the reach of children . | [RIDADR ]
UN 3261 8/PG 3
| [WGK Germany ]
1
| [RTECS ]
MB9120000
| [TSCA ]
TSCA listed | [HS Code ]
2922.49.8000 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Eye Dam. 1 | [Toxicity]
LD50 orally in rats: 3925 mg/kg; dermally in rabbits: >5010 mg/kg (Ahlrichs) |
| Hazard Information | Back Directory | [Description]
Glyphosine was introduced in 1973 and is preferably used in sugar beets. The synthesis starting with glycine uses two equivalents of formaldehyde and of phosphorous trichloride under oxidative conditions. A second derivative of Glyphosate is a cyclic phosphaoxazole being formed from Glyphosate and formaldehyde. This compound is claimed to control the growth of some grasses without dis- coloration or phytotoxicity.
| [Uses]
Application: Complexing agent; pK-values: pK1: ·2, pK2: 2.0, pK3: 5.20, pK4: 6.77, pK5: 10.89
Anti-diabetic; delay onset of diabetes in non-obese NOD mice
Glyphosine binds to a pocket of MHC class II molecules I-Ag7 and DQ8, and modify T cell responses to the autoantigenic insulin B chain fragment 9–23 (B:9–23) peptide. Glyphosine stimulate IL-10 production and delay onset of diabetes in non-obese NOD mice.? | [Uses]
Chemical ripener; plant growth regulator. | [Definition]
ChEBI: A tertiary amino compound that consists of glycine bearing two N-phosphonomethyl substituents. | [Production Methods]
Detailed information on the synthesis of glyphosine is not readily available in open literature. However, it was probably produced through a multistep process typical of aminomethyl phosphonate herbicides, beginning with the preparation of an amino acid–derived intermediate such as iminodiacetic acid or a substituted glycine analogue. Industrial manufacturers introduce the phosphonomethyl group via reaction with phosphorus trichloride and formaldehyde under controlled acidic conditions, forming a phosphonomethylated amino acid similar to the PMIDA and glycine based routes documented for glyphosate production. This condensation–oxidation sequence is followed by hydrolysis and neutralisation to yield the free acid or salt form of glyphosine. Purification typically involves aqueous work up, pH adjustment, and crystallisation to achieve technical grade purity | [General Description]
N,N-Bis(phosphonomethyl)glycine was present in the ligand bound to human apotransferrin. | [Biochem/physiol Actions]
Anti-diabetic; delay onset of diabetes in non-obese NOD mice | [Mechanism of action]
Absorbed by foliage and translocated, increases the partioning of dry matter towards sucrose storage and away from fibre production | [Pesticide Type]
Plant Growth Regulator; Herbicide |
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