142434-81-9

Basic information

• Product Name: 4-Phosphonomethyl-L-Phenylalanine
• Synonyms: 4-Phosphonomethyl-L-Phenylalanine;4-phosphonomethylphenylalanine;H-L-Pmp-OH;L-4-phosphonomethyl-Phenylalanine
• CAS NO: 142434-81-9
• Molecular Formula: C₁₀H₁₄NO₅P
• Molecular Weight: 259.195621
• Mol File: 142434-81-9.mol

Chemical Properties

• Boiling Point: 544.7 °C at 760 mmHg
• Flash Point: 283.2 °C
• Appearance: /
• Density: 1.499 g/cm³
• Vapor Pressure: 1.07E-12mmHg at 25°C
• Refractive Index: 1.615
• PKA: 2.19±0.10(Predicted)
• CAS DataBase Reference: 4-Phosphonomethyl-L-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phosphonomethyl-L-Phenylalanine(142434-81-9)
• EPA Substance Registry System: 4-Phosphonomethyl-L-Phenylalanine(142434-81-9)

Safety Data

• Hazardous Substances Data: 142434-81-9(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
4-Phosphonomethyl-L-Phenylalanine is used as a research compound for its structural similarity to phenylalanine, which aids in the study of protein formation and related biochemical processes.
Used in Biochemistry:
4-Phosphonomethyl-L-Phenylalanine is used as a biochemical tool to investigate the role of phenylalanine in protein synthesis and its potential applications in understanding various biological mechanisms.
Used in Flame Retardant Formulation:
Although its use is mainly restricted to laboratory research, 4-Phosphonomethyl-L-Phenylalanine is used as a phosphonate in the development of flame retardants, contributing to the creation of safer materials that resist ignition and slow the spread of fire.
Used in Corrosion Inhibition:
4-Phosphonomethyl-L-Phenylalanine is used as a phosphonate in the formulation of corrosion inhibitors, helping to protect materials from the damaging effects of corrosion and extending their lifespan.
Used in Water Softening Products:
As a phosphonate, 4-Phosphonomethyl-L-Phenylalanine is used in the development of water softening products, which are designed to reduce the hardness of water and prevent the buildup of mineral deposits in plumbing systems and appliances.

InChI:InChI=1/C10H14NO5P/c11-9(10(12)13)5-7-1-3-8(4-2-7)6-17(14,15)16/h1-4,9H,5-6,11H2,(H,12,13)(H2,14,15,16)

Upstream product

• 257628-04-9 L-4-((di-tert-butyl)phosphonomethyl)phenylalanine 
• 2361-96-8 ethyl N-acetyl-(L)-phenylalaninate 
• 130887-73-9 L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 142348-46-7 ethyl 4-(diethylphosphonomethyl)-D,L-phenylalaninate 
• 142348-45-6 ethyl N-(diphenylmethylene)-4-(diethylphosphonomethyl)-D,L-phenylalaninate 
• 142348-47-8 ethyl (N-tert-butyloxycarbonyl)-(4-diethylphosphonomethyl)-D,L-phenylalaninate 
• 108228-81-5 4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl 
• 229180-63-6 N-Ac-L-Phe(p-CH₂PO₃Et₂).OEt 
• 142348-55-8 (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propanoic acid 

Downstream Products

• 229180-64-7 Fmoc-(4-phosphonomethylphenyl)alanine 

Relevant articles and documents

Composition, synthesis and therapeutic applications of polyamines

This invention relates to a process of synthesis and composition of open chain (ring), closed ring, linear branched and or substituted polyamines, polyamine derived tyrosine phosphatase inhibitors and PPAR partial agonists/partial antagonists via a series of substitution reactions and optimizing the bioavailability and biological activities of the compounds. Polyamines prevent the toxicty of neutoxins and diabetogenic toxins including paraquat, methyphenyl pyridine radical, rotenone, diazoxide, streptozotocin and alloxan. These polyamines can be to treat neurological, cardiovascular, endocrine acquired and inherited mitochondrial DNA damage diseases and other disorders in mammalian subjects, and more specifically to the therapy of Parkinson's disease, Alzheimer's disease, Lou Gehrig's disease, Binswanger's disease, Olivopontine Cerebellar Degeneration, Lewy Body disease, Diabetes, Stroke, Atherosclerosis, Myocardial Ischemia, Cardiomyopathy, Nephropathy, Ischemia, Glaucoma, Presbycussis, Cancer, Osteoporosis, Rheumatoid Arthritis, Inflammatory Bowel Disease, Multiple Sclerosis and as Antidotes to Toxin Exposure.

An efficient synthesis of N(α)-FMOC-4(phosphonomethyl)-L- and D- phenylalanine

A simple and efficient synthesis for N(α)-Fmoc-4-(phosphonomethyl)L- phenylalanine and N(α)-Fmoc-D-phenylalanine with high optical purity by using the commercially available L and D-phenylalanine as the starting material is described.

Enantioselective synthesis of N-Fmoc protected di-tert-butyl 4-phosphonomethyl-L-phenylalanine: A hydrolytically stable analogue of O-phosphotyrosine

Fmoc-L-Pmp(tBu)2-OH was prepared with high enantiomeric purity by an asymmetric synthetic pathway, using a camphor sultam as chiral auxiliary.

Improved synthesis of [p-phosphono and p-sulfo]methylphenylalanine. Resolution of [p-phosphono-, p-sulfo-, p-carboxy- and p-N-hydroxycarboxamido-]methylphenylalanine

To analyse the role of post-translational phosphorylation and sulfation of tyrosine in peptides and proteins, we recently synthesized the new amino acids, p(CH2PO3H2)Phe and p(CH2SO3H)Phe (D,L mixture