19730-77-9

Basic information

• Product Name: {2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl}phosphonic acid
• CAS NO: 19730-77-9
• Molecular Formula: C₉H₁₂NO₅P
• Molecular Weight: 245.169
• Mol File: 19730-77-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 649°C at 760 mmHg
• Flash Point: 346.3°C
• Density: 1.583g/cm³
• Vapor Pressure: 9.98E-18mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: {2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl}phosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: {2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl}phosphonic acid(19730-77-9)
• EPA Substance Registry System: {2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl}phosphonic acid(19730-77-9)

Safety Data

• Hazardous Substances Data: 19730-77-9(Hazardous Substances Data)

Usage

Description

2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenylphosphonic acid is a phosphonic acid derivative with a unique molecular structure featuring a pyridinyl ethenyl group attached to a phosphonic acid moiety. This chemical compound, with the molecular formula C10H13NO6P, is characterized by its potential to inhibit the enzyme farnesyl diphosphate synthase, which is involved in the mevalonate pathway and isoprenoid biosynthesis. The presence of hydroxy and hydroxymethyl groups on the pyridinyl ring enhances its potential for medicinal applications, while its phosphonic acid nature allows for strong and stable interactions with metal ions, making it valuable in various industrial and research contexts.

Uses

Used in Pharmaceutical Industry:
2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenylphosphonic acid is used as a potential inhibitor for the enzyme farnesyl diphosphate synthase, which plays a crucial role in the mevalonate pathway. This application is significant for the development of new drugs targeting the mevalonate pathway and related metabolic pathways, potentially leading to treatments for various diseases associated with these pathways.
Used in Medicinal Chemistry:
As a phosphonic acid derivative with a pyridinyl ethenyl group, 2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenylphosphonic acid is used for the development of new drugs in medicinal chemistry. The hydroxy and hydroxymethyl groups on the pyridinyl ring make this compound a promising candidate for targeting specific enzymes and metabolic pathways, contributing to the advancement of novel therapeutic strategies.
Used in Industrial Applications:
The ability of 2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenylphosphonic acid to form strong and stable interactions with metal ions makes it useful in various industrial applications. This characteristic can be exploited in the development of new materials, catalysts, or other products that require metal ion interactions for their functionality.
Used in Research and Development:
In the field of research and development, 2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenylphosphonic acid serves as a valuable compound for studying the mevalonate pathway and its role in isoprenoid biosynthesis. Its potential as an enzyme inhibitor and its interactions with metal ions make it an interesting subject for further investigation, potentially leading to new discoveries and applications in both medicinal and industrial contexts.

Upstream product

• 6560-65-2 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxaldehyde 
• 1136-52-3 (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol 
• 65-23-6 5-hydroxy-6-methyl-3,4-pyridinedimethanol 

Relevant articles and documents

SAR of non-hydrolysable analogs of pyridoxal 5′-phosphate against low molecular weight protein tyrosine phosphatase isoforms

Kinases and phosphatases are key enzymes in cell signal transduction pathways. Imbalances in these enzymes have been linked to numerous disease states ranging from cancer to diabetes to autoimmune disorders. The two isoforms (IFA and IFB) of Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) appear to play a role in these diseases. Pyridoxal 5′-phosphate (PLP) has been shown to act as a potent but, impractical micromolar inhibitor for both isoforms. In this study, a series of non-hydrolysable phosphonate analogs of PLP were designed, synthesized and tested against the two isoforms of LMW-PTP. Assay results demonstrated that the best inhibitor for both isoforms was compound 5 with a Kis of 1.84 μM (IFA) and 15.6 μM (IFB). The most selective inhibitor was compound 16, with a selectivity of roughly 370-fold for IFA over IFB.

Vitamin B6 analogs. 4. 4-Desoxyisopyridoxal and the phosphonic acid analog of 4-desoxypyridoxine phosphate.

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