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Sigma-Aldrich

11-Hydroxyundecylphosphonic acid

≥95% (GC)

Synonyme(s) :

P-(11-Hydroxyundecyl)phosphonic acid

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About This Item

Formule empirique (notation de Hill):
C11H25O4P
Numéro CAS:
83905-98-0
Poids moléculaire :
252.29
Numéro MDL:
MFCD11982869
Code UNSPSC :
12352103
ID de substance PubChem :
329767889
Nomenclature NACRES :
NA.23

Pureté

≥95% (GC)

Forme

powder

Pf

107-111 °C

Chaîne SMILES 

OCCCCCCCCCCCP(O)(O)=O

InChI

1S/C11H25O4P/c12-10-8-6-4-2-1-3-5-7-9-11-16(13,14)15/h12H,1-11H2,(H2,13,14,15)

Clé InChI

PPCDEFQVKBXBPS-UHFFFAOYSA-N

Description générale

11-Hydroxyundecylphosphonic acid (HUPA) is an alkyl phosphonic acid that forms a self-assembled monolayer (SAM) on a variety of metal oxides and metal surfaces. It forms a hydroxyl terminated SAM that provides a physiological stability and controls the surface density of the coating.

Application

An organophosphonate surface modifier for label-free and low-cost biosensing applications;
Organophosphonic acid self-assembled monolayers (SAMs);
A hydroxyalkylphosphonate monolayer used to covalently bind primary amine groups in protein domains using chloroformate-derived crosslinking
HUPA is mainly used as a spacer/linker that forms a SAM on titanium oxide (TiO2) surfaces to immobilize the surface atoms for the formation of biocompatible materials for biomedical applications. It can also be used to functionalize the silicon-photonic resonators for biosensing applications.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Covalent functionalization of TiO2 nanotube arrays with EGF and BMP-2 for modified behavior towards mesenchymal stem cells
Bauer S, et al.
Integrative Biology : Quantitative Biosciences from Nano to Macro, 3(9), 927-936 (2011)
Copper oxide surfaces modified by alkylphosphonic acids with terminal pyridyl-based ligands as a platform for supported catalysis
Andrews B, et al.
Polyhedron, 114, 360-369 (2016)
Chunyi Chiang et al.
Langmuir : the ACS journal of surfaces and colloids, 28(1), 548-556 (2011-11-23)
We report a robust strategy for conjugating mixtures of two or more protein domains to nonfouling polyurethane surfaces. In our strategy, the carbamate groups of polyurethane are reacted with zirconium alkoxide from the vapor phase to give a surface-bound oxide
Crystalline TiO2 grafted with poly (2-methacryloyloxyethyl phosphorylcholine) via surface-initiated atom-transfer radical polymerization
Zhao Y, et al.
Applied Surface Science, 257(5), 1596-1601 (2010)
Jing Shang et al.
Langmuir : the ACS journal of surfaces and colloids, 28(6), 3338-3344 (2012-01-10)
Silicon photonic microring resonators have established their potential for label-free and low-cost biosensing applications. However, the long-term performance of this optical sensing platform requires robust surface modification and biofunctionalization. Herein, we demonstrate a conjugation strategy based on an organophosphonate surface
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