All Photos(2)
Synonym(s):
P-(11-Hydroxyundecyl)phosphonic acid
Empirical Formula (Hill Notation):
C11H25O4P
CAS Number:
Molecular Weight:
252.29
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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Quality Level
Assay
≥95% (GC)
form
powder
mp
107-111 °C
SMILES string
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)
InChI key
PPCDEFQVKBXBPS-UHFFFAOYSA-N
Related Categories
General description
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
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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
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)
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)
Phosphonic acid monolayers for binding of bioactive molecules to titanium surfaces.
Adden N
Langmuir, 22(19), 8197-8204 (2006)
Qianli Ma et al.
Biomaterials, 230, 119650-119650 (2019-12-07)
A multitude of micro- and nano-surface structures have been developed to improve the clinical performance of endosseous titanium (Ti) implants. However, most of these surface structures only simulate the topographic elements on a micro- or nano-scale. In this study, a
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