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Sigma-Aldrich

11-Hydroxyundecylphosphonic acid

≥95% (GC)

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Synonym(s):
P-(11-Hydroxyundecyl)phosphonic acid
Empirical Formula (Hill Notation):
C11H25O4P
CAS Number:
83905-98-0
Molecular Weight:
252.29
MDL number:
MFCD11982869
PubChem Substance ID:
329767889
NACRES:
NA.23

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
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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)
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)
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)
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
Phosphonic acid monolayers for binding of bioactive molecules to titanium surfaces.
Adden N
Langmuir, 22(19), 8197-8204 (2006)
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