Merck
CN
All Photos(1)

730300

Sigma-Aldrich

Methacrylic acid N-hydroxysuccinimide ester

98%

Sign Into View Organizational & Contract Pricing

Select a Size

Change View
Synonym(s):
N-(Methacryloxy)succinimide, N-(Methacryloyloxy)succinimide
Empirical Formula (Hill Notation):
C8H9NO4
CAS Number:
Molecular Weight:
183.16
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

98%

form

solid

mp

101-105 °C

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)ON1C(=O)CCC1=O

InChI

1S/C8H9NO4/c1-5(2)8(12)13-9-6(10)3-4-7(9)11/h1,3-4H2,2H3

InChI key

ACGJEMXWUYWELU-UHFFFAOYSA-N

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
56189E325746920
form

solid

form

-

form

powder

form

powder

mp

101-105 °C

mp

132-133 °C (lit.)

mp

-

mp

150-153 °C (lit.)

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

General description

Methacrylic acid N-hydroxysuccinimide ester(NHS-MA) belongs to the class of reactive monomers known as N-hydroxysuccinimide (NHS) esters. It is commonly used for functionalizing biomolecules through amine-reactive coupling reactions infields such as bioconjugation, protein labeling, and peptide synthesis. It also serves as a crosslinking agent or linker molecule for the conjugation of drugs or targeting ligands to carrier materials.

Application

Methacrylic acid N-hydroxysuccinimide ester can be used:
  • As a monomer to prepare degradable amphiphilic diblock copolymer microparticles via RAFT polymerization, for low pH-triggered drug delivery. NHS-MA can shield the drug molecule from degradation, enhance its solubility, and improve its pharmacokinetic properties.
  • For the surface functionalization of poly-ε-caprolactone (PCL) scaffolds used for tissue engineering. NHS groups are used to couple with chitosan of various molecular weights.
  • To prepare biocompatible polymer hydrogel for enzymatic biofuel cells. The hydrogel can serve as an enzyme-immobilizing matrix for enzymatic bioelectrodes.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - 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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Electrosprayed cysteine-functionalized degradable amphiphilic block copolymer microparticles for low pH-triggered drug delivery
Marie Finnegan, et al
Introduction to Polymer Chemistry, 10 (2019)
Postpolymerization modification of poly (pentafluorophenyl methacrylate): Synthesis of a diverse water-soluble polymer library
Gibson MI, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 47(17), 4332-4345 (2009)
Chitosan functionalized poly-?-caprolactone electrospun fibers and 3D printed scaffolds as antibacterial materials for tissue engineering applications
Myriam G. Tardajos, et al.
Carbohydrate Polymers, 191, 127-135 (2018)
A Modifiable, Spontaneously Formed Polymer Gel with Zwitterionic and N-Hydroxysuccinimide Moieties for an Enzymatic Biofuel Cell
Yixuan Huang, et al.
ACS applied polymer materials, 3, 631-639 (2021)
Water-soluble reactive copolymers based on cyclic N-vinylamides with succinimide side groups for bioconjugation with proteins
Peng H, et al.
Macromolecules, 48(13), 4256-4268 (2015)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service