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Sigma-Aldrich

Methacrylic acid N-hydroxysuccinimide ester

98%

Synonym(s):

N-(Methacryloxy)succinimide, N-(Methacryloyloxy)succinimide

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About This Item

Empirical Formula (Hill Notation):
C8H9NO4
CAS Number:
38862-25-8
Molecular Weight:
183.16
MDL number:
MFCD15072193
UNSPSC Code:
12162002
PubChem Substance ID:
329764554
NACRES:
NA.23
Pricing and availability is not currently available.

Quality Level

100

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

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.[1]
  • 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.[2]
  • To prepare biocompatible polymer hydrogel for enzymatic biofuel cells. The hydrogel can serve as an enzyme-immobilizing matrix for enzymatic bioelectrodes.[3]

Pictograms

Exclamation mark
GHS07

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8177
MKCV6197
MKCV9424
MKCS4447
MKCR4190

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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)
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)
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)
Theato, P.
Journal of Polymer Science Part A: Polymer Chemistry, 46, 6677-6677 (2008)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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