Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

568600

Sigma-Aldrich

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

98%

Synonym(s):

6-Maleimidocaproic acid N-succinimidyl ester, N-(ε-Maleimidocaproyloxy)succinimide, N-Succinimidyl 6-maleimidocaproate, EMCS

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C14H16N2O6
CAS Number:
55750-63-5
Molecular Weight:
308.29
Beilstein:
1499815
MDL number:
MFCD00043043
UNSPSC Code:
12352100
PubChem Substance ID:
24880215
NACRES:
NA.22

Assay

98%

reaction suitability

reagent type: cross-linking reagent

mp

70-73 °C (lit.)

functional group

NHS ester
imide
maleimide

storage temp.

−20°C

SMILES string

O=C(ON(C(CC1)=O)C1=O)CCCCCN2C(C=CC2=O)=O

InChI

1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2

InChI key

VLARLSIGSPVYHX-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

6-Maleimidohexanoic acid N-hydroxysuccinimide ester can be used in:
  • Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.
  • Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.
  • Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBZ3468V
MKBL7769V
MKBR7741V
MKBH3139V
MKBH6545V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis and antitumor efficacy of a β-glucuronidase-responsive albumin-binding prodrug of doxorubicin.
Legigan T, et al.
Journal of Medicinal Chemistry, 55(9), 4516-4520 (2012)
Microarray fabrication with covalent attachment of DNA using bubble jet technology.
Okamoto T, et al.
Nature Biotechnology, 18(4), 438-438 (2000)
Synthesis of maleimide-activated carbohydrates as chemoselective tags for site-specific glycosylation of peptides and proteins.
Ni J, et al.
Bioconjugate Chemistry, 14(1), 232-238 (2003)
Y Nakano et al.
International archives of allergy and immunology, 120(3), 199-208 (1999-12-11)
We have previously reported that ovalbumin (OVA) coupled with liposome via glutaraldehyde (GA) induced OVA-specific- and IgE-selective unresponsiveness in mice. In this study, OVA-liposome conjugates were made using four different coupling protocols: via GA, N-(6-maleimidocaproyloxy) succinimide (EMCS), disuccinimidyl suberate (DSS)
N J Maeji et al.
Journal of immunological methods, 146(1), 83-90 (1992-01-21)
Recently, the multipin approach for simultaneous multiple peptide synthesis was applied to the analysis of T cell determinants by using a novel cleavage method (Maeji et al., 1990). A diketopiperazine forming linker allowed cleavage of peptides into aqueous buffer which
View All Related Papers

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