4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (CAS 64987-85-5) is a heterobifunctional cross-linking reagent. With a molecular weight of 334.32 g/mol and formula C16H18N2O6, it features amine-reactive NHS ester and sulfhydryl-reactive maleimide groups connected by a 9-atom aliphatic spacer. This reagent is valuable for preparing bioconjugates, such as enzyme-carrier molecule conjugates and hapten-carrier molecule conjugates.
- IUPAC
- N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate,SMCC
Amine-Sulfhydryl Crosslinking
This reagent enables selective crosslinking between molecules possessing primary amines and free sulfhydryl groups. The NHS ester reacts with amines at pH 7.5 to form stable amide bonds, while the maleimide group reacts with thiols at pH 6.8 to form thioether linkages.
Bioconjugation
It is employed in the synthesis of bioconjugates, including enzyme immunoconjugates and hapten-carrier molecule conjugates, facilitating the study of biological interactions and protein structure.
Protein Modification
The heterobifunctional nature allows for precise modification of proteins, enabling targeted attachment of labels, drugs, or other molecules for various research applications in molecular biology and proteomics.
| Molecular weight | 334.32 |
|---|---|
| Empirical formula | C16H18N2O6 |
| Assay | ≥98% |
| Form | powder |
| Solubility | chloroform: soluble50 mg/mLDMF: soluble |
| Storage temperature | −20°C |
| Application | A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers. |
| Melting point | 180-182 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
| Shipped In | wet ice |
|---|
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester used for?
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This compound is a heterobifunctional cross-linking reagent used for selectively linking molecules containing primary amines to molecules containing free sulfhydryl groups, useful in bioconjugation and protein modification.
What is the CAS number and formula for this product?
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The CAS number is 64987-85-5 and the empirical formula is C16H18N2O6.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product at an assay of ≥98%. We do not represent this product as USP, BP, or EP grade.
What are the safety precautions when handling this chemical?
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This compound is a Warning hazard. It causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Handle with appropriate personal protective equipment including a dust mask (N95 type), eyeshields, and gloves. Ensure good ventilation.
How is this product shipped?
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This product is shipped on wet ice and stored at -20°C.
How can I request a quote or sample?
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Please contact our sales department via the website or direct enquiry line to request a quote or sample.
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