• Chemical structure of Sulfo-SMCC sodium salt (sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate), CAS 92921-24-9, ≥97% — the water-soluble version of SMCC (C16H17N2NaO9S): an amine-reactive sulfo-NHS ester and a thiol-reactive maleimide. Unlike membrane-permeable SMCC, the sulfonate keeps it out of cells, conjugating extracellular proteins in aqueous buffer; ideal for maleimide-activated carrier proteins and antibody-enzyme conjugates. Supplied by NorrChemica with DDP shipping. CoA and SDS
  • NorrChemica product reference card for Sulfo-SMCC sodium salt, CAS 92921-24-9, ≥97%, an amine-to-thiol heterobifunctional crosslinker. Shows the chemical structure with its sulfo-NHS ester (amine-reactive), cyclohexane spacer, and maleimide (thiol-reactive), and labelled sections: identity (C₁₆H₁₇N₂NaO₉S, MW 436.4, PubChem CID 4618794, MFCD00054978); maleimide–thiol selectivity over pH 6.5–7.5 with limited hydrolysis; and bioconjugate applications such as antibody–drug conjugates and conjugate vaccines.
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NorrChemica™

Sulfo-SMCC sodium salt

CAS 92921-24-9 ≥97%

Sulfo-SMCC sodium salt | CAS 92921-24-9 | ≥97%

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Technical Specifications

CAS Number 92921-24-9
MDL Number MFCD00054978
SMILES C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+]
InChI InChI=1S/C16H18N2O9S.Na/c19-12-5-6-13(20)17(12)8-9-1-3-10(4-2-9)16(23)27-18-14(21)7-11(15(18)22)28(24,25)26;/h5-6,9-11H,1-4,7-8H2,(H,24,25,26);/q;+1/p-1
InChIKey VUFNRPJNRFOTGK-UHFFFAOYSA-M
PubChem CID 4618794
Molecular Formula C₁₆H₁₇N₂NaO₉S
Molecular Weight 436.36 g/mol
Melting Point >270 °C (dec.)
Solubility Soluble in: water, N,N-dimethylformamide (DMF)
Purity ≥97%
Physical Form White to almost white powder to crystal
HS Code 2925.19
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store at 2–8 °C (OK to freeze). Keep under inert gas and protect from moisture; purge headspace with inert gas after each use.

Product Description & Scientific Applications

Sulfo-SMCC sodium salt (Sulfo SMCC) is a heterobifunctional crosslinker that conjugates amines to free thiols.

Stability. This class of maleimide-based heterobifunctional crosslinker is known for limited hydrolysis and thiol exchange due to its sterically hindered cyclohexyl moiety.

Thiol selectivity. The maleimide–thiol reaction is specific for thiol groups in the pH range of 6.5 to 7.5. At higher pH values, crossreactivity with amine groups occurs.

Maleimide–thiol conjugation. Maleimides have been used to link thiol groups to bioactive molecules: N-ethylmaleimide on solid-supported surfaces, antibody–enzyme and hapten–carrier conjugates, and carrier proteins with thiol groups in solution.

Bioconjugate applications. This heterobifunctional crosslinker class has been applied to the synthesis of peptide–protein conjugates, hapten–carrier complexes, antigen–antibody and enzyme–antibody fusions, immunotoxins, and antibody–drug conjugates. The thiol–maleimide reaction is used for the synthesis of antibody–drug conjugates (ADC) and conjugate vaccines. Sulfo-SMCC was used, together with attachment of a leucine zipper peptide (HiA CLZ) to the surface of extracellular vesicles, to create Zippersomes.

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  • Worldwide: 7–14 business days, selected locations.

Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements H315 - H319 - H335
P-Statements P280 - P302+P352 - P304+P340 - P312 - P332+P313 - P337+P313 - P501
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