SMCC crosslinker
- CAS No.
- 64987-85-5
- Chemical Name:
- SMCC crosslinker
- Synonyms
- SMCC;2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)Methyl)cyclohexanecarboxylate;NSC 344483;SMCC Crosslinker;N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC;LKA;R3-RM1;SMCC，98%;25MG/100MG/10G;N-SucciniMidyl 4-(N-MaleiMi
- CBNumber:
- CB6748487
- Molecular Formula:
- C16H18N2O6
- Molecular Weight:
- 334.32
- MOL File:
- 64987-85-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/5/24 15:44:31
| Melting point | 180-182 °C (lit.) |
|---|---|
| Boiling point | 501.7±42.0 °C(Predicted) |
| Density | 1.42±0.1 g/cm3(Predicted) |
| storage temp. | -20°C |
| solubility | chloroform: 50 mg/mL |
| form | powder |
| pka | -2.24±0.20(Predicted) |
| color | White to Off-White |
| Sensitive | Moisture & Light Sensitive |
| BRN | 1555271 |
| InChI | InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2 |
| InChIKey | JJAHTWIKCUJRDK-UHFFFAOYSA-N |
| SMILES | C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1 |
| CAS DataBase Reference | 64987-85-5(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-36-60-37 | |||||||||
| WGK Germany | 3 | |||||||||
| F | 10-21 | |||||||||
| HS Code | 29280000 | |||||||||
| NFPA 704 |
|
SMCC crosslinker price More Price(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | M5525 | 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester ≥98%, powder | 64987-85-5 | 5MG | ₹3009.35 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M5525 | 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester ≥98%, powder | 64987-85-5 | 25MG | ₹12795.15 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M5525 | 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester ≥98%, powder | 64987-85-5 | 100MG | ₹36491.08 | 2022-06-14 | Buy |
| TCI Chemicals (India) | S0853 | N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate | 64987-85-5 | 100MG | ₹8700 | 2022-05-26 | Buy |
| TCI Chemicals (India) | S0853 | N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate | 64987-85-5 | 1G | ₹13700 | 2022-05-26 | Buy |
SMCC crosslinker Chemical Properties,Uses,Production
Description
SMCC crosslinker is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. SMCC crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then can be added to an aqueous crosslinking reaction. SMCC crosslinking reagent is permeable across the lipid bilayer of the cell membrane and can be used to crosslink intracellular proteins and peptides.
Chemical Properties
White Crystalline Solid
Uses
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(abTaIII)2 fragments to l-B-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms.
Definition
ChEBI: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate is an N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. It is a member of maleimides and a N-hydroxysuccinimide ester.
General Description
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is 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). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.
Chemical Reactivity
Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a non-cleavable and membrane permeable crosslinker. It contains an amine-reactive N -hydroxysuccinimide (NHS ester) and a sulfhydryl-reactive maleimide group. NHS esters react with primary amines at pH 7-9 to form stable amide bonds. Maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. The maleimide groups of SMCC and Sulfo-SMCC and are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm.
SMCC crosslinker Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Sisco Research Laboratories Pvt. Ltd. | +91-22-4268 5800 | Mumbai, India | 4317 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Jiangxi Huihe Chemical Co., Ltd. | +86-19189228086 +8618858568638 | China | 886 | 58 | Inquiry |
| Hongxiong | +undefined18915499068 | China | 120 | 58 | Inquiry |
| Hebei Zhuanglai Chemical Trading Co.,Ltd | +8613343047651 | China | 3002 | 58 | Inquiry |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | China | 32760 | 60 | Inquiry |