Smcc

Base Information

• Chemical Name: Smcc
• CAS No.: 64987-85-5
• Molecular Formula: C16H18N2O6
• Molecular Weight: 334.329
• Hs Code.: 29280000
• European Community (EC) Number: 613-734-7,694-914-2
• NSC Number: 344483
• UNII: B357P1G1IF
• DSSTox Substance ID: DTXSID30215307
• Nikkaji Number: J416.284F,J555.938C
• Wikipedia: Succinimidyl_4-(N-maleimidomethyl)cyclohexane-1-carboxylate
• Wikidata: Q27132436,Q27274295
• RXCUI: 1426703
• Metabolomics Workbench ID: 62644
• Mol file: 64987-85-5.mol

Synonyms:N-(4-carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester;N-hydroxysuccinimidyl 4-(N-maleimidomethylcyclohexane)-1-carboxylate;N-SMC-carboxylate;N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid;SMCC compound

Chemical Property of Smcc

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 3.38E-10mmHg at 25°C
• Melting Point: 180-182 °C(lit.)
• Refractive Index: 1.598
• Boiling Point: 501.7 °C at 760 mmHg
• PKA: -2.24±0.20(Predicted)
• Flash Point: 257.2 °C
• PSA: 101.06000
• Density: 1.42 g/cm³
• LogP: 0.20080
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: chloroform: 50 mg/mL
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 334.11648630
• Heavy Atom Count: 24
• Complexity: 599

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Succinimidyl4-(Maleimidomethyl)cyclohexane-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-60-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CCC3=O
• Description: SMCC is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules.
• Uses: A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab’)2 fragments to ?-galactosidase. Conjugates hIgG to alkaline phosphatase. Spacer Arm: 11.6 Angstroms A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab’)2 fragments to ?-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms

Technology Process of Smcc

There total 5 articles about Smcc which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

maleic anhydride (108-31-6) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-aminomethyl-cyclohexanecarboxylic acid (1197-17-7,1197-18-8,701-54-2) → 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester (64987-85-5)

Guidance literature:

maleic anhydride; 4-aminomethyl-cyclohexanecarboxylic acid; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

1-hydroxy-pyrrolidine-2,5-dione; With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.3390/molecules25010229

Reference yield: 71.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid (64987-82-2) → 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester (64987-85-5)

Guidance literature:

With 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2021.113297

Reference yield:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) → 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester (64987-85-5)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1002/jps.2600750720

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

maleic anhydride

4-aminomethyl-cyclohexanecarboxylic acid

4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid

Downstream raw materials:

4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl-methyl)-cyclohexanecarboxylic acid [5-(6-chloro-2-methoxy-acridin-9-ylamino)-pentyl]-amide

Refernces

• 1、 Hu, Xinyue,Jiang, Hailun,Bai, Weiqi,Liu, Xiujun,Miao, Qingfang,Wang, Linlin,Jin, Jie,Cui, Along,Liu, Rui,Li, Zhuorong. "Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates". supporting information. . Retrieved 2021/03/08.