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64987-85-5 molecular structure
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2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate

ChemBase ID: 104274
Molecular Formular: C16H18N2O6
Molecular Mass: 334.32392
Monoisotopic Mass: 334.11648631
SMILES and InChIs

SMILES:
O=C1CCC(=O)N1OC(=O)C1CCC(CC1)CN1C(=O)C=CC1=O
Canonical SMILES:
O=C(C1CCC(CC1)CN1C(=O)C=CC1=O)ON1C(=O)CCC1=O
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

Cite this record

CBID:104274 http://www.chembase.cn/molecule-104274.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate
IUPAC Traditional name
2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate
SMCC
Synonyms
4-(Maleimidomethyl)cyclohexane-1-carboxylic acid N-hydroxysuccinimide ester
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate
Succinimidyl 4-[N-maleimidomethyl]-cyclohexane-1-carboxylate
4-(N-MALEIMIDOMETHYL)-CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
SMCC
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate
4-(N-Maleimidomethyl)cyclohexane-1-carboxylic Acid N-Hydroxysuccinimide Ester
NSC 344483
N-Succinimidyl 4-(Maleimidomethyl)cyclohexane-1-carboxylate
N-琥珀酰亚胺基4-(马来酰亚胺基甲基)环己烷羧酸酯
4-(N-马来酰亚胺基甲基)环己烷-1-羧酸琥珀酰亚胺酯
CAS Number
64987-85-5
MDL Number
MFCD00009634
Beilstein Number
1555271
PubChem SID
162091875
24897020
24882450
PubChem CID
125175

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 17.70829  H Acceptors
H Donor LogD (pH = 5.5) 0.2943863 
LogD (pH = 7.4) 0.2943863  Log P 0.2943863 
Molar Refractivity 80.7868 cm3 Polarizability 31.288792 Å3
Polar Surface Area 101.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
chloroform: soluble50 mg/mL expand Show data source
Dichloromethane expand Show data source
DMF: soluble expand Show data source
Ethyl Acetate expand Show data source
Apperance
powder expand Show data source
White Crystalline Solid expand Show data source
Melting Point
175-180 °C expand Show data source
179°C expand Show data source
180-182 °C(lit.) expand Show data source
180-182°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
2-8°C, Desiccate expand Show data source
Storage Warning
Moisture & Light Sensitive expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
~95% (HPLC) expand Show data source
≥98% expand Show data source
98% expand Show data source
98+% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C16H18N2O6 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02155309 external link
(Succinimidyl 4-[N-maleimidomethyl]-cyclohexane-1-carboxylate) Crystalline
Sigma Aldrich - M5525 external link
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.
Sigma Aldrich - 63181 external link
Other Notes
Derivatization of monoclonal antibodies with SMCC and conjugation with oligonucleotide for 2-step radioimmunotherapy1
Toronto Research Chemicals - S690400 external link
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab')2 fragments to Δ-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Yoshitake, S., et al., J. Biochem., 92: 1413, (1982)
  • • Maham, D.G., et al.: Anal. Biochem., 162, 163 (1987)
  • • Yoshitake, S., et al.: Eur. J. Biochem., 101, 395 (1987)
  • • Freytag, J.W., et al.: Clin. Chem., 30(1987)
  • • 1494 (1987)
  • • Mahan, D.E., et al.: Anal. Biochem., 162, 163 (1987)
  • • Peeters, J.M., et al.: J. Immunol
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PATENTS

PATENTS

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INTERNET

INTERNET

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