ChemicalBook > CAS DataBase List > SMCC crosslinker

SMCC crosslinker

Product Name
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;SMCC, 10 mM in DMSO
CBNumber
CB6748487
Molecular Formula
C16H18N2O6
Formula Weight
334.32
MOL File
64987-85-5.mol
More
Less

SMCC crosslinker Property

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)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-60-37
WGK Germany 
3
10-21
HS Code 
29280000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M5525
Product name
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
Purity
≥98%, powder
Packaging
5mg
Price
$37.7
Updated
2024/03/01
Sigma-Aldrich
Product number
573114
Product name
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
Packaging
100mg
Price
$270
Updated
2024/03/01
TCI Chemical
Product number
S0853
Product name
N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$88
Updated
2024/03/01
TCI Chemical
Product number
S0853
Product name
N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate
Purity
>98.0%(HPLC)
Packaging
1g
Price
$283
Updated
2024/03/01
Alfa Aesar
Product number
H54627
Product name
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, 98+%
Packaging
100mg
Price
$179
Updated
2021/12/16
More
Less

SMCC crosslinker Chemical Properties,Usage,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.

reaction suitability

reagent type: linker

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

Raw materials

Preparation Products

More
Less

SMCC crosslinker Suppliers

Suzhou Highfine Biotech Co., Ltd
Tel
0512-68311833 13962195826
Fax
0512-68417696
Email
wuhao@highfine.com
Country
China
ProdList
499
Advantage
75
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
Advantage
60
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
More
Less

View Lastest Price from SMCC crosslinker manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate 64987-85-5
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-24
Henan Aochuang Chemical Co.,Ltd.
Product
N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate 64987-85-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-26
Zhuozhou Wenxi import and Export Co., Ltd
Product
N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate 64987-85-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

64987-85-5, SMCC crosslinkerRelated Search:


  • N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC
  • SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester]
  • trans-4-(Maleimidomethyl)-cyclohexane carboxylic acid-NHS ester
  • N-SucciniMidyl 4-(N-MaleiMidoMethyl)cyclohexanecarboxylate
  • 4-(N-MaleiMidoMethyl)cyclohexane-1-carboxylic acid N-hydroxysucciniMide ester, 98+%
  • NSC 344483
  • 4-(N-Maleimidomethyl)cyclohexanecarboxylic Acid N-Succinimidyl Ester SMCC
  • 25MG/100MG/10G
  • 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)Methyl)cyclohexanecarboxylate
  • SMCC N-SucciniMidyl 4-(N-MaleiMidoMethyl)cyclohexane-1-carboxylate
  • N-SucciniMidyl 4-(MaleiMidoMethyl)cyclohexane-1-carboxylate(SMCC)
  • 4-(MaleiMidoMethyl)cyclohexane-1-carboxylic acid N-hydroxysucciniMide ester, 98+%
  • N-SucciniMidyl 4-(N-MaleiMi
  • SucciniMidyl-4-(N-MaleiMidoMethyl)cyclohexane-1-carboxylate (SMCC)
  • SMCC Crosslinker
  • N-SucciniMidyl 4-(N-MaleiMidoMethyl)cyclohexanecarboxylate , 98.0%(LC)
  • N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-
  • N-Succinimidyl 4-(N-maleimidomethyl)cycl
  • 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester
  • LKA
  • <i>N</i>-Succinimidyl 4-(<i>N</i>-Maleimidomethyl)cyclohexanecarboxylate
  • 4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-*
  • 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylat
  • n-(4-carboxycyclohexylmethyl)maleimiden-hydroxysuccinimideester
  • SMCC
  • SUCCINIMIDYL TRANS-4-(MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
  • SUCCINIMIDYL-TRANS-4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
  • SUCCINIMIDYL-TRANS-4-(N-MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
  • SUCCINIMIDYL 4-[N-MALEIMIDO-METHYL]CYCLOHEXANE-1-CARBOXYLATE
  • N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
  • N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLATE
  • TRANS-4-(N-MALEIMIDYLMETHYL)-CYCLO-HEXANE-1-CARBOXYLATE-N-HYDROXYSUCCINIMIDE ESTER
  • 4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
  • 4-(N-MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
  • N-succinimidyl 4-(maleimidome.)cyclo-hexanecarboxylate
  • 4-(N-MALEIMIDOMETHYL)-CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER CRYSTALLINE
  • N-Succinimidyl-4-(N-maleimidomethyl)-cyclohexane-1-carboxylate
  • 4-(Maleimidomethyl)cyclohexane-1-carboxylic acid N-hydroxysuccinimide ester
  • trans-4-(Maleimidomethyl)-cyclohexane carboxylic
  • 4-(maleimidomethyl)-1-cyclohexanecarboxylic acid N-hydroxy
  • SMCC [4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester] *CAS 64987-85-5*
  • N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate &gt
  • Cyclohexanecarboxylic acid, 4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]-, 2,5-dioxo-1-pyrrolidinyl ester
  • Succinimidyl 4-(N-maleimidomethyl)cyclohexanecarboxylate
  • N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate (2mg*5)
  • 2,5-Dioxopyrrolidin-1-yl 4-[(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate
  • 4-(N-Maleimidomethyl)cyclohexanecarboxylic Acid N-Succinimidyl Ester
  • R3-RM1
  • Succinimidyl-4-(N- (N-maleimidomethyl) cyclohexane-1-carboxylate (SMCC), 98%
  • (2,5-dioxopyrrolidin-1-yl) 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate
  • SMCC,98%
  • 4-(N-maleimidyl methyl) cyclohexane-1-carboxylic acid succinimide ester
  • N-Succinimidyl-4-[2-(4,4-Dimethoxytrityl)]Butyrate
  • SMCC, heterobifunctional cross-linker
  • SMCC, 10 mM in DMSO
  • 64987-85-5
  • C16H18N2O6
  • BioChemical