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SMCC crosslinker

SMCC crosslinker structure

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%;SMCC[573114];25MG/100MG/10G

CBNumber:: CB6748487

Molecular Formula:: C16H18N2O6

Molecular Weight:: 334.32

MDL Number:: MFCD00009634

MOL File:: 64987-85-5.mol

MSDS File:: SDS

Last updated:2025-10-09 14:55:14

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SMCC crosslinker Properties

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)
FDA UNII	B357P1G1IF
UNSPSC Code	41116133
NACRES	NC.07

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

Risk Statements

36/37/38

Safety Statements

26-36-60-37

WGK Germany

10-21

HS Code

29280000

NFPA 704

	1
2		0

SMCC crosslinker price More Price(40)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	M5525	4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester ≥98%, powder	64987-85-5	5mg	$38.8	2025-07-31	Buy
Sigma-Aldrich	573114	4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester	64987-85-5	100mg	$292	2025-07-31	Buy
TCI Chemical	S0853	N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate >98.0%(HPLC)	64987-85-5	100mg	$88	2025-07-31	Buy
TCI Chemical	U0143	N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate (2mg×5)	64987-85-5	1SET	$163	2025-07-31	Buy
TCI Chemical	S0853	N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate	64987-85-5	5G	$768	2025-07-31	Buy

Product number	Packaging	Price	Buy
M5525	5mg	$38.8	Buy
573114	100mg	$292	Buy
S0853	100mg	$88	Buy
U0143	1SET	$163	Buy
S0853	5G	$768	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.

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 synthesis

Synthesis of SMCC crosslinker from N-Hydroxysuccinimide

SMCC crosslinker Preparation Products And Raw materials

Raw materials

Preparation Products

Doxorubicin-SMCC

SMCC crosslinker Suppliers

Global( 330)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Suzhou Highfine Biotech Co.,Ltd.	+86-0512-68071238 +86-13771819922	june@highfine.com	China	458	58
Jiangxi Huihe Chemical Co., Ltd.	+86-19189228086 +8618858568638	wuzhouding@huihecrop.com	China	886	58
Hongxiong	+undefined18915499068	Suzhouhongxiong@163.com	China	120	58
Wuhan Fortuna Chemical Co., Ltd	+86-027-59207850 +86-13986145403;	info@fortunachem.com	China	5987	58
Hebei Zhuanglai Chemical Trading Co.,Ltd	+8613343047651	admin@zlchemi.com	China	3692	58
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	33024	60
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29852	58
SHANDONG ZHI SHANG CHEMICAL CO.LTD	+86 18953170293	sales@sdzschem.com	China	2930	58
Jinan Carbotang Biotech Co.,Ltd.	+8615866703830	figo.gao@foxmail.com	China	8497	58
Jinan Finer Chemical Co., Ltd	+86-531-88989536 +86-15508631887	sales@finerchem.com	China	2953	58

Supplier	Advantage
Suzhou Highfine Biotech Co.,Ltd.	58
Jiangxi Huihe Chemical Co., Ltd.	58
Hongxiong	58
Wuhan Fortuna Chemical Co., Ltd	58
Hebei Zhuanglai Chemical Trading Co.,Ltd	58
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
SHANDONG ZHI SHANG CHEMICAL CO.LTD	58
Jinan Carbotang Biotech Co.,Ltd.	58
Jinan Finer Chemical Co., Ltd	58

View Lastest Price from SMCC crosslinker manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2025-10-09	N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate 64987-85-5	US $0.00-0.00 / KG	1KG	99.8%	100kg	WUHAN FORTUNA CHEMICAL CO., LTD
2025-10-09	SMCC 64987-85-5	US $30.00-85.00 / mg		99.53%	10g	TargetMol Chemicals Inc.
2025-04-15	N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate 64987-85-5	US $10.00 / kg	1kg	99%	20ton	Hebei Zhuanglai Chemical Trading Co.,Ltd

N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate
64987-85-5
US $0.00-0.00 / KG
99.8%
WUHAN FORTUNA CHEMICAL CO., LTD

SMCC
64987-85-5
US $30.00-85.00 / mg
99.53%
TargetMol Chemicals Inc.

N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
64987-85-5
US $10.00 / kg
99%
Hebei Zhuanglai Chemical Trading Co.,Ltd

SMCC crosslinker Spectrum

SMCC crosslinker(64987-85-5)¹HNMR SMCC crosslinker(64987-85-5)IR

64987-85-5(SMCC crosslinker)Related Search:

Bismaleimide N-Chlorosuccinimide Succinimide Methyl acrylate RESMETHRIN

Tris(trimethylsilyl)phosphate Cyclohexane Cyclohexanecarboxylic acid O-Phthalimide Alendronic acid

Phosphonic acid, P,P'-[4-[[[4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]cyclohexyl]carbonyl]amino]-1-hydroxybutylidene]bis- Tranexamic Acid 6-Aminocaproic acid N-ETHYL ACRYLAMIDE DIALIFOS

Maleimide Methylcyclohexane Acetohydroxamic acid

1of4

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 N-Succinimidyl 4-(N-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 > 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 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester N-(4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylicacidsuccinimideester SMCC[573114]