N-Succinimidyl 6-maleimidohexanoate
- Product Name
- N-Succinimidyl 6-maleimidohexanoate
- CAS No.
- 55750-63-5
- Chemical Name
- N-Succinimidyl 6-maleimidohexanoate
- Synonyms
- 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate;EMCS;MCOSU;6-maleimidohexanoic acid N-hydroxylsuccinimide ester;6-MALEIMIDOCAPROIC ACID N-SUCCINIMIDYL ESTER;6-Maleimidohexanoic acid N-hydroxysuccinimide ester;(2,5-Dioxopyrrolidin-1-yl) 6-(2,5-dioxopyrrol-1-yl)hexanoate;EMCS Crosslinker;maleimide-(CH2)5-NHS;NHS-(CH2)5-Mal (EMCS)
- CBNumber
- CB8212960
- Molecular Formula
- C14H16N2O6
- Formula Weight
- 308.29
- MOL File
- 55750-63-5.mol
N-Succinimidyl 6-maleimidohexanoate Property
- Melting point:
- 70-73 °C(lit.)
- Boiling point:
- 480.6±47.0 °C(Predicted)
- Density
- 1.40±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- chloroform: 100mg/mL
- form
- powder
- pka
- -2.21±0.20(Predicted)
- color
- Off-white to pale brown
- Sensitive
- Light & Moisture Sensitive & Hygroscopic
- BRN
- 1499815
- InChI
- InChI=1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2
- InChIKey
- VLARLSIGSPVYHX-UHFFFAOYSA-N
- SMILES
- N1(CCCCCC(ON2C(=O)CCC2=O)=O)C(=O)C=CC1=O
- CAS DataBase Reference
- 55750-63-5(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36/37/38-40
- Safety Statements
- 26-36/37-36
- WGK Germany
- 3
- F
- 8-10-21
- HS Code
- 29280000
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.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 63177
- Product name
- 6-Maleimidohexanoic acid N-hydroxysuccinimide ester
- Purity
- ≥98.0% (HPLC)
- Packaging
- 25mg
- Price
- $227
- Updated
- 2025/07/31
- Product number
- 568600
- Product name
- 6-Maleimidohexanoic acid N-hydroxysuccinimide ester
- Purity
- 98%
- Packaging
- 500mg
- Price
- $597.55
- Updated
- 2025/07/31
- Product number
- S0428
- Product name
- N-Succinimidyl 6-Maleimidohexanoate [Cross-linking Reagent]
- Purity
- >98.0%(N)
- Packaging
- 1g
- Price
- $98
- Updated
- 2025/07/31
- Product number
- M9794
- Product name
- 6-Maleimidohexanoic acid N-hydroxysuccinimide ester
- Purity
- ≥98%, powder
- Packaging
- 10mg
- Price
- $144
- Updated
- 2025/07/31
- Product number
- M9794
- Product name
- 6-Maleimidohexanoic acid N-hydroxysuccinimide ester
- Purity
- ≥98%, powder
- Packaging
- 25mg
- Price
- $227
- Updated
- 2025/07/31
N-Succinimidyl 6-maleimidohexanoate Chemical Properties,Usage,Production
Description
Mal-heptanoic NHS ester contains a maleimide group and an NHS ester. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.
Chemical Properties
White to cream colored crystals
Uses
6-Maleimidohexanoic acid N-hydroxysuccinimide ester can be used in:
- Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.
- Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.
- Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.
reaction suitability
reagent type: linker
Synthesis
6066-82-6
55750-53-3
55750-63-5
Under nitrogen protection, 4.7 g (22 mmol) of 6-maleimidohexanoic acid (MC) and 25 g (22 mmol) of N-hydroxybutanediimide (HOSu) were dissolved in 50 ml of acetonitrile. Another 4.5 g (22 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was dissolved in 25 ml of acetonitrile and the internal temperature was maintained. The DCC solution was slowly added dropwise to the reaction mixture at 0°C. The reaction mixture was stirred at 0 °C for 2 h. The reaction was then brought to room temperature and continued overnight. After completion of the reaction, the precipitate was removed by filtration and the filter cake was washed with acetonitrile (10 ml x 3). The filtrates were combined and concentrated to dryness under reduced pressure. The resulting oily product was dried under reduced pressure for 6 h at room temperature to give 6.4 g of a light brown solid, i.e., succinimidyl 6-(maleimido)hexanoate, in 95% yield.
IC 50
Non-cleavable Linker
References
[1] Patent: CN107789630, 2018, A. Location in patent: Paragraph 0064; 0065; 0066
[2] Patent: WO2018/178060, 2018, A1. Location in patent: Page/Page column 58; 60; 61
[3] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[4] Patent: WO2015/95953, 2015, A1. Location in patent: Page/Page column 118
[5] Patent: WO2016/41082, 2016, A1. Location in patent: Page/Page column 97; 98
N-Succinimidyl 6-maleimidohexanoate Preparation Products And Raw materials
Raw materials
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View Lastest Price from N-Succinimidyl 6-maleimidohexanoate manufacturers
- Product
- N-Succinimidyl 6-maleimidohexanoate 55750-63-5
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-13
- Product
- N-Succinimidyl 6-maleimidohexanoate 55750-63-5
- 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
- Product
- N-Succinimidyl 6-maleimidohexanoate 55750-63-5
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-08