6-Maleimidocaproic acid

Base Information

• Chemical Name: 6-Maleimidocaproic acid
• CAS No.: 55750-53-3
• Molecular Formula: C10H13 N O4
• Molecular Weight: 211.218
• Hs Code.: 29251900
• European Community (EC) Number: 611-311-1
• DSSTox Substance ID: DTXSID10876051
• Nikkaji Number: J685.630F
• Wikidata: Q72488095
• ChEMBL ID: CHEMBL47391
• Mol file: 55750-53-3.mol

Synonyms:6-Maleimidocaproic acid;55750-53-3;6-Maleimidohexanoic acid;6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid;1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-;6-Maleimidocapronic acid;6-(2,5-dioxopyrrol-1-yl)hexanoic acid;Maleimide-(CH2)5-COOH;N-(5-Carboxypentyl)maleimide;CHEMBL47391;N-Maleoyl-6-aminocaproic acid;MFCD00043140;6-Maleimidocaproicacid;N-maleoyl-6-aminohexanoic acid;Mal-(CH2)5-COOH;(EMCA);SCHEMBL43969;DTXSID10876051;CHEBI:176414;BCP12780;CS-M1809;N-(6-oxo-6-hydroxyhexyl)maleimide;BDBM50471014;6-Maleimidohexanoic acid, 90% (GC);AKOS000139285;GS-6853;AC-25055;BP-20415;HY-77959;SY030571;6-Maleimidohexanoic acid, >=98% (HPLC);A8047;AM20100367;FT-0604083;M2338;6-Maleimidohexanoic acid, >=98.0% (HPLC);A14037;EN300-395442;6-Maleimidohexanoic acid (6-Maleimidocaproic acid);J-518825;6-[2,5-Dioxo-2,5-dihydro-pyrrol-1-yl]hexanoic acid;Z245319376;6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid #;6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid

Chemical Property of 6-Maleimidocaproic acid

Chemical Property:

• Vapor Pressure: 8.97E-08mmHg at 25°C
• Melting Point: 86-91 ºC
• Refractive Index: 1.536
• Boiling Point: 407.3°C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 200.1°C
• PSA: 74.68000
• Density: 1.285g/cm³
• LogP: 0.49430
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Soluble in water, methanol, ethanol, dimethyl sulfoxide. Insoluble in ether.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 211.08445790
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

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

6-MaleimidocaproicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)N(C1=O)CCCCCC(=O)O
• Description: 6-Maleimidocaproic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.
• Uses: 6-Maleimidohexanoic acid is used as a probe for introducing maleimides groups into biomolecules and active pharmaceutical ingredients. Further, it is used with N-hydroxysuccinimide ester as a bifunctional cross-linking reagent. In addition to this, it acts as a probe for thiol groups in membrane proteins.

Technology Process of 6-Maleimidocaproic acid

There total 13 articles about 6-Maleimidocaproic acid 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: 80.0%

maleic anhydride (108-31-6) + 6-aminohexanoic acid (60-32-2,93208-38-9) → 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3)

Guidance literature:

With acetic acid; at 120 ℃;

Reference yield: 77.4%

succinic acid anhydride (108-30-5) + 6-aminohexanoic acid (60-32-2,93208-38-9) → 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3)

Guidance literature:

With acetic acid; at 20 ℃; for 10h; Time; Reflux;

Reference yield: 74.0%

6-(3-carboxyacryloylamino)caproic acid (57079-14-8) → 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3)

Guidance literature:

With sodium acetate; acetic anhydride; at 90 ℃; for 2h;

DOI:10.1039/b507096a

upstream raw materials:

6-(3-carboxyacryloylamino)caproic acid

6-aminohexanoic acid

maleic anhydride

C₁₀H₁₅NO₅

Downstream raw materials:

6-maleimidohexanoic acid N-hydroxylsuccinimide ester

C₅₀H₇₃N₇O₁₁S₂

C₅₅H₈₁N₇O₁₁S₂

tert-butyl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentylcarbamate

Refernces

• 1、 Wei tang,Chang, Yuan,Liu, Xin-Yuan. "Preparation of a New PEGylation Reagent for Sulfhydryl-containing Polypeptide". . p. 6515 - 6516. Retrieved 1994.
• 2、 Cai, Xingguang,Sun, Lidan,Dai, Yuxuan,Avraham, Yosefa,Liu, Chunxia,Han, Jing,Liu, Yuan,Feng, Dazhi,Huang, Wenlong,Qian, Hai. "Novel fatty acid chain modified GLP-1 derivatives with prolonged in vivo glucose-lowering ability and balanced glucoregulatory activity". . p. 2599 - 2609. Retrieved 2018.
• 3、 Xiao, Dian,Luo, Longlong,Li, Jiaguo,Wang, Zhihong,Liu, Lianqi,Xie, Fei,Feng, Jiannan,Zhou, Xinbo. "Development of bifunctional anti-PD-L1 antibody MMAE conjugate with cytotoxicity and immunostimulation". . . Retrieved 2021/09/27.
• 4、 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.