11-Maleimidoundecanoic acid

Base Information

• Chemical Name: 11-Maleimidoundecanoic acid
• CAS No.: 57079-01-3
• Molecular Formula: C15H23NO4
• Molecular Weight: 281.352
• Hs Code.: 2925190090
• UNII: LG78EY7HVB
• ChEMBL ID: CHEMBL298171
• DSSTox Substance ID: DTXSID50205689
• Nikkaji Number: J1.108.805H
• Wikidata: Q27282968
• Mol file: 57079-01-3.mol

Synonyms:11-Maleimidoundecanoic acid;57079-01-3;11-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)undecanoic acid;11-(2,5-dioxopyrrol-1-yl)undecanoic Acid;N-(10-Carboxydecyl)maleimide;AM-10;1H-Pyrrole-1-undecanoic acid, 2,5-dihydro-2,5-dioxo-;Maleimide-(CH2)10-COOH;LG78EY7HVB;CHEMBL298171;UNII-LG78EY7HVB;11-Maleimidoundecanoic?acid;SCHEMBL43882;MAL-(CH2)10-COOH;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-undecanoic Acid;DTXSID50205689;UVZTZBRGZXIBLZ-UHFFFAOYSA-N;AMY21531;11-Maleimidoundecanoic acid (KMUA);BDBM50471015;MFCD00941279;AKOS015893060;GS-5929;11-Maleimidoundecanoic acid, 95% (GC);HY-130908;CS-0116431;FT-0604077;H10004;A869766;Q27282968;11-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-undecanoic acid

Chemical Property of 11-Maleimidoundecanoic acid

Chemical Property:

• Vapor Pressure: 1.86E-09mmHg at 25°C
• Melting Point: 89-90 °C
• Refractive Index: 1.515
• Boiling Point: 452.8 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 227.6 °C
• PSA: 74.68000
• Density: 1.139 g/cm³
• LogP: 2.44480
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in methanol, and chloroform.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 358

Purity/Quality:

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

11-Maleimidoundecanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)N(C1=O)CCCCCCCCCCC(=O)O
• Uses: A sulfhydryl reactive heterobifunctional crosslinking reagent. Spacer Arm: 15.7 Angstroms The maleimide functional group can be used to conjugate a variety of biomolecules such as enzymes and DNA to the polymer chain.

Technology Process of 11-Maleimidoundecanoic acid

There total 5 articles about 11-Maleimidoundecanoic 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: 61.2%

N-(10-carboxy-n-decyl)maleamic acid → 11-(2,5-dioxopyrrol-1-yl)undecanoic acid (57079-01-3)

Guidance literature:

With tributyl-amine; 1-nitro-4-trifluoroacetoxy-benzene; In N,N-dimethyl-formamide; at -5 - -2 ℃; for 3h;

Reference yield: 58.0%

11-((Z)-3-Carboxy-acryloylamino)-undecanoic acid (57079-16-0) → 11-(2,5-dioxopyrrol-1-yl)undecanoic acid (57079-01-3)

Guidance literature:

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

DOI:10.1021/jm950872p

Reference yield: 45.0%

→ 11-(2,5-dioxopyrrol-1-yl)undecanoic acid (57079-01-3)

Guidance literature:

upstream raw materials:

11-((Z)-3-Carboxy-acryloylamino)-undecanoic acid

11-aminoundecanoic acid

11-(4-(2-carboxyethyl)-1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindol-2(3H)-yl)undecanoic acid

Downstream raw materials:

N-[10-((4-(((4'-n-hexyloxy)benzoyl)oxy)phenoxy)carbonyl)-n-decyl]maleimide

11-(maleimidyl)undecanoic acid succinimidyl ester

k-maleimidoundecanoic acid N-hydrazide

Refernces

• 1、 Schütz, Markus B.,Lê, Khan,Ilyas, Shaista,Mathur, Sanjay. "Reversible Covalent Assembly of Nanoparticles through On-Surface Diels-Alder Reaction". . p. 1552 - 1558. Retrieved 2020.
• 2、 De Ojeda, J. M. Bautista,Quijada-Garrido,Barrales-Rienda. "Synthesis, characterization and properties of N-maleimide side-chain liquid crystalline copolymers". . p. 495 - 510. Retrieved 2012/01/12.