CAS 55750-53-3 6-Maleimidohexanoic acid (HCID 573683)

Substructure search Find similar structures

Basic information

CAS: 55750-53-3
Standard SMILES: O=C(O)CCCCCN1C(=O)C=CC1=O
InChIKey: WOJKKJKETHYEAC-UHFFFAOYSA-N
Molecular formula: C10H13NO4
Average molar mass: 211.21 g/mol
Monoisotopic mass: 211.0844579

Names & identifiers

Preferred name: 6-Maleimidohexanoic acid
IUPAC: 6-(2,5-dioxopyrrol-1-yl)hexanoic acid
English name: 6-Maleimidocaproic acid
Molecular formula: C10H13NO4
Molecular weight: 211.21

Names & synonyms

6-Maleimidocaproic acid6-Maleimidohexanoic acidRefChem:543501611-311-155750-53-36-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid6-Maleimidocapronic acid1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-6-(2,5-dioxopyrrol-1-yl)hexanoic acidMFCD00043140Maleimide-(CH2)5-COOHN-(5-Carboxypentyl)maleimide

Show more names

EMCA6-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)hexanoic acidMalHex6-MaleimidocaproicAciMal-(CH2)5-COOH (EMCA)

N-Maleoyl-6-aminocaproic acidSCHEMBL43969CHEMBL47391CS-M1809N-(6-oxo-6-hydroxyhexyl)maleimideBP-20415PD127389SY030571

Database identifiers

CAS: 55750-53-3
PubChem CID: 573683
DTXSID: DTXSID10876051
ChEMBL: CHEMBL47391
ChEBI: CHEBI:176414
EC Number: 611-311-1
Nikkaji: J685.630F

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 74.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 6
Heavy atoms: 15
Formal charge: 0
Complexity: 291

Physicochemical properties

Melting point: 86 · 86-91 °C
Boiling point: 407.3 · 407.3±28.0 °C(Predicted)
Density: 1.285 · 1.285±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
form: Powder
pka: 4.74 · 4.74±0.10(Predicted)
color: White to pale yellow
Water Solubility: Soluble in water, methanol, ethanol, dimethyl sulfoxide. Insoluble in ether.
Sensitive: Moisture Sensitive
BRN: 1532405 · 1532405
InChI: InChI=1S/C10H13NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h5-6H,1-4,7H2,(H,14,15)
InChIKey: WOJKKJKETHYEAC-UHFFFAOYSA-N
SMILES: N1(CCCCCC(O)=O)C(=O)C=CC1=O
CAS DataBase Reference: 55750 · 55750-53-3(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (73.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (98.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 56 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Dam. 1 (73.2%)；Eye Irrit. 2 (25%)；STOT SE 3 (98.2%)

Safety data

F: 10-21
wgk: 3
hs_code: 29251900
risk_code: 36/37/38-41-37/38
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: Xi
safety_code: 26-36-39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system

Chemistry & industry

Applications · 2 items

Description6-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.

Uses6-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.