6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid

• ChemBase ID: 69304
• Molecular Formular: C10H13NO4
• Molecular Mass: 211.21452
• Monoisotopic Mass: 211.0844579
• SMILES: C(=O)(CCCCCN1C(=O)C=CC1=O)O
• Canonical SMILES: OC(=O)CCCCCN1C(=O)C=CC1=O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid
• IUPAC Traditional name: N-maleoyl-6-aminohexanoic acid
• Synonyms: 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic Acid; 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic Acid; 6-Maleimidohexanoic Acid; N-(5-Carboxy-n-pentyl)maleimide; ε-Maleimidocaproic Acid; ε-Maleimidohexanoic Acid; EMCA; 6-Maleimidocaproic Acid; 6-Maleimidohexanoic acid; ε-MALEIMIDOCAPROIC ACID; 6-Maleimidocaproic acid; N-Maleoyl-6-aminocaproic acid; N-(5-Carboxypentyl)maleimide; 6-Maleimidohexanoic acid

Database IDs

• CAS Number: 55750-53-3
• MDL Number: MFCD00043140
• Beilstein Number: 1532405
• PubChem SID: 24882443; 162035031
• PubChem CID: 573683

CALCULATED PROPERTIES

• Acid pKa: 4.269142
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7729127
• LogD (pH = 7.4): -2.5046744
• Log P: 0.48056772
• Molar Refractivity: 52.9891 cm^3
• Polarizability: 20.07729 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 86-91 °C; 87-89°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC); 95+%; 98%
• Empirical Formula (Hill Notation): C10H13NO4

DETAILS

MP Biomedicals - 02155308

Purity: 98% min. Probe for thiol groups in membrane proteins

Sigma Aldrich - M8904

Application

• Probe for thiol groups (SH-groups) in membrane proteins

Sigma Aldrich - 63176

Application

• Probe for thiol groups (SH-groups) in membrane proteins

Toronto Research Chemicals - M137950

A sulfhydryl reactive heterobifunctional crosslinking reagent. Widely used probe for introducing maleimides groups into biomolecules. A probe for thiol groups in proteins.Spacer Arm: 9.4 Angstroms

REFERENCES

• Griffith, D.G., et al., FEBS Left., 134: 261, (1981).
• Griffith, D.G., et al.: FEBS Lett., 134, 261 (1981)