8-(phenylamino)naphthalene-1-sulfonic acid amine

• ChemBase ID: 103021
• Molecular Formular: C16H16N2O3S
• Molecular Mass: 316.37484
• Monoisotopic Mass: 316.08816338
• SMILES: N.OS(=O)(=O)c1c2c(Nc3ccccc3)cccc2ccc1
• Canonical SMILES: OS(=O)(=O)c1cccc2c1c(ccc2)Nc1ccccc1.N
• InChI: InChI=1S/C16H13NO3S.H3N/c18-21(19,20)15-11-5-7-12-6-4-10-14(16(12)15)17-13-8-2-1-3-9-13;/h1-11,17H,(H,18,19,20);1H3
• InChIKey: IPBNQYLKHUNLQE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(phenylamino)naphthalene-1-sulfonic acid amine
• IUPAC Traditional name: phenyl-peri acid amine; ANS amine
• Synonyms: 1,8-ANS NH4; 8-Anilino-1-naphthalenesulfonic acid ammonium salt; 1,8-ANS NH₄; Ammonium 8-anilino-1-naphthalenesulfonate; ANSA; N-Phenyl peri acid; 8-ANILINO-1-NAPHTHALENE SULFONIC ACID AMMONIUM SALT; 8-苯胺基萘-1-磺酸; N-苯基周位酸; 8-苯氨基-1-萘磺酸 铵盐

Database IDs

• CAS Number: 28836-03-5
• EC Number: 249-265-6
• MDL Number: MFCD00012560
• Beilstein Number: 3581235
• PubChem SID: 162089801; 24846428
• PubChem CID: 12877595

CALCULATED PROPERTIES

• Acid pKa: -2.0288842
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2071737
• LogD (pH = 7.4): 1.2071565
• Log P: 2.1060174
• Molar Refractivity: 81.6169 cm^3
• Polarizability: 33.139984 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble; Do you have solubility information on this product that you would like to share?; H2O: soluble; methanol: soluble; NaOH: soluble1 N
• Melting Point: 242- 244°C
• Fluorescence: λex 388 nm; λem 470 nm in 0.1 M Tris, 0.2 M KCl, pH 9.0, BSA

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-36; S:20-25-26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ~95%; ≥90% (NT); ≥97.0% (HPLC)
• Grade: for fluorescence; technical
• Linear Formula: C16H13NO3S · NH3

DETAILS

MP Biomedicals - 02150380

Ammonium Salt
Purity: ~95%

Sigma Aldrich - 10417

Application
ANS forms an inclusion complex with cyclodextrin. Such model systems are useful to mimic biological recognition and can be studied by measuring the change in fluorescence of free-ANS to complexed-ANS. When ANS enters the hydrophobic core of cyclodestrin, it’s fluorescence increases 1,2. Utilized in the reagent phase of a sodium-selective fiber-optic sensor. The reagent phase also contains a copper(II) polyelectrolyte, which binds to ANSA in the absence of sodium and quenches the fluorescence. In the presence of sodium, ANSA forms a cationic complex creating ion-pairs, causing it to fluoresce 3. ANS is often incorporated into di-block polymers and can be released by changes in the local environment (i.e., temperature, pH, etc.) 4,5,6. ANS is commonly used as a fluorescence probe to investigate molecular assemblies of surfactants and amphiphilic polymers because a blue shift of the emission maximum indicates the fluorophore is located in less polar media 7,8. Fluorescent probe for protein studies using methodologies such as steady-state and dynamic fluorescence measurements 9,10.
This product is an amphiphilic fluorescent probe for protein studies . Excitation of the unbound dye at 380 nm results in a low fluorescent emission with a maximum at 545 nm. The fluorescence intensity of ANS increases when the dye binds to the hydrophobic regions of a protein . The protein-ANS complex has an emission spectrum which is shifted to a broad maximum at 470 nm. At pH 8, protein causes a 40-fold increase in the relative quantum yield compared to free ANS in solution . ANS has been used to monitor protein conformational changes by binding to the hydrophobic regions of a protein , to gain new insight into protein binding interactions, often by acting as reporter or competitor ligands9,10, to investigate the visual excitation process and structural aspects of photoreceptor cell membranes , and to probe (and disrupt) the structure of both high- and low-density lipoproteins. It has also been used as a substrate in a chemiluminescent enzyme immunoassay system and as a dye for yeast viability determination. The conformational states for apo- and holo- yeast alcohol dehydrogenase were reported under conditions of low pH using ANS fluorescence . ANS is also commonly used as a fluorescence probe to investigate molecular assemblies of surfactants and amphiphilic polymers because a blue shift of its emission maximum indicates the probe is located in less polar environment 7

Sigma Aldrich - 10416

Application
ANS forms an inclusion complex with cyclodextrin. Such model systems are useful to mimic biological recognition and can be studied by measuring the change in fluorescence of free-ANS to complexed-ANS. When ANS enters the hydrophobic core of cyclodestrin, it’s fluorescence increases 1,2. Utilized in the reagent phase of a sodium-selective fiber-optic sensor. The reagent phase also contains a copper(II) polyelectrolyte, which binds to ANSA in the absence of sodium and quenches the fluorescence. In the presence of sodium, ANSA forms a cationic complex creating ion-pairs, causing it to fluoresce 3. ANS is often incorporated into di-block polymers and can be released by changes in the local environment (i.e., temperature, pH, etc.) 4,5,6. ANS is commonly used as a fluorescence probe to investigate molecular assemblies of surfactants and amphiphilic polymers because a blue shift of the emission maximum indicates the fluorophore is located in less polar media 7,8. Fluorescent probe for protein studies using methodologies such as steady-state and dynamic fluorescence measurements 9,10.