trisodium 8-(acetyloxy)pyrene-1,3,6-trisulfonate

• ChemBase ID: 156687
• Molecular Formular: C18H9Na3O11S3
• Molecular Mass: 566.42177
• Monoisotopic Mass: 565.90000695
• SMILES: CC(=O)Oc1cc(c2ccc3c(cc(c4c3c2c1cc4)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: CC(=O)Oc1cc(c2c3c1ccc1c3c(cc2)c(cc1S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C18H12O11S3.3Na/c1-8(19)29-13-6-14(30(20,21)22)10-4-5-12-16(32(26,27)28)7-15(31(23,24)25)11-3-2-9(13)17(10)18(11)12;;;/h2-7H,1H3,(H,20,21,22)(H,23,24,25)(H,26,27,28);;;/q;3*+1/p-3
• InChIKey: AVWTVIHOBLSYNA-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium 8-(acetyloxy)pyrene-1,3,6-trisulfonate
• IUPAC Traditional name: trisodium 8-(acetyloxy)pyrene-1,3,6-trisulfonate
• Synonyms: 1-Acetoxypyrene-3,6,8-trisulfonic acid trisodium salt; Trisodium-8-acetoxypyrene-1,3,6-trisulfonate; 8-Acetoxypyrene-1,3,6-trisulfonic acid trisodium salt

Database IDs

• CAS Number: 115787-83-2
• MDL Number: MFCD00135685
• Beilstein Number: 9538267
• PubChem SID: 24845099; 162250824
• PubChem CID: 13931984

CALCULATED PROPERTIES

• Acid pKa: -2.845918
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): -5.6952815
• LogD (pH = 7.4): -5.6952877
• Log P: 1.4339086
• Molar Refractivity: 106.3574 cm^3
• Polarizability: 47.401028 Å^3
• Polar Surface Area: 197.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble; methanol: soluble
• Melting Point: 238-248 °C (dec.)(lit.)
• Fluorescence: λex 460 nm; λem 510 nm in 0.1 M potassium phosphate pH 8.0 (esterase)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C18H9Na3O11S3

DETAILS

Sigma Aldrich - 00879

Application
suitable as fluorogenic substrate for esterases
A membrane permeable, nonfluorescent reagent 1. This fluorochrome enters the cell cytoplasm, where its acetic group is cleaved by intracellular, nonspecific esterases, which forms the impermeable, fluorescent form of the molecule1. Utilized as a phloem-mobile symplasmic tracer having staining characteristics that differ from the commonly used CFDA (5-(6-)carboxyfluorescein diacetate)1,2,3,4,5.
Other Notes
Highly water soluble enzyme substrate for the fluorimetric assay of esterases at longwave excitation and emission wavelengths6