c.i. azoic coupling component 10
Naphthol AS-E
CAS: 92-78-4
Molecular Formula: C17H12ClNO2
c.i. azoic coupling component 10 - Names and Identifiers
| Name | Naphthol AS-E |
| Synonyms | C.I. 37510 NAPTHOL AS-E NAPHTHOL AS-E Naphthol AS-E AcnaNaphtholPC DaitoGrounderE AZOIC COUPLING COMPONENT 10 C.I.Azoic Coupling Component 10 c.i. azoic coupling component 10 C.I. Azoic Coupling Component 10 4'-CHLORO-3-HYDROXY-2-NAPHTHANILIDE 2-Hydroxy-3-Naphthoyl-p-Chloraniline N-(4-CHLOROPHENYL)-3-HYDROXY-2-NAPHTHAMIDE N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide 2-Naphthalenecarboxamide, N-(4-chlorophenyl)-3-hydroxy- |
| CAS | 92-78-4 |
| EINECS | 202-189-7 |
| InChI | InChI=1/C17H12ClNO2/c18-13-5-7-14(8-6-13)19-17(21)15-9-11-3-1-2-4-12(11)10-16(15)20/h1-10,20H,(H,19,21) |
c.i. azoic coupling component 10 - Physico-chemical Properties
| Molecular Formula | C17H12ClNO2 |
| Molar Mass | 297.74 |
| Density | 1.399±0.06 g/cm3(Predicted) |
| Melting Point | 255°C |
| Boling Point | 416.5±30.0 °C(Predicted) |
| Flash Point | 205.7°C |
| Solubility | soluble in Dimethylformamide |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | Beige solid |
| Color | White to Light yellow to Dark green |
| pKa | 8.69±0.40(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.735 |
| Physical and Chemical Properties | Properties light beige powder. melting point 258~259 ℃ solubility: soluble in O-dichlorobenzene. Dissolved in caustic soda solution was yellow. Insoluble in water and soda ash solution. |
| Use | It is used as a priming agent for cotton fiber dyeing and printing, and can also be used as an intermediate for lake pigments |
| In vitro study | CREB (cyclic AMP-response element-binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors.CREB can not be activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through the kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP.In a cell-based CREB Renilla luciferase reporter assay, Naphthol AS-Einhibits CREB-mediated gene transcription with an IC 50 of 2.29 µM. In HEK293T-based complementation assay, Naphthol AS-Edose-dependently inhibited Renilla luciferase activity with an IC 50 of 2.9 µM by directly binding to CBP's KIX domain (K d ~8.6 µM using a recombinant KIX).Naphthol AS-Eexhibits low µM activity in inhibiting the proliferation of all these cancer cells, which is consistent with its cellular CREB inhibition potency. The average GI 50 values for A549, MCF-7, MDA-MB-231 and MDA-MB-468 are approximately2.9µM, 2.81µM, 2.35µM and 1.46µM, respectively.Naphthol AS-E (2.5 µM-10 µM; 48 hours) decreases the expression of anti-apoptotic protein Bcl-2. The expression of VEGF is also decreased. |
c.i. azoic coupling component 10 - Reference Information
| Color index | 37510 |
| LogP | 2.97 at 23℃ and pH7.2 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| biological activity | Naphthol AS-E is a potent, KIX-KID interacting inhibitor of cell permeability. Naphthol AS-E directly binds to the KIX domain of CBP (Kd: 8.6 μm), blocking the interaction of the KIX domain and the kiddomain (IC50: 2.26 μm). Naphthol AS-E is available for cancer research. |
| Use | as a priming agent for dyeing and printing of cotton fibers, also can be used as an intermediate of lake pigment phenol AS-E is mainly used for cotton dyeing, also used for dyeing viscose fiber, silk, generally not used for printing, often with blue base or Blue salt with dark blue and blue dye. It is also used in the manufacture of lake pigments. |
| production method | with 2,3-acid and p-chloroaniline as raw materials, with chlorobenzene as solvent. The 2, 3-acid is first made into a sodium salt and then condensed with P-chloroaniline in the presence of PCl3, neutralized, distilled, filtered and dried to a finished product.. |
Last Update：2024-04-09 21:54:55
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