Xylenol orange

Catalog NumberHG1611354

CAS Number1611-35-4

CategoryAmphoteric Surfactants

Synonyms

glycine,n,n'-[3h-2,1-benzoxathiol-3-ylidenebis[(6-hydroxy-5-methyl-3,1-phenyle; ne)methylene]]bis[n-(carboxymethyl)-,s,s-dioxide

Molecular Weight

672.66

Molecular Formula

C31H32N2O13S

Appearance

Solid

Application

Use as indicator.

Active Content

95%

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Case Study

Xylenol Orange Dye Doping Enhances NLO, Piezoelectric and Mechanical Properties of ADP Single Crystals

Goel, Sahil, et al. Arabian Journal of Chemistry 13.1 (2020): 146-159.

Xylenol orange (XO; C₃₁H₃₂N₂O₁₃S), a water-soluble triphenylmethane dye, was used to dope ammonium dihydrogen phosphate (ADP; NH₄H₂PO₄) single crystals to improve their nonlinear optical (NLO) performance.
Experimental Protocol: Pure and XO-doped (0.01, 0.05 and 0.1 mol%, labelled XADP-1/2/3) ADP crystals were grown by slow evaporation from 25 g ADP in 50 mL double-distilled water at 35 °C. Characterization used powder XRD, FTIR (400-4000 cm^-1), UV-vis-NIR (200-1100 nm), photoluminescence (λ_exc = 350 nm), TG/DTA, the piezoelectric charge coefficient d₃₃ (PM-300, 0.25 N at 110 Hz), Kurtz-powder SHG (Nd:YAG, 1054 nm) and Vickers microhardness.
Performance Evaluation: XO selectively stained the {100} growth sectors of ADP, confirmed by fluorescence and an orange emission at 597 nm. Doping lowered the direct band gap from 6.13 to 5.72 eV and transmittance from 88% to 84.2%. The piezoelectric coefficient rose from 1.80 to 2.92 pC/N, SHG output from 4.83 to 5.84 mJ/pulse, and microhardness increased, while the decomposition temperature fell from 216.9 to 213.9 °C and the honey contact angle dropped from 81.8° to 61.9°.

Ferric-Xylenol Orange Assay for High-Throughput Substrate-Specificity Screening of VAO and EUGO

Ewing, Tom A., et al. Molecules 23.1 (2018): 164.

Xylenol orange (XO) forms a colored ferric complex exploited here as a screening assay for the substrate specificity of the flavin-dependent para-phenol oxidases vanillyl alcohol oxidase (VAO) and eugenol oxidase (EUGO).
Experimental Protocol: In the xylenol orange assay, a hydroperoxide oxidizes Fe²⁺ to Fe³⁺, which complexes XO and is quantified at 560 nm. His-tagged enzymes were purified by a single Ni-NTA affinity step; steady-state kinetics used 50 mM potassium phosphate buffer, pH 7.5, with 2 mM substrate at 19-20 °C. Twenty-four potential substrates and fourteen active-site variants were screened in 96-well format, and products were confirmed by GC and GC/MS.
Performance Evaluation: The assay's detection limit corresponded to a reaction rate of 0.83 s^-1. His-VAO gave k_cat 2.5 s^-1 and K_m 129 µM for vanillyl alcohol; EUGO-His gave 8.0 s^-1 and 47 µM. Screening identified 4-cyclopentylphenol as a new substrate of both enzymes (His-VAO rate 3.9 s^-1, >99% conversion to 4-(1-cyclopenten-1-yl)phenol) and 4-cyclohexylphenol as a new VAO substrate. Variant T457Q His-VAO gave a threefold higher rate with vanillyl alcohol, while V436I EUGO-His raised activity three- and fourfold toward chavicol and 4-cyclopentylphenol.

Xylenol Orange-Based Colorimetric LAMP for Naked-Eye Detection of Escherichia coli

Jaroenram, Wansadaj, et al. Journal of microbiological methods 156 (2019): 9-14.

Xylenol orange (XO), a low-cost pH-dependent dye that shifts from yellow (< pH 6.7) to violet, was combined with loop-mediated isothermal amplification (LAMP) for naked-eye detection of Escherichia coli.
Experimental Protocol: LAMP primers were designed against the E. coli yaiO gene, and 25 µL reactions containing 2 µM inner and loop primers, 0.2 µM outer primers, 1.4 mM dNTPs, 0.6 M betaine, 4 mM MgSO₄ and 8 U Bst 2.0 DNA polymerase were run in a low-buffer solution (100 mM (NH₄)₂SO₄, 500 mM KCl, 20 mM MgSO₄, 1% Tween-20). Optimal conditions were 63 °C, initial pH 8.5 and 0.06 mM XO; DNA from E. coli ATCC 10536 was tested in spiked milk samples alongside AGE confirmation.
Performance Evaluation: Amplification dropped the pH from about 8.5 to 6.0-6.5, turning positive samples from purple to yellow/orange. The assay detected as little as 1 CFU/reaction after 120 min-100,000 times more sensitive than multiplex PCR (10⁵ CFU/reaction)-with no cross-reaction against eight other foodborne pathogens. Across 83 milk samples (51 spiked, 32 non-adulterated), sensitivity, specificity and accuracy were all 100%.

• Synonyms: glycine,n,n'-[3h-2,1-benzoxathiol-3-ylidenebis[(6-hydroxy-5-methyl-3,1-phenyle; ne)methylene]]bis[n-(carboxymethyl)-,s,s-dioxide
• Molecular Weight: 672.66
• Molecular Formula: C31H32N2O13S
• Appearance: Solid
• Application: Use as indicator.
• Active Content: 95%