Phenyl sulfate

The sulfotransferases catalyze formation of sulfate esters of compounds having hydroxy or amino groups. The donor in this transfer of a sulfuryl group is 3 -phosphoadenylsulfate, also named previously as 3 -phosphoadenosine-5 -phos-phosulfate (PAPS). An example of this reaction is seen in Eq. (11) for phenol as the sulfuryl (S03) acceptor, with the products of the reaction being phenyl sulfate and adenosine 3, 5 -bisphosphate (PAP). 

Figure 4.22 High temperature size-exclusion liquid chromatography of an engineering plastic, poly (phenyl sulfate). Column, SSC GPS-3506, 50 cm x 8 mm i.d. eluent, 1-chloronaphthalene flow rate, 1.0 ml min-1 column temperature, 210 °C detector, refractive index detector.

Cats and pigs have low activities of phenol glucuronyltransferase, and metabolize phenol to phenyl sulfate nearly exclusively (Capel et al. 1972 French et al. 1974 Miller et al. 1976). Because humans have a greater capacity to glucuronidate phenol, cats and pigs would not be good models for the metabolism of phenol by humans. 

Ogata M, Yamasaki Y, Kawai. 1986. Signficance of urinary phenyl sulfate and phenylglucuronide as indices of exposure to phenol. Int Arch Occup Environ Health 58 197-202. 

Sunamoto et al. 94) have studied the reaction of (14) with 2,4-dinitro-phenyl sulfate in aqueous organic solvent with 0.1 A sodiiun hydroxide. The rate of esterolysis by (14) was greater than the rate of the reaction catalyzed by -cyclodextrin. Better binding by the paracyclophane cavity and the greater nucleophilicity of the oxime group as compared to the secondary hydroxyl group of jS-cycdextrin were cited to explain the difference in catalytic efficiency. 

Fig. 7. Plot of log for the hydrolysis (at 48.6°C) of a series of substituted phenyl sulfates vs. the p/Ca of the corresponding phenols. The solid line represents meta- and para-substtuted substrates ort/io-substituted compounds of interest are indicated individually.

Phenyl N-phenylphosphoramidochloridatc, 416 Phenylselenenylation, 219 Phenyl selenocyanate, 33, 416-417 (3-Phcnylselcnoindole, 37, 38 N-Phenylselenophthalimide, 417-418 3-Phenylseleno sulfones, 407, 408 (3-(Phenylseleno)vinyl sulfones, 408 Phenyl sulfates, 410 Phenylsulfinylacetonitrile, 418-419 4-(Phenylsulfmyl)butyric acids, 1... 

Serum Uremic syndrome Control rats (6/5) LC-MS Indoxyl sulfate, phenyl sulfate, hippuric acid, and p-cresyl-sulfate (57)... 

There are quantitative differences in the benzene metabolites produced by different species (Sabourin et al. 1988). Fischer 344 rats exposed to 50 ppm benzene had undetectable amounts of phenol, catechol, and hydroquinone in the liver, lungs, and blood. The major water-soluble metabolites were muconic acid, phenyl sulfate, prephenyl mercapturic acid, and an unknown The unknown was present in amounts equal to the amounts of phenyl sulfate in the liver phenyl sulfate and the unknown were the major metabolites in the liver. B6C3Fj mice exposed to 50 ppm benzene had detectable levels of phenol and hydroquinone in the liver, lungs, and blood catechol was detectable only in the liver and not in the lungs or blood. As in the rat, the unknown was present in amounts equal to the amounts of phenyl sulfate in the liver. Mice had... 

The primary metabolite of benzene is phenol. Phenol is excreted as glucuronide and sulphate conjugates in urine. Total phenolic metabolites (phenol, phenyl sulfate, and phenyl glucuronide) have been determined by hydrolyzing urine samples either enzymatically or by acid, then extracting the phenol with solvent. Phenol is then measured by GC or HPLC techniques. Enzymatic hydrolysis coupled with GC/FID has been reported the detection limit is 1 mg/L and recovery is excellent (92-98%) (Buchet 1988). Acid hydrolysis followed by HPLC provides quantitative recovery ( 100%) and a detection limit of 0.01 nmol/g (Murray and Adams 1988). Sulfate and glucuronide conjugates... 

Urine (phenol, phenyl sulfate, phenyl glucuronide) Digestion (enzymatic and with acid) extraction with diethyl ether GC/FID (IARC Method 6) 1 mg/L 92-98 Buchet 1988... 

Fig. 8. Plot of va. surfactant concentration, Cn, for the hydrolysis of 2,4-dinitro-phenyl sulfate at pH 8 00 and 25-0° (Fendler et al., 1970a).

Blei Bis-[3-nitro-phenyl]- -sulfat (Hydrat) XIII/7, 172... 

Phenol is absorbed from the gastrointestinal tract, skin, and mucous membranes and is metabolized to phenylglucuronide and phenyl sulfate, which are excreted in the urine. 

Digest sample enzymatically and with acid extract phenol, phenyl sulfate, and phenyl glucuronide with ethyl ether... 

Phenol, phenyl gluouronJde,phenyl sulfate Benzene... 

Instrument detection limits were estimated from the linear calibration curve using two times the average peak height of the baseline noise for each ion monitored as the minimum detectable signal. Estimated instrument limits of detection (ng) are phenol, 51 4-nitrophenol, 3.6 1-naphthol, 165 4-nitrophenyl glucuronide, 0.25 1-naphthy.l glucuronide, 5.3 phenyl sulfate, 7.7 4-nitrophenyl sulfate, 0.29 1-naphthyl sulfate, 3.1. For the UV detector at 254 nm, the corresponding limits of detection (ng) were phenol, 5.0 4-nitrophenol, 8.2 1-naphthol, 4.0 4-... 

Peaks are identified as phenol (A), phenyl sulfate (B), 4-nitrophenol (C), 4-nitrophenyl glucuronide (I)), 4 -nitrophenyl sulfate (E), 1-naphthol (F). 1-naphthyl glucuronide (G), and 1-naphthyl sulfate (H). 

Phenol, [108-95-2] phenyl sulfate potassium salt, [1733-88-6] phenyl glucuronide, [17685 05 1] 4-nitrophenol, [100-02 7] 4-nitrophenyl sulfate potassium salt, [6217-68-1] 4-nitrophenyl glucuronide, [10344-94-2] 1-naphthol, [90-15-3] 1-naphthyl sulfate potassium salt, [6295 74-5] 1-naphthyl glucuronide, [17238-47-0]. 

Figure 1. Strong anion exchange LC separation of phenols, aryl glucuronides and aryl sulfates using a UV absorbance detector. Compounds eluted are 1, phenol 2, 4-nitrophenol 3, 1-naphthol 4, phenyl-be ta-D-glucuronide 5, 4-nitrophenyl-beta-D-glucuronide 6, 1- naphthyl-beta-D-glucuronide 7, phenyl sulfate 8, 4-nitrophenyl sulfate 9, 1-naphthyl sulfate. (Reproduced with permission from Ref. 19. Copyright 1989 Elsevier Science Publishers B.V.)...

Figure 2. TSP SIM traces for metabolic conjugates eluted from a strong anion exchange column. Deprotonated molecule ions are plotted as follows m/z 173, phenyl sulfate m/z 269, phenyl-beta-D- glucuronide m/z 218, 4-nitrophenyl-beta-D-glucuronide m/z 314, 4-nitrophenyl-beta-D-glucuronide m/z 223, 1-naphthyl sulfate m/z 319, 1-naphthyl-beta-D-glucuronide.

Figure 3. Selected reaction monitoring of aryl glucuronides and sulfates eluted from a strong anion exchange column. Glucuronides are detected by neutral loss of 176 mass units as in phenyl-beta-D- glucuronide (269" --> 93"), 4-nitrophenyl-beta-D-glucuronide (314" --> 138"), and 1-naphthyl-beta-D-glucuronide (319" > 143"). Sulfate conjugates are detected by neutral loss of S03 as in phenyl sulfate (173 — > 93"), 4-nitrophenyl sulfate (218 — > 138") and 1-naphthyl sulfate (223" > 143"). Compounds with a 4-nitrophenol moiety are detected with Q1 at m/z 138 and Q3 at m/z 108 scan 74, 4-nitrophenol scan 133, 4-nitrophenyl-beta-D-glucuronide and scan 269, 4- nitrophenyl sulfate.

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