Naphthyl 2-sulfate

Figure 10 Conversion of 1-naphthol to 1-naphthyl sulfate by sulfotransferases.

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.

Some other examples of selective alteration will now be given. Whereas vertebrates convert phenols to j8-glucuronides, most insects form phenyl-)8-glucosides instead. In a patient whose normal lung tissue converted 1-naphthol to 1-naphthyl sulfate, squamous carcinoma tissue made 1-naphthyl glucu-ronide from the same phenol (see Section 3.5, p. 87 for the biochemistry of these alternative routes) (Cohen, Gibby and Mehta, 1981). 

Cytochrome C 6-Bromo-2-naphthyl sulfate Cytochrome C (oxidized) 1.8 0.2 203... 

Phosphorescent inclusion complex can be used to probe heme accessibihty in heme proteins [27]. The phosphorescence lifetime of 6-bromo-2-naphthyl sulfate (BNS) is several hundred microseconds and is self-quenched. Quenching of BNS phosphorescence does not occur for the non-heme protein lysoz3me and apomyoglobin but occurs by a dynamic mechanism with a quenching constant of 12 X lO M s for cytochrome c and myoglobin and with a quenching constant of 6.2 x 10 s for protoporphyrin IX. The phosphorescence of... 

Benzanthrone has been prepared by three general methods, the first of which is generally regarded as the best (i) by heating a reduction product of anthraquinone with sulfuric acid and glycerol,1 or with a derivative of glycerol, or with acrolein. The anthraquinone is usually reduced in sulfuric acid solution, just prior to the reaction, by means of aniline sulfate, iron, , or copper. It has also been prepared (2) by the action of aluminum or ferric chloride on phenyl-a-naphthyl ketone, and (3) from i-phenylnaphthalene-2-carboxylic acid. ... 

Dinitro-5-methoxy-naphthol-(l), methyl-[6,8-Dinitro-5-hydroxy-naphthyl-(])] -ether). (O2N)2C10H4(0H).O.CH3, mw 264.21, N 10.61%, OB to C02 —121.12%, orange needles from CCI4, mp 173° (decompn). Sol in CCI4. Prepn from 2,4-dinitro-naphthalenediol-(l,5) by reacting with an excess of dimethyl sulfate in dil NaOH... 

Eight isomers are in the literature 1 -A zido-2-nitronaphthalene (2-Nitro-l-naphthyl azide). Long yel needles from aq acet, mp 103—4° with decompn (Refs 1 4) CA Registry No 16714-21-9. Prepd by the action of Na azide on 2-nitro-1-naphthalenediazonium sulfate with urea in glac acet ac (Ref 4). It decomps at 150° with N evolution, and in toluene at 110° to give a 90% yield of... 

Roubal et al. (8) applied TLC to the separation and identification of metabolites of l c-iabeled naphthalene administered to coho salmon fingerlings via intraperitoneal injection. 1-Naphthol, a dihydrodiol, mercapturic acid, 1-naphthyl glucuronic acid and a glycoside/sulfate fraction were identified in brain, liver, gall bladder, and muscle 1-naphthol, a dihydrodiol, and 1-naphthyl glucuronic acid were the only metabolites found in heart. 

Micellar media created by sodium dodecyl sulfate or cetyltrimethylammon-ium bromide have also a positive effect on the ortho selectivity [262,269-271]. In a recent article, the PFR of 1-naphthyl acetate in aqueous solutions of an antenna polyelectrolyte like poly(sodium styrenesulfonate-co-2-vinylfluorene) has been reported, which, in addition to the micellar effect, also provides singlet sensitization by means of fluorene chromophores. In this particular case, the occurrence of in-cage versus out-of-cage processes can be clearly correlated with the different packing of the microdomains, which depends on the molar fraction of monomers in the antenna copolymer [272]. 

C. Regeneration of 0-tetralone. Fifty grams (0.20 mole) of /3-tetralone bisulfite addition product is suspended in 250 ml. of water, and 75 g. (0.6 mole) of sodium carbonate monohydrate is added. At this point the pH of the solution is approximately 10. The mixture is extracted with five 100-ml. portions of ether (Note 8). The combined extract is washed with 100 ml. of 10% hydrochloric acid, then with 100-ml. portions of water until the washings are neutral to litmus, and is dried over anhydrous magnesium sulfate. The ether is removed by distillation, and the residue is distilled from a Claisen flask under reduced pressure, preferably in a nitrogen atmosphere. The pure /3-tetralone is obtained as a colorless distillate b.p. 70-71°/0.25 mm. (92-940/1.8 mm., 114-11674.5 mm.) n 1.5594. The yield is 17-21 g. (40-50% based on /3-naphthyl ethyl ether). 

Fused oxygen and nitrogen-containing rings may also be prepared in reactions with thioureas thus, dihydrobenzoxazine products are obtained on treatment of salicyloyl chloride with thioureas371 or on fusion of salicylate esters with thiopseudoureas.320 When the thio-pseudoureas are treated with o-aminophenol, the products are benzoxa-zoles.320 A naphthyl analog of a benzoxazole is produced on treatment of l-(2-hydroxy-l-naphthyl)-2-thiourea with dimethyl sulfate.372... 

Methyl- or 2-ethyl-benzo[Z> ]thiophenes are conveniently prepared by treatment of 2-benzo[6]thienyllithium with the appropriate alkyl sulfate <70AHC(11)177). Clemmensen or Wolff-Kishner reductions of the 2-acylbenzo[Z>]thiophenes are useful, but since acylation produces a mixture of the 2- and 3-acyl isomers (Section 3.14.2.4), these must be separated. Cyclization of phenyl phenacyl sulfide with hydrofluoric acid leads exclusively to 2-phenyl-benzo[6]thiophene, and 3-phenylbenzo[6]thiophene can be rearranged to the 2-isomer in hydrofluoric acid (Section 3.15.2.3.2). Aromatization of 2-cycIohexenylbenzo[6]thiophene, obtained by condensation of the 2-lithio reagent with cyclohexanone, gives 2-phenyl-benzo[6]thiophene, and the reaction is adaptable to the 2-(l-naphthyl) derivative also. 

---