Phenols, acid sulfates

Todd, J.S., Zimmerman, R.C., Crews, P., and Randall, S.A., The antifouling activity of natural and synthetic phenolic acid sulfate esters, Phytochemistry, 34, 401, 1993. 

Allied-Signal Process. Cyclohexanone [108-94-1] is produced in 98% yield at 95% conversion by liquid-phase catal57tic hydrogenation of phenol. Hydroxylamine sulfate is produced in aqueous solution by the conventional Raschig process, wherein NO from the catalytic air oxidation of ammonia is absorbed in ammonium carbonate solution as ammonium nitrite (eq. 1). The latter is reduced with sulfur dioxide to hydroxylamine disulfonate (eq. 2), which is hydrolyzed to acidic hydroxylamine sulfate solution (eq. 3). 

Finally, the fact that anthocyanins can reach the brain represents a beginning of an explanation of the purported neuroprotection effects of anthocyanins. Anthocyanins may be eliminated via urinary and biliary excretion routes. " The extent of elimination of anthocyanins via urine is usually very low (< 0.2% intake) in rats and in humans, indicating either a more pronounced elimination via the bile route or extensive metabolism. As mentioned earlier, in the colon, non-absorbed or biliary excreted anthocyanins can be metabolized by the intestinal microflora into simpler break-down compounds such as phenolic acids that may be (re)absorbed and conjugated with glycine, glucuronic acid, or sulfate and also exhibit some biological... 

A wide range of anionic surfactants (Fig. 23) has been classified into groups, including alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), alcohol sulfates (AS), alcohol ether sulfates (AES), alkyl phenol ether sulfates (APES), fatty acid amide ether sulfates (FAES), alpha-olefin sulfates (AOS), paraffin sulfonates, alpha sulfonated fatty acids and esters, sulfonated fatty acids and esters, mono- and di-ester sulfosuccinates, sulfosuccinamates, petroleum sulfonates, phosphate esters, and ligno-sulfonates. Of the anionic surfactants, ABS and LAS continue to be the major products of anionic surfactants [314, 324]. Anionic surfactants have been extensively monitored and characterized in various environmental matrices [34,35,45,325-329]. 

Anastasio, C., B. C. Faust, and C. J. Rao, Aromatic Carbonyl Compounds as Aqueous-Phase Photochemical Sources of Hydrogen Peroxide in Acidic Sulfate Aerosols, Fogs, and Clouds. 1. Non-Phenolic Methoxybenzaldehydes and Methoxyacetophe-nones with Reductants (Phenols), Environ. Sci. Techno ., 31, 218-232 (1997). 

The conjugation of phenol with glucuronic acid is zero in the cat but the facility is present in many other species. Conversely the conjugation of phenol with sulfate is zero in the pig but the facility is present in many other species. There are many... 

Purity was confirmed by gel-filtration using a HPLC column packed with Asahipak GS-520HQ and elution with 100 mM sodium phosphate buffer containing 300 mM sodium chloride (pH 6.7). The content of total protein, total sugars, uronic acids, sulfates, nucleic acids, phosphate or fatty acids was assayed by the BCA [32] and Lowry method [33], the phenol-sulfuric acid method [34], the Blumenkrantz method [35], nephelometry [36], absorption at 260 nm, the Bartlett method [37] and the GLC method after methyl-esterification [38], respectively. 

Figure 2.8 Summary of behavior of phenolic acid esters and free forms in the GIT and the liver. 5-O-CQA, 5-O-caffeoylquinic acid 5-O-FAAF, 5-O-feruloyl-L-arabinofura-nose C, conjugate (sulfate, glucuronide or methyl) CA, caffeic acid FA, ferulic acid FA-FA, dimer of ferulic acid FA-oligosac., ferulic acid esterified to an oligosaccharide FA-Xy, ferulic acid esterified to xylan R, alkyl group.

The glycosidic linkage of III bears a physiological resemblance to that of another conjugation product found in urine, the phenolic acid (or ethereal ) sulfate (V). Many phenols can be conjugated with either D-glucuronic acid or sulfuric acid ... 

In an analytical experimental series (Fig. 1), the effluent was collected in fractions. These fractions were analyzed with respect to pH, fermentable sugars, furan aldehydes, phenolic compounds, aliphatic acids, sulfate, and ultraviolet (UV) absorption at 280 nm. 

It is significant that, on treatment with water, pentabromobenzene-diazomum acid sulfate does not yield the expected phenol. Instead, part of the salt is converted into pentabromobenzene and part is resinified.82... 

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... 

Note F = flavonoid glu = glucose PA = phenolic acid gIcA = glucuronide SO4 = sulfate, Me = methyl rha = rhamnose. 

Many other groups may be present in the alcohol or phenol during alkylation. Dimethyl sulfate and chlorohydrins give chloro ethers. Halo ethers are also prepared by the action of this reagent on halogenated phenols, e.g., w-bromoanisole (91%)- Phenolic aldehydes are converted in excellent yields to alkoxy aldehydes with dimethyl sulfate or alkyl p-toluenesulfonates. The conversion of a phenolic ketone to an alkoxy ketone is illustrated by the preparation of p-methoxypropiophenone (88%). Phenolic acids, esters, and cyanides, and nitrophenols respond favorably to this method for methylation. The sodium salt of mandelic acid, C H, CHOHCOOH, is methylated with dimethyl sulfate to furnish, after acidification, a-methoxyphenylacetic acid (42%). ... 

Methylation by diazomethane is a simple method for derivatization of relatively acidic compounds [e.g., phenols (pA = 9-10) or carboxylic acids (pi = 4.4 0.2)]. The application of this reagent for methylation of aliphatic alcohols requires additional acid catalysis. Methyl iodide is the most convenient reagent for synthesis of permethylated derivatives of polyols (including carbohydrates) and phenols. Dimethyl sulfate [(01130)2802] can be used in basic aqueous media for methylation of phenols, but the yields of methyl ethers, in this case, are not enough for quantitative determinations of initial compounds by GC. 

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

Phenol + B -phosphoadenosine 5 -phosphosulfuric acid phenylsulfuric acid (sulfate conjugation) Phenol + glucuronic acid -> phenyl glucuronide (alucuronide conjugation)... 

Water resource quality/ effluents BOD. suspended solids, salts, toxic metals, sulfates BOD, suspended solids, oil, metals, acids, phenol, sulfides, sulfates, ammonia, cyanides, effluents from wet gas scrubbers Organic chemicals, heavy metals, suspended solids, COD, cyanide Contamination of water by toxic chemicals, accidental spillage of toxic materia] Used effluent... 

These metabolites were generated during digestion and intestinal absorption as a result of phase II enzymes and were converted into glucuronidated and sulfated metabolites as well as methylated metabolites. The procyanidins, which were not absorbed in the small intestine, passed into the large intestine where they were degraded by the colonic microflora into phenolic acids, which could be absorbed into the circulatory system and subjected to phase II metabolism prior to excretion. Serra et al. [34] used a colonic fermentation model with rat colonic microflora and reported that the phen-ylacetic acid and its hydroxylated forms were the main fermentation products, and hydroxy-y-valerolactone was specifically from procyanidin compounds. 

---