Sodium 4-hydroxybenzoate

The solubility of the antitubercular drug, pyrazinamide, is directly proportional to the concentration of sodium p-aminosalicylate (sodium PAS) or sodium hydroxybenzoate in aqueous solution [305]. Thermal analysis has confirmed the complex formation between the drug and sodium PAS, but the authors [305] list the alternatives of complexation and normal increase in solubility in the presence of additive as the causes of solubilization. As the antituberculars are always used clinically in combination - sodium PAS is also an effective drug-this study may have some bearing on the efficacy of the combinations. It might be of interest for an investigation to be carried out on the solution properties of isoniazid, streptomycin, and sodium PAS mixtures, especially as streptomycin is thought to have some colloidal electrolyte properties of its own. 

Kolbe-Schmitt reaction (Section 24 10) The high pressure re action of the sodium salt of a phenol with carbon dioxide to give an o hydroxybenzoic acid The Kolbe-Schmitt reac tion IS used to prepare salicylic acid in the synthesis of as pinn... 

Amino-2-hydroxybenZOiC acid. This derivative (18) more commonly known as 4-aminosa1icy1ic acid, forms white crystals from ethanol, melts with effervescence and darkens on exposure to light and air. A reddish-brown crystalline powder is obtained on recrystallization from ethanol —diethyl ether. The compound is soluble ia dilute solutioas of nitric acid and sodium hydroxide, ethanol, and acetone slightly soluble in water and diethyl ether and virtually insoluble in benzene, chloroform or carbon tetrachloride. It is unstable in aqueous solution and decarboxylates to form 3-amiaophenol. Because of the instabihty of the free acid, it is usually prepared as the hydrochloride salt, mp 224 °C (dec), dissociation constant p 3.25. 

The model was tested by the micellar liquid chromatography separ ation of the five rarbornicin derivatives and four ethers of hydroxybenzoic acid. Micellar mobile phases were made with the sodium dodecylsulfate and 1-pentanol or isopentanol as modifier. In all cases the negative signs of the coefficients x and y indicate that at transition of the sorbat from the mobile on the stationar y phase the number of surfactant monomers as well as the number of modifier molecules increases in its microenvironment. 

The mixture was heated under reflux and a solution of 0.2 g of ethyl iodide in 5 ml of dry tetrahydrofuran was allowed to flow into the reaction medium. When the reaction started, a solution of 6.2 g of 7heated under reflux until the complete disappearance of the magnesium turnings. The reaction medium was then cooled in an ice bath, after which there was added thereto a solution in 45 ml of tetrahydrofuran of 7 g of 6-oxo-benzo[b] -benzofurano[2,3-e] oxepin. The reaction mixture was allowed to stand for 20 hours at a temperature of 20°C, and was then poured into a saturated aqueous solution of ammonium chloride maintained at a temperature of 5°C. The mixture was extracted with ether and the organic portion was washed and dried over anhydrous sodium sulfate. After evaporation of the solvent, 9.4 g of crude product were obtained, which after recrystallization from isopropanol, provided 6.7 g of pure 6-(3-dimethylam nopropyl)-8-hydroxybenzo[b] benzofurano-[2,3-e] oxepin, melting point 160°C (yield, 71 %). 

Oxabicydo[2.2.2]octan-3-one 50, which is readily prepared by hydr(>genation of p-hydroxybenzoic acid followed by dehydration40 , can be polymerized by heating with phosphoric acid or sodium hydride to give a polyester23 . jn contrast, 6-oxabi-... 

Sodium or potassium phenoxide can be carboxylated regioselectively in the para position in high yield by treatment with sodium or potassium carbonate and carbon monoxide. Carbon-14 labeling showed that it is the carbonate carbon that appears in the p-hydroxybenzoic acid product. The CO is converted to sodium or potassium formate. Carbon monoxide has also been used to carboxylate aromatic rings with palladium compoimds as catalysts. In addition, a palladium-catalyzed reaction has been used directly to prepare acyl fluorides ArH —> ArCOF. ... 

Actually, the reaction seems to be more complicated than this. At least part of the potassium p-hydroxybenzoate that forms comes from a rearrangement of initially formed potassium salicylate. Sodium salicylate does not rearrange. See Shine, FI.J. Ref. 402, p. 344. See also Ota, K. Bull. Chem. Soc. Jpn., 1974, 47, 2343. 

Esters of aromatic acids are not reduced by this procedure, so an aromatic COOH group can be reduced in the presence of a COOR group. However, it is also possible to reduce aromatic ester groups, by a variation of the trichlorosilane procedure. The o- and p-hydroxybenzoic acids and their esters have been reduced to cresols (HOC6H4CH3) with sodium bis(2-methoxyethoxy)aluminum hydride, NaAlH2(0C2H40Me)2 Red-Al). ... 

Condensation of aromatic methylesters such as methyl 4-methoxybenzoate 351 a or methyl 4-hydroxybenzoate 351b with excess sodium-HMDS 486 in a mixture of THF-l,3-dimethyl-imidazolin-2-one (DMEU) at 185 °C in a closed vessel affords 59 or 93% of 4-hydroxybenzonitrile 298 as well as 26% 352 with smooth cleavage of the aromatic methyl ether in 351a (Scheme 4.47). Methyl indole-3-carboxylate gives hkewise 3-cyanoindole in 81% yield [127] (cf. also ref [92] in section 4.3). 

C12 to C20, primarily Ci6 to ( is), used as surface lubricants in the manufacture of food-contact articles. The method, which uses ethyl palmitate (Eastman Chemicals No. 1575 Red Label) as an internal standard, has been validated at 200 ppm total FAME [185]. Other FAME standards (methyl palmitate, methyl stearate, methyl oleate, methyl linoleate and methyl linolenate) are available (Applied Science Laboratories) [116], Worked out examples of additive determinations are given in the Food Additives Analytical Manual [116], which also describes a great many of indirect food additives, such as BHA, BHT, TBHQ, l-chloro-2-propanol, DLTDP, fatty acid methyl esters, w-heptyl-p-hydroxybenzoate, propyl-gallate, sodium benzoate, sodium stearoyl-2-lactylate, sorbitol and phenolic antioxidants. EPA methods 606 and 8060 describe the CGC separation of phthalate esters (direct injection) (cf. Figure 4.2). 

The product is almost exclusively sodium o-hydroxybenzoate (salicylate, 71) only traces of the p-isomer being obtained if, however, the reaction is carried out on potassium phenoxide the salt of the p-acid becomes the major product. It has been suggested that the preferential o-attack with sodium phenoxide may result from stabilisation of the T.S. (72) through chelation by NaP in the ion pair ... 

Annex III lays down the conditions of use for permitted preservatives and antioxidants, with lists of foods and maximum levels in each case. Part A lists the sorbates, benzoates and p-hydroxybenzoates, E 200-E 219 part B lists sulphur dioxide and the sulphites, E 220-E 228 part C lists other preservatives with their uses, including nisin, dimethyl dicarbonate and substances allowed for surface treatment of certain fruits, E 249 potassium nitrite, E 250 sodium nitrite, E 251 sodium nitrate and E 252 potassium nitrate, E 280-E 283 propionic acid and the propionates part D lists the antioxidants E 320 butylated hydroxyanisole (BHA), E 321 butylated hydroxytoluene (BHT), E 310 propyl gallate, E 311 octyl gallate, E 312 dodecyl gallate, E 315 eiythorbic acid and E 316 sodium erythorbate. 

There is a recent trend towards simultaneous CE separations of several classes of food additives. This has so far been applied to soft drinks and preserved fruits, but could also be used for other food products. An MEKC method was published (Lin et al., 2000) for simultaneous separation of intense sweeteners (dulcin, aspartame, saccharin and acesulfame K) and some preservatives (sorbic and benzoic acids, sodium dehydroacetate, methyl-, ethyl-, propyl- and isopropyl- p-hydroxybenzoates) in preserved fruits. Ion pair extraction and SPE cleanup were used prior to CE analysis. The average recovery of these various additives was 90% with good within-laboratory reproducibility of results. Another procedure was described by Frazier et al. (2000b) for separation of intense sweeteners, preservatives and colours as well as caffeine and caramel in soft drinks. Using the MEKC mode, separation was obtained in 15 min. The aqueous phase was 20 mM carbonate buffer at pH 9.5 and the micellar phase was 62 mM sodium dodecyl sulphate. A diode array detector was used for quantification in the range 190-600 nm, and limits of quantification of 0.01 mg/1 per analyte were reported. The authors observed that their procedure requires further validation for quantitative analysis. 

Sodium aluminium phosphate, acidic Sodium aluminium silicate Sodium benzoate Sodium calcium polyphosphate Sodium carbonate Sodium ethyl p-hydroxybenzoate Sodium ferrocyanide Sodium gluconate... 

Preservative 215 Sodium ethyl p-hydroxybenzoate 10 35th Series 2001... 

A sample of aspirin of accurately known mass is reacted with a known excess amount of sodium hydroxide solution. The alkali first catalyses the hydrolysis of aspirin to ethanoic acid and salicylic acid (2-hydroxybenzoic acid) and then neutralises these acids. The overall balanced equation for the reaction is ... 

A method was proposed for the preparation of p-hydroxybenzoic acid by oxidation of p-cresol with atmospheric oxygen in an acetic acid-acetic anhydride mixture under catalysis of cobalt acetate, manganese(II) acetate, and sodium bromide (Litvintsev et al. 1994). This procedure ensures 60% yield of p-acetoxybenzoic acid and 100% conversion of the initial p-cresol. 

Kj, or the ratios of solution-phase solute concentration and adsorbed-phase concentration were calculated to estimate the relative affinity of the soils for phenolic acids. The Kj values for p-hydroxybenzoic acid, p-coumaric, vanillic, ferulic, and syringic icids were 67, 75, 69, 92 and 376, respectively for a 48-hr equilibration of 0.1 nmol mL phenolic acid solution with a sample of an alfisol preextracted in boiling water. The sorption capacity was greatly reduced by pretreatment of soil samples with sodium acetate-hydrogen peroxide to remove organic matter and metal sesquioxides. 

Reactions. w-Hydroxybenzoic acid affords a variety of products, depending on the catalyst and conditions employed. Catalytic reduction over platinum black or platinum oxide in alkaline solution gives 3-hydroxycyclohexanecarboxylic acid [22267-35-2]. Reduction of a warm aqueous solution over platinum oxide or over colloidal platinum yields cyclohexanecarboxylic acid. w-Hydroxybenzaldehyde can be prepared by reducing ///-hydroxybenzoic acid with sodium amalgam. Finally, reduction over Raney nickel gives cydohexanol. 

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