Sulfate derivatives

Mixtures containing sulfated castor oil were used to increase the lubricity of water base drilling fluids (123). Sulfated castor oil is also used in dishwashing compounds as a hand softener. A typical cleaning composition contains sodium dodecylben2ene sulfonate, sulfated castor oil, ethanol, and water. A sulfated derivative of castor oil is used as a dispersant for plaster of Paris, reducing the water needed to form a plastic slurry (124). Pesticide emulsions can be stabilized using ethoxylated castor oil (125). 

Natural products Vegetable oils waxes, mineral oils plus their sulfated derivatives (including those of animal oils and fats) Sugar extraction glue manufacture cutting oils... 

The thermochemical data for the sulfoxides, sulfones, sulfites and sulfates, derived from calorimetric measurements, are given in Tables 1-5. All entries in the tables were checked by examination of the original sources. Where available, data are given for the gas phase and either the liquid (lq) or solid (c) phase. Preference was given to gas and liquid phase data. 

The reaction is usually carried out at 120-130°C for several hours but care must be taken to avoid local acidic conditions, which can adversely effect the reaction producing hydrolysis of the sulfated derivative. 

Although the Sharpless asymmetric epoxidation is an elegant method to introduce a specific defined chirality in epoxy alcohols and thus, in functionalized aziridines (see Sect. 2.1), it is restricted to the use of allylic alcohols as the starting materials. To overcome this limitation, cyclic sulfites and sulfates derived from enantiopure vfc-diols can be used as synthetic equivalents of epoxides (Scheme 5) [12,13]. 

Tosylate derivatives are not usually found in nature, but sulfate derivatives of alcohols are common (52). They are formed by the reaction of an alcohol with sulfate, catalyzed by a sulfotransferase enzyme. 

Polycarboxylated polyalkoxylates and their sulfate derivatives may be prepared by reacting an ethoxylated or propoxylated alcohol with a water-soluble, alkali or earth alkali metal salt of an unsaturated carboxylic acid [339]. The reaction occurs in aqueous solution in the presence of a free radical initiator and gives products of enhanced yield and reduced impurity levels, compared with the essentially anhydrous reactions with free carboxylic acids, which have been used otherwise. The method provides products that give solutions that are clear on neutralization, remain clear and homogeneous on dilution, and are useful as cleaning agents in drilling and other oil field operations. 

Barzu T, Level M, Petitou M, Lormeau J-C, J. Choay J, Schols D, Baba M, Pauwels R, Witvrouw M, De Clercq E. Preparation and anti-HIV activity of O-acylated heparin and dermatan sulfate derivatives with low anticoagulant effect. J Med Chem 1993 36 3546-3555. 

Depending on diet and systemic (whole body) metabolism, which produces so-called fixed acids such as sulfate derived from sulfur-containing amino acids and phosphate, mainly from nucleic acid metabolism, there is a tendency for pH of body fluids to fall. 

Work on the chemical structure and properties of the poisons from Alaska butter clam siphons, the hepatopancreas of California mussels, and axenic cultures of G. catenella carried on in the Biological Laboratories and with Rapoport at the University of California definitely established that the sea mussel did not alter the poison obtained from G. catenella. The poison from all three sources had identical structures (31). The situation with the Alaska butter clam may be different however in light of the different saxitoxin derivatives recently found in the dinoflagellates in that region. Perhaps the clam converts the sulfo and sulfate derivatives to the more toxic saxitoxin. 

Polysiloxanes are widely employed as biomaterials. Artificial skin can be fabricated from a bilayer fabricated from a cross-linked mixture of bovine hide, collagen, and chondroitin sulfate derived from shark cartilage with a thin top layer of polysiloxane. The polysiloxane acts as a moisture and oxygen-permeable support and protects the lower layer from the outer world. A number of drug delivery systems use polysiloxanes because of the flexibility and porous nature of the material. 

VD Nadkami, T Toida, CL Van Gorp, TL Schubert, JM Weiler, KP Hanse, EEO Caldwell, RJ Linhardt. Preparation and biological activity of N-sulfated chondroitin sulfate derivatives. Carbohydr Res 290 87—96, 1996. 

Conjugated equine estrogens (Premarin) are the most commonly used estrogens in the treatment of menopause-associated vasomotor symptoms and osteoporosis. Premarin is a mixture of estrogen sulfates, including estrone, equilin, and 17-(3-dihydroequilin. The sulfate derivatives are orally active and are cleaved within the body to yield the active, unconjugated estrogen. 

Difficulties encountered in the postsynthetic chemical sulfation of peptides and the correspondingly low yields have led to the proposal of an alternative approach. This approach makes use of appropriate tyrosine 0-sulfate derivatives for the chain elongation steps in solution and on solid supports by applying protection strategies compatible with the acid sensitivity of the sulfate ester. Moreover, the analytical characterization of the peptides synthesized with tyrosine 0-sulfate derivatives is greatly facilitated since contaminations deriving from the preparation of the intermediates are easily detected by chromatographic (HPLC and CE) and spectroscopic methods (see Table 2). 

Reaction of benzyl a-D-glucopyranosyl cyclic sulfate 44 or benzyl a-D-galactopyranosyl cyclic sulfate 45 with 1,4-anhydro-2,3,5-tri-0-benzyl-4-thio-D-arabinol 46, followed by debenzylation and reduction, gave novel sulfonium sulfate derivatives 47a and 47b, respectively, which were used to prepare homologs of salacinol 48, a natural human maltase glucoamylase inhibitor, as lead candidates for the treatment of type 2 diabetes (Scheme 3) <2006JOC1111>. 

The only stable 1,3,2-dioxathietanes known are fluorinated sulfate derivatives formed by addition of sulfur trioxide to bis(trifluoromethyl)ketene. These structures are fairly well characterized from spectral data and from reactions with nucleophiles. Hexafluoroisopropy-lidene-l,3,2-dioxathietane 2,2-dioxide acts as a sulfur trioxide transfer agent to alkenes and is in equilibrium with a dimeric form as indicated by 19F NMR (Scheme 138) (71KGS1645, 72KGS306, 73KGS178, 132l). 

The directly sulfonated CDs were the second family of compounds studied. The substituent was introduced, after multiple synthetic steps, at the C6 position with a metabolically stable C-S bond. Like the sulfate derivatives, the sulfonates have the negative charge of the substituent in proximity to the carbohydrate backbone. 

The zinc content of EAF dust can be removed by sulphating, using iron sulfate derived from a waste product in some steelmaking processes, pickle liquor residue, as the main... 

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