Organosulfur Compound

organosulfur compound

[ȯr¦gan·ə¦səl·fər ′käm‚pau̇nd]
(organic chemistry)
One of a group of substances which contain both carbon and sulfur.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Organosulfur Compound

 

any of a group of substances whose molecules contain a carbon-sulfur bond. There are a large number of such compounds, and the compounds are of various types; sulfur, together with hydrogen, oxygen, nitrogen, and the halogens, is one of the principal elements forming organic compounds. The sulfur atom in these compounds can be in any of its characteristic (–2, +4, +6) oxidation states.

There are three main types of organosulfur compounds. The first type (R, R’, and Ar designate organic residues)) contains sulfur atoms in the - 2 oxidation state and includes mercaptans (thioalcohols, RSH), thiophenols (ArSH), thioaldehydes (R—CH=S), and thioketones (R—CS—R’). Also included here are the thio acids

as well as the various derivatives of these acids, and thioethers (organic sulfides, R—S—R’), disulfides and polysulfides (R—Sx—R’, where x ≥ 2), sulfonium salts (RR’S+x-, where X is an anion, such as Cl-), such sulfur-containing heterocycles as thiophene, and numerous compounds of various classes that have sulfur-containing groups, such as mercaptoamino acids.

The second type of organosulfur compound contains sulfur atoms in the +4 oxidation state and includes sulfinic acids, which have the structural formula

and sulfoxides (RSOR’). The third type contains sulfur atoms in the + 6 oxidation state and includes sulfonic acids (RSO3H) and sulfones (R—SO2—R’).

The principal method for the synthesis of organosulfur compounds involves reactions between organic compounds and either elemental sulfur or the following simple inorganic sulfur compounds: H2S, Na2S, NaSH, SCl2, SO2, SO3, and H2SO4. The reactions proceed according to the following schemes:

A second important method of synthesis involves mutual inter-conversions of organosulfur compounds.

Organosulfur compounds include such important natural substances as the amino acids cystine and methionine and a series of coenzymes (coenzyme A, lipoic acid), vitamins (thiamine, biotin), and antibiotics (penicillins). The sulfhydryl groups of cystine play an important role in the active site of many enzymes. The disulfide bonds of cysteine, formed as a result of the bonding of two cysteine residues, help support the structure of proteins and peptides. Organosulfur compounds also include many medicinal and physiologically active synthetic substances, such as sulfanilamide drugs, radioprotectors (cystamine, cystaphos), insecticides, fungicides, growth stimulants, poisons (yperite), and various classes of dyes, such as sulfur dyes and certain aniline, anthraquinone, and phthalocya-nine dyes. Certain high-molecular-weight compounds, for example, polysulfide rubbers (Thiokols), may be considered organosulfur compounds. The vulcanization of rubber by sulfur (and sulfur derivatives) is based on the formation of organosulfur compounds. Organosulfur compounds are used as inhibitors of polymerization and oxidation, stabilizers of polymer materials (mercaptobenzimidazole), and solvents (tetramethy-lene sulfone, dimethyl sulfoxide). The salts of organic sulfonic acids are used as surfactants (detergents). Many organosulfur compounds, for example, aromatic sulfonic acids, are important intermediates in heavy organic synthesis.

B. L. DIATKIN

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.
References in periodicals archive ?
According to new report available with Million Insights, Thiourea is an organosulfur compound also termed as thiocarbamide that resembles urea but contains sulfur instead of oxygen.
* A case-control study found that working inside greenhouse 7, which had been fumigated with the organosulfur compound metam sodium the night of October 13, was strongly associated with illness.
Allicin, an organosulfur compound, which prevents lipid biosynthesis, was proved to damage Candida albicans cell wall [7] and cause inhibition of RNA synthesis in bacteria [8].
Dashwood, "Allylmercaptan, a garlic derived organosulfur compound inhibits histone deacetylase and enchances Sp3 binding on the P21WAF1," Carcinogenesis, vol.
The garlic compound whose antimicrobial activity is attributed to is known as allicin, an organosulfur compound from which the metabolites diallyl sulfide and diallyl disulfide are formed.
Among them, DADS, an oil-soluble organosulfur compound, has been described as the major one responsible for therapeutic properties against prostate and colon in in vitro models and gastric, breast, and leukemia in in vivo models (Table 2).
Allicin, an organosulfur compound which is converted from alliin by alliinase of garlic, has been shown to participate in chondrocytes proliferation [20], so we examined the effect of SAMC in chondrocytes growth.
Aside from these, the leafy vegetable is also a good anti-oxidant to fight skin problems and a good cancer protection thanks to its organosulfur compound, which is said to reduce the risk of cancer.
To identify effective adsorbents, we need to quantify the monomer properties similar to the evaluation of organosulfur compound properties.
DADS, an organosulfur compound up-regulate [p21.sup.[waf/dP1]] protein expression and induce apoptosis which was due to the hyperacetylation of histone H3 and H4 (Arunkumar et al.
evaluated the underlying mechanism for reduced live fibrosis by diallyl trisulfide (DATS), the primary organosulfur compound in garlic.