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.

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.


References in periodicals archive ?
About DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)[sub.
An organosulfur compound isolated from oil-macerated garlic extract, and its antimicrobial effect.
8 nmoles sulfhydryl (SH) group/ml suggesting that this protein could be an organosulfur compound.
However, this suggests that garlic organosulfur compounds could preserve the tissue structural integrity [30].
Phyto- and organosulfur compounds do wonders for your skin.
It contains a variety of organosulfur compounds such as allicin, ajoene, S allylcysteine, diallyl disulfide, S-methylcysteine sulfoxide and S-allylcysteine (Chi et al.
Contributed by pharmaceutics, pathology, cancer, nutrition, and other specialists from North America and Asia, chapters address the basic mechanisms of inflammation/oxidative stress-driven cancer, including preventing carcinogenesis, the role of obesity, and antioxidant properties of common dietary phytochemicals; cellular signal transduction, molecular targets, and biomarkers of these cancer-preventive phytochemicals; challenges with in vivo absorption and pharmacokinetics of phytochemicals; cancer prevention and vitamins A, D, and E, omega-3 and omega-6 fatty acids, flavonoids and polyphenols, garlic organosulfur compounds and crucifer glucusinolates, and selenium, herbal medicines, and alpha lipoic acid; and epigenetics and chronic inflammation.
Organosulfur compounds will see significant growth in these applications, particularly in paint, thanks to performance advantages and environmental concerns about competing products.
Two previous works published last year by Lu and WSU colleagues in Applied and Environmental Microbiology and Analytical Chemistry found diallyl sulfide and other organosulfur compounds effectively kill important foodborne pathogens, such as Listeria monocytogenes and Escherichia coli O157:H7.
1996, "Protective effects of garlic and related organosulfur compounds on acetaminophen-induced hepatotoxicity in mice," Toxicol.
Organosulfur compounds, found in garlic and onions, are strong supporters of good health by increasing the activity of immune cells that fight cancer and indirectly help break down cancer-causing substances.