Эрисульфоксид

Identification

Erysulfoxide is a chemical reagent with CAS 98043-37-9, gross formula C7H12O3S. Systematic name according to IUPAC: (5R)-5-(2-methylsulfinylethyl)oxolan-2-one, synonyms in databases: 6-methylsulfinyl-4-hydroxyhexanoic acid lactone, 2(3H)-furanone, dihydro-5-(2-(methylsulfinyl)ethyl)-, (R-(R*,S*))-. IDs: CHEMBL446822, CTK3I7010, DTXSID90913493.

Basic Attributes

• CAS No: 98043-37-9
• Chemical formula: C7H12O3S
• Molecular weight: 176.23338
• Exact weight: 176.051
• PSA characteristic: 62.6
• XLogP3: -0.3

Chemical class and structure

The substance belongs to the section “Lactones” - a cyclic ester of gamma-butyric acid (oxolan-2-one), in the side chain of which there is a methylsulfinylethyl group. The presence of a sulfoxide center makes the molecule chiral and polar, which is reflected in the negative XLogP3 value (-0.3): the compound is more hydrophilic than most organic lactones of similar molecular weight. The topological polar surface (PSA 62.6 Å2) consists of the carbonyl oxygen of the lactone ring, the ether oxygen of the ring, and the sulfinyl oxygen of the side chain.

According to the structural motif - a methylsulfinyl group on an aliphatic chain - the substance is close to the family of sulfinyl derivatives found among the products of the breakdown of glucosinolates from plants of the genus Erysimum (brassicas, cruciferous plants): methylthioalkyl, methylsulfinylalkyl and methylsulphonylalkyl glucosinolates are described in this genus, and the name of the compound itself - erysulfoxide - reflects this taxonomic and biosynthetic lineage. Unlike erizoline and erucin, in which the sulfinyl or thio group retains an open isothiocyanate function, in erysulfoxide the chain is closed in a five-membered lactone cycle, that is, we are not looking at a product of enzymatic hydrolysis of glucosinolate by myrosinase, but an independent oxygen-containing metabolite of the same structural series.

Properties and application

The compound is supplied as a laboratory reagent for preparative organic chemistry and analytical studies - a reference standard for the identification of structurally related sulfoxide lactones by mass spectrometry and NMR. Used in research laboratories working with the chemistry of glucosinolates and their oxidation products, including the construction of fragmentation libraries for targeted searches for organosulfur metabolites of plants of the cabbage family using the LC-MS/MS method.

Storage and handling

Like most sulfoxides, the substance is sensitive to heat and reducing agents - upon heating, dismutation or reduction of the sulfinyl group to sulfide is possible, and upon contact with strong oxidizing agents, additional oxidation to sulfone is possible. Store in a tightly closed container, in a cool, dry place, away from heat sources and strong reducing and oxidizing agents, preferably in a package protected from light, since the sulfoxide group is photosensitive. Work using standard personal protective equipment for laboratory technicians - gloves, safety glasses, fume hood, since the toxicological profile of the substance is not described in open sources and there is no data on the GHS classification.