45127-11-5

Basic information

• Product Name: Coenzyme
• Synonyms: 2,2'-dithiodiethanesulfonic acid;16208-51-8 (Di-hydrochloride salt);2,2'-Dithidi-1-ethanesulfonic acid;Bis(2-sulfoethyl)disulfide;Ethanesulfonic acid, 2,2'-dithiobis-;Omega,omega'-ethanedisulfidedisulfonic acid;2-[(2-sulfoethyl)disulfanyl]ethane-1-sulfonic acid;2,2'-disulfanediyldiethanesulfonic acid
• CAS NO: 45127-11-5
• Molecular Formula: C4H10O6S4
• Molecular Weight: 282.38
• Mol File: 45127-11-5.mol

Chemical Properties

• Appearance: /
• Density: 1.769±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.637
• CAS DataBase Reference: Coenzyme(CAS DataBase Reference)
• NIST Chemistry Reference: Coenzyme(45127-11-5)
• EPA Substance Registry System: Coenzyme(45127-11-5)

Safety Data

• Hazardous Substances Data: 45127-11-5(Hazardous Substances Data)

Usage

Uses

Coenzyme M can be used for F430 Biosynthesis and insertion.

InChI:InChI=1/C4H10O6S4/c5-13(6,7)3-1-11-12-2-4-14(8,9)10/h1-4H2,(H,5,6,7)(H,8,9,10)

Upstream product

• 3375-50-6 2-Mercaptoethanesulfonic acid 
• 19767-45-4 mesna 
• 98022-97-0 2,2'-dithiobisethanesulfonyl chloride 
• 4263-52-9 sodium 2-bromethanesulfonate 

Relevant articles and documents

Medicinal disulfide salts

This invention relates to novel salts of medicinal disulfides. The compounds include a terminal sulfonate or phosphonate moiety, and have many uses, such as toxicity reducing agents when administered with many antineoplastic agents.

Reducing toxic effects of carboplatin using dithioethers

To reduce the toxic effect of carboplatin, particularly myelosuppression and emesis, a dithioether having the formula R1 -(CH2)n --S--S--(CH2)m --R2 (I) wherein: PA1 each of R1 and R2 individually is SO3 H or PO3 H2 ; and PA1 each of m and n is individually 1, 2, 3 or 4; PAL or a pharmaceutically acceptable salt thereof, preferably disodium 2,2'-dithiobis(ethane sulfonate) (dimesna), is administered in combination with carboplatin to a patient, at substantially the same time or sequentially, whereby the dithioether and the carboplatin become co-present in the blood of the patient. Compositions comprising carboplatin and the dithioether are included in the invention.

The reaction of S-nitrosothiols with thiols at high thiol concentration

Reactions of S-nitrosothiols (RSNO) with their corresponding thiols (RSH) present in a large excess (>20-fold) proceed readily to give the disulfide. Ammonia is formed together with some nitrite anion, and these constitute >90% of the 'nitrogen' products. This is in marked contrast with the reaction at low thiol concentration, where nitric oxide is the major initial 'nitrogen' product, which is rapidly converted in the presence of oxygen in water to nitrite anion. Also in marked contrast to the 'low thiol concentration' reaction, the reaction at high thiol concentration is not affected by added Cu2+, nor by the metal-ion scavenger EDTA. Kinetically all reactions were excellent first-order processes, and the reactions were also strictly first order in thiol concentration. A large range of nitrosothiols were studied and the generality of the reaction established. Some reactions of RSNO with other thiols (R'SH) were examined and the results readily interpreted in terms of a prior rapid equilibrium transnitrosation. The pH dependence for the reaction of S-nitrosocysteine with cysteine clearly showed that the reactive species is the cysteine thiolate anion. The results are discussed along with those of two other recent reports of these reactions, in terms of thiolate attack initially at the nitroso nitrogen atom, and subsequently at sulfur atoms, eliminating RSSR and yielding hydroxylamine, which is rapidly reduced by thiolate ion to ammonia. The results are also discussed in connection with the release of NO from nitrosothiols and with the important biological consequences, both for the in vivo reactions of NO and for the potential of nitrosothiols as NO-releasing drags for medical use.