3-Mercaptopropionate

Additions of mercaptans with alkaline catalysts give 3-alk5ithiopropionates (29). In the case of hydrogen sulfide, the initially formed 3-mercaptopropionate reacts with a second molecule of acrylate to give a 3,3 -thiodipropionate (30,31). 

Other products of commercial value, such as laurylthiopropionic acid [1462-52-8], C22H24SCH2CH2COOH, are produced starting from 3-mercaptopropionic acid [107-96-0], HSCH2CH2COOH, and unsaturated products.. 7- Alkylthiocarhoxylic acids and their potassium salts have been described and evaluated as surfactants (qv). They provide exceUent thermally stable behavior and good surface activity for their alkaline salts (4). 

Among other mercaptocarboxyhc acids, the mercaptopropionic acids have undergone a promising development. Thiolactic acid or 2-mercaptopropionic acid [79 2-5] HSCH(CH2)COOH, is manufactured by usiag 2-chloropropionic acid [598-78-7]. 3-Mercaptopropionic acid [107-96-0] HSCH2CH2COOH, competes with thioglycohc acid ia plastic additives or as modifiers ia various polymers. Mercaptopropionic acid is... 

Acute Toxicity. ThioglycoHc acid, its esters and 3-mercaptopropionic acid are considered moderately toxic on the basis of acute toxicity studies. These are presented in Table 4. 

Michael-Type Additions. Michael additions are generally used to prepare methyl 3-mercaptopropionate (eq. 10) and mercaptopropionitrile (eq. 11) by the reaction of methyl acrylate or acrylonitrile and hydrogen sulfide using a basic catalyst. This reaction proceeds as shown ... 

Condensation of p-chlorobenzaldehyde with 3-mercaptopropionic acid in the presence of ammonium carbonate leads to the thiazi-none, 179. The reaction very probably proceeds by the intermediacy of the carbonyl addition product, I7S lactamization completes formation of the observed product. Oxidation of 179 to the sulfone by means of potassium permanganate in acetic acid gives chlormezanone (180), a minor tranquilizer with muscle-relaxant properties. 

A solution of 4-chlorobenzaldehyde is reacted with (3-mercaptopropionic acid and with methylamine. The mixture is refluxed in benzene and water is removed from an overhead separator. The reaction mixture was cooled, washed with dilute ammonium hydroxide and water, and the benzene was removed by distillation in vacuo. The oily residue was taken up in ether from which it crystallized. The precipitate was recrystallized twice from ether to yield 2-(4-chlorophenvl)-3-methyl-4-metathiazanone. 

Chemicai Name 1-(3-Mercaptopropionic acid)-8D-arginine vasopressin Common Name —... 

Mercaptopropionic acid (HRSH) has been oxidised with ferricyanide in aqueous solution to give 3,3 -dithiodipropionic acid in 95 % yield. Whilst individual runs showed second-order disappearance of oxidant, the magnitude of 2 varied with increasing thiol, oxidant and ferrocyanide concentrations , viz. 

Ester-thioester copolymers were enzymatically synthesized (Scheme 7). ° The lipase CA-catalyzed copolymerization of e-caprolactone with 11-mercaptoundecanoic acid or 3-mercaptopropionic acid under reduced pressure produced the polymer with molecular weight higher than 2 x 10". The thioester unit of the resulting polymer was lower than the feed ratio. The transesterification between poly(8-caprolactone) and 11-mercaptoundecanoic acid or 3-mercaptopropionic acid also took place by lipase CA catalyst. Recently, aliphatic polythioesters were synthesized by lipase CA-catalyzed polycondensation of diesters with 1,6-hexanedithiol. ... 

An alternative pathway for the degradation of dimethylsulfoniopropionate involves successive de-S-methylation to 3-thiomethylpropionate and 3-mercaptopropionate ... 

S. pomeroyi could grow at the expense of dimethylsulfoniopropionate and a number of putative degradation products including acrylate, R. nubinhibens was unable to grow with acrylate and neither strain could utilize 3-mercaptopropionate for growth (Gonzalez et al. 2003). 

Shea and MacCrehan [10] determined hydrophillic thiols in sediment pore water using ion-pair chromatography coupled to an electrochemical detector. Down to 2p mole absolute of these compounds could be determined including cysteine, monothiogylcerol, glutathione, mercaptopyruvic acid, 3-mercaptopropionic acid and 2-mercaptopropionic acid. 

Fig. 8.3 Dimethylsulfoniopropionate and dimethyl sulfide cycling in the open ocean. DMSO dimethylsulfoxide, CCN cloud condensation nuclei, MMPA 3-methylpropionate, ji-HP (S-hydrox-ypropionate, 3-MPA 3-mercaptopropionate, MeSH methanethiol, X-CH unidentified molecule with a terminal methyl group. (Reprinted from Yoch 2002, with permission from D. Yoch and the American Society for Microbiology)...

Marc J, van der Maarel C, Jansen M, Hansen T (1995) Methanogenetic conversion of 3-S-methy-lmercaptopropionate to 3-mercaptopropionate. Appl Environ Microbiol 61 48-51... 

Ligand exchange with small charged adsorbants, e.g., 3-mercaptopropionic acid (MPA) [34]... 

PROPYLENE OXIDE ETHYL FORMATE METHYL ACETATE PROPIONIC ACID 3-MERCAPTOPROPIONIC ACID LACTIC ACID METHOXYACETIC ACID TRIOXANE THIACYCLOBUTANE 1-BROMOPROPANE... 

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