Chemistry:2-Hydroxy-4-(methylthio)butyric acid
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| C5H10O3S | |
| Molar mass | 150.19 g·mol−1 |
| Appearance | colorless or white solid |
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| GHS Signal word | Danger |
| H315, H318, H412 | |
| P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P273, P280, P302+352, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P317Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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2-Hydroxy-4-(methylthio)butyric acid is an organic compound with the structural formula CH3SCH2CH2CH(OH)CO2H. It is a white solid. In terms of functional groups, the molecule is a α-hydroxy carboxylic acid and a thioether. The compound is structurally related to the amino acid methionine by replacement of the amine with a hydroxy group.
The compound is produced commercially in racemic form from acrolein by conjugate addition of methanethiol followed by formation and hydrolysis of a cyanohydrin.[2] it is used as a substitute for methionine in animal feed.[3]
In nature, the compound is also an intermediate in the biosynthesis of 3-dimethylsulfoniopropionate, precursor to natural dimethyl sulfide.[4]
References
- ↑ "2-Hydroxy-4-(methylthio)butyric acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/11427#section=Safety-and-Hazards.
- ↑ Rey, Patrick; Rossi, Jean-Christophe; Taillades, Jacques; Gros, Georges; Nore, Olivier (2004). "Hydrolysis of Nitriles Using an Immobilized Nitrilase: Applications to the Synthesis of Methionine Hydroxy Analogue Derivatives". Journal of Agricultural and Food Chemistry 52 (26): 8155–8162. doi:10.1021/jf048827q. PMID 15612811.
- ↑ Lemme, A.; Hoehler, D.; Brennan, JJ; Mannion, PF (2002). "Relative Effectiveness of Methionine Hydroxy Analog Compared to DL-Methionine in Broiler Chickens". Poultry Science 81 (6): 838–845. doi:10.1093/ps/81.6.838. PMID 12079051.
- ↑ Curson, Andrew R. J.; Liu, Ji; Bermejo Martínez, Ana; Green, Robert T.; Chan, Yohan; Carrión, Ornella; Williams, Beth T.; Zhang, Sheng-Hui et al. (2017). "Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process". Nature Microbiology 2 (5): 17009. doi:10.1038/nmicrobiol.2017.9. PMID 28191900. https://ueaeprints.uea.ac.uk/id/eprint/62649/1/Todd_Figure_1.pdf.
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