2-Hydroxy-4-(methylthio)butyric acid

2-Hydroxy-4-(methylthio)butyric acid
Names
Other names
    • 2-Hydroxy-4-(methylthio)-butanoic acid
    • α-Hydroxy-γ-(methylthio)-butyric acid
    • Desmeninol
    • Alimet
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.659 Edit this at Wikidata
EC Number
  • 209-523-0
UNII
  • InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
    Key: ONFOSYPQQXJWGS-UHFFFAOYSA-N
  • CSCCC(O)C(O)=O
Properties
C5H10O3S
Molar mass 150.19 g·mol−1
Appearance colorless or white solid
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H315, H318, H412
P264, P264+P265, P273, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ^ "2-Hydroxy-4-(methylthio)butyric acid". pubchem.ncbi.nlm.nih.gov. Retrieved 28 April 2022.
  2. ^ 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.
  3. ^ 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.
  4. ^ Curson, Andrew R. J.; Liu, Ji; Bermejo Martínez, Ana; Green, Robert T.; Chan, Yohan; Carrión, Ornella; Williams, Beth T.; Zhang, Sheng-Hui; Yang, Gui-Peng; Bulman Page, Philip C.; Zhang, Xiao-Hua; Todd, Jonathan D. (2017). "Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process" (PDF). Nature Microbiology. 2 (5): 17009. doi:10.1038/nmicrobiol.2017.9. PMID 28191900. S2CID 21460292.