2-Hydroxy-4-(methylthio)butyric acid

Base Information

• Chemical Name: 2-Hydroxy-4-(methylthio)butyric acid
• CAS No.: 583-91-5
• Deprecated CAS: 110518-19-9,120-91-2,96661-25-5
• Molecular Formula: C5H10O3S
• Molecular Weight: 150.199
• European Community (EC) Number: 209-523-0
• UNII: Z94465H1Y7
• DSSTox Substance ID: DTXSID50862236
• Nikkaji Number: J21.888J
• Wikipedia: 2-Hydroxy-4-(methylthio)butyric_acid
• Wikidata: Q27295171
• NCI Thesaurus Code: C77373
• Metabolomics Workbench ID: 47619
• ChEMBL ID: CHEMBL2104213
• Mol file: 583-91-5.mol

Synonyms:(+-)-isomer of alpha-hydroxy-gamma-methylmercaptobutyric acid;2-hydroxy-4-methylthiobutanoic acid;2-hydroxy-4-methylthiobutyrate;4-methylthio-2-hydroxybutyrate;Alimet;alpha-hydroxy-gamma-methylmercaptobutyric acid;alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt;alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt (2:1);alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt(+-)-isomer;alpha-hydroxy-gamma-methylmercaptobutyric acid, monosodium salt;alpha-hydroxy-gamma-methylmercaptobutyric acid, monosodium salt (S)-isomer;alpha-hydroxy-gamma-methylthiobutyrate;alpha-hydroxymethionine;methionine hydroxy analog

Chemical Property of 2-Hydroxy-4-(methylthio)butyric acid

Chemical Property:

• Appearance/Colour: Light brown liquid
• Vapor Pressure: 3.45E-05mmHg at 25°C
• Refractive Index: 1.529
• Boiling Point: 316.5 °C at 760 mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 145.2 °C
• PSA: 82.83000
• Density: 1.277 g/cm³
• LogP: 0.18500
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 150.03506535
• Heavy Atom Count: 9
• Complexity: 94.2

Purity/Quality:

99.9% ^*data from raw suppliers

2-Hydroxy-4-(methylthio)butyricAcid ^*data from reagent suppliers

Safty Information:

• Statements: 23/24/25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Animal Feed Additives
• Canonical SMILES: CSCCC(C(=O)O)O
• Recent ClinicalTrials: Study of CPX-351 (VYXEOS) in Individuals < 22 Years With Secondary Myeloid Neoplasms
• Uses: Methionine hydroxy analogue 2-Hydroxy-4-(methylthio)butyric Acid is used to improve stem activity to eliminate deoxynivalenol-induced intestinal injury.

Technology Process of 2-Hydroxy-4-(methylthio)butyric acid

There total 23 articles about 2-Hydroxy-4-(methylthio)butyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-hydroxyoxolan-2-one (19444-84-9) + sodium thiomethoxide (5188-07-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Guidance literature:

3-hydroxyoxolan-2-one; sodium thiomethoxide; In N,N-dimethyl-formamide; at 153 ℃; for 3h;

With hydrogenchloride; water; Product distribution / selectivity;

Reference yield: 99.0%

2-hydroxy-4-(methylthio)butyronitrile (17773-41-0) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Guidance literature:

With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC₈₇₅₀; at 30 ℃; for 48h; pH=7.3;

DOI:10.1021/jf048827q

Reference yield: 90.0%

α-hydroxy-4-methylthiobutyramide (49540-21-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Guidance literature:

With sodium hydroxide; In water; for 3h; Heating;

DOI:10.1016/S0040-4039(00)95254-7

upstream raw materials:

DL-methionine

L-methionine

2-hydroxy-4-(methylthio)butyronitrile

α-hydroxy-4-methylthiobutyramide

Downstream raw materials:

D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester

(R)-2-hydroxy-4-(methylthio)butanoic acid

C₆H₁₃O₃S⁽¹⁺⁾*I^(1-)

C₁₂H₁₇O₃S⁽¹⁺⁾*Br^(1-)

Refernces

• 1、 -. "METHOD AND DEVICE FOR PREPARING 2-HYDROXY-4-METHYLTHIOBUTYRIC ACID AND INTERMEDIATES THEREOF". Paragraph 0166-0169; 0185-0188; 0204-0207. . Retrieved 2021/05/21.
• 2、 -. "METHOD FOR MANUFACTURING 2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID". Paragraph 0050-0055. . Retrieved 2021/06/26.