Basic information
- CAS
120-91-2- Standard SMILES
CSCCC(O)C(=O)O- InChIKey
ONFOSYPQQXJWGS-UHFFFAOYSA-N- Molecular formula
- C5H10O3S
- Average molar mass
- 150.2 g/mol
- Monoisotopic mass
- 150.03506518
Overview
2-hydroxy-4-(methylthio)-butanoic acid is a light brown liquid. (USCG, 1999)
Names & identifiers
- Preferred name
- alpha-Hydroxy-gamma-methylmercaptobutyric acid
- IUPAC
- 2-hydroxy-4-methylsulfanylbutanoic acid
- English name
- 2-Hydroxy-4-(methylthio)butyric acid
- Molecular formula
- C5H10O3S
- Molecular weight
- 150.2
Names & synonyms
2-Hydroxy-4-methylthiobutanoic acidalpha-Hydroxy-gamma-methylmercaptobutyric acidRefChem:5858004-methylthio-2-hydroxybutyratealpha-hydroxy-gamma-methylthiobutyrate2-Hydroxy-4-(methylthio)butyric acid583-91-5DesmeninolAlimet2-Hydroxy-4-(methylthio)butanoic acidDesmeninol [INN]Butanoic acid, 2-hydroxy-4-(methylthio)-
Show more names
HMTBAmhaacidHMTBA-13C4Desmenidol-13C4(68-72% in Water)Ipradol (feed grade)MHA acid (feed grade)methioninehydroxyanalog
MHA acid2-hydroxy-4-(methylsulfanyl)butanoic acidMHA-FA2-hydroxy-4-methylsulfanylbutanoic acidMFCD000704902-Hydroxy-4-(methylthio) butanoic acidButyric acid, 2-hydroxy-4-(methylthio)-alpha-Hydroxy-gamma-(methylthio)butyric acid
Database identifiers
- CAS
120-91-2、583-91-5
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 82.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 94.2
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Animal Feed Additives
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]
Density1.21 to 1.23 (USCG, 1999)
Flash Point250 °F (USCG, 1999)
Melting Point250 °C
Vapor Pressure16.0 [mmHg]
Physical Description
2-hydroxy-4-(methylthio)-butanoic acid is a light brown liquid. (USCG, 1999)
Light brown liquid; [CAMEO] Light brown to brown liquid with an odor of sulfur; [MSDSonline]
Solid
Collision Cross Section167.3 Ų [M-H]-
Autoignition Temperature320 °F (USCG, 1999)
Physicochemical properties
Safety & regulation
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
Danger
Hazard information
Regulatory Information
Regulation (EC) No 1831/2003 (amended)
2-Hydroxy-4-(methylthio)butanoic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Butanoic acid, 2-hydroxy-4-(methylthio)-: Environment tier I assessment
Health HazardsCorrosive to the eyes and moderately irritating to the skin. (USCG, 1999)
Hazards SummaryAn irritant; [HSDB] A moderate skin irritant; Corrosive to eyes; [CAMEO] An irritant; Causes burns to eyes; [MSDSonline]
Reactive GroupAcids, Carboxylic
Reactivity Profile
An organosulfide, alcohol, and organic acid. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt.
Chemistry & industry
Pharmacology
Mechanism of Action
METHIONINE PRECURSORS & METHIONINE ANALOGS WERE TESTED FOR THEIR ABILITY TO REPLACE OR TO ANTAGONIZE L-METHIONINE IN THE GROWTH OF PHYSARUM POLYCEPHALUM. 2-HYDROXY-4-(METHYLTHIO)BUTANOIC ACID SUPPORTED GROWTH, WHEN SUBSTITUTED FOR L-METHIONINE.
Metabolism/Metabolites
CHICK LIVER HOMOGENATES CATALYZED THE OXIDATION OF 2-HYDROXY-4-(METHYLTHIO)BUTANOIC ACID TO KETOMETHIONINE & BOTH CHICK LIVER SUPERNATANTS & RAT LIVER SUPERNATANTS CONVERTED KETOMETHIONINE TO THE HYDROXY DERIVATIVE OR TO METHIONINE.
IN RAT TISSUE, BOTH FLAVINE COENZYME & GLUTAMINE ARE REQUIRED FOR THE CONVERSION OF 2-HYDROXY-4-METHYLTHIOBUTYRIC ACID INTO METHIONINE. PER GRAM OF TISSUE, THE KIDNEY POSSESSES GREATER CONVERSION ACTIVITY THAN THE LIVER, BRAIN, SMALL INTESTINE, & MUSCLE, ALTHOUGH ON A TOTAL ORGAN BASIS THE LIVER IS THE MOST IMPORTANT. MOST OF THE CONVERSION ACTIVITY IS LOCATED IN THE SUPERNATANT FRACTION OF THE LIVER.
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Methionine hydroxy analog is used as a livestock dietary supplement; [Merck Index]
Farming (Pesticides) [Category: Industry]
CALCIUM SALT IN POULTRY FEED
Methods of ManufacturingBLAKE, WINEMAN, US PATENTS 2,745,745 AND 2,938,053 (1956 AND 1960 TO MONSANTO)
General Manufacturing InformationButanoic acid, 2-hydroxy-4-(methylthio)-: ACTIVE
Applications
UsesMethionine hydroxy analogue
Uses2-Hydroxy-4-(methylthio)butyric Acid is used to improve stem activity to eliminate deoxynivalenol-induced intestinal injury.
Related reactions
11 records
Compound notes
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